“You Make the Memories, We’ll Make the Arrangements”
Caribbean sailing vacations

The Caribbean is known to be one of the best spots for sailing vacations. Due to its outstanding natural beauty, it is among the most popular tourist attractions. Therefore, you must determine a schedule to get the best out of your 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
Scuba  Scuba Diving On Board
$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 sailing 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’s considered the “High Season,” so please keep this in mind and consider booking early.

This is also the prime time when travelers from around the world rush to the location and enjoy a lovely Caribbean vacation. During these months, the temperature is mild, with calmer 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, you can also expect numerous people to visit since everyone’s escaping the harsh winters and looking to relax amidst the warmth of the Caribbean Sea.

January and February are great times for a 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 vacation.

The Rainy Season

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 beaches are spectacular. Many yachts will leave the British and US Virgin Islands at the end of July to head south to the Grenadines for the hurricane season. If you wish to enjoy a long-distance charter visiting many islands, it’s an excellent opportunity.

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 catamarans, and has beautiful weather.

August and September tend to be very 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.

It will depend 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. There are many different Caribbean destinations for sailing trips. 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.

Looking for something right now in 2023? Let us know what you’re looking for.

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