Sailing Caribbean Islands

catamaran in the Caribbean Islands. Sailing Caribbean Islands

Whether you are an experienced sailor or a novice looking for an unforgettable adventure, the Caribbean offers plenty of sailing opportunities. If you’re eager to embark on a sailing escapade in this tropical paradise, we have a wide selection of boats and yachts for sale and charter in Florida and the Caribbean. 

Best Places to sail in the Caribbean 

When it comes to the best places to sail in the Caribbean and surrounding areas, everyone has their favorites. It depends on how you want to spend your trip, your interests and what you want to see.   


Known as the “Gateway to the Caribbean,” Florida offers excellent sailing opportunities with its convenient proximity to the islands. From Miami to Fort Lauderdale to West Palm Beach, the Sunshine State boasts world-class marinas and a vibrant sailing community.

You can find exceptional boats and yachts for sale in Florida through our comprehensive listings:

1. Miami   
2. Fort Lauderdale   
3. West Palm Beach 

Caribbean Islands

The Caribbean archipelago comprises a myriad of sailing destinations. From the Dominican Republic’s pristine beaches to Saint Lucia’s dramatic volcanic landscapes, each island possesses its own unique charm.

We have an extensive range of boats and yachts for sale in the Caribbean in the following areas:  

  1. Dominican Republic 
  2. Saint Lucia 
  3. Antigua and Barbuda 
  4. Bahamas 
  5. Trinidad and Tobago 
  6. Grenada 
  7. Barbados 
  8. Sint Maarten/Saint Martin 
  9. Haiti

Best Sailing trips in the Caribbean

When it comes to the best sailing trips in the Caribbean, it again depends on the type of vacation you want and the journey you want to enjoy. However, some trips are always popular, including: 

  • Caribbean and Atlantic – Experience ultimate luxury by chartering a yacht to explore the Caribbean and Atlantic. Discover hidden coves, delectable cuisine and vibrant marine life. We offer yacht charter services in Florida and the Keys, allowing you to embark on a mesmerizing journey. 
  • Windward Islands – Set sail to the Windward Islands, a chain of picturesque islands in the southeastern Caribbean. From the lush rainforests of Dominica to the allure of St. Barts, this sailing trip promises breathtaking beauty at every turn. Explore our Windward Islands yacht charter options

Best sailing destinations in the Caribbean 

Some trips aren’t just about sailing, they’re about the destination too. Part of the beauty of a sailing trip is that you can travel flexibly, create a vacation that’s exactly what you’re looking for and explore beautiful destinations such as: 

  • Virgin Islands – Discover paradise in the Virgin Islands, known for pristine beaches and coral reefs. Explore the enchanting underwater world. We provide yacht charter services in the Virgin Islands
  • Jamaica – Immerse yourself in the vibrant culture of Jamaica while sailing along its stunning coastline. Explore hidden coves, visit world-famous attractions, and savor the local cuisine. We offer yacht charters in Jamaica for an unforgettable experience.  

Where to sail in the Caribbean 

If sailing is your priority on your trip, and you want to spend as many hours on the water as possible, then there are some areas of the Caribbean that are better suited to all-day sailing, such as:  

Whether you’re looking to buy or charter a yacht, our extensive listings and professional services ensure that you’ll find the perfect vessel for your journey. Explore our yacht search feature or discover more about charter options in the Caribbean.  

Read our Caribbean Islands Boating & Yachting Guide to find out more.

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