Star Collector: Caribbean Explorations
 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Jan 31, 2026 - Sat Feb 14, 2026,
 14 days
 on Wind Spirit
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Starting from $4,099 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
Expand
Sat Jan 31
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
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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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Sun Feb 1
St. John's
Arrive:8:00 AM
Depart:6:00 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
+
_
St. Johns, Beach EscapeBeach | Essentials Collection
Duration4 Hours
Activity LevelEasy
$79
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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
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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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Mon Feb 2
Road Bay
Arrive:9:00 AM
Depart:6:00 PM
Watersports Platform: 
2 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.
2 Shore Excursions Available
+
_
Road Bay, Iconic Island Highlights with Salt Tasting and Beach TimeBeach | Sightseeing | Refreshments
Duration4 Hours
Activity LevelEasy-Moderate
$189
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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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Tue Feb 3
Soper's Hole
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
4 Available
+_
Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away. 
4 Shore Excursions Available
+
_
Tortola, Snorkel Adventure at Peter IslandBoating | Essentials Collection | Sightseeing | Refreshments | Snorkeling
Duration3 Hours
Activity LevelModerate-Strenuous
$135
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Soper's Hole: Cane Garden Bay Beach BreakBeach | Essentials Collection | Refreshments
Duration4 Hours
Activity LevelModerate
$89
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Tortola, Tortola Jeep & Beach TourBeach | Essentials Collection | Sightseeing
Duration4 Hours
Activity LevelModerate
$199
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Tortola, Scenic Drive & Beach Outdoors | Sightseeing | Beach | Essentials Collection
Duration4.5 Hours
Activity LevelEasy
$109
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Tue Feb 3
Jost Van Dyke, Great Harbour
Arrive:7:00 PM
Depart:
Watersports Platform: 
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
Wed Feb 4
Jost Van Dyke, Great Harbour
Arrive:
Depart:10:00 PM
Watersports Platform: 
2 Available
+_
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
2 Shore Excursions Available
+
_
Jost Van Dyke, Catamaran Cruise & Swim to Norman IslandBeach | Boating | Essentials Collection | Snorkeling
Duration4.5 Hours
Activity LevelModerate-Strenuous
$259
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Jost Van Dyke, Sail and SnorkelBoating | Essentials Collection | Sightseeing | Refreshments | Watersports
Duration4 Hours
Activity LevelModerate-Strenuous
$159
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Thu Feb 5
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
2 Available
+_
  • The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns.
 
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.
2 Shore Excursions Available
+
_
Virgin Gorda: Highlights & Bath TourBeach | Boating | Essentials Collection | Walking
Duration4 Hours
Activity LevelStrenuous
$89
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Virgin Gorda: Snorkel AdventureBoating | Essentials Collection | Refreshments | Snorkeling
Duration2.75 Hours
Activity LevelModerate-Strenuous
$239
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Fri Feb 6
Gustavia
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
5 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.
5 Shore Excursions Available
+
_
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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St. Barts, Concierge Collection: Sunset CruiseBoating | Concierge Collection | Sightseeing | Refreshments
Duration1.5 Hours
Activity LevelEasy-Moderate
$199
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Sat Feb 7
Philipsburg, St. Maarten
Arrive:6:00 AM
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 Feb 8
Charlestown
Arrive:8:00 AM
Depart:4:00 PM
Watersports Platform: 
6 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.
6 Shore Excursions Available
+
_
Charlestown, Yachtsman Grill Beach EscapeBeach | Essentials Collection | Outdoors | Refreshments
Duration3.5 Hours
Activity LevelModerate
$69
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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
Duration4 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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Charlestown, Quad Biking AdventureOutdoors | Sightseeing
Duration2.5 Hours
Activity LevelStrenuous
$159
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Mon Feb 9
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
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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, Concierge Collection: Cooking Caribbean Flavors & Lifestyles Culture | Dining | Sightseeing | Concierge Collection
Duration3.5 Hours
Activity LevelEasy
$129
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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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Tue Feb 10
Mayreau
Arrive:8:00 AM
Depart:5:00 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
+
_
Mayreau, Grenadines Island Escape Snorkeling | Outdoors | Refreshments | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$89
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Wed Feb 11
Anse Mitan
Arrive:7:30 AM
Depart:2:00 PM
Watersports Platform: 
5 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.
5 Shore Excursions Available
+
_
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, Creole VillageCulture | Essentials Collection | Sightseeing | Walking
Duration2.75 Hours
Activity LevelModerate-Strenuous
$99
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Thu Feb 12
Basseterre
Arrive:1:00 PM
Depart:10:00 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
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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
VIEW DETAILS
Fri Feb 13
Gustavia
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
5 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.
5 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
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St. Barts, Concierge Collection: Sunset CruiseBoating | Concierge Collection | Sightseeing | Refreshments
Duration1.5 Hours
Activity LevelEasy-Moderate
$199
VIEW DETAILS
Sat Feb 14
Philipsburg, St. Maarten
Arrive:6:00 AM
Depart:
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
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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