Windward Islands Surf & Sunsets

Mar 13, 2026 — Mar 20, 2026

Starting from

See more routes around Caribbean

SAN JUAN → SAN JUAN

7 Nights on Star Seeker

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
MAR 13, 2026
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 14, 2026
Marigot, St. Martin
ARRIVE
11:00 AM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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
11:30 AM
Duration
5 Hours
Activity Level
Easy
Price
$259

Marigot, French Creole Cooking Class

Time
11:30 AM
Duration
5 Hours
Activity Level
Easy-Moderate
Price
$319
3
MAR 15, 2026
Les Saintes
ARRIVE
8:00 AM
DEPART
3:00 PM
MARINA
YES
SHORE EXCURSIONS
1

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, Blue Escape Kayaking *

Time
8:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$149
4
MAR 16, 2026
Mayreau
ARRIVE
8:00 AM
DEPART
6:00 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
5
MAR 17, 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 Snorkel Adventure

Time
8:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$119

Bequia, Concierge Collection: Rum Tasting at Firefly Plantation

Time
10:30 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, Taste of Bequia

Time
10:00 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$149

Bequia Highlights

Time
9:00 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$89
6
MAR 18, 2026
Pigeon Island
ARRIVE
8:00 AM
DEPART
2:30 PM
MARINA
NO
SHORE EXCURSIONS
8

The UNESCO site Pitons' with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.

Pigeon Island, Catamaran Cruise to the Pitons

Time
8:30 AM
Duration
5 Hours
Activity Level
Easy
Price
$159

Pigeon Island, Concierge Collection: Half Day Private Car & Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$399

Pigeon Island, Concierge Collection: Half Day Private Van & Guide

Time
8:30 AM
Duration
4 Hours
Activity Level
Easy
Price
$499

Pigeon Island, Rainforest Canopy Zip Line Adventure

Time
8:30 AM
Duration
4.5 Hours
Activity Level
Moderate-Strenuous
Price
$119

Pigeon Island, Panoramic St. Lucia

Time
9:00 AM
Duration
3 Hours
Activity Level
Easy
Price
$59

Pigeon Island, St. Lucian Walking Food Tour

Time
9:45 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$189

Pigeon Island, Discover Sailing

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$129

Pigeon Island, Aerial Tram Park

Time
9:00 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$159
The Pitons
ARRIVE
5:30 PM
DEPART
6:30 PM
MARINA
NO
SHORE EXCURSIONS
0

Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.

7
MAR 19, 2026
AT SEA

Star Seeker

number of decks
6 Decks
yacht length
ft (0 meters)
yacht crew size
Crew Members
yacht guest capacity
224 Guests

Staterooms

Room Size 268 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 246 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 225 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 225 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 301 sq ft
Max. Occupancy 3 Passengers
Amenities

Starting from

Room Size 280 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 203 sq ft
Max. Occupancy 2 Passengers
Amenities

Starting from

Room Size 548 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 380 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 353 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 288 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 225 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 225 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 280 sq ft
Max. Occupancy 2 Passengers
Amenities

Room Size 280 sq ft
Max. Occupancy 2 Passengers
Amenities
Expand all

Available Dates

Date Yacht
Starting from
Actions
Feb 13 (Fri) – Feb 20 (Fri), 2026February 13 (Fri) – February 20 (Fri), 2026Star Seeker$5,927
Feb 27 (Fri) – Mar 6 (Fri), 2026February 27 (Fri) – March 6 (Fri), 2026Star Seeker$5,836
Nov 8 (Sun) – Nov 15 (Sun), 2026November 8 (Sun) – November 15 (Sun), 2026Star Pride$3,330
Nov 22 (Sun) – Nov 29 (Sun), 2026November 22 (Sun) – November 29 (Sun), 2026Star Pride$3,330
Dec 6 (Sun) – Dec 13 (Sun), 2026December 6 (Sun) – December 13 (Sun), 2026Star Pride$3,130
Dec 20 (Sun) – Dec 27 (Sun), 2026December 20 (Sun) – December 27 (Sun), 2026Star Pride$3,330
Jan 3 (Sun) – Jan 10 (Sun), 2027January 3 (Sun) – January 10 (Sun), 2027Star Pride$4,030
Nov 8 (Mon) – Nov 15 (Mon), 2027November 8 (Mon) – November 15 (Mon), 2027Star Pride$2,930
Nov 22 (Mon) – Nov 29 (Mon), 2027November 22 (Mon) – November 29 (Mon), 2027Star Pride$2,930
Dec 27 (Mon) – Jan 3 (Mon), 2028December 27 (Mon) – January 3 (Mon), 2028Star Legend$3,230
Jan 10 (Mon) – Jan 17 (Mon), 2028January 10 (Mon) – January 17 (Mon), 2028Star Legend$3,030
Jan 24 (Mon) – Jan 31 (Mon), 2028January 24 (Mon) – January 31 (Mon), 2028Star Legend$3,030
Feb 7 (Mon) – Feb 14 (Mon), 2028February 7 (Mon) – February 14 (Mon), 2028Star Legend$3,030
Feb 21 (Mon) – Feb 28 (Mon), 2028February 21 (Mon) – February 28 (Mon), 2028Star Legend$3,030
Mar 13 (Mon) – Mar 20 (Mon), 2028March 13 (Mon) – March 20 (Mon), 2028Star Pride$3,030
Mar 27 (Mon) – Apr 3 (Mon), 2028March 27 (Mon) – April 3 (Mon), 2028Star Pride$3,030