San Juan & the Virgin Islands

Mar 20, 2028 — Mar 27, 2028

Starting from

DATA ART TEST PROMO

See more routes around Caribbean

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.

Popular Highlights

Additional Information

Map routes may vary by sailing. Actual itineraries are listed below.
1
MAR 20, 2028
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
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.

2
MAR 21, 2028
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

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy
Price
$99

St. John, Lind Point Trail Eco Hike

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$129

St. John, Champagne Catamaran Sail

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$139

St. John, Champagne Catamaran Sail

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$149

St. John, Trunk Bay Snorkeling Experience

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$149
3
MAR 22, 2028
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

4
MAR 23, 2028
Gustavia
ARRIVE
7:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

5
MAR 24, 2028
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

6
MAR 25, 2028
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

7
MAR 26, 2028
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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

8
MAR 27, 2028
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

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 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 2 Passengers
Amenities

Starting from

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

San Juan & the Virgin Islands

SAN JUAN → SAN JUAN

7 Nights on Star Pride

Mar 20, 2028 — Mar 27, 2028

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
MAR 20, 2028
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
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.

2
MAR 21, 2028
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, 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, 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

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, 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

3
MAR 22, 2028
Basseterre
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

4
MAR 23, 2028
Gustavia
ARRIVE
7:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

5
MAR 24, 2028
Philipsburg, St. Maarten
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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.

6
MAR 25, 2028
Jost Van Dyke, Great Harbour
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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.

7
MAR 26, 2028
Virgin Gorda / Prickly Pear, British Virgin Islands
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

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

8
MAR 27, 2028
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.