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Sunset over Philipsburg

Philipsburg Small Ship Cruises

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Travel to the blissful island and capital of St. Martin, Philipsburg located in the Leeward Island chain. The island of St. Martin is located in the Caribbean, and it is divided between the French Republic and the Kingdom of the Netherlands splitting the territory roughly 60/40 but with a pretty equal population. Philipsburg sits on the side that is owned by the Kingdom of the Netherlands. This port town has a population of nearly 2,000 inhabitants and sits on the Southernmost part of the island. Take a walk through the beautiful boardwalk or relax on Great Bay Beach. Take a small ship cruise with Adventure Life around the Caribbean Islands with the advantage of size, allowing the boat to access smaller coves, reefs, and ports that are impossible to access on larger vessels. Contact our travel experts to start planning your ideal trip to Philipsburg today!
All Philipsburg Small Ship Cruises

5 Best Philipsburg Cruises for 2025-2026

Trip Name From Days Next Departure Summary
Western Antilles $2,480 8 Oct 05, 2026 Explore the Caribbean in this 8-day itinerary. Start in Philipsburg, Sint Maarten, Gustavia, Saint-Barthelemy, Deshaies in Guadeloupe, Saint-Pierre, Martinique, Soufriere, St Lucia, and conclude in Bridgetown, Barbados.
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Leeward Islands $1,960 8 Nov 29, 2025 The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches, or hike to the tropical mountaintops.
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Caribbean Yachting Hideaways $7,740 8 Mar 14, 2026 Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz Bay’s scenic hikes, and Virgin Gorda’s famous Baths. Discover Philipsburg’s vibrant culture, Gustavia’s idyllic beaches, and Montserrat’s volcanic history.
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Treasure Islands $1,960 8 Nov 22, 2025 Don't miss the opportunity to relax on one of the beaches and enjoy the tropical sun's warmth. Soak up the sun in one of the world's most gorgeous locations, the Caribbean. Visit St. Maarten, Anguilla, Jost Van Dyke, St. Kitts, and St. Barts on this 8-day small ship trip!
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Westbound Atlantic Ocean Crossing $4,820 25 Oct 29, 2025 Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San Sebastian, and Philipsburg. Explore historic sites, natural beauty, charming towns, golden beaches, and unique shopping experiences.
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All St Martin Small Ship Cruises

3 Top-Rated Philipsburg Small Ship Cruises for 2025-2026

Trip Name From Days Next Departure Summary
Star Flyer $1,630 Apr 18, 2025 The Star Flyer is a stylish vessel designed to accommodate 170 passengers in an intimate and comfortable atmosphere. This true clipper ship reflects its proud heritage in every inch of its polished brass and gleaming brightwork. The décor of Star Flyer is reminiscent of the grand age of sail with spacious accommodations and expansive teak decks.
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SH Vega $2,480 May 21, 2025 5-star elegant Scandi-design boutique ship offers you an intimate setting from which you will be fully immersed in all the sights and scenery of your voyage.
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Emerald Azzurra $7,190 Apr 26, 2025 As Emerald's first-ever ocean superyacht, the luxurious Emerald Azzurra is designed to take up to 100 passengers sailing along the Adriatic Coast, Red Sea, and the Eastern and Western Mediterranean.
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Philipsburg & Leeward Islands Travel Guide

Explore charming Charlotte Amalie

Leeward Islands Politics

The Leeward Islands, a geographical grouping with an essentially shared history, have developed over time into six separate nations. They have a common interest in tourism, and in economic and cultural advancement for their ethnically diverse but essentially harmonious populations.
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Enjoy the natural beauty of the Caribbean

Leeward Islands Geography

Along with the Windward Islands, the small Leeward Islands form the Lesser Antilles on the eastern border of the Caribbean Sea. The geography of the Leeward Islands is comprised primarily by coral and volcanic islands. The soil on the coral islands is not well suited to agriculture, making these countries' primary economic engine tourism.
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Stroll along the white sandy beaches of St. Barth's

Leeward Islands Weather

As long as you avoid the hurricane season during the latter half of the year, you'll enjoy pleasant tropical temperatures between 81°F and 95°F (27°C and 35°C) and bright sunny days that never seem to end.
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Philipsburg: Bird's Eye View on the Liberty Clipper Video

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