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San Juan & the Virgin Islands

Dec 27, 2026 — Jan 3, 2027

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SAN JUAN → SAN JUAN

7 Nights on Star Pride

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.

Additional Information
Map routes may vary by sailing. Actual itineraries are listed below.
1
DEC 27, 2026
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
5

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

Available Excursions

San Juan

Time
8:30 AM
Duration
4 Hours
Activity Level
N/A

Add during booking

$729

San Juan

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous

Add during booking

$159

San Juan

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Moderate-Strenuous

Add during booking

$159

San Juan

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

Add during booking

$829

San Juan

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate

Add during booking

$289

2
DEC 28, 2026
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
5

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Available Excursions

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy

Add during booking

$99

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$149

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$129

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$149

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$139

3
DEC 29, 2026
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
9

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

Available Excursions

Gustavia

Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate

Add during booking

$349

Gustavia

Time
5:00 PM
Duration
1.5 Hours
Activity Level
Easy-Moderate

Add during booking

$199

Gustavia

Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate

Add during booking

$519

Gustavia

Time
8:30 AM
Duration
1 Hours
Activity Level
Easy

Add during booking

$139

Gustavia

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous

Add during booking

$349

Gustavia

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate

Add during booking

$349

Gustavia

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$299

Gustavia

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous

Add during booking

$509

Gustavia

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$499

4
DEC 30, 2026
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
8

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Available Excursions

Basseterre

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy

Add during booking

$109

Basseterre

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy

Add during booking

$99

Basseterre

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous

Add during booking

$129

Basseterre

Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$119

Basseterre

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate

Add during booking

$79

Basseterre

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$99

Basseterre

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate

Add during booking

$59

Basseterre

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate

Add during booking

$139

5
DEC 31, 2026
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
4

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

Available Excursions

Philipsburg, St. Maarten

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous

Add during booking

$169

Philipsburg, St. Maarten

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

Add during booking

$99

Philipsburg, St. Maarten

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

Add during booking

$799

Philipsburg, St. Maarten

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate

Add during booking

$189

6
JAN 01, 2027
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
1

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

Available Excursions

Jost Van Dyke, Great Harbour

Time
9:30 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous

Add during booking

$259

7
JAN 02, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
2

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

Available Excursions

Virgin Gorda / Prickly Pear, British Virgin Islands

Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

Add during booking

$269

Virgin Gorda / Prickly Pear, British Virgin Islands

Time
8:00 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$89

8
JAN 03, 2027
San Juan
ARRIVE
7:00 AM
DISEMBARK
8:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

Star Pride

number of decks
6 Decks
yacht length
440 ft (134 meters)
yacht crew size
140 Crew Members
yacht guest capacity
312 Guests
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Staterooms

Room Size 575 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 400 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 468 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Room Size 277 sq ft
Max. Occupancy 3 Passengers
Amenities

Room Size 277 sq ft
Max. Occupancy 2 Passengers
Amenities
Expand all

Available Dates

Date Yacht
Starting from
Actions
Nov 15 (Sun) – Nov 22 (Sun), 2026November 15 (Sun) – November 22 (Sun), 2026Star Pride
Nov 29 (Sun) – Dec 6 (Sun), 2026November 29 (Sun) – December 6 (Sun), 2026Star Pride
Dec 13 (Sun) – Dec 20 (Sun), 2026December 13 (Sun) – December 20 (Sun), 2026Star Pride
Jan 10 (Sun) – Jan 17 (Sun), 2027January 10 (Sun) – January 17 (Sun), 2027Star Pride
Nov 1 (Mon) – Nov 8 (Mon), 2027November 1 (Mon) – November 8 (Mon), 2027Star Pride
Nov 15 (Mon) – Nov 22 (Mon), 2027November 15 (Mon) – November 22 (Mon), 2027Star Pride
Dec 20 (Mon) – Dec 27 (Mon), 2027December 20 (Mon) – December 27 (Mon), 2027Star Legend
Jan 3 (Mon) – Jan 10 (Mon), 2028January 3 (Mon) – January 10 (Mon), 2028Star Legend
Jan 17 (Mon) – Jan 24 (Mon), 2028January 17 (Mon) – January 24 (Mon), 2028Star Legend
Jan 31 (Mon) – Feb 7 (Mon), 2028January 31 (Mon) – February 7 (Mon), 2028Star Legend
Feb 14 (Mon) – Feb 21 (Mon), 2028February 14 (Mon) – February 21 (Mon), 2028Star Legend
Mar 20 (Mon) – Mar 27 (Mon), 2028March 20 (Mon) – March 27 (Mon), 2028Star Pride

San Juan & the Virgin Islands

SAN JUAN → SAN JUAN

7 Nights on Star Pride

Dec 27, 2026 — Jan 3, 2027

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.

