Cruising in the Caribbean: Everything You Need To Know
Find out how sailors can enjoy the best of the Caribbean both off-the-beaten path and better-known sailing hotspots.
May 9, 2025
Sailors are drawn to the Caribbean for its calm cruising conditions, making it an incredible cruising ground to brush up your seafaring skills. While the tropical islands are grouped closely together, they provide distinct cultural differences. Each island has a nuanced fusion of nationalities, spices, and customs. Many of the unique and remote locations are only accessible by boat.
Since the Caribbean's water conditions are largely predictable during the winter season, with calm waters and stable winds, island-hopping holds constant appeal with less experienced sailors as well as more seasoned helmsmen. If you are new to sailing, be mindful that no coast guards or sea tows will be available to bail you out and haul-out services are close to non-existent.
Cruising couples often charter out a boat in winter for a dose of winter sun and enjoy it so much that they end up selling their homes in exchange for an adventurous liveaboard life. Read about Family Cruising: Meet the Montague's Navigating The World And Raising A Newborn
Explore the tropical islands via folding bikes, SUPs, canoes, and hiking trails, and enjoy soaking up the scenery filled with an array of biodiverse wildlife.
Above: Sailing to remote anchorages in Southern Panama. Image via The Camerons.
Nelson’s Dockyard: The Most Historic Harbor in the Caribbean
Nelson’s Dockyard at English Harbour where Admiral Horatio Nelson lived in the 1780s is where cruising sailors dock. There are 30 stern-to berths, along with modern services such as shore power, internet and TV cable hookups.
Popular Bareboat Charter Destinations In The Caribbean
Antigua, Anegada, Anguilla, St Barts, Bequia, Carriacou, Tobago, British Virgin Islands, St. Martin, Barbuda, Grenada, St. Lucia, Dominica and Puerto Rico are the best-known cruising islands among the sailing community.
Many sailors chose to begin their journey at the Virgin Islands in the northern Caribbean. Due to the close proximity of the islands, you have flexibility over your schedule and can decide where you want to drop anchor on the day. Ports of entry include Road Harbour and West End Harbour on Tortola; Gun Creek in North Sound on Virgin Gorda; Great Harbour on Jost Van Dyke and Thomas Bay on Virgin Gorda. From here, sailors descend down south to the reef-lined Grenadines.
St. Barths
St Barts marina. Image via Zuzana Prochazka.
The glitziest of the Caribbean islands St.Barths attracts a well-heeled crowd. It gets busy during tourist season, therefore you may want to visit early in the season to avoid overcrowding and queues. Beths at the moorings have limited availability, and you may need to drop anchor a little further offshore and use a tender, or even swim ashore. Inland, there are hikes and trail paths marked up between rock formations. Pack a pair of binoculars and camera and be careful to keep them dry as you trail through the sprawling wilderness, ascending ladders and wading through turquoise grotto pools in rock cavities. For lunch with a view, walk up to the top of the Baths Bar where there are phenomenal 360-degree views of the BVI, as well as live entertainment.
Off-The-Beaten Path: The Windward Islands
Boats in the Windwards are less common, and the cruising grounds here provide a quieter and more serene sailing experience. The islands are vast, many of them shaped by sprawling rainforests, rugged mountains with volcanic-tipped peaks, and coral reef-rich waters. There is less tourism trade and while it's less developed and modern conveniences are harder to come by, you will find real locals living a simple lifestyle, similar to that of a bygone era.
Guadeloupe is a string of islands, part of the French territory in the southern Caribbean Sea. Seas near the Hilly Grande-Terre Island provide consistent trade winds between 10 and 20 knots which make for great sailing conditions. Ashore you will find long pristine beaches and sugarcane fields.
On Basse-Terre Island, you can find the Parc National de la Guadeloupe Carbet Falls and the volcano La Grande Soufrière. Smaller, thumb-sized islands include Marie-Galante and La Désirade.
Pigeon Island, on the west coast of Guadeloupe, has offers a wide range of dive boats for charter, especially during the prime months of December through to May. Sailors should keep a watchful eye out for scuba flags and divers in the water.
Terre-de-Haute, a small island with the look and feel of a quaint French village, is well worth visiting. Zip from boat to dinghy and enjoy a drink in an intimate French-style café, then hike to old French forts steeped in history. Many inhabitants still wear traditional Creole dress on the quieter, nearby islands of Les Saintes, Marie Galante. Here, there is a fusion of African, European, and East Indian cultures and cuisine.
