This is the peak travel period, so book early to secure your yacht.
Unique Activities:
Enjoy outdoor adventures and island festivities.
Annual Carnivals occur on some islands, such as St. Thomas, where Carnival runs from mid-April to early May. You can enjoy parades, concerts, and cultural events.
Therefore, NOW is the best time to contact us regarding your Caribbean sailing family vacation.
The Rainy Season | Best Time for Caribbean Sailing Vacations
If you are on a smaller budget and are looking to plan a trip, you can visit between June and November. The weather is still beautiful, and the snorkeling and the white sand beaches are spectacular.
August and September tend to be too hot with the usual rain showers. For some travelers, rain can be a refreshing experience helping to keep you cool. Dancing in the rain can be fun like singing and snorkeling to explore the marine life.
The Shoulder Season | May-June & September-October
A Caribbean sailing vacation before or after peak season offers lower prices and a more intimate yachting experience. While the islands are warm year-round, this season tends to be more humid, making it ideal for exploring historical sites, like museums.
Sailing catamaran with water toys
Water Sports and Nature:
Enjoy water sports in Jumby Bay, Antigua, or marvel at the island’s natural beauty without the peak season crowds.
Weather and Pricing:
Take advantage of good weather and lower prices at sailing resorts Caribbean.
Expect occasional rain showers in May, though the chance of hurricanes remains low during the shoulder season.
The Low Season | May to November
Affordable Rentals: The low season offers more affordable boat rental rates, allowing you to stretch your budget and extend your trip.
Peaceful Atmosphere: From May to October, enjoy quieter waters, warm beaches, and fewer boats crowding the Caribbean.
Local Connection: With fewer tourists around, you’ll have more opportunities to connect with locals and enjoy the relaxed island lifestyle.
Limited Activities: This period isn’t ideal for shopping and restaurant hopping, as many establishments operate on reduced schedules.
Weather Considerations: While the hurricane season (June to November) can bring rough weather, most charters are equipped to handle storms, ensuring safety during your adventure.
Caribbean Sailing Vacations With BVI SAIL
It depends on your schedule and preference when you visit the Caribbean on a yacht charter vacation.
Depending on what time of the year you are currently viewing this page. Possibly the live WebCam below will give you a good indication of the weather. Regardless it’s nice to see a beautiful “live” view from a hilltop on the gorgeous USVI Island of St. John.
*Tip: Check this live Cam sometime in the evening as the sun sets; you won’t regret it!
The Leeward Islands of The British Virgin Islands, U.S. Virgin Islands, St Martin, Anguilla, Antigua, and Montserrat. Set sail to your ideal Caribbean islands of choice, and get ready to have that rum punch in hand. Or an excellent Carib Beer.
On the other hand, Virgin Gorda has fewer crowds and perfect weather during high season. Hence, worth adding to your family catamaran vacations.
Looking for something right now in 2024? Let us know what you’re looking for.
FAQ about Caribbean Sailing Vacations
What should I pack for a sailing trip?
Duffel bags are ideal for sailing trips. You should pack light including breathable outfits, non-slip shoes, and swimsuits. Also, bring travel documents and personal medications.
How to choose the right yacht?
Pick a catamaran, sailing yacht, or motor yacht based on your needs. Also, think about the activities you want to do on and off the boat. Then, let our charter brokers help you find the perfect match.
Client Reviews
Xandros
Cam, Jada & Sam, You all are truly first-class in all regards. Xandros and her special crew are incredible memories for this family. From pet barracuda, scuba life saves, map briefs, seabob excessive use, endless laughs, chess tournaments that never end, food menus that constantly amaze, this is the trip for the record books. Hope to run into you all again soon, if only someday in an airport.
Mahasattva
Captain Ryan, Chef Glen and Jessica You are absolutely INCREDIBLE human beings! We felt so safe, so well cared for, so full of joy onboard the beautiful Mahasattva! We cannot thank you enough for this once in a lifetime experience.
You created unreal, magical experiences for us and for our children. Fishing, e-foiling, scuba diving, exploring the baths, the caves and beaches. This trip has surpassed our wildest imagination and we TRULY cannot thank you enough.
Scuba Diving On Board
