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Philipsburg Beach Trips

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Unlock the treasure chest of the Caribbean with one of our 6 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
EXPLORE

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
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
Explore beautiful Jost van Dyke
from $8,390
2for1
EXPLORE

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
Hiking
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
0
Explore the famous rock formations of the baths
from $6,995
No SS
EXPLORE

Across a sea of idyllic Islands

Philipsburg, St. Maarten Round - 8 Day Itinerary aboard Sea Cloud Spirit
  • Explore chic St. Barths
  • Relax at Great Bay
  • Visit Virgin Gorda
  • Cruise Sir Francis Channel
Starts / Ends
Philipsburg / Philipsburg
Activities
Small Ship Sailing, Snorkeling, Stand Up Paddle Boarding
Activity Level
Variable
Set sail on an unforgettable 8-day Caribbean cruise aboard the Sea Cloud Spirit. Experience the charm of St. Maarten, Antigua, St. Barths, and the Virgin Islands as you explore paradise by sea. Discover rich culture, pristine beaches, and lively island towns filled with color and charm.
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
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
0
Caribbean landscapes and harbors
from $21,180
2for1
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Discover the Yachting Islands of the Caribbean

Roundtrip Saint John’s - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Barbuda’s iconic pink sands
  • Visit Les Saintes’ quaint towns
  • Discover Deshaies’ lush hills
  • Swim off Norman Island’s shores
Starts / Ends
St. John's / St. John's
Activity Level
Variable
Embark on a 15-day cruise with Emerald Azzurra, exploring the Caribbean from St. John’s, Antigua, with stops at stunning destinations like Barbuda, Guadeloupe, and the British Virgin Islands. Enjoy snorkeling in Culebra and the relaxed vibe of Esperanza on Vieques, all amidst beautiful beaches and vibrant island culture.
Cruise Details
0
Learn about Spanish colonial history in Old San Juan
from $21,980
2for1
EXPLORE

Discover the Yachting Islands of the Caribbean

Roundtrip San Juan - 15 Day Itinerary aboard Emerald Azzurra
  • Snorkel Culebra’s coral reefs
  • Wander Vieques’ Esperanza
  • Explore St. John’s plantation ruins
  • Stroll Philipsburg’s streets
Starts / Ends
San Juan / San Juan
Activities
Local Market Visits, Village Visits, Archaeological Site Visits, Wildlife Viewing, Kayaking
Activity Level
Variable
Embark on a 15-day Caribbean cruise from San Juan aboard Emerald Azzurra, exploring serene spots like Culebra, Vieques, and St. Barts. Experience stunning beaches, rich culture, and scenic ports, all in a relaxed yacht-style setting.
Cruise Details
0
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