1
DEC 27, 2026
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
5

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

Shore Excursion

Port
San Juan
Time
8:30 AM
Duration
4 Hours
Activity Level
N/A

Add during booking

$729 USD

San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Airport

Not every day will you get an opportunity to visit the 2nd oldest city in America. For about 90 minutes you will walk the cobblestone streets accompanied by an expert guide who will give you interesting information on many amazing structures and relate events that make Old San Juan a must-do on your bucket list. You will visit San Cristobal Fort, the largest fort built by the Spanish in the New World. Learn the mystery of the sentry boxes and other memorable facts. On the way to the airport you will also have the opportunity to visit and learn the history of the Tapia Theater, Plaza Colon, Plaza de Armas, La Rogativa, The San Jose Church, The Governor's Main House, San Juan Cathedral, and other interesting sites. Please note : Wear comfortable attire and walking shoes.

Port
San Juan
Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous

Add during booking

$159 USD

San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Windstar Hotel

Not every day will you get an opportunity to visit the 2nd oldest city in America. For about 90 minutes you will walk the cobblestone streets accompanied by an expert guide who will give you interesting information on many amazing structures and relate events that make Old San Juan a must-do on your bucket list . You will visit San Cristobal Fort, the largest fort built by the Spanish in the New World. Learn the mystery of the sentry boxes and other memorable facts. On the way to the airport you will also have the opportunity to visit and learn the history of the T apia Theater, Plaza Colon, Plaza de Armas, La Rogativa, The San Jose Church, The Governor's Main House, San Juan Cathedral , and other interesting sites. You will be transferred to the Windstar Hotel. Please note : Wear comfortable attire and walking shoes.

Port
San Juan
Time
8:30 AM
Duration
3.25 Hours
Activity Level
Moderate-Strenuous

Add during booking

$159 USD

San Juan, Concierge Collection: Half Day Private SUV with Guide

Explore at your leisure with a private vehicle, driver, and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own car. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites or create your own personal stops to make the experience your own. Please note : Capacity: 3-6 guests. Private cars are ordered per vehicle (not per person). This tour includes transport in a private car, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 4 hours. Recommended for physically challenged guests.

Port
San Juan
Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

Add during booking

$829 USD

San Juan, Bacardi Rum Tour & Tasting- With Transfer to Windstar Hotel

San Juan, Bacardi Rum Tour & Tasting- With Transfer to Windstar Hotel

Port
San Juan
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate

Add during booking

$289 USD

2
DEC 28, 2026
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
ARRIVE
8:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
5

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

St. John, Island tour Featuring Annaberg Ruins

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy

Add during booking

$99 USD

St. John, Champagne Catamaran Sail

Set sail on a relaxing three-hour catamaran cruise through Virgin Islands National Park, enjoying shaded seating or sun deck views as you head to a vibrant snorkel site. Explore colorful reefs teeming with tropical fish and maybe even a sea turtle, or simply float on the crystal-clear water. Visit secluded Honeymoon Beach (conditions permitting) before unwinding with snacks and drinks on a scenic sail back to St. John.

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$149 USD

St. John, Lind Point Trail Eco Hike

Set out from Cruz Bay with an ecologist guide for a scenic hike through lush tropical forest, learning about local wildlife, native history, and island culture. Take in sweeping views of St. Thomas and the British Virgin Islands before reaching tranquil Honeymoon Beach, where you can swim or relax beneath coconut trees. Continue along the Lind Point trail back to Cruz Bay.

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$129 USD

St. John, Trunk Bay Snorkeling Experience

St. John is a breathtaking island known for its pristine white-sand beaches and lush tropical landscapes. Enjoy scenic views of Cruz Bay, Hawksnest Bay, and the historic Caneel Bay Plantation as you make your way to the highlight of the tour—iconic Trunk Bay. Here, a unique underwater snorkeling trail awaits. Spend more than 90 minutes swimming and snorkeling along the marked route, where vibrant corals and tropical fish are easy to spot, or simply unwind beneath the shade of a palm tree. Snorkel gear, instruction, and a lounge chair are all included.

