Windward Islands Surf & Sunsets
 
San Juan to San Juan
Fri Feb 27, 2026 - Fri Mar 6, 2026,
 7 days
 on Star Seeker
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Starting from $3,099 USD
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ITINERARY AND SHORE EXCURSIONS

The best on land brought to you by the best at sea. Get to the heart of local cultures with Windstar shore excursions. You don't want to just dip a toe in local culture, you want to dive into the deep end, and that's exactly what Windstar shore excursions are designed to do. All of our excursion are created to provide authentic local experience - the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you're an outdoor enthusiast, a foodie, a history buff, or someone who loves to get to know the faces behind the many places we travel.

Date
Port
Arrive
Depart
Watersports
Platform
Shore
Excursions
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Fri Feb 27
San Juan
Arrive:
Depart:7:00 PM
Watersports Platform: 
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.
Sat Feb 28
Philipsburg, St. Maarten
Arrive:12:00 PM
Depart:6:30 PM
Watersports Platform: 
10 Available
+_
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.
10 Shore Excursions Available
+
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St. Maarten, Concierge Collection: Half Day Private Island Tour in SUV or Deluxe Mini VanConcierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$799
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St. Maarten: Americas Cup Sailboat Racing Refreshments | outdoor | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$149
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St. Maarten: Soualiga Sky Explorer & Flying Dutchman Sightseeing | Essentials Collection
Duration4.25 Hours
Activity LevelStrenuous
$339
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St. Maarten, Post Island Tour with Transfer to AirportEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$99
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St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$99
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St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$99
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St. Maarten: Americas Cup Sailboat Racing with Transfer to AirportBoating | Essentials Collection | Outdoors | Refreshments
Duration2.5 Hours
Activity LevelModerate
$179
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St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel Outdoors | Refreshments | Boating | Essentials Collection
Duration2.5 Hours
Activity LevelModerate
$179
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St. Maarten: Soualiga Sky Explorer & 360 Views Sightseeing | Essentials Collection
Duration4.5 Hours
Activity LevelEasy
$219
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St. Maarten: Under Two Flags Island Tour Sightseeing | Walking | Essentials Collection
Duration4 Hours
Activity LevelEasy
$99
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Sun Mar 1
Les Saintes
Arrive:9:00 AM
Depart:6:00 PM
Watersports Platform: 
8 Available
+_
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.
8 Shore Excursions Available
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Les Saintes, Blue Escape Kayaking *Boating | Essentials Collection | Outdoors | Sightseeing | Refreshments
Duration2 Hours
Activity LevelModerate
$149
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Les Saintes, Sample Culinary Treasures of GuadeloupeBeach | Concierge Collection | Culture | Dining
Duration3 Hours
Activity LevelEasy-Moderate
$209
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Les Saintes, Explore Terra de Haut by FootCulture | Essentials Collection | Refreshments | Walking
Duration1.25 Hours
Activity LevelModerate
$109
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Les Saintes, Sailing the BayBoating | Concierge Collection | Refreshments
Duration3 Hours
Activity LevelModerate
$199
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Les Saintes, Historic Tastes & Treasures of Fort NapoleonCulture | Essentials Collection | Sightseeing | Refreshments
Duration2.5 Hours
Activity LevelModerate
$129
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Les Saintes, Terre de Haut Panoramic TourEssentials Collection | Sightseeing
Duration Hour
Activity LevelEasy
$119
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Les Saintes, Snorkel Experience in Les Saintes *Boating | Essentials Collection | Refreshments | Snorkeling | Wildlife
Duration2 Hours
Activity LevelStrenuous
$119
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Les Saintes, Relax & Snorkel *Beach | Boating | Essentials Collection | Refreshments | Snorkeling
Duration3 Hours
Activity LevelModerate-Strenuous
$169
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Mon Mar 2
Soufriere
Arrive:9:00 AM
Depart:9:00 PM
Watersports Platform: 
5 Available
+_
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.
5 Shore Excursions Available
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Soufriere, Chocolate Heritage tour at Fond Doux Estate Sightseeing | Walking | Refreshments | Essentials Collection
Duration2.5 Hours
Activity LevelEasy-Moderate
$99
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Soufriere, Green Haven Organic Farm to Table LunchCulture | Dining | Essentials Collection | Sightseeing
Duration3 Hours
Activity LevelEasy-Moderate
$129
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Soufriere, Botanical Gardens, Toraille Waterfall & Beach Sightseeing | Beach | Essentials Collection
Duration4 Hours
Activity LevelEasy-Moderate
$69
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Soufriere, Snorkel at Marine Park Snorkeling | Boating | Wildlife | Essentials Collection
Duration2.5 Hours
Activity LevelModerate-Strenuous
$109
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Soufriere, Concierge Collection: Taste of St. Lucia Dining | Culture | Concierge Collection
Duration2.5 Hours
Activity LevelEasy-Moderate
$179
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Tue Mar 3
Bequia
Arrive:9:00 AM
Depart:10:00 PM
Watersports Platform: 
6 Available
+_
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.
6 Shore Excursions Available
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Bequia, Bequia Fort & Lower Beach Getaway *Beach | Essentials Collection | Refreshments
Duration3 Hours
Activity LevelEasy-Moderate
$95
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Bequia, Bequia Heritage and Scenic TouEssentials Collection | Sightseeing | Refreshments
Duration3 Hours
Activity LevelEasy-Moderate
$99
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Bequia Highlights Outdoors | Wildlife | Culture | Sightseeing | Essentials Collection
Duration2.5 Hours
Activity LevelEasy-Moderate
$89
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Bequia, Mustique Magic with Lunch Dining | Sightseeing | Boating | Essentials Collection
Duration6 Hours
Activity LevelModerate
$269
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Bequia Snorkel Adventure Snorkeling | Outdoors | Wildlife | Refreshments | Boating | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$119
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Bequia, Taste of BequiaCulture | Dining | Essentials Collection | Refreshments
Duration3.5 Hours
Activity LevelEasy-Moderate
$149
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Wed Mar 4
Mayreau
Arrive:8:00 AM
Depart:4:30 PM
Watersports Platform: 
1 Available
+_
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.
1 Shore Excursion Available
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Mayreau, Grenadines Island Escape Snorkeling | Outdoors | Refreshments | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$89
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Thu Mar 5
AT SEA
Arrive:
Depart:
Watersports Platform: 
Fri Mar 6
San Juan
Arrive:7:00 AM
Depart:
Watersports Platform: 
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.