Windward Islands Surf & Sunsets

Feb 27, 2026 — Mar 6, 2026

Starting from $6,872 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.

See more routes around Caribbean

SAN JUAN → SAN JUAN

7 Nights in 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
FEB 27, 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
FEB 28, 2026
Philipsburg, St. Maarten
ARRIVE
12:00 PM
DEPART
6:30 PM
MARINA
NO
SHORE EXCURSIONS
6

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: Soualiga Sky Explorer & 360 Views

Time
12:30 PM
Duration
4.5 Hours
Activity Level
Easy-Moderate
Price
$219

St. Maarten: Soualiga Sky Explorer & Flying Dutchman

Time
12:30 PM
Duration
4.25 Hours
Activity Level
Strenuous
Price
$339

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

Time
12:30 PM
Duration
4 Hours
Activity Level
Easy
Price
$799

St. Maarten: Under Two Flags Island Tour

Time
12:30 PM
Duration
4 Hours
Activity Level
Easy
Price
$99

St. Maarten: Americas Cup Sailboat Racing

Time
12:30 PM
Duration
3.5 Hours
Activity Level
Moderate-Strenuous
Price
$149

Philipsburg, Savor St. Maarten Foodie Tour

Time
12:30 PM
Duration
4.5 Hours
Activity Level
Easy-Moderate
Price
$189
3
MAR 01, 2026
Les Saintes
ARRIVE
9:00 AM
DEPART
3:00 PM
MARINA
NO
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, Sample Culinary Treasures of Guadeloupe

Time
10:00 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$209

Les Saintes, Blue Escape Kayaking *

Time
9:30 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$149

Les Saintes, Snorkel Experience in Les Saintes *

Time
10:00 AM
Duration
2 Hours
Activity Level
Strenuous
Price
$119

Les Saintes, Historic Tastes & Treasures of Fort Napoleon

Time
12:30 PM
Duration
2.5 Hours
Activity Level
Moderate
Price
$129

Les Saintes, Relax & Snorkel *

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$169

Les Saintes, Sailing the Bay

Time
9:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$199

Les Saintes, Terre de Haut Panoramic Tour

Time
9:30 AM
Duration
1 Hours
Activity Level
Easy
Price
$119

Les Saintes, Explore Terra de Haut by Foot

Time
9:30 AM
Duration
1.25 Hours
Activity Level
Moderate
Price
$109
4
MAR 02, 2026
Mayreau
ARRIVE
8:00 AM
DEPART
6:00 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.

5
MAR 03, 2026
Bequia
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
5

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, Taste of Bequia

Time
9:30 AM
Duration
3.5 Hours
Activity Level
Easy-Moderate
Price
$149

Bequia, Mustique Magic with Lunch

Time
9:30 AM
Duration
6 Hours
Activity Level
Moderate
Price
$269

Bequia, Bequia Fort & Lower Beach Getaway *

Time
9:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$95

Bequia Snorkel Adventure

Time
9:30 AM
Duration
3 Hours
Activity Level
Strenuous
Price
$119

Bequia Highlights

Time
9:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$89
6
MAR 04, 2026
Soufriere
ARRIVE
9:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
5

Nestled in the shadows of the UNESCO Pitons, Soufriere represents the heart and soul of St. Lucia. The tiny town center is full of street vendors and stores and some of the best resorts on the island can be found here. Nearby are secluded waterfalls and the waters here boast some of the best diving around. Sights to see include the Edmund Rainforest Trail, fond Doux Holiday plantation, Robot Estate and the Gros Piton Nature Trail.

Soufriere, Botanical Gardens, Toraille Waterfall & Beach

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

Soufriere, Chocolate Heritage tour at Fond Doux Estate

Time
9:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$99

Soufriere, Snorkel at Marine Park

Time
9:30 AM
Duration
2.5 Hours
Activity Level
Moderate-Strenuous
Price
$109

Soufriere, Concierge Collection: Taste of St. Lucia

Time
9:30 AM
Duration
2.5 Hours
Activity Level
Easy-Moderate
Price
$179

Soufriere, Bean to Bar & Market Style Lunch

Time
9:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$235
7
MAR 05, 2026

Star Seeker

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

Available Staterooms

Premier Veranda Suite VS1

Cabin
6 Cabins
Max. Occupancy
2 Passengers
Room Size
Sqft
Amenities

Deluxe Suite

Cabin
4 Cabins
Max. Occupancy
2 Passengers
Room Size
288 Sqft
Amenities

Veranda Suite

Cabin
16 Cabins
Max. Occupancy
2 Passengers
Room Size
225 Sqft
Amenities

Oceanview Suite

Cabin
10 Cabins
Max. Occupancy
2 Passengers
Room Size
203 Sqft
Amenities

Triple Infinity Suite

Cabin
2 Cabins
Max. Occupancy
3 Passengers
Room Size
301 Sqft
Amenities

Premier Veranda Suite VSS

Cabin
12 Cabins
Max. Occupancy
2 Passengers
Room Size
Sqft
Amenities

Premier Veranda Suite

Cabin
14 Cabins
Max. Occupancy
2 Passengers
Room Size
225 Sqft
Amenities

Triple Infinity Suite IN3

Cabin
2 Cabins
Max. Occupancy
3 Passengers
Room Size
Sqft
Amenities

Horizon Owner's Suite

Cabin
2 Cabins
Max. Occupancy
2 Passengers
Room Size
548 Sqft
Amenities

Available Dates