Have questions? We're here.
Sunset over Philipsburg

Philipsburg St. Martin Cruises

Travel made your way ™
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
Experience the captivating Caribbean destination of St. Martin with Adventure Life's array of 7 Cruises for 2025. Join us on a cruise journey through the turquoise waters of Philipsburg, where you can explore the vibrant culture, pristine beaches, and charming streets of this island paradise. From snorkeling in crystal-clear waters to savoring delicious Caribbean cuisine, each moment offers a unique opportunity to immerse yourself in the wonders of this region. Engage in wildlife viewing, village visits, and beach relaxation, all while surrounded by the natural beauty that has made St. Martin a favorite destination for travelers. With activities suitable for all ages and interests, don't miss this chance to discover the magic of St. Martin. Contact one of Adventure Life's Caribbean specialists for help planning your next seamless trip.
Filter (7 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Philipsburg
Learn about the history of the Caribbean
$2,880
EXPLORE

Western Antilles

Saint Martin to Barbados - 8 Day Itinerary aboard SH Vega
  • Explore Philipsburg, Sint Maarten
  • Discover the town of Gustavia
  • Explore the village of Deshaies
  • Admire the Pitons in Soufriere
  • Discover Saint-Pierre, Martinique
  • Explore Bridgetown, Barbados
Starts / Ends:
Philipsburg / Bridgetown
Activities:
Archaeological Site Visits, Kayaking, Small Ship Cruises, Village Visits
Activity Level:
Variable
Experience the best of the Caribbean with this 8-day itinerary. Start your trip in Philipsburg, Sint Maarten, and soak in the vibrant atmosphere of this Dutch capital. Enjoy the lively beachfront establishments, excellent shopping, and stunning beaches like Great Bay and Little Bay. In Gustavia, …
Cruise Details
0
Relax on the beaches of St. Maarten
$1,640
EXPLORE

Leeward Islands

8 Day Itinerary aboard Star Flyer
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Variable
Embark on an 8-day cruise aboard the Star Flyer. With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this unique region, …
Cruise Details
0
Tropical waterfall and turquoise pool in lush forest
$1,640
EXPLORE

Treasure Islands

8 Day Itinerary aboard Star Flyer
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
Starts / Ends:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Variable
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
Cruise Details
0
Play on the famously beautiful beaches of St. Barth's
$11,595
EXPLORE

Enjoy Caribbean Rhythms at the Turn of the Year

Caribbean: Round-trip Philipsb - 15 Day Itinerary aboard Sea Cloud
  • Snorkel the famed Virgin Gorda
  • See luxurious St. Barthelemy
  • Explore the culture of Grenada
  • Admire beautiful St. Lucia
Starts / Ends:
Philipsburg / St. Barth
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Variable
Explore the best of the Caribbean on this round-trip cruise from Philipsburg aboard the Sea Cloud sailing ship. From the charming Dutch Colonial port town of Philipsburg, make your way to the British Virgin Islands. Snorkel the famed baths, or simply relax on the white sandy beaches before sailing …
Cruise Details
0
Relax on the beaches of St. Maarten
$8,995
EXPLORE

Barefoot through Balmy January

St Maarten to Barbados - 10 Day Itinerary aboard Sea Cloud
  • Explore St. Maarten’s charm
  • Relax on Bequia beaches
  • Snorkel in Tobago Cays
  • Discover Soufriere’s sulfur springs
Starts / Ends:
Philipsburg / Barbados
Activities:
Small Ship Sailing, Snorkeling
Activity Level:
Variable
Embark on a 10-day journey through the Caribbean, starting in Philipsburg, St. Maarten. Discover European charm in the heart of the Caribbean, stroll along the Boardwalk, or relax on Great Bay Beach. Visit the island of St. Barths, renowned for its elegant atmosphere and vibrant harbor. In …
Cruise Details
0
Explore beautiful Jost van Dyke
$7,190
EXPLORE

Caribbean Yachting Hideaways

St Thomas - St John's - 8 Day Itinerary aboard Emerald Azzurra
  • Visit The Baths’ granite formation
  • Explore Culebra's white-sand beach
  • Experience swimming off the yacht
  • Discover the history of St. John
Starts / Ends:
St. Thomas / Antigua
Activities:
Adventure Options, Hiking, Kayaking, Snorkeling
Activity Level:
Variable
Experience an 8-day Caribbean journey aboard the luxurious Emerald Azzurra. Explore Culebra’s pristine beaches and vibrant reefs, then sail to Vieques for its beautiful waterfront and Sun Bay. Discover Cruz Bay on St. John with its charming town and scenic hikes. Experience the natural …
Cruise Details
0
Explore the beautiful Canary Islands
$4,600
EXPLORE

Westbound Atlantic Ocean Crossing

25 Day Itinerary aboard Star Flyer
  • Discover the Rock of Gibraltar
  • Experience Tangier
  • Visit Cadiz
  • Explore Safi
Starts / Ends:
Malaga / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
Embark on a 25-day cruise aboard the Star Flyer through Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San Sebastian, and Philipsburg. Immerse yourself in the rich history and exquisite architecture of Malaga's Alcazaba and Gibralfaro Castle. Witness the …
Cruise Details
0
1-7 of 7 Results
TrustScore 4.8 | 383 reviews
TrustScore 4.8 of 5
total score
Based on 383 reviews on
review score
6 hours ago
Kassandra is knowledgeable, efficient and very pleasant to work with.
Fred Weeman
review score
2 days ago
The booking was processed efficiently and quickly. We got what we wanted.
Doug Laporte
review score
2 days ago
Great company. Good communications. Great accommodations, excursions, transport. Guide Elvira was spectacular along with transport, driver, Cesar and activities
Kathy S
review score
3 days ago
Very responsive to questions. Helpful with all arrangements
Roz
review score
4 days ago
The ship company they sent us on was perfect in every detail
lisa wegener

Caribbean Travel Guide

Favorite Caribbean Caribbean All Trips

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By

Sandra Fernandez employee profile
Sandra F
Plan My Trip
We love travel, talk with an expert 1.800.344.6118