When is Yachting Season in the Caribbean?

Busy harbor in St. Thomas, Virgin Islands, Caribbean, When is Yachting Season in the Caribbean?

Yachting seasons are divided into winter and summer. Generally, yachtsmen and women will travel to the Mediterranean in the summer time, while winter season is reserved for the Caribbean. This has a lot to do with the weather, and the ideal times to take a yachting vacation.

Image caption: Busy harbor in St. Thomas, Virgin Islands, Caribbean

Yachting in the Winter Season

Luxury yachts and boats in the marina of Marigot, St Martin, Caribbean.
Luxury yachts and boats in the marina of Marigot, St Martin, Caribbean.

Because of the agility and flexibility that owning a yacht affords an owner, traveling to various parts of the world is simply easier. Yacht owners know that the best time to travel to the Caribbean is in the winter, when the weather is best in the islands.

“Generally, the winter season in the Caribbean begins in December and ends in late April/early May. The timing of the winter Caribbean yachting season corresponds with hurricane season, as yachts do not want to be around during that time.”

There are of course, hurricane holes in the Caribbean where you can escape hurricanes, but insurance prices will skyrocket during that time, and so often, owners will leave the Caribbean for better climes.

Yachting Season in the Caribbean Islands

Yachts on the island of Saint Martin in the Caribbean
Yachts on the island of Saint Martin in the Caribbean

Yacht owners love to visit the Caribbean, as the culture is vibrant, and rich with history. Known to thrive with festivals and carnivals, visitors can relish in the local street dances and cuisine. There are various islands in the Caribbean that you will want to visit with your yacht; here are the main areas that yachtsmen and women flock to during the popular winter season.

Yachting Season in The British Virgin Islands: Sea, Mountains, and More

The BVIs include Tortola, Jost Van Dyke, Virgin Gorda, and many more islands; these islands are the northern most islands in the Caribbean where you can take your yacht.

“Get pampered by your yacht crew while you soak in the sun on one of the many anchorages where you can take in the stunning mountainous views. Because of their prime location, it’s convenient to fly in and meet your yacht and its crew from the United States.”

The BVIs offer 20 picturesque islands that yacht captains are most familiar with. Work with the yacht captain to form the ideal yachting itinerary where you can island hop and enjoy the many picture-perfect beaches, visit the islands and enjoy their local fare. There are many marinas looking to welcome you to the islands and care for your motor yacht or sailboat while you take a break and enjoy life ashore for a couple of days.

Be sure to visit Cane Garden Bay, Dolphin Discovery, and Smuggler’s Cove. Dive underwater with friends and family and get up close and personal with reefs and marine life where you will be amazed at all the different species. You may want to seek out The Bight on Norman Island, where you can snorkel with parrotfish, sea fans, sponges, and much more.

Stop at the capital of the BVIs in Road Town, Tortola where some of the action is. The town is abuzz with activity and is home to a wonderful collection of spices. Its dramatic landscape also offers peaceful beaches. Be sure to take your camera to Sage Mountain national park and take in the scenery.

Yachting Season in The United States Virgin Islands: Charter a Yacht and Live Life to the Fullest

The USVIs are made up of St. Thomas, St. John, and St. Croix, each one offering its unique gifts to the visiting yachtsmen and women that gather to its shores every winter. Since St. Thomas has an international airport, it’s by far the most popular of the USVIs. Most yacht charters will begin here for ease of access. Whether your ideal holiday includes excitement and adventure or peace and tranquility, you will find it here.

St. John

St. John is the smallest island of the three. It has been intentionally preserved and distinguished as a natural treasure in which the locals take great pride. Enjoying the fare on St. John can either be casual or high-end, as both types of cuisine are offered here. Two-thirds of St. John is actually considered a national park. If you are into tourism and want to explore some of the island, visit the Battery, a fort from 1735. For hikers, Annaberg Trail is not to be missed. If you need a break, stop at the many restaurants and bars that make up Coral Bay, a popular hang-out for boaters and visitors alike.

St. Croix

St. Croix is the largest of the three islands, and welcomes both adventurers and those seeking a tranquil escape. This island is an eco-tourism dream. There is a special mooring system kept to protect underwater life, which goes to show how much preservation means here. Locals are highly supportive of recycling on the island, and offer handmade items at its local shops. There are also solar-powered lodgings as well as farm stays that encourage natural activities such as hiking, horse-back riding, snorkeling, kayaking, and of course, scuba diving. The beaches of St. Croix offer crystal-clear waters and soft sand beaches. Cramer’s Park beach on the east end offers a festive environment. You will also find Tamarind Beach and Shoys Beachin this area; be sure to bring a snorkel to discover underwater life.