Culebra: The Spanish Virgin Islands
Above: Culebra beach. Image via Zuzana Prochazka.
If your idea of bliss is on a beach with nobody around except a few fishermen bobbing on ramshackle boats and a trail of sandy footprints, then you will enjoy the quiet life in Culebra. Part of the Virgin Islands, midway between St Thomas and Puerto Rico, Culebra is the perfect place to unwind. There are no major hotels, drawing a more intrepid crowd. Anchorages are quiet and the mooring balls are free to use as you please.
The vibrant rainbow-hued pop-up shacks in Culebra Town serve Puerto Rican street food and cerveza. “La Isla Bonita” is what locals call Culebra, one of the two central Spanish Virgin Islands.
Bahia Tortuga is a stunning porcelain-white sandy beach near Culebrita, visited mainly by cruising crowds. Here, you can hike to the tumbledown lighthouse or snorkel with Tortuga turtles in the azure shallows near the appropriately named Tortuga Beach.
Buying Or Chartering A New or Used Boat
The most popular vessels to charter in the Caribbean are catamarans. If you appreciate nautical heritage and are happy to charter a crew-manned yacht, you can charter a classic sailing boat such as a schooner or a sloop and experience what the Caribbean was like in days gone by. If you want to charter a boat in the Caribbean, or are considering buying a boat to ship down from the U.S. here are some of the most popular boat builders best-suited to the temperate climates; Leopard, Lagoon, Leopard, Fountaine Pajot, Sunreef, and Outremer.
Bear in mindful that if you decide to charter a boat that you will be taxed on the book value of the boat.
To find out more about sailboats read a guide to the Different Types of Sailboats on our sister site YachtWorld.
Read our popular Q&A’s to find out everything you need to know about cruising in the Caribbean:
What Month Is Hurricane Season In The Caribbean?
The hurricane season for the Atlantic Basin (the Atlantic Ocean, Caribbean Sea and Gulf of Mexico) is from the beginning of June until the end of November.
How Long Does To take To Sail Around the Caribbean?
Most cruisers plan an itinerary from as little as one or two weeks.
When Is The Best Month To Cruise The Caribbean?
In general, from December through April is the best time of year because the weather is fair and the sea conditions are calm.
How Can Cruising Families Help Their Kids To Connect With Other Kids?
There are loads of cruising kid boats around with whom to connect. Family cruisers tend to be open-minded and friendly people. If you are on a long cruise and want to prevent your children from becoming isolated or bored lots of families organize daily meet-ups.
- Join Kids4Sail is a wonderful support and community group available on Facebook with over 7.6K members on their database.
- Join WhatsApp groups that connect cruising kid boats up with other families.
- If you are intending to do a long passage with children, Kindles are great for kids to read and require less storage space. Audible books are a good idea for nightime when the light is low.
If you are interested in family cruising you might enjoy Family Cruising: Meet the Montague's Navigating The World and Raising a Newborn.
Where Are The Best Destinations for Cruising Families To Meet?
Georgetown, Bahamas is a children's favorite because there are so many kids. The beaches and sandbars of the Bahamas’ Exuma Cays provided plenty of places for kids to explore. Most people meet in cruising hubs such as Grenada, St Anne Martinique, and St Martin.
Le Phare Bleu, Grenada is known as the family marina, and at Halloween lots of families gather and connect here and stay within close proximity for the rest of the sailing season.
Why Are Catamarans Popular In The Caribbean?
Catamarans' shallow drafts allow greater access to shallower waters, small coves, and secluded hideaways without grounding or damaging coral reefs, ideal for cruising tropical waters. Also, the catamaran’s two-hull structure and wide beam allow for a smooth sailing experience, with minimal rocking — a huge benefit for anybody who suffers from seasickness.
Catamarans have a broader deck space compared with their monohull counterparts, which since they sit above the waterline tend to be larger, brighter and more airy.
Shop for new and used catamaran boats for sale.
Dining Aboard A Boat In The Caribbean
Boat ovens can get overheated and cooking food evenly can be a challenge. Barbecues are a great way of enjoying the great outdoors while soaking up the sun-kissed views. You can source fresh local ingredients from the larger islands and cooking on a boat is a great way to try different local fresh fruits, vegetables, and fish. Some of the smaller islands do not cater to tourists, therefore you need to make sure that you are stocked up with dry food.
Read more about liveaboard life in the Caribbean on our sister site Buying A Liveaboard Sailing Yacht: A Rollercoaster Journey
