Windward Islands Surf & Sunsets

Dec 27, 2027 — Jan 3, 2028

Starting from

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SAN JUAN → SAN JUAN

7 Nights on Star Legend

Revel in seven days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean’s Windward Islands. It’s a perfect vacation getaway for anyone craving a quick escape from life’s everyday obligations. Swim among sea turtles and glide above dazzling coral reefs with a highly skilled diving guide off the coast of Les Saintes’ volcanic shoreline. Vacation time is always well spent among the Windward Islands, but nothing makes it more perfect than the personalized attention and unique excursion opportunities offered by Windstar.

Popular Highlights

Additional Information

Map routes may vary by sailing. Actual itineraries are listed below.
1
DEC 27, 2027
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
DEC 28, 2027
AT SEA
3
DEC 29, 2027
St. George's
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

4
DEC 30, 2027
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.

5
DEC 31, 2027
Mayreau
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.

6
JAN 01, 2028
Les Saintes
ARRIVE
10:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

7
JAN 02, 2028
Marigot, St. Martin
ARRIVE
8:00 AM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
4

Established around 1689, Marigot is the attractive capital of French St. Martin, with its brightly colored houses, a lively open-air market, secluded beaches, and pretty waterfront promenade. Because of its tax-free status, Marigot is a popular center for duty-free shopping, where all of the world's most prestigious brands can be found.  Originally the area was marshy, and surrounded by mangroves. In the 1970s part of the bay was filled in to extend Marigot into a larger city with a marina. Overlooking Marigot is Fort St. Louis, the largest historical monument in St. Martin with an impressive panoramic view of the bay.

Marigot, Beach Day at KKO With Lunch

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy
Price
$259

Marigot, Rhum and Rhythm

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$299

Marigot, French Creole Cooking Class

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$319

Marigot, French and Dutch Island Discovery

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$99
8
JAN 03, 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 Legend

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

Windward Islands Surf & Sunsets

SAN JUAN → SAN JUAN

7 Nights on Star Legend

Dec 27, 2027 — Jan 3, 2028

Revel in seven days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean’s Windward Islands. It’s a perfect vacation getaway for anyone craving a quick escape from life’s everyday obligations. Swim among sea turtles and glide above dazzling coral reefs with a highly skilled diving guide off the coast of Les Saintes’ volcanic shoreline. Vacation time is always well spent among the Windward Islands, but nothing makes it more perfect than the personalized attention and unique excursion opportunities offered by Windstar.

1
DEC 27, 2027
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
DEC 28, 2027
AT SEA
3
DEC 29, 2027
St. George's
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
0

Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

4
DEC 30, 2027
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
0

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.

5
DEC 31, 2027
Mayreau
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.

6
JAN 01, 2028
Les Saintes
ARRIVE
10:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
0

This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

7
JAN 02, 2028
Marigot, St. Martin
ARRIVE
8:00 AM
DEPART
3:00 PM
MARINA
NO
SHORE EXCURSIONS
4

Established around 1689, Marigot is the attractive capital of French St. Martin, with its brightly colored houses, a lively open-air market, secluded beaches, and pretty waterfront promenade. Because of its tax-free status, Marigot is a popular center for duty-free shopping, where all of the world's most prestigious brands can be found.  Originally the area was marshy, and surrounded by mangroves. In the 1970s part of the bay was filled in to extend Marigot into a larger city with a marina. Overlooking Marigot is Fort St. Louis, the largest historical monument in St. Martin with an impressive panoramic view of the bay.

Marigot, Beach Day at KKO With Lunch

Escape to paradise with a scenic 25-minute drive to the charming French village of Orient Bay, where your experience begins at KKO Beach Restaurant. Enjoy a welcome drink before settling into your reserved beach lounge chair, then savor breathtaking ocean views, the soothing sound of the waves, and a beautifully crafted three-course French lunch prepared in advance for a seamless dining experience. Spend the rest of the day soaking up the sun, swimming in the turquoise sea, or browsing the boutique shops along the beach. As the day winds down, you’ll return to port with unforgettable memories of this idyllic French Caribbean escape.
Port
Marigot, St. Martin
Time
8:30 AM
Duration
5 Hours
Activity Level
Easy

Add during booking

$259 USD

Marigot, Rhum and Rhythm

This curated half-day tour offers an immersive taste of Sint Maarten, ideal for cruise guests wanting to experience local rhum culture, coastal relaxation, and authentic cuisine in a short time. Begin at the Rusty Parrot with a pirate-themed rhum tasting and ship tour, then continue to the Lolo’s in Grand Case for a traditional Creole BBQ meal. Next, visit Colombier Traditions to experience the heritage of the historic Colombier hills while sampling a variety of locally crafted rhums. The journey concludes in the heart of Marigot with a refreshing Guavaberry Slushie or Passionfruit Rum Punch at the Sugar Apple. Blending storytelling, island flavors, plane spotting, beachside charm, and a lively musical ride back to port, this unique four-stop adventure delivers far more than most guests expect—all in just four hours.
Port
Marigot, St. Martin
Time
8:30 AM
Duration
4 Hours
Activity Level
Easy

Add during booking

$299 USD

Marigot, French Creole Cooking Class

Located just 25 minutes from the port, Creole Culinary is renowned for its lively atmosphere and hands-on Cooking Masterclasses. Spend time with Chef Anna or Francky as they share their expertise and guide you in crafting a delicious Creole-inspired meal. Along the way, enjoy a brief history of the region, and afterward, savor your culinary creation while sipping a cocktail or a glass of wine. 
Port
Marigot, St. Martin
Time
8:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate

Add during booking

$319 USD

Marigot, French and Dutch Island Discovery

Depart Marigot port for a scenic drive toward Paradise Peak, the island’s highest point, passing Grand Case and continuing by Orient Beach to Paradise Lookout Point for stunning views of Orient Beach and St. Barth. Travel through Quartier d’Orleans, or French Quarter, before crossing into the Dutch side of the island. In Philipsburg, the Dutch capital, enjoy about an hour of free time to shop along Front Street or stroll the Boardwalk with its restaurants, bars, and ice cream parlors, as well as views of the cruise ships at the Dr. A.C. Wathey Cruise & Cargo Facility. The tour continues to Cay Hill Lookout Point for photo-worthy views of Simpson Bay Lagoon—the Caribbean’s largest land-enclosed lagoon—Simpson Bay Beach, and the approach to Princess Juliana International Airport. At the famous Sunset Beach Bar, witness planes landing dramatically overhead before returning to Marigot port to tender back to the ship.
Port
Marigot, St. Martin
Time
8:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate

Add during booking

$99 USD

8
JAN 03, 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.