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Philipsburg Beach Trips

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Unlock the treasure chest of the Caribbean with one of our 4 hand-picked beach tours in 2025 and 2026 to Philipsburg, St Martin. Picture yourself soaking up the sun on a white sand beach, exploring tropical jungles or taking a dip in crystal-clear waters. Our expertly-crafted itineraries will provide you with endless opportunities to experience all the best that this beautiful region has to offer. From vibrant cities like Philipsburg and Marigot, to hidden coves and secluded bays, there's something for everyone in this magical part of the world. Don't miss out on your chance for an unforgettable adventure! Contact one of our St Martin beach vacation specialists today and start planning your perfect island getaway!
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    • Philipsburg
Stroll along the beautiful beaches of the Caribbean
from $3,420
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Eastbound Atlantic Ocean Crossing

Philipsburg - Malaga - 21 Day Itinerary aboard Star Flyer
  • Explore Philipsburg’s Dutch side
  • Experience Marigot’s markets
  • Unwind while crossing the Atlantic
  • Visit Ponta Delgada’s churches
Starts / Ends
Philipsburg / Malaga
Activities
Small Ship Sailing, Local Market Visits, Archaeological Site Visits
Activity Level
Variable
Set sail on a 21-day cruise aboard the Star Flyer, starting in Philipsburg and visiting Ponta Delgada in the Azores. End your journey in Malaga, Spain, exploring its Moorish heritage while enjoying 18 days at sea.
Cruise Details
0
Enjoy the natural beauty of the Caribbean
from $5,270
EXPLORE

Caribbean Flair Away from the Everyday

9 Day Itinerary aboard Sea Cloud Spirit
  • Fort Napoleon island lookout
  • Hike Tet Paul, St. Lucia springs
  • Snorkel Tobago Cays reefs
  • Dominica hikes and river tours
Starts / Ends
Philipsburg / Philipsburg
Activities
Hiking, Snorkeling, Stand Up Paddle Boarding
Activity Level
Variable
Sail roundtrip from St. Maarten on a 9-day Sea Cloud Spirit cruise through the Lesser Antilles. Visit Îles des Saintes, St. Lucia, Union Island, Bequia, and Dominica. Highlights include volcanic hikes, rainforest tours, snorkeling in Tobago Cays, and tall ship sailing days with sunset views and sea air.
Cruise Details
0
Gustavia Harbor in St. Barths
from $1,970
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Antigua to Antigua

Roundtrip St John - 8 Day Itinerary aboard Star Clipper
  • Explore St. John's dockyards
  • Sail Sir Francis Drake Channel
  • Stroll Norman Island's beach
  • Tour Basseterre's old plantations
Starts / Ends
St. John's / St. John's
Activities
Village Visits
Activity Level
Variable
Embark on an 8-day cruise in the Caribbean aboard the Star Clipper, starting and ending in Antigua. Discover the beaches and boutiques of St. Barts, explore Norman Island, and enjoy the charm of Jost van Dyke, while swimming at Virgin Gorda and experiencing St. Kitts’ history and nature.
Cruise Details
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Explore beautiful Jost van Dyke
from $8,390
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
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.
Cruise Details
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