Lush & Lovely Islands of the Lesser Antilles
 
Philipsburg, St. Maarten to Bridgetown
Sat Feb 28, 2026 - Sat Mar 7, 2026,
 7 days
 on Wind Spirit
VIEW ALL DATES
Starting from $2,499 USD
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST

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 Feb 28
Philipsburg, St. Maarten
Arrive:
Depart:7:00 PM
Watersports Platform: 
5 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.
5 Shore Excursions Available
+
_
St. Maarten, Post Island Tour with Transfer to AirportEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$99
VIEW DETAILS
St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$99
VIEW DETAILS
St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$99
VIEW DETAILS
St. Maarten: Americas Cup Sailboat Racing with Transfer to AirportBoating | Essentials Collection | Outdoors | Refreshments
Duration2.5 Hours
Activity LevelModerate
$179
VIEW DETAILS
St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel Outdoors | Refreshments | Boating | Essentials Collection
Duration2.5 Hours
Activity LevelModerate
$179
VIEW DETAILS
Sun Mar 1
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
+
_
Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. KittsConcierge Collection | Culture | Dining | Sightseeing
Duration3.5 Hours
Activity LevelEasy
$99
VIEW DETAILS
Basseterre, Brimstone Hill Fortress & Fairview Great HouseCulture | Essentials Collection | Sightseeing | UNESCO
Duration3.25 Hours
Activity LevelEasy
$79
VIEW DETAILS
Basseterre, Island History & Rum TastingEssentials Collection | Sightseeing | Refreshments
Duration2.5 Hours
Activity LevelEasy
$59
VIEW DETAILS
Basseterre, Nevis Panoramic and Beach TourBeach | Boating | Dining | Essentials Collection | Sightseeing
Duration5 Hours
Activity LevelEasy-Moderate
$139
VIEW DETAILS
Basseterre: Caribbean Scenic Railway Refreshments | Culture | Sightseeing | Essentials Collection
Duration3 Hours
Activity LevelEasy
$109
VIEW DETAILS
Basseterre: Sky Safari Zipline Adventure Outdoors | Wildlife | Essentials Collection
Duration4 Hours
Activity LevelStrenuous
$119
VIEW DETAILS
Basseterre: Snorkel Safari Snorkeling | Wildlife | Refreshments | Boating | Essentials Collection
Duration3 Hours
Activity LevelModerate
$99
VIEW DETAILS
Basseterre: St Kitts Quad ATV Adventure Outdoors | Refreshments | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$129
VIEW DETAILS
Mon Mar 2
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
+
_
St Barts, Concierge Collection: St. Barthelemy Beach DayBeach | Concierge Collection | Dining
Duration6 Hours
Activity LevelEasy-Moderate
$499
VIEW DETAILS
St. Barts: Sailing Catamaran AdventureBeach | Boating | Essentials Collection | Refreshments | Snorkeling | Wildlife
Duration3 Hours
Activity LevelModerate
$299
VIEW DETAILS
St. Barts: Independent Explorer by CarEssentials Collection | Sightseeing
Duration6 Hours
Activity LevelEasy-Moderate
$349
VIEW DETAILS
St. Barts: Intimate Island TourEssentials Collection | Sightseeing
Duration Hour
Activity LevelEasy
$139
VIEW DETAILS
St. Barts, Concierge Collection: Sunset CruiseBoating | Concierge Collection | Sightseeing | Refreshments
Duration1.5 Hours
Activity LevelEasy-Moderate
$199
VIEW DETAILS
St. Barts: Yellow Semi-Sub ExplorationBoating | Essentials Collection | Wildlife
Duration Hour
Activity LevelEasy
$119
VIEW DETAILS
Tue Mar 3
St. John's
Arrive:8:00 AM
Depart:9:00 PM
Watersports Platform: 
8 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.
