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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 $1,030 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 $2,010 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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Emerald Sakara 100 $6,295 Emerald Cruises brings our award-winning reputation and service to the world's oceans and coastlines as we introduce Luxury yacht cruising on our brand new, innovative superyachts, custom-designed to allow unique access to the fascinating ports and harbors only small yachts can reach.
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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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All Philipsburg Deals

8 Best Philipsburg Small Ship Cruise Deals for 2026-2027

Trip Name From Days Summary
Cruising the Leeward Islands $6,395 8 Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara, starting in Philipsburg, Sint Maarten. Visit Anguilla's coral reefs, explore Virgin Gorda's grottos, and enjoy local cuisine while discovering unique island architecture.
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Eastern Caribbean with St. Barths $6,295 8 Set sail on an 8-day Eastern Caribbean cruise from Bridgetown on Emerald Sakara, visiting St. Lucia's mud baths, Antigua's Nelson's Dockyard, and the stunning beaches of Iles des Saintes. End your journey in Philipsburg, the lively capital of Dutch Sint Maarten.
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Discover Eastern Caribbean & Grenadines $13,340 15 Set sail on a 15-day Caribbean cruise from Philipsburg on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Visit charming islands like Virgin Gorda, Saint Barthelemy, and Bequia for stunning beaches, local cuisine, and water activities amidst breathtaking views.
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Discover Eastern Caribbean & Grenadines $13,390 15 Join a 15-day Caribbean cruise from Bridgetown on the Emerald Sakara, exploring the Eastern Caribbean and Grenadines. Experience local culture in Speightstown, enjoy water sports in Kingstown, and relax in natural hot springs in Soufriere before returning to Barbados.
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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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Treasure Islands $2,010 8 Set sail on an 8-day Caribbean cruise aboard the Star Flyer, starting and ending in Philipsburg, St. Maarten. Explore scenic spots like St. Barts, Jost Van Dyke, Virgin Gorda, and Anguilla, blending natural beauty and rich history.
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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

Jane Packer Adventure Life employee profile
Jane P.
Philipsburg, St Maarten, Old Street market
Caribbean

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