Sublime Southern Caribbean
 
Bridgetown to Philipsburg, St. Maarten
Sun Jan 4, 2026 - Wed Jan 14, 2026,
 10 days
 on Wind Spirit
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Starting from $3,399 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
Marina
Shore
Excursions
Expand
Sun Jan 4
Bridgetown
Arrive:
Depart:6:00 PM
Watersports Platform: 
3 Available
+_
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
3 Shore Excursions Available
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Bridgetown: Barbados Island Tour with Airport Transfer Dining | Sightseeing | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$129
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Bridgetown, Bajan Rum and Beer Tour with Transfer to Airport
Duration3.5 Hours
Activity Level
$219
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Bridgetown, Bajan Rum and Beer Tour with Transfer to Windstar Hotel
Duration3.5 Hours
Activity Level
$219
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Mon Jan 5
Mayreau
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
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.
Tue Jan 6
Roseau
Arrive:1:00 PM
Depart:6:00 PM
Watersports Platform: 
9 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.
9 Shore Excursions Available
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Roseau, 4X4 Waterfall & RainforestBeach | Essentials Collection | Outdoors | Refreshments
Duration3 Hours
Activity LevelModerate
$89
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Roseau, Whale & Dolphin Adventure Wildlife | Refreshments | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelEasy-Moderate
$159
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Roseau, Champagne Reef Snorkel AdventureEssentials Collection | Snorkeling | Wildlife
Duration2 Hours
Activity LevelStrenuous
$79
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Roseau, A Historical Roseau Walking TourSightseeing | Refreshments | Walking
Duration2.5 Hours
Activity LevelModerate
$59
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Roseau, Dominica in a DayCulture | Sightseeing | Refreshments | Snorkeling | Walking
Duration4.5 Hours
Activity LevelStrenuous
$159
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Roseau, Indian River Rowboat Wildlife | Culture | Walking | Boating | Essentials Collection
Duration4.5 Hours
Activity LevelModerate
$89
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Roseau, River Tubing AdventureEssentials Collection | Outdoors | Refreshments | Watersports
Duration4 Hours
Activity LevelModerate
$109
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Roseau, Trafalgar Falls & Hot Springs Outdoors | Wildlife | Refreshments | Walking | Essentials Collection
Duration3 Hours
Activity LevelModerate
$99
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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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Wed Jan 7
Anse Mitan
Arrive:7:00 AM
Depart:5:00 PM
Watersports Platform: 
6 Available
+_
Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.
6 Shore Excursions Available
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Anse Mitan, VIP Experience at La Mauny Plantation and Rum TastingConcierge Collection | Culture | Refreshments
Duration3.5 Hours
Activity LevelEasy-Moderate
$259
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Anse Mitan, Martinique Heritage Refreshments | Culture | Sightseeing | Essentials Collection
Duration4 Hours
Activity LevelModerate
$169
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Anse Mitan, Kayaking Mangrove DiscoveryBoating | Essentials Collection | Sightseeing
Duration2.5 Hours
Activity LevelModerate-Strenuous
$139
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Anse Mitan, Southern Panoramic MartiniqueCulture | Sightseeing | Refreshments
Duration3.75 Hours
Activity LevelModerate
$149
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Anse Mitan, Snorkel Adventure Long
Duration3 Hours
Activity LevelStrenuous
$209
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Anse Mitan, Creole VillageCulture | Essentials Collection | Sightseeing | Walking
Duration2.75 Hours
Activity LevelModerate-Strenuous
$99
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Thu Jan 8
Deshaies
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
Situated near the Grand Anse beach, Deshaies has the deepest bay of all the Caribbean coasts with the best natural protection which made it a shelter for pirates of days gone by and is said to still be housing treasures on the Island. Grand Anse beach is one of the most beautiful of the islands with its over half a mile of fine golden sand and coconut palms.
Fri Jan 9
Basseterre
Arrive:8:00 AM
Depart:9:00 PM
Watersports Platform: 
8 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.
8 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
$99
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Basseterre, Brimstone Hill Fortress & Fairview Great HouseCulture | Essentials Collection | Sightseeing | UNESCO
Duration3.25 Hours
Activity LevelEasy
$79
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Basseterre, Island History & Rum TastingEssentials Collection | Sightseeing | Refreshments
Duration2.5 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: St Kitts Quad ATV Adventure Outdoors | Refreshments | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$129
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Sat Jan 10
St. John's
Arrive:9:00 AM
Depart:11:00 PM
Watersports Platform: 
9 Available
+_
St. John’s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.  The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you.  Sites to see include St. John’s Cathedral with its white Baroque towers, the Botanical Garden, St. John’s Antigua Lighthouse, and Fort James.