Please note: Wear a swimsuit and bring a towel, sunscreen, and a hat.

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$149 USD

St. John, Champagne Catamaran Sail

Spend a relaxing self-guided day at Cinnamon Bay Beach, with at least three hours to swim, explore historic ruins, or unwind beneath the palms in complimentary lounge chairs. Enjoy a casual snack lunch and drinks from the beachside snack shack whenever you’re feeling thirsty or hungry.

Port
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate

Add during booking

$139 USD

3
DEC 29, 2026
Gustavia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
9

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

St. Barts: Independent Explorer by Car

Here is a chance for the adventuresome to get away from the crowds, get behind the wheel, and enjoy the lush countryside on a self-guided tour . You will be escorted from the pier to the nearby starting point and after brief formalities you will be given the keys to your rental car. Armed with a map of the island, some suggested itineraries, and some details about historical facts and points of interest, you're ready to explore this beautiful island at your own pace . The cost is for the car; one to four people can explore at just one rate. Please note : Participants must be comfortable driving winding and hilly conditions. Bring your swimsuit, a credit card, and a current driver's license. The tour price is per car and includes CDW insurance, a $1200 euro deductible which will be fully or partially charged to the driver's credit card in the event the car is returned damaged. Fuel costs are included. Pricing is per car, and can hold up to 4 guests. Only one person in the party needs to purchase the tour. Your tour time may vary depending on when your ship docks.

Port
Gustavia
Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate

Add during booking

$349 USD

St. Barts, Concierge Collection: Sunset Cruise

Boarding your sailing cat you will depart from Gustavia's tender pier. Your Captain will give a safety briefing as you set sail. You will have a peaceful and quiet sailing time in the vicinity of the harbor area to enjoy scenic views of the sunset. You will appreciate the scenic panorama, passing the mega yachts at anchor. The Captain will offer you Champagne, mineral water, soft drinks or beer and some assorted light snacks. The crew will be attentive and helpful. Please note : You will board the ship with a gangway that can be tricky because of the recurrent swell in Gustavia harbor. You will have to remove your shoes and be barefoot before boarding the vessel. The Captain is solely responsible and has the right to refuse boarding to a guest who would be judged unable to participate. Cancellations must be made 48 hours prior to cruise time for refunds.

Port
Gustavia
Time
5:00 PM
Duration
1.5 Hours
Activity Level
Easy-Moderate

Add during booking

$199 USD

St Barts, Concierge Collection: St. Barthelemy Beach Day

You will find Le Barthélemy Resort and Spa at the end of a beautiful bay right on a stunning beach. Le Barthélemy is sheer luxury, so let yourself be spoiled. In the rare beauty of the natural setting, you will understand the spirit of St. Barts; elegance, refinement, and discretion. Enjoy your lunch, swim, make use of the non-motorized watersport equipment provided, or do nothing at all, enjoy yourself. Le Barthélemy lets you forget all worries for the day and slips you into a cocoon of comfort and contentment. ENJOY! This is the life, St. Bart's style. This excursion was arranged specifically for and is exclusive to Windstar guests. Please note : Bring your swimsuit, sunscreen, and a cover up for the restaurant. Lunch is included at the resort restaurant.

Port
Gustavia
Time
8:30 AM
Duration
6 Hours
Activity Level
Easy-Moderate

Add during booking

$519 USD

St. Barts: Intimate Island Tour

This is an exclusive panorama island tour for five people with a local, English speaking driver/guide in an air-conditioned vehicle. Experience the local highlights as you wish, at your pace. Please note : Wear comfortable shoes and clothes.

Port
Gustavia
Time
8:30 AM
Duration
1 Hours
Activity Level
Easy

Add during booking

$139 USD

Gustavia, Concierge Collection: Scuba Dive 1 Tank

Explore the vibrant flora and fauna of St. Barthélemy with our expert, accredited instructors as they guide you through the stunning sites of the Protected Marine Reserve on this one tank dive. Please note: any electronic devices (such as cell phones, cameras, etc.) and valuable items should be securely stored in a waterproof, sealable dry bag. Guests are responsible for any damage to these items. Please bring copies of your PADI scuba certification.

