Sailing in the Caribbean

Explore the stunning islands of the Caribbean

It is every sailor’s dream to sail the Caribbean. Amongst the 5,000 and more islands, steady trade winds take you through cerulean blue waters, past coral reefs to sandy cays, sheltered coves, sun-soaked beaches and spectacularly stunning anchorages. With any luck, a pod of dolphins will join you at the bow, and, quite often, you’ll be the only boat there. Step ashore and find that no two islands are the same. Mountainous and volcanic; flat and sandy; quiet fishing villages and pulsing harbours full of colourful restaurants and bars. It’s an intoxicating mix.

Why sail here?

Every sailor dreams of sailing in the Caribbean – it is one of the most fabulous destinations, with Tortola often called the sailing capital of the world. Over 60 islands and cays, surrounded by clear, turquoise water and the rich, local laid back culture, make for a thrilling week. Or two. The climate is near perfect, with warm weather and cooling, steady trade winds, whilst the islands form a barrier to the Atlantic, resulting in calmer seas. Then of course, there’s the stunning scenery.

Each island is different from the next, with secluded coves and long paradisical beaches, and great stops along the way for sundowners at a tiny beach shack or a white linen restaurant. You can see one island from the next, giving you “line of sight” sailing and a choice of a short hop between each, or a long beat out on a steady breeze. Beneath the waves, the marine life is vibrant and colourful, promising spectacular snorkelling and diving. However you want to soak up island life, whether it’s on a monohull yacht or catamaran, we can assure you that nothing comes close to island hopping in these waters.

A day in the life

Before you set sail, your skipper will talk through what kind of sailing you’d like to do and agree your itinerary. The options in the Caribbean mean there’s something for every type of sailor and every kind of wishlist. On day one you might head for Cooper Island, where there’s a protected anchorage in Manchioneel Bay and a beach club facing west – perfect for a sundowner and not a bad way to end the day. Have an evening swim off the boat, or watch life sail by from the foredeck.

Start each day with a refreshing dip, or perhaps don a snorkel and marvel at the coral and abundant marine life. With luck you may see a turtle or two. Then once your crew has pulled up the anchor, let the crew hoist the sails and point to your next island for a day on the beach, or a hike up to the highest point for a view over the archipelago. You might stop for lunch on Scrub Island or overnight in a bay off Anegada. And how about taking the helm and sailing the boat yourself under the expert guidance of your skipper?

View a sample sailing itinerary

Food & Drink

It’s very easy to become accustomed to a week or two on a crewed yacht. The team know exactly where to source all the best ingredients, and sometimes even catch it on the go. Breakfast is laid out each morning for you, with bowlfuls of fresh fruit and juices and delicious, gourmet lunches magically appear whilst you’re out paddle boarding or enjoying a well-deserved rest on some idyllic beach! Depending where you are, the evening might involve dinner at a beach shack, to the sounds of live music or freshly grilled seafood onboard.

Many of the islands are well-known for certain local delicacies. Anegada is famous for its spiny lobster, and you’ll find it on many a menu. Mahi mahi is a staple, and when it’s coupled with some Caribbean spices, is delicious. And you’re likely to come across a Painkiller if you stop at any bar – cream of coconut, pineapple juice, nutmeg, and a healthy shot (or two) of rum!

Activities & Experiences

Depending on the type of boat you charter, there are a range of toys, and the experienced crew are on hand to set everything up for you. You can be as active as you like with a choice of kayaks to paddle boards and snorkelling equipment. The Caribbean has some fabulous snorkelling and diving – with coral atolls, abundant marine life and stunningly clear water. The protected bays and anchorages beckon you out on a paddle board, and of course, the miles upon miles of perfect beaches will keep you happy for days.

Some of the boats come equipped with waterskiing kit or a windsurf rig – a great afternoon pursuit before you set sail once more. There are plenty of places for some excellent kite and windsurfing. If you want to stretch your legs, each island has so much to explore – from the salt ponds of Anegada Island, full of flamingos, to visiting the geological wonder that is the giant boulders on Virgin Gorda, and their tidal pools and caves. Rent a bike, scooter or a Jeep and head inland to explore. On the east coast of Jost Van Dyke at Diamond Cay, try a natural jet bath at the “Bubbly Pool”. The Caribbean is the place to go deep sea fishing – so, in between islands, see if you can catch supper. And if you find that you’re not quite relaxed enough, then ask your skipper to head to the Floating Spa.

Our favourite spots

We’d happily sail in the Caribbean whenever we could – there’s so much water to sail, and so many islands to hop – it can be impossible to decide where to anchor! We love Virgin Gorda for its scenery and hiking – the island is full of trails and the views from the top are spectacular. The “Baths” – the enormous granite boulders – are a must-see too. Have dinner at Leverick Bay – Jumbies Beach Bar is a fun place to hang out, with live music and even a pirate show.

The very low-lying Anegada has some of the best beaches in the BVIs – head for Loblolly Bay or Cow Wreck Beach. It’s worth going for the names alone! And the beaches at Cane Island Bay on Tortola are also definitely made for spending some time on. They are beautiful. Norman Island is great for snorkelling, whilst Cooper Island is one of the most relaxed and charming you’ll find. And our favourite place for a sundowner is at the infamous Soggy Dollar Bar, where you probably shouldn’t order too many of the aforementioned Painkiller cocktails.

Example Yachts

Find out more about the yachts you could be sailing on:

A 5 Cabin Catamaran