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INTERNATIONAL NUMBERS HEALTH & SAFETY YACHT CLUB WISHLIST MY WINDSTAR
Call Your Travel Advisor or800.258.7245

Beach Fun & Sun: A Remote Caribbean Getaway

 
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Sat Nov 20, 2027 - Sun Nov 28, 2027,
 8 days
 on Wind Surf
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Starting from $2,999 USD
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OVERVIEW & ITINERARY
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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.

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Date
Port
Arrive
Depart
Marina
Shore
Excursions
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Sat Nov 20
Philipsburg, St. Maarten
Arrive:
Depart:7:00 PM
Watersports Platform: 
+_
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.
Sun Nov 21
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.
Mon Nov 22
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.
Tue Nov 23
Deshaies
Arrive:7:00 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.
Wed Nov 24
Road Bay
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
+_
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.
Thu Nov 25
Soper's Hole
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
+_
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. 
Thu Nov 25
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.
Fri Nov 26
Jost Van Dyke, Great Harbour
Arrive:
Depart:10:00 PM
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.
Sat Nov 27
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
+_
  • 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.
Sun Nov 28
Philipsburg, St. Maarten
Arrive:6:00 AM
Depart:
Watersports Platform: 
+_
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.