Port
Gustavia
Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous

Add during booking

$349 USD

Gustavia, Concierge Collection: Savor St Barts

St. Barthélemy offers a unique culinary experience that blends French and Caribbean flavors into a delicious fusion. Stroll through the charming streets of Gustavia, where luxury boutiques and hidden gems await, all while savoring some of the island's finest gastronomic delights at every stop. Your culinary adventure begins with a classic French treat: a crepe, served with a choice of lemon and sugar or warm homemade chocolate. Discover the origins of this beloved dish from the Bretagne region, and enjoy it with a refreshing glass of hard apple cider. Next, head to the iconic "Le Select" bar, famous for being the place where Jimmy Buffett wrote his hit song "Cheeseburger in Paradise" in 1978. Known for its legendary rum punch, called "Planteur" (available with or without alcohol), this stop promises a fun and flavorful experience. Then, wander to a cozy restaurant nestled in the heart of Gustavia, where you'll enjoy a healthy "Tartine," a French open-faced sandwich topped with smoked salmon, lemon Greek yogurt, avocado, and sesame seeds, paired with a chilled Passion Fruit Iced Tea. The grand finale of your culinary tour takes you to the elegant Barons de Rothschild lounge, where you'll indulge in two glasses of their signature champagne: the Blanc de Blanc and the Rose Champagne, accompanied by the unforgettable Baron de Rothschild cheese. It's the perfect way to unwind and savor the finest flavors of St. Barth. At the end of the tour, your guide will escort you back to the tender, or you may choose to stay and explore the shops of Gustavia at your own pace.

Port
Gustavia
Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate

Add during booking

$349 USD

St. Barts: Sailing Catamaran Adventure

Caribbean music and the friendly crew of a well-appointed, full-sail catamaran will welcome you aboard. This boat is specially designed to offer shade and refreshing breezes as you sail along the beautiful west coast of the island to the Marine Park at Colombier Bay . You will anchor about 80 feet offshore, close to coral reefs teeming with schools of colorful fish. A professional instructor will give you a full orientation and explain the use of the snorkel equipment. You will have time to swim and snorkel, or simply bask in the sun. On the return to Gustavia, soft drinks, beer, or refreshing rum punch or fruit punch will be offered. Please note : This exclusive experience is limited to 12 guests and sells out quickly. No previous sailing experience necessary. The catamaran will offer refreshments throughout the trip. Restrooms are located on board the catamaran. Bring sunscreen, hat, swimsuit, and underwater camera and towel. Snorkeling gear is available on the boat.

Port
Gustavia
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

Add during booking

$299 USD

Gustavia, Concierge Collection: Jet Ski

Embark on an exciting adventure to discover St. Barth's most stunning beaches! Accompanied by professional instructors, you'll begin your journey from Gustavia Harbor, making stops at the picturesque Shell Beach, the secluded Gouverneur Beach, and the beautiful Salines Beach, before heading south to Coco Island, located 0.62 miles from St. Barth. Along the way, enjoy a 15-minute swim break in the calm waters before hopping back onto your jet-ski for the return ride to Gustavia. Please note: participants must be at least 16 years old. You will be required to sign a waiver prior to participating in this tour.

Port
Gustavia
Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous

Add during booking

$509 USD

Gustavia, Concierge Collection: Scuba Dive 2 Tank

Explore the vibrant flora and fauna of St. Barthélemy with our expert, accredited instructors as they guide you through the stunning sites of the Protected Marine Reserve on this two tank dive. Please note: any electronic devices (such as cell phones, cameras, etc.) and valuable items should be securely stored in a waterproof, sealable dry bag. Guests are responsible for any damage to these items. Please bring copies of your PADI scuba certification.

Port
Gustavia
Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

Add during booking

$499 USD

4
DEC 30, 2026
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
8

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Basseterre: Caribbean Scenic Railway

Completely circle the island of St. Kitts by road and rail in just a few hours. The St. Kitts Scenic Railway is a narrow-gauge railroad that was built almost a century ago to deliver sugar cane from the fields to the mill in Bassetèrre. Each railcar features seating on two levels. The upper level features a spacious open-air observation deck offering panoramic views of the surrounding countryside, while the lower level provides air-conditioned comfort. Island ambiance will be evoked with comfortable rattan furniture, complimentary specialty drinks, island music by the Scenic Railway Choir , and an informative narrative history of the Caribbean. In addition to your rail experience, your sightseeing will also feature a scenic drive by bus along the southwestern coast. Enjoy unparalleled vistas of Brimstone Hill Fortress , the British "Gibraltar of the West Indies," Middle Island where Thomas Jefferson's great-grandfather is buried, and the neighboring island of Nevis, birthplace of American statesman Alexander Hamilton. Please note : Bring your camera, sunscreen, sunglasses, and a hat if you are planning on sitting on the upper level.

