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Top Philipsburg Tours & Cruises in 2025

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Discover the best the world has to offer with Adventure Life’s expert-curated Philipsburg tours 2025. From to hidden gems off the beaten path, our 4 top-rated itineraries take you deep into Philipsburg’s breathtaking landscapes. Guided by bilingual experts, these immersive experiences cater to adventurers seeking unique journeys in small groups or customizable private tours.

Choose from a variety of 8 to 25 days itineraries starting at $1,960 to $31,240. You’ll find options that suit your travel style. Whether you’re passionate about Small Ship Sailing, Snorkeling, Hiking, Local Market Visits, and Village Visits or eager to explore Philipsburg’s rich culture and natural beauty, our Philipsburg tours 2025 deliver unforgettable moments. Each itinerary blends awe-inspiring exploration with a commitment to sustainability to ensure your adventure supports the preservation of our planet.

Adventure Life’s dedication to personalized travel promises your Philipsburg tour 2025 is seamless from start to finish. From arranging transportation to selecting accommodations tailored to your preferences, we’ll take care of every detail. Our expert recommendations and insider tips make your journey even more enriching.

Contact our specialists today to start planning your Philipsburg tour 2025. Whether you’re a solo traveler, a couple, or part of a group, Adventure Life will create a transformative experience you’ll treasure forever.
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    • Philipsburg
Relax on the beaches of St. Maarten
from $1,960
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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
Snorkeling
Activity Level
Variable
The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Dominica, Iles des Saintes, Guadeloupe, Antigua, and St. Barts. As the wind blows your ship across turquoise waters through thousands of cays, snorkel in the clear water, relax on sunny beaches, or hike to the tropical mountaintops.
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Tropical waterfall and turquoise pool in lush forest of Dominica
from $1,960
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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
Activity Level
Variable
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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Explore beautiful Jost van Dyke
from $10,590
2for1
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Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Azzurra
  • Discover Culebra Island’s shores
  • Explore Vieques Island waterfront
  • Tour St. John’s Annaberg ruins
  • Relax on Jost Van Dyke’s White Bay
Starts / Ends
San Juan / St. John's
Activities
Small Ship Sailing, Local Market Visits, Hiking, Village Visits
Activity Level
Variable
Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.
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Explore the beautiful Canary Islands
from $4,820
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
Activity Level
Variable
Embark on a 25-day cruise aboard the Star Flyer, visiting Malaga, Gibraltar, Tangier, Cadiz, Safi, Arrecife, Puerto del Rosario, Las Palmas, San Sebastian, and Philipsburg. Explore historic sites, natural beauty, charming towns, golden beaches, and unique shopping experiences.
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1-4 of 4 Results
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TrustScore 4.8 | 568 reviews
TrustScore 4.8 of 5
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Based on 568 reviews on
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2 months ago
Jess is funtastic! She listens and fines the adventure I want to share with my granddaughter
carolynn basque

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