Hold times may be longer than usual: We're currently undergoing a reservation system upgrade and are still fixing some issues. Please contact us if you have any questions.
Lush & Lovely Islands of the Lesser Antilles
 
Philipsburg, St. Maarten to Bridgetown
Sun Jan 11, 2026 - Sun Jan 18, 2026,
 7 days
 on Wind Surf
?All-inclusive from
$3,122
?Cruise Only From
$2,499
VIEW ALL SAILING
DATES & FARES
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
Sun Jan 11
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
+
_
St. Maarten, Post Island Tour with Transfer to AirportEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$79
VIEW DETAILS
St. Maarten, Post Island Tour with Transfer to HotelEssentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$79
VIEW DETAILS
St. Maarten: Americas Cup Sailboat Racing with Transfer to AirportBoating | Essentials Collection | Outdoors | Refreshments
Duration2.5 Hours
Activity LevelModerate
$149
VIEW DETAILS
St. Maarten: Americas Cup Sailboat Racing with Transfer to Windstar Hotel Outdoors | Refreshments | Boating | Essentials Collection
Duration2.5 Hours
Activity LevelModerate
$149
VIEW DETAILS
Mon Jan 12
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
+
_
Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. KittsConcierge Collection | Culture | Dining | Sightseeing
Duration3.5 Hours
Activity LevelEasy
$89
VIEW DETAILS
Basseterre, Brimstone Hill Fortress & Fairview Great HouseCulture | Essentials Collection | Sightseeing | UNESCO
Duration3.25 Hours
Activity LevelEasy
$69
VIEW DETAILS
Basseterre, Island History & Rum TastingEssentials Collection | Sightseeing | Refreshments
Duration3.25 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, Irie Rider Speed BoatBoating | Essentials Collection | Refreshments | Snorkeling
Duration3.25 Hours
Activity LevelModerate-Strenuous
$109
VIEW DETAILS
Basseterre: St Kitts Quad ATV Adventure Outdoors | Refreshments | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$119
VIEW DETAILS
Tue Jan 13
Gustavia
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
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.
Wed Jan 14
St. John's
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
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.
Thu Jan 15
Les Saintes
Arrive:8:00 AM
Depart:9:00 PM
Watersports Platform: 
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.
Fri Jan 16
Pigeon Island
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
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.
Sat Jan 17
Kingstown
Arrive:7:00 AM
Depart:2:00 PM
Watersports Platform: 
Charming Kingstown, the capital and main commercial center of St. Vincent & the Grenadines is known for its churches, cobblestone streets, colonial buildings and the St. Vincent Botanical Gardens, founded in 1765.  Steep hills surround the town, with Fort Charlotte sitting high on a ridge north of the city, offering panoramic views of Kingstown and the surrounding islands.  Other sites to see include St. George’s Anglican Cathedral, an 1820s structure adorned with stained glass windows, St. Mary’s Catholic Cathedral, built in 1823, with its lovely Gothic spires and Romanesque columns and arches.
Sun Jan 18
Bridgetown
Arrive:5:00 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
$119
VIEW DETAILS
Bridgetown: Barbados Island Tour with Transfer to Windstar Hotel Sightseeing | Dining | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$119
VIEW DETAILS