Port
Basseterre
Time
8:30 AM
Duration
3 Hours
Activity Level
Easy

Add during booking

$109 USD

Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts

A unique culinary experience! You may have previously enjoyed the exotic flavors of West Indian cooking, but do you know the actual ingredients of the dishes or their history? Regardless of whether you are a seasoned cook or just a lover of tasty cuisine, this demonstration will appeal to you. After a short drive you will arrive at Fairview Great House & Tropical Garden. Enjoy regional dishes prepared before your eyes . As ingredients are added, the historian cook will recount tales about the history of the regional foods, and talk about the development of dishes that use African, European, and Indian cooking methods. Then you will sample the dishes along with homemade refreshments. Explore the Fairview Great House & Botanical Garden. You may also choose to meander through the different areas of the beautifully landscaped 2.5-acre botanical garden at your leisure. Complimentary copies of the recipes of the dishes prepared during your tour will be yours to take home as a souvenir of your unique experience in St. Kitts. Please note : Due to the limited space available on this tour, it will sell out quickly.

Port
Basseterre
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy

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$99 USD

Basseterre: St Kitts Quad ATV Adventure

Here is a unique way to experience the Caribbean! This exciting exploration will begin with a transfer from the dock to the Quad Bike (ATV) base. After an introduction and full orientation on the use of the bikes and safety precautions, you will be ready to mount the four-wheel ATV bikes for a wildly exhilarating adventure. Your experienced guide will lead you on a thrilling ride through cane fields and down country dirt tracks and up scenic slopes with views of neighboring islands. On the way you may also be able to taste local fruits in season. Then it will be time once more to get back on the bikes and return to the tour base. Enjoy a cool drink before you will be transferred back to the pier. Please note : You will be provided with a helmet. This tour is not recommended for those with mobility issues or back problems as you will be traveling off road over hilly and bumpy terrain. You will be required to sign a waiver to participate on this tour. Maximum weight is 250 lbs.

Port
Basseterre
Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous

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$129 USD

Basseterre: Sky Safari Zipline Adventure

Fly along zip lines up to 1,400 feet in length, 25 stories above the ground! This is a spectacular 5-line zip line journey based at the Historic Wingfield Estate . After a short orientation, training session, and riding the first (trainer) line, you will hop into vehicles for a trek up the famous Valley of the Giants . You will see fantastic panoramic views of Brimstone Hill Fortress, Old Road Village , former sugar estates, the Caribbean Sea, and Mount Liamuiga. With a mile of zip lines you will soar at speeds up to 50 miles per hour . Thanks to the cutting edge technology of this system you will fly hands and feet free, just like a bird. All you have to do is sit back, and enjoy the experience! You will also be given an opportunity to walk around the Wingfield Estate Ruins. View the first British masonry in the entire New World as well as the remnants of the different methods of processing sugar which are all on site. As an additional treat your tour also includes a short walk to the Romney Manor , home of Caribelle Batik, where you can enjoy the enchanting gardens, batik studios, and gift shop. Please note : This tour is not available for guests who are pregnant, have a heart condition or serious medical condition, previous neck or back injuries. To participate on this tour guests must wear closed-toe shoes, weigh at least 60 pounds but no more than 275 pounds and sign a waiver. Any guests wishing to bring along personal items will have the option to leave items at the base and rent a locker to store them in. Price per locker is $3 US and payable directly to the Sky Safari facility.

