itinerary & excursions

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

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OVERVIEW & ITINERARY

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

Watersports
Platform

Shore
Excursions

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Sat Feb 28

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 Mar 1

Basseterre

Arrive:8:00 AM

Depart:9:00 PM

Watersports Platform:

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.

Mon Mar 2

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.

Tue Mar 3

St. John's

Arrive:8:00 AM

Depart:9:00 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.

Wed Mar 4

Les Saintes

Arrive:8:00 AM

Depart:5:00 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.

Thu Mar 5

Roseau

Arrive:8:00 AM

Depart:1:00 PM

Watersports Platform:

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.

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:

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.