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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

6 Best Philipsburg Cruises for 2025-2026

Trip NameFromDaysNext DepartureSummary
Westbound Atlantic Ocean Crossing$460025Oct 29, 2025Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San …
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Caribbean Yachting Hideaways$77408Mar 14, 2026Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz …
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Save the Best for Last$39808Mar 27, 2025Sail aboard the Sea Cloud on a 10-day Caribbean adventure through the British Virgin Islands, St. Barths, Nevis, and St. Maarten. Explore Virgin …
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Treasure Islands$16408Feb 15, 2025Don'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 …
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Western Antilles$24808Oct 5, 2026Explore the Caribbean in this 8-day itinerary. Start in Philipsburg, Sint Maarten, Gustavia, Saint-Barthelemy, Deshaies in Guadeloupe, Saint-Pierre, …
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Leeward Islands$16408Feb 8, 2025The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des …
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All Philipsburg Luxury Small Ship Cruises

2 Best Philipsburg Luxury Small Ship Cruises for 2025-2026

Trip NameFromDaysNext DepartureSummary
Westbound Atlantic Ocean Crossing$460025Oct 29, 2025Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San …
0
Caribbean Yachting Hideaways$77408Mar 14, 2026Embark on an 8-day Caribbean adventure aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches, Vieques’ lovely waterfront, Cruz …
0
All St Martin Small Ship Cruises

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

Ship NameMax PassengersFromSummary
Star Flyer170$1640The Star Flyer is a stylish vessel designed to accommodate 170 passengers in an intimate and comfortable atmosphere. This true clipper ship reflects …
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Emerald Azzurra100$7740As Emerald's first-ever ocean superyacht, the luxurious Emerald Azzurra is designed to take up to 100 passengers sailing along the Adriatic Coast, …
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Sea Cloud64$3980With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. …
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Sea Cloud Spirit136$7500Sea Cloud Spirit is a modern and elegant windjammer with occupancy for 136 guests and a crew of 85. It gives you an amazing opportunity of traveling …
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SH Vega152$24805-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 …
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Philipsburg & Leeward Islands Travel Guide

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Philipsburg: Bird's Eye View on the Liberty Clipper Video

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