Port
Basseterre
Time
8:30 AM
Duration
4 Hours
Activity Level
Strenuous

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$119 USD

Basseterre, Brimstone Hill Fortress & Fairview Great House

On this tour, you will enjoy an overview of the capital of St. Kitts & Nevis and get an up-close look at the island's colonial splendor. Board your motor coach for the 30-minute drive with your guide into Basseterre, one of the oldest towns in the Eastern Caribbean. Admire impressive Victorian and Georgian architecture and view important landmarks such as the Berkeley Memorial Clock Tower and Independence Square, once a slave market and today host to a picturesque fountain and a centuries-old church. You will stop at the Fairview Great House and Tropical Garden. At this 300-year-old colonial property, you will explore perfectly preserved rooms, including the original kitchen with its volcanic stone and brick oven and the bathing room with its sun-warmed bath. Follow the stone bridge to the lush tropical botanical garden, where many of the plants such as palms and fruit trees date back as far as the 1700s. Then explore the 300-year-old Brimstone Fortress, perched 780 feet above sea level. This magnificent structure is the second largest of its type in the entire Western Hemisphere and is one of the best preserved. This Gibraltar of the West Indies is a UNESCO World Heritage Site and more battles were fought here than at any other single site in British and French naval history. Its spectacular panoramic views include part of the Kittitian coastline, countryside and five neighboring islands. Please note : This tour is not wheelchair accessible.

Port
Basseterre
Time
8:30 AM
Duration
3.25 Hours
Activity Level
Easy-Moderate

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$79 USD

Basseterre: Snorkel Safari

Experience the pleasure of snorkeling at several sites that are abundant with tropical fish and coral life . There will be a short 10-minute walk from the pier to the marina where your boat awaits. Then you will cruise the island's pristine southeast peninsula, inhabited by the shy green vervet monkey. Snorkeling opportunities include Ballets Bay, Shitten Bay, and Bugs Hole . Marine life varies but you may see: turtles, eagle rays and stingrays, schools of saltwater chub, snapper, angel fish, parrot fish, squirrel fish, and sand sharks. Many virgin reefs and extensive soft corals, fans, and sponges make up the reef life. Thirst-quenching non-alcoholic drinks, local beer and water will be provided. Please note : Wear your swimsuit under your clothing and bring a towel. (Towels will be available at the gangway.) Your waiver release form must be signed and medical conditions must be disclosed. Access to and from the water is done by a ladder on the side of the boat.

Port
Basseterre
Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate

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$99 USD

Basseterre, Island History & Rum Tasting

Your tour will begin with a narrated drive around historic Basseterre, one the oldest towns in the Eastern Caribbean. You will view Victorian and Georgian style architecture, important monuments such as the Berkeley Memorial Clock Tower, Independence Square (once a former slave market) with its prominent fountain and impressive centuries-old Catholic Co-Cathedral across the street. See the newly restored Fairview Great House & Botanical Garden. Here you will enjoy a guided tour around the Great House, which is believed to have been originally built in 1701 by the French. The inhabitants who have been recorded to reside here include American legal luminary John Gardiner and Lawyer James Stephen -advocate of the enslaved. The rich history of the site and the island is well displayed with its superbly furnished historical information room that brings to life the 1700s - 1800 with true impressions of what life was like on an Estate in St. Kitts during that era. From the cobblestone courtyard view the original kitchen building with its volcanic stone and brick oven; the original bathing room with its large sun warmed volcanic stone bath; the stone bridge leading from the rear veranda of the Great House to the rear area of the tropical botanical garden. While in the courtyard don't forget to wander into the old stone cellar where you will find a slavery exhibit. This self guided exhibit provides a glimpse of the African-Caribbean slavery story which began in Africa. The experience includes details of the journey through the Middle Passage to the Caribbean. Learn about the life of the slaves on the plantation during the pre and post emancipation period. You will be given the opportunity to taste several flavors of rum, hear the history of where rum came from in the Caribbean and how Caribbean people made their own rum. Hear stories of when the Irish settled on St. Kitts and the rum legacies they left and how and where rum drinking has evolved on the island. After your rum tasting experience, take time to wander in the 2 1/2 acre Botanical Garden. Don't forget to peek inside the gift shop and pick up some keepsakes that will remind you of this unique experience for years to come. Please note: Bring your camera, cash, credit card, sunscreen, sunglasses, and hat.

