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Philipsburg, St Maarten, Old Street market

Philipsburg Trips with Village Visits

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Explore remote villages on one of the below 3 unique Philipsburg cultural experiences for 2026 or 2027. Visit the local village, meet the people, experience local cuisine with a local English speaking guide on your own private tour or small group guided tour. Discover unique local cultures on trips that include activities like Local Market Visits, Small Ship Sailing, and Snorkeling and cost from $1,970 for experiences of 8 to 17 days. Tell us about your ideal Philipsburg cultural trip and our Philipsburg experts will help you plan every detail of your next trip.

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Gustavia Harbor in St. Barths
from $1,970
EXPLORE

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
Snorkeling
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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Relax on the beaches of St. Maarten
from $6,955
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Sailing On The Trade Winds

Philipsburg Roundtrip - 11 Day Itinerary aboard Sea Cloud II
  • Explore Philipsburg harbor
  • Walk Terre-de-Haut
  • See Piton peaks
  • Sail Drake Channel
Starts / Ends
Philipsburg / Philipsburg
Activities
Local Market Visits
Activity Level
Variable
Experience an 11-day Caribbean sailing itinerary from and to Philipsburg, St. Maarten aboard Sea Cloud II. Visit St. Lucia, Martinique, Îles des Saintes, St. Barths, and the British Virgin Islands, with time at sea focused on hands-on sailing and relaxed days ashore.
Cruise Details
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Visit Las Palmas’ Santa Ana Cathedral, a central landmark in the city
from $13,695
EBD 30%
EXPLORE

Dream Of A Lifetime. Atlantic Crossing

Las Palmas to Philipsburg - 17 Day Itinerary aboard Sea Cloud Spirit
  • Experience Transatlantic Crossing
  • See the Gran Canaria landscapes
  • Explore Las Palmas old town
  • Climb rigging and set sails
Starts / Ends
Las Palmas / Philipsburg
Activities
Small Ship Sailing, Village Visits
Activity Level
Variable
Experience 17 days aboard Sea Cloud Spirit on a transatlantic crossing from Las Palmas to Philipsburg. Relax on deck, enjoy wellness programs, and explore Gran Canaria’s landscapes before arriving in the Caribbean.
Cruise Details
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