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Classic Caribbean
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Jan 18, 2025 - Sat Jan 25, 2025,
 7 days
 on Wind Surf
?All-inclusive from
$3,199
?Cruise Only From
$3,199
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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
Expand
Sat Jan 18
Philipsburg, St. Maarten
Arrive:
Depart:7:00 PM
Watersports Platform: 
4 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.
4 Shore Excursions Available
+
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St. Maarten, Post Island Tour with Transfer to AirportEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$79
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St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$79
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St. Maarten: Americas Cup Sailboat Racing with Transfer to AirportBoating | Essentials Collection | Outdoors | Refreshments
Duration2.5 Hours
Activity LevelModerate
$149
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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
$149
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Sun Jan 19
Charlestown
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
4 Available
+_
This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney’s Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.
4 Shore Excursions Available
+
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Charlestown, Coastal Boat Cruise Snorkel AdventureBoating | Essentials Collection | Sightseeing | Wildlife
Duration3 Hours
Activity LevelModerate-Strenuous
$85
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Charlestown, Concierge Collection: Deep Sea FishingBoating | Concierge Collection | Outdoors | Wildlife
Duration5 Hours
Activity LevelModerate-Strenuous
$279
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Charlestown, Nevis Half Island & Botanical Garden Sightseeing | Outdoors | Refreshments | Essentials Collection
Duration2.5 Hours
Activity LevelEasy
$99
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Charlestown, Montravers Hike & Beach Break with Lunch Hiking | Dining | Wildlife | Outdoors | Essentials Collection
Duration5 Hours
Activity LevelModerate
$89
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Mon Jan 20
Roseau
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
8 Available
+_
Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you’re up for an optional hike, don’t miss Boiling Lake and the Valley of Desolation at Dominica’s Morne Trois Pitons National Park, a UNESCO World Heritage Site.
8 Shore Excursions Available
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Roseau, 4X4 Waterfall & RainforestBeach | Essentials Collection | Outdoors | Refreshments
Duration3 Hours
Activity LevelModerate
$79
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Roseau, Whale & Dolphin Adventure Wildlife | Refreshments | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelEasy-Moderate
$109
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Roseau, Champagne Reef Snorkel AdventureEssentials Collection | Snorkeling | Wildlife
Duration2 Hours
Activity LevelStrenuous
$79
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Roseau, Concierge Collection: Cooking Caribbean Flavors & Lifestyles Culture | Dining | Sightseeing | Concierge Collection
Duration3.5 Hours
Activity LevelEasy
$119
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Roseau, Indian River Rowboat Wildlife | Culture | Walking | Boating | Essentials Collection
Duration4.5 Hours
Activity LevelModerate
$79
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Roseau, River Tubing AdventureEssentials Collection | Outdoors | Refreshments | Watersports
Duration4 Hours
Activity LevelModerate
$99
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Roseau, Trafalgar Falls & Hot Springs Outdoors | Wildlife | Refreshments | Walking | Essentials Collection
Duration3 Hours
Activity LevelModerate
$89
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Roseau, Concierge Collection: Wet & Rugged DominicaConcierge Collection | Dining | Hiking | Sightseeing | Walking
Duration5.5 Hours
Activity LevelStrenuous
$225
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Tue Jan 21
Pigeon Island
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
12 Available
+_
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.
