Explore the best of sailing in the Caribbean

The quintessential destination for a yacht charter, the Caribbean is what often comes to mind when people think of sailing. It is no wonder, given the excellent conditions for this area’s cruising grounds which are home to some of the world’s most stunning beaches and secluded shores. Enjoy all this and more when you book a boat holiday in the Caribbean with Zizoo.

  • Islands of Antigua, the Bahamas and B.V.I.
  • Smooth sailing and picturesque beaches
  • Vibrant culture and entertainment
Quick Info

Martinique Aimé Césaire (FDF), Lynden Pindling (NAS), Beef Island Tortola (EIS)

Boat base locations
Martinique, Bahamas, Tortola, BVI

Wreck Diving, Watersports, Pristine Beaches

Best time to sail
December – May


Language spoken
English, French, Spanish, Dutch, Creole Languages

Things to do and see when sailing in the Caribbean

popular destinations for us travelers

Visit in the Caribbean:

  • Historical coastal towns to visit while sailing in the Caribbean:  Nassau in the Bahamas and Fort-de-France in Martinique.
  • The main attractions of the Caribbean are its beaches including those on Virgin Gorda in the BVI, where you’ll find a stunning national park surrounded by pristine beaches.
  • You could also make a stop in Eagle Beach in Aruba or Majors Bay in St Kitts.
  • For food lovers, Sugar Mill Restaurant in Montego Bay, Jamaica, is considered one of the country’s best, or enjoy fine dining at The Dove in Road Town, BVI.
  • Jamaica, the Bahamas and Antigua are well known for their vibrant nightlife. Check out the Ibiza Bahama Beach Club facing the water in Nassau, Bahamas, or Rush Night Club near Cedar Grove in Antigua while cruising the crystal waters during your Caribbean sailing holidays. 

The BVI has one of the world’s best wreck dives at the RMS Rhone off Salt Island:

  • Montego Bay is another excellent site for scuba diving in Jamaica, a sailor’s paradise among turquoise waters and white sandy shores.
  • The crystal clear waters are also inviting for snorkellers. You can request snorkeling equipment with your sailing booking with Zizoo to get a better look at the Caribbean’s tropical sea life while on your sailing holiday. 

Boats in the Caribbean

Rent a Sailboat in the Caribbean
Rent a Catamaran in the Caribbean
Rent a Motorboat in the Caribbean

Sailing conditions

The Caribbean covers a wide range of topographically diverse islands so it is worth noting that the islands offer slightly differing climates. On average, the Caribbean is blessed with ideal temperatures in the mid to upper 20’s. In some islands, like Martinique, expect air temperatures in the 30s and similar sea temperatures, with wave heights usually well under a meter.

Check individual destinations for information on the best times and any physical obstacles to be aware of while navigating these gorgeous sailing waters. Generally speaking, early morning sailing in the early part of the year will make for the calmest conditions. Remember, you can also book a skippered sailing holiday in the Caribbean with Zizoo. Find out if you need a skipper for your next trip. 

Average temperatures in the Caribbean (BVI)
Average temperatures in the Caribbean
Sailing Conditions
  • Conditions vary along this long island chain, from the calmer waters around the BVI to more energetic conditions in the south along the Windward Islands trail.
  • You can expect winds of 10 to 25 knots.
  • The Easterly Trade wind is the most prominent and consistent wind in the Caribbean which is strongest in December and January.
  • Consistent currents and trade winds around the BVI, for example, are calmer, usually well below 20 knots.
  • From June to November, the trade wind is often less predictable and stable making the winter months the best time to go on a sailing holiday in the Caribbean.
  • The months between December and May are also the driest months in the Caribbean. Learn more about winter sailing in the Caribbean in our guide.

Suggested sailing route

sailing bvi

There are several possible routes for your island hopping holiday in the Caribbean. Some sailors prefer to stick to their favourite locales, getting to know the waters and shores of certain island clusters. Others may prefer to discover new destinations and practice sailing in different conditions. Choose from a relaxed retreat on a luxury yacht or an island hopping adventure with friends. For those looking for the best nightlife, check out our list of the best party islands in the Caribbean.

The British Virgin Islands are popular with beginner sailors because of the ideal steady currents and wind speed. More experienced seafarers may enjoy sailing the Windward Islands. These take you from Martinique to Saint Lucia and on to Saint Vincent and Grenada.

Either way, choosing one base as a starting point is a good idea, and it allows you to begin planning how to fit in scuba diving and beach time between seeing all the varied sights on your trip. Major marinas that also offer anchorage include Port Saint Charles on Barbados, Fort-de-France on Martinique, and Rodney Bay on St Lucia. Many land-dwelling travelers visit the Caribbean to relax at its pristine beaches, and boat rental gives you the opportunity to see many more of them than the average visitor.

One of the most popular sailing routes in the BVI begins in Tortola and takes you to some of the Caribbean’s best beaches and incredible natural reserves. Discover the seven-day sailing route here.

Read helpful articles for your next sailing holiday