Windward Islands Surf & Sunsets

Nov 22, 2026 — Nov 29, 2026

Starting from

See more routes around Caribbean

SAN JUAN → SAN JUAN

7 Nights on Star Pride

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.

Additional Information

1
NOV 22, 2026
San Juan
EMBARK
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
8

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.

San Juan: Rainforest Eco Wonder Tour with Transfer to Airport

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate-Strenuous
Price
$199

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

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$159

Time
8:30 AM
Duration
4 Hours
Activity Level
N/A
Price
$729

San Juan: Rainforest Eco Wonder Tour with Transfer to Windstar Hotel

Time
8:30 AM
Duration
5 Hours
Activity Level
Moderate-Strenuous
Price
$199

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

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$289

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

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$289

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

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Moderate-Strenuous
Price
$159

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

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$829
2
NOV 23, 2026
AT SEA
3
NOV 24, 2026
St. George's
ARRIVE
9:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
10

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.

St. Georges, Powerboat & Snorkeling at the Statues Park *

Time
9:30 AM
Duration
2 Hours
Activity Level
Moderate-Strenuous
Price
$119

St. Georges, Certified Two-Tank Dive

Time
9:30 AM
Duration
4.25 Hours
Activity Level
Moderate-Strenuous
Price
$319

St. Georges, The Best of Grenada

Time
9:30 AM
Duration
7.5 Hours
Activity Level
Easy
Price
$169

St. Georges, Discover Scuba

Time
9:30 AM
Duration
4.5 Hours
Activity Level
Moderate
Price
$279

St. Georges, Izzie's Great House Discovery

Time
9:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$119

St. Georges, Certified One-Tank Dive

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$215

St. Georges, Sailing Cruise to the Statue Park

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$99

St Georges, Spice of Our Lives

Time
9:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$69

St. Georges, Fort Frederick Rainforest & Waterfall

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$99

St. Georges, Clear Bottom Kayaking

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$89
4
NOV 25, 2026
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
YES
SHORE EXCURSIONS
6

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.

Bequia, Bequia Fort & Lower Beach Getaway *

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$99

Bequia, Taste of Bequia

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$149

Bequia, Concierge Collection: Rum Tasting at Firefly Plantation

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$169

Bequia, Mustique Magic with Lunch

Time
8:30 AM
Duration
6 Hours
Activity Level
Moderate
Price
$269

Bequia Highlights

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$89

Bequia Snorkel Adventure

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$119
5
NOV 26, 2026
Mayreau
ARRIVE
8:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
1

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.

Mayreau, Grenadines Island Escape

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$89
6
NOV 27, 2026
Les Saintes
ARRIVE
10:00 AM
DEPART
5:00 PM
MARINA
YES
SHORE EXCURSIONS
8

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.

Les Saintes, Relax & Snorkel *

Time
10:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$179

Les Saintes, Sample Culinary Treasures of Guadeloupe

Time
10:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$209

Les Saintes, Blue Escape Kayaking *

Time
10:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$149

Les Saintes, Sailing the Bay

Time
10:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$249

Les Saintes, Snorkel Experience in Les Saintes *

Time
10:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$119

Les Saintes, Historic Tastes & Treasures of Fort Napoleon

Time
10:30 AM
Duration
2.5 Hours
Activity Level
Moderate
Price
$129

Les Saintes, Terre de Haut Panoramic Tour

Time
10:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$119

Les Saintes, Explore Terra de Haut by Foot

Time
10:30 AM
Duration
1.25 Hours
Activity Level
Moderate
Price
$109
7
NOV 28, 2026
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, French and Dutch Island Discovery

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

Marigot, French Creole Cooking Class

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

Marigot, Rhum and Rhythm

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

Marigot, Beach Day at KKO With Lunch

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

Star Pride

number of decks
6 Decks
yacht length
522 ft (159 meters)
yacht crew size
200 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