St. Thomas

St. Thomas, the most lively of the islands, is where most yachtsmen and women visit when coming to the USVIs. In 1917, the US purchased St. Thomas when it was a base for pirates. It’s now the heart of luxury yacht charters in the area. St. Thomas offers secluded beaches and lush greenery and is a word-wide renowned destination from visitors all over the world. They come to enjoy the beaches, shopping, restaurants and more. Voted one of the most beautiful beaches in the world by National Geographic is Magens Bay Beach – one you won’t want to miss while visiting St. Thomas. Take in the sweeping views at Drake’s Seat, and bring your camera so you can reminisce at a later time.

Yachting Season in The Leeward Islands

Located in the center of the Caribbean island chain are the Leeward islands. The main airports are located in St. Maarten and Antigua. In this chain of islands, you will find influences of the Dutch, English and French everywhere you look. In fact, St. Maarten is divided into two sides- the Dutch side, and the French side so you can get exposed to two major cultures when on island.

St. Barts

For glitz and glamour, you will want to visit St. Barts, which is a must-stop for many luxury yacht charters. The island itself is small, as is its main harbor town, Gustavia, which is less than 10 square miles in size. Since the terrain in St. Barts is rugged, many get around island with an ATV or a Jeep unless you remain in Gustavia. The port town is a “see and be seen” of superyachts, and is where the famous St. Barths Bucket regatta takes place from. By far the busiest time of year in St. Barts is Christmas and New Year’s where celebrations abound. Book your stay early if you intend to visit during this bustling time.

St. Maarten

St. Maarten is just 17 nautical miles away from St. Barts, which is where many choose as their yachting destination in the central Caribbean. The island is known for its buoyant and entertaining vibe, especially on the Dutch side, where casinos and nightlife are abundant. The French side is known for its cuisine, where the fare is French and the language is, too.


Antigua is rich with history and UNESCO World Heritage sites, as well as several preserved military fortifications. Shirley Heights is among one of these, as is Nelson’s Dockyard in English Harbor. Falmouth Harbor is well-known among the yacht set, and is where you will find many superyachts docked. For watersports, be sure to visit Nonsuch Bay, and to enjoy a nice long walk, take a trip to nearby Green Island.

Yachting Season in The Grenadines

Also called the Windward islands, the Grenadines are less developed than other Caribbean islands and the locals live on their own time, which is what is so special about these islands.

“You can relish in the rainforests here, as well as its beaches and reefs. There is countless opportunity for SCUBA diving and hiking, as well plenty of other exciting activities.”

The southern coast of St. Vincent, one of the islands in the Grenadines is filled with stunning anchorages, restaurants, and hotels. Situated between St Lucia and Grenanda, the Grenadines are famous for their black sand beaches due to the surrounding semi-submerged volcanic mountains. Popular islands in this region include St. Vincent, Bequia, Canouan, Mustique, and more.

St. Vincent

St. Vincent is filled with rugged beauty, and offers a popular airport so you can start your yacht charter from here. Next stop is Bequia, which is only accessible by boat; enjoy the local shops of Admiralty Bay, and for stunning view of the Grenadines, take a ride up to The Old Fort Hotel. Visit the Maritime Museum here, and watch local craftsmen working on small boat building. Seek out Port Elizabeth for beaches, bars and restaurants.

Tobago Cays

Tobago Cays is a must-stop for excellent diving and is within easy cruising distance of other islands on your Grenadines yacht charter vacation. This impressive group of uninhabited cays offers secluded anchorages among stunning reefs. Superior snorkeling, diving, windsurfing and kayaking flourish in this area. Take out the water toys and simply enjoy what the ocean has to offer here. See the green turtles, reefs, and all types of fish.

Escaping to the Caribbean in the winter yachting season has so much to offer visitors.

“Relish in the local cuisine, take in the spectacular views and seclude yourself among marine life. Take the time to get to know some of the local culture, which is deep rooted in the histories of each island. Enjoy what yachting truly is – an escape from the world and into another, where you are well-looked after by your crew and captain who will assure you have a memorable time.”

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