12 Shore Excursions Available
+
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Pigeon Island, Concierge Collection: Full Day Private Car & Guide Sightseeing | Concierge Collection
Duration8 Hours
Activity LevelEasy
$699
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Pigeon Island, Concierge Collection: Full Day Private Van & Guide Sightseeing | Concierge Collection
Duration8 Hours
Activity LevelEasy
$899
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Pigeon Island, Aerial Tram Park Wildlife | Refreshments | Walking | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$155
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Pigeon Island, Catamaran Cruise to the PitonsBeach | Boating | Essentials Collection | Sightseeing | Refreshments | UNESCO
Duration5 Hours
Activity LevelEasy
$139
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Pigeon Island, St. Lucian Walking Food TourCulture | Essentials Collection | Sightseeing | Refreshments | Walking
Duration3.5 Hours
Activity LevelEasy-Moderate
$179
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Pigeon Island, Mt. Pimard Nature Trail & HikeEssentials Collection | Hiking | Sightseeing
Duration2.5 Hours
Activity LevelModerate
$109
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Pigeon Island, Panoramic St. LuciaSightseeing | Refreshments
Duration3 Hours
Activity LevelEasy
$55
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Pigeon Island, Discover Sailing Boating | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$129
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Pigeon Island, Off Road Segway Adventure Outdoors | Refreshments | Sightseeing | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$149
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Pigeon Island, Rainforest Canopy Zip Line Adventure Wildlife | Refreshments | Sightseeing | Essentials Collection
Duration4.5 Hours
Activity LevelStrenuous
$115
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Pigeon Island, Concierge Collection: Half Day Private Car & Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$399
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Pigeon Island, Concierge Collection: Half Day Private Van & Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$499
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Wed Jan 22
Les Saintes
Arrive:8:00 AM
Depart:5:00 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
Duration3.5 Hours
Activity LevelModerate
$139
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Les Saintes, Sample Culinary Treasures of GuadeloupeBeach | Concierge Collection | Culture | Dining
Duration3 Hours
Activity LevelEasy-Moderate
$199
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Les Saintes, Explore Terra de Haut by FootCulture | Essentials Collection | Refreshments | Walking
Duration1.25 Hours
Activity LevelModerate
$99
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Les Saintes, Sailing the BayBoating | Concierge Collection | Refreshments
Duration3 Hours
Activity LevelModerate
$209
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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
$99
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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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Thu Jan 23
Gustavia
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
6 Available
+_
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.
6 Shore Excursions Available
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St Barts, Concierge Collection: St. Barthelemy Beach DayBeach | Concierge Collection | Dining
Duration6 Hours
Activity LevelEasy-Moderate
$399
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St. Barts: Sailing Catamaran AdventureBeach | Boating | Essentials Collection | Refreshments | Snorkeling | Wildlife
Duration3 Hours
Activity LevelModerate
$299
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St. Barts: Independent Explorer by CarEssentials Collection | Sightseeing
Duration6 Hours
Activity LevelEasy-Moderate
$279
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St. Barts: Intimate Island TourEssentials Collection | Sightseeing
Duration Hour
Activity LevelEasy
$99
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St. Barts: Sailing the Leeward CoastBoating | Essentials Collection | Refreshments
Duration3 Hours
Activity LevelEasy-Moderate
$199
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St. Barts, Concierge Collection: Sunset CruiseBoating | Concierge Collection | Sightseeing | Refreshments
Duration1.5 Hours
Activity LevelEasy-Moderate
$159
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Fri Jan 24
Basseterre
Arrive:8:00 AM
Depart:9:00 PM
Watersports Platform: 
9 Available
+_
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
9 Shore Excursions Available
+
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Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. KittsConcierge Collection | Culture | Dining | Sightseeing
Duration3.5 Hours
Activity LevelEasy
$89
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Basseterre, Brimstone Hill Fortress & Fairview Great HouseCulture | Essentials Collection | Sightseeing | UNESCO
Duration3.25 Hours
Activity LevelEasy
$69
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Basseterre, Island History & Rum TastingEssentials Collection | Sightseeing | Refreshments
Duration3.25 Hours
Activity LevelEasy
$59
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Basseterre, Nevis Panoramic and Beach TourBeach | Boating | Dining | Essentials Collection | Sightseeing
Duration5 Hours
Activity LevelEasy-Moderate
$139
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Basseterre: Caribbean Scenic Railway Refreshments | Culture | Sightseeing | Essentials Collection
Duration3 Hours
Activity LevelEasy
$109
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Basseterre: Sky Safari Zipline Adventure Outdoors | Wildlife | Essentials Collection
Duration4 Hours
Activity LevelStrenuous
$119
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Basseterre: Snorkel Safari Snorkeling | Wildlife | Refreshments | Boating | Essentials Collection
Duration3 Hours
Activity LevelModerate
$99
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Basseterre, Irie Rider Speed BoatBoating | Essentials Collection | Refreshments | Snorkeling
Duration3.25 Hours
Activity LevelModerate-Strenuous
$109
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Basseterre: St Kitts Quad ATV Adventure Outdoors | Refreshments | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$119
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Sat Jan 25
Philipsburg, St. Maarten
Arrive:6:00 AM
Depart:
Watersports Platform: 
4 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.
4 Shore Excursions Available
+
_
St. Maarten, Post Island Tour with Transfer to AirportEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$79
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St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$79
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St. Maarten: Americas Cup Sailboat Racing with Transfer to AirportBoating | Essentials Collection | Outdoors | Refreshments
Duration2.5 Hours
Activity LevelModerate
$149
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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
$149
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