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Philipsburg, St Maarten, Old Street market

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

8 Best Philipsburg Small Ship Cruises for 2026-2027

All Philipsburg Small Ship Cruises
All Philipsburg Small Cruise Ships

4 Top-Rated Philipsburg Small Cruise Ships for 2026-2027

Ship Name Max Passengers From Summary
Star Clipper 170 $1,000 Star Clipper is a 170-passenger vessel designed to provide a unique traveling experience unlike any other cruise vacation. Step aboard and discover a new age of sailing, where the traditions of the past are happily married to the comforts and amenities of the present day.
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Star Flyer 170 $1,710 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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Sea Cloud Spirit 136 $6,995 Sea 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 with a high comfort level and enjoying the best panorama views.
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Sea Cloud II 94 $6,495 The Sea Cloud II is a legendary windjammer comparable to her sister ship, the Sea Cloud. Featuring her own unique character, the Sea Cloud II combines the high standards expected of a 5-star cruise ship with the unique atmosphere of a romantic tall ship.
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All Philipsburg Deals

8 Best Philipsburg Small Ship Cruise Deals for 2026-2027

Trip Name From Days Summary
Leeward Islands $2,010 8 Join an 8-day roundtrip Caribbean cruise from Philipsburg, St. Maarten, on the Star Flyer, visiting historic Nevis, scenic Dominica, and the vibrant yachting hub of Antigua. Enjoy snorkeling in Terre-de-Haut and explore Basseterre and South Friars Bay in St. Kitts before returning to St. Maarten.
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Treasure Islands $2,010 8 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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Leeward Islands $2,010 8 Embark on an 8-day roundtrip cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring St. Maarten, Nevis, Dominica, Antigua, and St. Barts. Experience stunning beaches, vibrant culture, and unique natural landscapes across the Leeward Islands.
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Antigua Roundtrip $2,010 8 Experience an 8-day round-trip cruise from St. John's, Antigua, aboard the Star Clipper, visiting destinations like St. Barts, the British Virgin Islands, and St. Maarten. Enjoy duty-free shopping, stunning beaches, and historic sites before concluding your journey in Antigua.
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Treasure Islands $2,010 8 Join an 8-day Caribbean cruise on the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore stunning beaches, historic sites, and vibrant islands like Anguilla, Tortola, Virgin Gorda, and St. Barts.
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Leeward Islands $2,010 8 Embark on an 8-day Caribbean cruise from Philipsburg, St. Maarten, aboard the Star Flyer, exploring charming towns, lush rainforests, and beautiful beaches. Enjoy duty-free shopping in Gustavia before returning to St. Maarten.
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Sun-Drenched Sailing Days $6,995 8 Sail 8 days aboard Sea Cloud Spirit through the Caribbean, Lesser Antilles & Grenadines. You explore St. Maarten, Martinique, St. Lucia, Dominica, Nevis, and Anguilla, combining colonial towns, volcanic peaks, rainforests, and white-sand beaches with authentic sailing experiences at sea.
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Dream Of A Lifetime. Atlantic Crossing $13,695 17 Experience 17 days aboard Sea Cloud Spirit on a transatlantic crossing from Las Palmas to Philipsburg. Relax on deck, enjoy wellness programs, and explore Gran Canaria’s landscapes before arriving in the Caribbean.
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Philipsburg & Leeward Islands Travel Guide

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

Jenna Fedyschyn Adventure Life employee profile
Jenna F.
Philipsburg, St Maarten, Old Street market
Caribbean

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