Port
Basseterre
Time
8:30 AM
Duration
2.5 Hours
Activity Level
Moderate

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$59 USD

Basseterre, Nevis Panoramic and Beach Tour

Experience the Best of St Kitts and Nevis when you choose this relaxing tour that includes an exhilarating boat ride, a panoramic island tour of Nevis crammed with spectacular views and historical interests, and a luxury beach break. You will board your fast and comfortable power catamaran and head to the beautiful island of Nevis, known in colonial days as the Queen of the Caribbean. Once in Nevis, you will board an air-conditioned van for a panoramic tour of the island, with its lush tropical vegetation and the spectacular vistas of the Caribbean Sea. You will pause for a photo stop at Hamilton House , the birthplace of the United States' first Secretary of the Treasury, Alexander Hamilton. The building is currently used as a museum and hosts the meetings of the Nevis House of Assembly. Your guide will point out interesting landmarks along the way, and you will have an opportunity to visit St. Thomas Lowland Church, built in 1643, the oldest Anglican Church in the Caribbean, where you will see spectacular views back to St Kittts. The highlight of your Island tour could well be Nisbet Plantation , the home of Fanny Nisbet, who, in 1778 married Admiral (then Lieutenant Horatio Nelson in Nevis). Next, your guide will take you through quaint villages to the sands of Pinney's Beach for a Caribbean-style lunch served at a beach-side restaurant. Enjoy delicious rum or fruit punch, as well as an included beach chair and shared umbrella .Perhaps take a refreshing dip in the blue Caribbean Sea. When it is time to reboard your catamaran for the return journey to Basseterre, you will board straight from the beach Please note: Dress in comfortable, casual clothing, bring a towel, your swimsuit and sunscreen. Lunch is included on this tour.

Port
Basseterre
Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate

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$139 USD

5
DEC 31, 2026
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
4

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

St. Maarten: Americas Cup Sailboat Racing

Experience the thrill of racing multi-million dollar America's Cup Race sailboats in the warm blue waters and brisk trade winds of St. Maarten. Previous sailing experience is not necessary for this excursion, which is one of the highest rated in the Caribbean. You will tender out from the 12 Metre Clubhouse dock at Dock Maarten where after a briefing you will take a 10-minute tender ride out to your allocated sailboat. Either Dennis Conner's America's Cup winning Stars & Stripes, Canada II , or True North IV are yours for this once-in-a-lifetime adventure. The expert crew will show you exactly what to do if you want to take a "crew member's" position. Then it's off to the racecourse - grind a winch - trim a sail - punch a stopwatch, or just sit back, relax and e njoy the included refreshments . After the race enjoy a victory rum punch party at the12 Metre Clubhouse where the tour ends. Please note : Wear soft-soled suitable footwear for the sailboat. This event is weather/wind dependent.

Port
Philipsburg, St. Maarten
Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous

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$169 USD

St. Maarten: Under Two Flags Island Tour

The best way to see the "friendly" island of St. Maarten/St. Martin, the smallest island shared between two nations, is to take the Under Two Flags Island Tour. You will depart Philipsburg Port and will be driven to beautiful Oyster Pond, to cross the border to the French side, and follow along Coralita Road to the first stop of your tour. There, you will have the opportunity to enjoy a picturesque lookout point over the impressive Atlantic coast and the islands of Tintamarre and St Bart's. After a short stop, drive through Quartier d'Orléans, better known as French Quarter, past well known Orient Beach and Grand Case, culinary capital of the Caribbean, before arriving in Marigot, capital of the French side. Here you will have time to visit the outdoor seaside market, where among Caribbean souvenirs, local art work and hand-made jewelry, products from Provence, France, can also be found. The West Indies Mall with its French boutiques is just around the corner. Leaving Marigot behind, stop at Cay Hill Lookout Point for another photo op overlooking Simpson Bay Lagoon, one of the largest lagoons in the West Indies, and the blue waters of the Caribbean. Then, for the last stop, you will be dropped off in Philipsburg for some more shopping on Front Street or a nice stroll along the Boardwalk before returning to the Port. Please note : This tour is not wheelchair accessible. Wear comfortable walking shoes, a hat, sunscreen and bring some cash.

Port
Philipsburg, St. Maarten
Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

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$99 USD

St. Maarten, Concierge Collection: Half Day Private Island Tour in SUV or Deluxe Mini Van

Explore at your leisure with a private vehicle, driver, and English-speaking guide. This exclusive tour will allow you to customize your time ashore and explore the most interesting sites in the comfort and privacy of your own car. With your private vehicle, and the personalized attention of your driver and English-speaking guide, you will have the flexibility and independence to design your itinerary ashore. See the iconic sites or create your own personal stops to make the experience your own. Please note : Capacity: 3-6 guests. Private cars are ordered per vehicle (not per person). This tour includes transport in a private car, driver and English Speaking Guide. Itinerary can be adjusted with tour guide as long as it's in the area and does not exceed the duration of 4 hours. Recommended for physically challenged guests.