9 Shore Excursions Available
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St.Johns, Concierge Collection: Sail Snorkel and Beach
Duration3 Hours
Activity Level
$239
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St. Johns, Beach EscapeBeach | Essentials Collection
Duration4 Hours
Activity LevelEasy
$79
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St Johns, Concierge Collection, Jet Ski AdventureBeach | Boating | Essentials Collection | Sightseeing
Duration1.75 Hours
Activity LevelModerate-Strenuous
$379
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St. Johns, Open Course Canopy Challenge Outdoors | Wildlife | Sightseeing | Essentials Collection
Duration4 Hours
Activity LevelStrenuous
$139
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St. Johns: Presidents TourEssentials Collection | Sightseeing
Duration3 Hours
Activity LevelEasy
$109
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St Johns, Chocolate and Rum MakingCulture | Refreshments
Duration3.25 Hours
Activity LevelEasy-Moderate
$209
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St. Johns, Segway Fort Conqueror Outdoors | Sightseeing | Refreshments | Beach | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$159
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St. Johns, Spectacular Antigua Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$79
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St Johns, Swim with the StingraysEssentials Collection | Refreshments | Watersports
Duration3 Hours
Activity LevelModerate
$109
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Sun Jan 11
Falmouth Harbour
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
1 Available
+_
It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
1 Shore Excursion Available
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Falmouth Harbour , Concierge Collection, Tuk Tuk Rainforest and BeachBeach | Sightseeing | Refreshments
Duration3.5 Hours
Activity LevelEasy
$379
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Mon Jan 12
Gustavia
Arrive:9:00 AM
Depart:10:00 PM
Watersports Platform: 
9 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.
9 Shore Excursions Available
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Gustavia, Concierge Collection: Scuba Dive 1 TankConcierge Collection | Outdoors | Watersports
Duration3 Hours
Activity LevelStrenuous
$339
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Gustavia, Concierge Collection: Scuba Dive 2 TankConcierge Collection | Outdoors | Wildlife
Duration4 Hours
Activity LevelStrenuous
$499
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St Barts, Concierge Collection: St. Barthelemy Beach DayBeach | Concierge Collection | Dining
Duration6 Hours
Activity LevelEasy-Moderate
$499
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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
$349
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St. Barts: Intimate Island TourEssentials Collection | Sightseeing
Duration Hour
Activity LevelEasy
$139
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Gustavia, Concierge Collection: Jet SkiBeach | Outdoors | Sightseeing | Watersports
Duration2 Hours
Activity Level(not specified)
$269
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Gustavia, Concierge Collection: Savor St BartsConcierge Collection | Culture | Refreshments | Walking
Duration2.5 Hours
Activity Level(not specified)
$349
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St. Barts, Concierge Collection: Sunset CruiseBoating | Concierge Collection | Sightseeing | Refreshments
Duration1.5 Hours
Activity LevelEasy-Moderate
$199
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Tue Jan 13
Road Bay
Arrive:7:00 AM
Depart:7:00 PM
Watersports Platform: 
4 Available
+_
With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean.  It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats.  Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
4 Shore Excursions Available
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Road Bay, Iconic Island Highlights with Salt Tasting and Beach TimeBeach | Sightseeing | Refreshments
Duration4 Hours
Activity LevelEasy-Moderate
$189
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Road Bay, Concierge Collection: Relaxing Day at Savi with LunchBeach | Concierge Collection | Dining
Duration5 Hours
Activity LevelEasy-Moderate
$439
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Road Bay, Shoal Bay Beach TransferBeach | Culture | Essentials Collection | Outdoors | Sightseeing
Duration4 Hours
Activity LevelEasy
$125
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Concierge Collection: Road Bay, Snorkel Adventure by SpeedboatBoating | Concierge Collection | Refreshments | Snorkeling | Wildlife
Duration3 Hours
Activity LevelModerate-Strenuous
$329
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Wed Jan 14
Philipsburg, St. Maarten
Arrive:6:00 AM
Depart:
Watersports Platform: 
6 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.
6 Shore Excursions Available
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Philipsburg, Savor St. Maarten Foodie Tour
Duration4.5 Hours
Activity Level
$189
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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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