8 Shore Excursions Available
+
_
St. Johns, Beach EscapeBeach | Essentials Collection
Duration4 Hours
Activity LevelEasy
$79
VIEW DETAILS
St. Johns, Concierge Collection, Birds Nest Eco Tour with Snorkeling and Caribbean LunchBeach | Concierge Collection | Dining | Sightseeing | Wildlife
Duration5.5 Hours
Activity LevelModerate-Strenuous
$269
VIEW DETAILS
St Johns, Concierge Collection, Jet Ski AdventureBeach | Boating | Essentials Collection | Sightseeing
Duration1.75 Hours
Activity LevelModerate-Strenuous
$379
VIEW DETAILS
St. Johns, Open Course Canopy Challenge Outdoors | Wildlife | Sightseeing | Essentials Collection
Duration4 Hours
Activity LevelStrenuous
$139
VIEW DETAILS
St. Johns: Presidents TourEssentials Collection | Sightseeing
Duration3 Hours
Activity LevelEasy
$109
VIEW DETAILS
St. Johns, Segway Fort Conqueror Outdoors | Sightseeing | Refreshments | Beach | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$159
VIEW DETAILS
St. Johns, Spectacular Antigua Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$79
VIEW DETAILS
St Johns, Swim with the StingraysEssentials Collection | Refreshments | Watersports
Duration3 Hours
Activity LevelModerate
$109
VIEW DETAILS
Wed Mar 4
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
+
_
Les Saintes, Blue Escape Kayaking *Boating | Essentials Collection | Outdoors | Sightseeing | Refreshments
Duration2 Hours
Activity LevelModerate
$149
VIEW DETAILS
Les Saintes, Sample Culinary Treasures of GuadeloupeBeach | Concierge Collection | Culture | Dining
Duration3 Hours
Activity LevelEasy-Moderate
$209
VIEW DETAILS
Les Saintes, Explore Terra de Haut by FootCulture | Essentials Collection | Refreshments | Walking
Duration1.25 Hours
Activity LevelModerate
$109
VIEW DETAILS
Les Saintes, Sailing the BayBoating | Concierge Collection | Refreshments
Duration3 Hours
Activity LevelModerate
$199
VIEW DETAILS
Les Saintes, Historic Tastes & Treasures of Fort NapoleonCulture | Essentials Collection | Sightseeing | Refreshments
Duration2.5 Hours
Activity LevelModerate
$129
VIEW DETAILS
Les Saintes, Terre de Haut Panoramic TourEssentials Collection | Sightseeing
Duration Hour
Activity LevelEasy
$119
VIEW DETAILS
Les Saintes, Snorkel Experience in Les Saintes *Boating | Essentials Collection | Refreshments | Snorkeling | Wildlife
Duration2 Hours
Activity LevelStrenuous
$119
VIEW DETAILS
Les Saintes, Relax & Snorkel *Beach | Boating | Essentials Collection | Refreshments | Snorkeling
Duration3 Hours
Activity LevelModerate-Strenuous
$169
VIEW DETAILS
Thu Mar 5
Roseau
Arrive:8:00 AM
Depart:1:00 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
+
_
Roseau, 4X4 Waterfall & RainforestBeach | Essentials Collection | Outdoors | Refreshments
Duration3 Hours
Activity LevelModerate
$89
VIEW DETAILS
Roseau, Whale & Dolphin Adventure Wildlife | Refreshments | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelEasy-Moderate
$159
VIEW DETAILS
Roseau, Champagne Reef Snorkel AdventureEssentials Collection | Snorkeling | Wildlife
Duration2 Hours
Activity LevelStrenuous
$79
VIEW DETAILS
Roseau, Concierge Collection: Cooking Caribbean Flavors & Lifestyles Culture | Dining | Sightseeing | Concierge Collection
Duration3.5 Hours
Activity LevelEasy
$129
VIEW DETAILS
Roseau, Indian River Rowboat Wildlife | Culture | Walking | Boating | Essentials Collection
Duration4.5 Hours
Activity LevelModerate
$89
VIEW DETAILS
Roseau, River Tubing AdventureEssentials Collection | Outdoors | Refreshments | Watersports
Duration4 Hours
Activity LevelModerate
$109
VIEW DETAILS
Roseau, Trafalgar Falls & Hot Springs Outdoors | Wildlife | Refreshments | Walking | Essentials Collection
Duration3 Hours
Activity LevelModerate
$99
VIEW DETAILS
Roseau, Concierge Collection: Wet & Rugged DominicaConcierge Collection | Dining | Hiking | Sightseeing | Walking
Duration5.5 Hours
Activity LevelStrenuous
$225
VIEW DETAILS
Fri Mar 6
Mayreau
Arrive:8:00 AM
Depart:4:00 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.
Sat Mar 7
Bridgetown
Arrive:7:00 AM
Depart:
Watersports Platform: 
2 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.
2 Shore Excursions Available
+
_
Bridgetown: Barbados Island Tour with Airport Transfer Dining | Sightseeing | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$129
VIEW DETAILS
Bridgetown: Barbados Island Tour with Transfer to Windstar Hotel Sightseeing | Dining | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$129
VIEW DETAILS