Port
Philipsburg, St. Maarten
Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

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$799 USD

Philipsburg, Savor St. Maarten Foodie Tour

Philipsburg, Savor St. Maarten Foodie Tour

Port
Philipsburg, St. Maarten
Time
8:30 AM
Duration
4.5 Hours
Activity Level
Easy-Moderate

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$189 USD

6
JAN 01, 2027
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
1

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.

Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

This outing contains all the right ingredients for a fun-filled and memorable day on the water in the BVI. Board a power catamaran from Great Harbor and take in the breathtaking and incredible views of the islands of both the USVI and BVI. Your captain and crew have extensive local knowledge and will share geographical and nautical facts and lore with you. The boat will dock at Pirates Bight on Norman Island, famously known as Treasure Island. The reputed history of piracy on this island is immortalized in Robert Louis Stevenson's famous book Treasure Island . Here, you have free time to snorkel from the beach, enjoy a stroll or simply relax. Please note : Wear your swimsuit under your clothing; bring a towel, sunscreen, and a hat. Guests with heart problems, epilepsy or asthma are not allowed to participate in snorkeling. A waiver must be signed, and medical conditions disclosed. Guests participating in snorkeling should be able to swim and be in good physical condition.

Port
Jost Van Dyke, Great Harbour
Time
9:30 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous

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$259 USD

7
JAN 02, 2027
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
2

The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns

Virgin Gorda: Snorkel Adventure

Board a 36-foot Newton Dive Special vessel for a fun and relaxing cruise through the islands surrounding Virgin Gorda. Motor across the stunning Virgin Gorda waters with views of neighboring islands. The boat will moor at your first snorkel spot, chosen by the Captain as the best location for the day. The crew will assist with getting your snorkel gear ready, give a safety briefing and guide you in the water while pointing out interesting sea life. Once back on board, the Captain will pick out a second snorkel spot for you to enjoy. The tour will end with refreshments on board and a cruise back to shore in time for your beach barbecue. Please note: wear your swimsuit under your clothes, bring a towel, a dry t-shirt or sweatshirt, reef friendly sunscreen, waterproof camera (if you want to record the boulders ashore), and a hat. Participants must sign a waiver before departing the dock. Depending on weather and sea state the snorkel locations might have to be adjusted. Minimum age is 7 years. The only way to experience this natural wonder is with our pre- arranged shore excursion being offered onboard.

Port
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AM
Duration
2.75 Hours
Activity Level
Moderate-Strenuous

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$269 USD

Virgin Gorda: Highlights & Bath Tour

Enjoy the best that Virgin Gorda has to offer when you take this Island Tour to the world famous Baths. Board your open air safari bus at Gun Creek and wind up the hills to Gorda Peak where you will have the opportunity to photograph the impressive archipelago of the B.V.I. Your route will take you on down the spine of this beautiful island. From here you will drive to The Baths. These massive granite boulders stand out against powdery white sand and crystal-clear waters, so seize this chance to scramble through narrow gaps, intricate pools and passages which comprise this adventurous footpath before it opens out to the spectacular white sands of Devil's Bay. The beach at The Baths boasts an appealing bar, souvenir stand and restrooms. For those not physically inclined, you can still be witness to these dramatic batholiths should you take a drink at the Top of The Baths, or the less strenuous path direct down to Devils Bay. Before boarding the safari busses, sample a complimentary rum punch, punch or water at the gazebo above the Baths, and then enjoy the remainder of your circular island tour via Nail Bay with homes of the rich and famous and Hog's Heaven for some stunning shots of the ship anchored in North Sound. Please note : Wear your swimsuit under your clothes, bring reef-friendly sun screen, towel, camera, reef or aqua shoes to explore the Baths, flip-flops are not recommended. This tour is not recommended for those with mobility issues. Use caution while walking down the trail and through the boulders in the caves. Path is uneven and slippery. On some days expect crowds. Please be aware of the National Flag Warning System and adhere to it at all times. Red Flag: Danger - No Swimming. Yellow Flag: Caution - Weak swimmers are discouraged from entering the water. Purple Flag: Jellyfish Warning. The only way to experience this natural wonder is with our pre- arranged shore excursion being offered onboard.

Port
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:00 AM
Duration
4 Hours
Activity Level
Strenuous

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$89 USD

8
JAN 03, 2027
San Juan
ARRIVE
7:00 AM
DISEMBARK
8:00 AM
MARINA
NO
SHORE EXCURSIONS
0

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.