Our top Caribbean islands for sailing 

07th Jul 2020

We’ve shared our top Caribbean islands for sailing and these islands offer amazing cruising grounds within their borders, so you can plan a fun-packed, exciting itinerary.

Our top Caribbean islands for sailing are bursting with history, coral reefs for snorkeling, hikes ashore, beaches perfect for quiet strolls and swimming and an exciting food scene. There’s just no need to cross any borders when there is this much to entertain you locally. 

For the foodies, we’ve taken a look at where to eat in the Caribbean. Many restaurants are ready to welcome you and waiting to serve mouth-watering Caribbean flavors to accompany your vacation. From tacos at relaxed beach bars to fine-dining restaurants, we’ve got the lowdown on who is open to enhance your Caribbean sailing experience*. 

US Virgin Islands 

You can sail freely between our base at Compass Point Marina and St. Thomas, St. John, St. Croix and Water Island in the US Virgin Islands. St. John has one of the most beautiful shorelines in the Caribbean and you’ll be spoilt for choice when planning your itinerary. Read our guide to the best beaches in the US Virgin Islands.

Where to eat in the US Virgin Islands

  • Lime Out,  Coral Bay, St. John – Satisfy your taco desires at this floating restaurant with boat pick up service or delivery to Coral Bay dock available. For opening hours, call +1.340.643.5333 or check them out on Instagram
  • Heidi’s Honeymoon Grill, Water Island – Serving pulled pork sandwiches, burgers, dogs and tacos. Open 10am-3pm. Call +1 340-690-0325 or check out their Facebook
  • Dinghy’s Beach Bar & Grill, Water Island – Sip a cold drink in a hammock or try the blackened shrimp wrap or jerk chicken. Call +1 340-227-5525 or check out their Facebook for opening hours
  • Pizza Pi, Great St. James – Delicious NY-style pizza from a floating restaurant. Opening hours vary so check their Instagram or call 340-643-4674 / VHF 16.


You can sail freely between our base at Palm Cay Marina, Nassau, and the outstanding islands within the Exumas. Public beaches and parks are open, so you can meet the iguanas and the famous swimming pigs, or explore all the wonderful cays in the Exuma chain. We’ve got everything you need to know about sailing the Exumas.

Where to eat in the Bahamas

  • Graycliff, Nassau – When thinking of where to eat in the Caribbean, this is a legendary restaurant with a jaw-dropping wine cellar and fine dining. Call ahead for their opening hours or check out their Instagram
  • Palm Cay Club House, Nassau – White sand beaches, 80ft lap pool make the perfect setting for a bite to eat and a cool drink
  •  Latitudes Restaurant, Nassau Harbour Club – Head here for waterfront dining, serving sushi, ramen, grill and pizza. Check Instagram for opening hours
  • Staniel Cay Yacht Club Plenty of dining space outside so you can watch the sunset and the Goombay Smash is recommended. Box picnics available, as well as lobster, conch, sandwiches and burgers
  • Highbourne Cay Marina – This Exumas restaurant offers waterfront and sunset views, as well as a tasty menu with local seafood, including lobster tails and mahi mahi. Reservations required for dinner

Flights to Nassau include Southwest Airlines from Baltimore and JetBlue Airways from New York and Fort Lauderdale.


With a beach for every day of the year, you won’t struggle to find remote spot in Antigua to relax without crowds. Antigua is a firm favorite among the Dream Yacht Charter team when it comes to Caribbean islands for sailing. If you love history you can trace the footsteps of Nelson and the battles that took place. Or you can sail over to Barbuda, where you’ll see some of the loveliest stretches of sandy beach in the world. Read our guide to five vacation ideas in Antigua.

