Have questions? We're here.
Sunset over Philipsburg

Philipsburg Small Ship Cruises

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
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

10 Best Philipsburg Cruises for 2022-2023

Trip NameFromDaysNext DepartureSummary
On the Sunny Side of Life$47558Dec 14, 2023Discover deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the islands' sugar cane …
0
Windjammer Rendezvous in the Lesser Antilles$678512Mar 27, 2023Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s …
0
Pirate Islands, Sailors' Haunts and Dream Beaches$44959Dec 14, 2022Join the Sea Cloud II on this fantastic 9-day cruise exploring Caribbean hot spots. Visit the colorful small cities and the exceptional beaches this …
0
Front Row Seat at the Famous Bucket Regatta$749511Mar 17, 2023Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s …
0
Philipsburg Round Trip$49208Nov 28, 2022Join the Sea Cloud Spirit on a roundtrip Caribbean cruise to St. Maarten which includes stops in Puerto Rico, the British Virgin Islands, and France. …
0
Treasure Islands$23608Dec 3, 2022Don'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 …
0
Leeward Islands$23608Nov 26, 2022The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Nevis, Dominica, …
0
Relaxed Festive Days Under Palms$1018517Dec 20, 2022Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious …
0
Pure Sailing- Crossing the Atlantic$1295517Nov 29, 2022Sail around the Atlantic ocean as Sea Cloud II sail from the island on the Southwest coast of Praia to Gustavia enjoying the beautiful beaches and …
0
Philipsburg to Puntarenas$968016Dec 5, 2022Relax and unwind as the Sea Cloud Spirit takes you to the best of the Caribbean, Colombia, Panama, and Costa Rica during this 16-day cruise from …
0
All Philipsburg Luxury Small Ship Cruises

4 Best Philipsburg Luxury Small Ship Cruises for 2022-2023

Trip NameFromDaysNext DepartureSummary
Relaxed Festive Days Under Palms$1018517Dec 20, 2022Cruising the perfect dream of tall ships: Encounter volcanic islands, laid-back sailors' haunts, and colorful underwater worlds. Join the luxurious …
0
Pure Sailing- Crossing the Atlantic$1295517Nov 29, 2022Sail around the Atlantic ocean as Sea Cloud II sail from the island on the Southwest coast of Praia to Gustavia enjoying the beautiful beaches and …
0
Pure Sailing- Crossing the Atlantic$1496018Nov 25, 2022Sail across the Atlantic Ocean on this exclusive 18-day, once-in-a-lifetime offshore adventure on the Sea Cloud schooner. Enjoy an authentic sailing …
0
Transatlantic:Malaga to St.Maarten$394025Nov 2, 2022This once-in-a-lifetime sailing expedition starts at the tropical paradise island of St. Maarten and voyages across the Atlantic Ocean all the way to …
0
All St Martin Small Ship Cruises

4 Top-Rated Philipsburg Small Ship Cruises for 2022-2023

Ship NameMax PassengersFromSummary
Star Flyer170$2330The Star Flyer is a stylish vessel designed to accommodate 170 passengers in an intimate and comfortable atmosphere. This true clipper ship reflects …
0
Sea Cloud64$4755With occupancy for just 64 guests, the Sea Cloud is a modern and elegant windjammer outfitted with modern amenities and uniquely decorated cabins. …
0
Sea Cloud II94$4495The Sea Cloud II is a legendary windjammer comparable to her sister ship, the Sea Cloud. Featuring her own unique character, the Sea Cloud II …
0
Sea Cloud Spirit136$4920Sea 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 …
0

Philipsburg & Leeward Islands Travel Guide

All Philipsburg Videos

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

Caribbean Travel Guide

Favorite Caribbean All Trips

Top Philipsburg Travel Destinations

Philipsburg Trips by Departure Date

Philipsburg Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By