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16-Day Leeward Islands Cruises & Trips

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Discover the best of Leeward Islands on one of these 3 recommended 16-day cruises. Explore Philipsburg, and St. Lucia where you will enjoy small ship cruises, small ship sailing, snorkeling, and village visits during the day as you sail port-to-port in your floating vacation home at night. We work with all of the top-rated small ships in Leeward Islands and can give you unbiased advice on which ship and itinerary best match your tastes and needs. Our cruises to Leeward Islands range from $2,330 to $18,220 for a 16-day itinerary. Contact one of Adventure Life's Leeward Islands cruise specialists for help deciding which itinerary is best for you and we'll assist you in planning every detail of your dream trip. 

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    • Leeward Islands
Colorful harbor of Bonaire

Philipsburg to Puntarenas

16 Day Itinerary aboard Sea Cloud Spirit
  • View a tropical paradise Grenada
  • Immerse in traditions and culture
  • Transit the famous Panama Canal
  • Explore spectacular Costa Rica
Starts/ Ends in:
Philipsburg / Quepos
Sailing Schooner, Small Ship Cruise, Snorkeling, Village Visit
Activity Level:
Fall in love with the crystal waters of the Caribbean, Panama and Costa Rica on this 16-day cruise aboard the Sea Cloud Spirit. Begin your exciting journey in Philipsburg, St. Maarten. Enjoy the tropical scenery of the best diving and snorkeling spots in the Carribean. Explore the colonial center …
Cruise Details
Visit vibrant Las Palmas

Westbound Atlantic Ocean

Las Palmas - St. Maarten - 16 Day Itinerary aboard Star Flyer
  • Explore Caldera de Bandama
  • Visit Las Palmas
  • Enjoy La Gomera
  • Experience Garajonay National Park
Starts/ Ends in:
Las Palmas / Philipsburg
Small Ship Cruise
Activity Level:
Set a course for the Atlantic Ocean.For those who value traveling in style and comfort, for romantic souls who want to experience the style and grace of the "good old days" but with all the modern conveniences, and for those who simply want to escape from the ordinary routine, nothing …
Cruise Details
Relax on the beaches of St. Maarten

Transatlantic: Praia - Philipsburg

16 Day Itinerary aboard Sea Cloud II
  • Visit endless field of sugarcane
  • Explore the island of Praia
  • Cross the Atlantic ocean
Starts/ Ends in:
Praia / Philipsburg
Sailing Schooner, Small Ship Cruise
Activity Level:
Sail around the Atlantic ocean as Sea Cloud II sail from the island on the Southwest coast Praia to Philipsburg, St Maarten. enjoying the beautiful beaches and exploring different shops and restaurants in the neighborhood.
Cruise Details
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