Where to eat in Antigua

  • Sheer Rocks, Cocobay Resort, St Mary’s – Treat yourself to tapas or the tasting menu in a stunning location. Awarded the Caribbean Journal’s best Caribbean restaurant 2020. Open now for lunch and dinner, Wednesday through Sunday. Check out their Instagram
  • Melini’s, Jolly Harbour Marina – Open for takeout lunch and dinner Tuesday through Saturday, 2pm-8pm. See their Facebook for the menu
  • Dennis Beach Bar and Restaurant, St Mary’s – Order lobster, shrimp or catch of the day with a Caribbean twist while on the beach
  • The Crow’s Nest, Jolly Harbour – Takeaway Italian baked goodies and restaurant dining available. Check their Facebook for details
  • Miracles Caribbean Restaurant and Bar – Call in advance to reserve a table to enjoy lobster pasta and much more. Check their Facebook for updates


Martinique offers plenty for a relaxing vacation sailing around the island with so much to see and do. Discover the white sandy beaches in the south and volcanic black sand in the north. Pack your snorkel to explore the amazing coral reefs, such as at Anse d’Arlet, or visit Les Gorges de la Falaise waterfalls. Finish up with some retail therapy in Fort-de-France.

Where to eat in Martinique

  • Zanzibar, Le Marin – Enjoy authentic modern cuisine with a sea view, close to our base. Open for lunch and dinner, Tuesday through Sunday noon.
  • Le Petibonum, Martinique – Head to this beach bar for access to a private beach and a menu full of tasty homemade delights and rum cocktails. Take a look at their Facebook for more information
  • Le Zandoli, Martinique – Found within La Suite Villa hotel, this restaurant is offering a sophisticated, refined menu under Chef Florent Boucher and Nicolas Magie. Open for lunch and dinner from Wednesday through Saturday and Sunday noon. Follow their Instagram for updates
  • Le Bolibar, Martinique Enjoy the 360º panoramic views on the terrace and the bistro menu. Follow their Facebook for details


This spectacular cruising ground is home to Les Saintes archipelago, which is one of the reasons why this is one of the top Caribbean islands for sailing. This region is also a marine life paradise with Pigeon Island’s Jacques Cousteau’s marine reserve and awesome snorkeling at Marie Galante. Take a look at our itinerary for the perfect week of cruising in Guadeloupe.

Where to eat in Guadeloupe

  • Ti Kaz’la, Les Saintes Bay, Terre de Haut – This classy restaurant is directly on the beach in Les Saintes Bay. It offers the best view in the area and really good food. Make a reservation in advance
  • Chez Henri, Marie-Galante – Enjoy a typical local beach bar/restaurant experience where you can enjoy rums of the island and local food at a reasonable price. Book ahead of your visit
  • Zoo Rock Café, Marina du Gosier, Le Gosier – Near our base is a real hub in the sailing community, where sailors and locals meet. Dine on BBQ specials in the garden, dance on the dancefloor or relax with a cold drink
  • Le Zagaya, Saint François – Known for really good fresh food with seafood coming directly off the fishing boats

St. Martin

Vacation in St. Martin for some of the best snorkeling in the Caribbean and the chance to visit the islands of Tintamarre, Pinel Island and many anchorages only accessible by boat (our base can advise). Don’t miss the local reefs and beaches, before setting sail over to island of billionaires, St. Barths – there’s just so much to see within this cruising ground. Read our guide to the top things to do in St. Barths.

Where to eat in St. Martin & St. Barths

  • Le Tamarin, St Barths – Mediterranean and French flavors with an Asian twist will enthrall foodies in a lush garden setting. Open from 6pm Tuesday-Sunday. Check out their Instagram
  • Le Cottage, St Martin – If you are looking for where to eat in the Caribbean that offers a warm welcome and great service then look no further. This is the place for beautiful presentation and authentic flavors. Take a look their Facebook for updates
  • Quarter Kitchen and Cocktail Lab, St Barths – Choose from an Asian-fusion menu, sit back and enjoy culinary expertise. For more information, check their Facebook
  • Le Telegraphe, St. Martin –  Book ahead for lunch or dinner and experience a welcoming atmosphere where foodies gather. Open every day except Wednesdays. Their Facebook has the latest information 

Find out more

If you are researching the top Caribbean islands for sailing, we’ve got some ideas for you. You can charter bareboat and sail yourself, or hire a skipper to sail the boat for you. For a luxurious sail, choose an all-inclusive crewed yacht for complete ease and relaxation on your cruise through paradise. We offer by the cabin charters in the Exumas, Martinique, St. Martin and Guadeloupe. Learn more about planning your perfect vacation of a lifetime on our blog.

*Restrictions and opening hours are subject to change at short notice and we are not responsible.