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Caribbean sailing vacations

The Caribbean is one of the best spots for sailing vacations. Because of its outstanding natural beauty, it is among the most popular tourist attractions. Therefore, you must determine a schedule to get the best time for Caribbean sailing vacations. Winter can be the best time for Caribbean Yacht Charters.

Recommended yachts for sailing the islands of the Caribbean.

$59,000 - $70,000 /wk
  • 4 Cabins
  • 65.00 Ft Cat
  • Built: 2021
Scuba  Scuba Diving On Board
$45,000 /wk
  • 3 Cabins
  • 64.00 Ft Cat
  • Built: 2021
$44,700 - $48,000 /wk
  • 4 Cabins
  • 62.00 Ft Cat
  • Built: 2018
Scuba  Scuba Diving On Board

What Is The Best Time To Go Sailing in the Caribbean Islands?

The Dry Season is one of the best times to charter a yacht for one of your Caribbean catamaran vacations.

The season runs between December and May. During this period, the weather is drier, sunny, and clear, which makes it suitable for sailing on most days.

However, you will pay a premium when chartering over Christmas and New Year’s. Also, it falls under the “High Season,” so please keep this in mind and consider booking early.

This is also the prime time when travelers rush to the location and enjoy a lovely Caribbean vacation. During these months, the temperature is mild, with calmer, crystal-clear waters during May. Furthermore, thanks to the dry season, you can expect great weather with unique outdoor activities. Some of the islands also have an annual Carnival.

In St. Thomas, Carnival starts from mid-April to the beginning of May. You can attend concerts, parades, and other events during this time.

During this season, many people come to visit, escaping the harsh winters. They can also relax in the warmth of the Caribbean Sea.

January and February are great for a family yacht charter vacation. The Christmas and New Year’s rush is over, and fewer boats are in the anchorages, especially in January. And there are more crewed catamarans available for charter. 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.

Many yachts will leave the British and US Virgin Islands at the end of July. They will head south to the Grenadines for the hurricane season. Indeed, an excellent way to enjoy a long-distance charter in the Caribbean.

The Best Time for Caribbean Sailing Vacations
Sailing catamaran with water toys

The Grenadines are an excellent yacht charter destination during the summer months. Less busy, has lots of choice crewed Caribbean catamaran charters, and has beautiful weather.

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 and after peak season escapes premium pricing for a more intimate yachting experience. Though the weather on the islands is warm year-round, during this season, it becomes more humid. Make it a great time to visit historical sites, such as museums.

Enjoy water sports in Jumby Bay, Antigua during summer. Or just cherish the island’s natural wonders without the peak season crowds.

Take benefit from the good weather by sailing resorts in the Caribbean at lower prices. However, expect for rain showers in May. Chances for hurricane to hit the Caribbean is low during the shoulder season.

The Low Season | May to November

Among the best times for Caribbean sailing vacations, the low season has more distinct advantages. Boat rentals tend to be lower during off-peak time, which allows you to maximize budget and trip duration.

Between May and October, you’ll appreciate cruising in the Caribbean with fewer boats and serene, warm beaches. With fewer tourists, grab the chance to meet the friendly locals and savor the island life unhurried. On the other hand, it’s not the best time for shopping and restaurant hopping.

Moreover, you might encounter rough weather, as the hurricane season runs from June to November. The good news is that most charters are well-equipped to deal with storms.

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!

We are here to assist you with a sailing yacht charter vacation in the Caribbean. Many different Caribbean destinations for sailing experiences. The Windward Islands, including St. Lucia, St Vincent, the Grenadines, and Grenada.

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.

Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.