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Sail and stay holidays in the Caribbean

Island hopping holidays

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Why choose a sail and stay holiday?

Have you ever dreamt of island-hopping in the Caribbean, setting sail and exploring tropical islands, weighing anchor in idyllic coves and beautiful bays full of vibrant culture? Your dreams may just have come true with Hayes and Jarvis’ amazing new partnership with The Moorings to provide you with a luxury sail and stay holiday on land and sea.

For the first time voyager with an interest in sailing you can be as involved as you want to be, or simply lie on the deck with a cocktail and let your experienced crew guide you from heavenly beach to colourful seaside town without a care in the world.

Captain's cocktails on a luxury catamaran

This could be the perfect honeymoon for newlyweds to celebrate their new lives together, while friends and families will enjoy cruising from bay to beach together, discovering history and culture, learning to snorkel and go fishing together and a variety of on-board water sport activities. Your luxury catamaran includes snorkelling gear and your skipper is sure to know the best spots to experience the underwater world. Then combine your cruise with a stay in the luxury resort of your choice to create an adventure you will never forget.

The catamarans are spacious and stylish, easily accommodating larger groups. Think ‘floating hotels’ with a qualified skipper and chef on board, allowing you to create your own sailing itinerary and daily menu while you sit back and enjoy life. Then, soak up Caribbean island life at a luxury resort to get your feet back on dry land. Here are two suggested itineraries to inspire you.

Sail Grenada and St Vincent and the Grenadines - stay in East Winds Hotel St Lucia.

What better way to explore the charming character, scenery and wildlife of Grenada and St Vincent and the Grenadines than on board a luxury catamaran.

You’ll be welcomed on board with a cocktail while your skipper prepares to set sail to Dragon Bay. Here, you’ll dive among moray eels, nursing sharks and turtles before exploring the Underwater Sculpture Park, a collection of statues depicting Grenadian life. Or simply ask your skipper to drop you ashore on powdery sands for sunbathing with your favourite book for company. It’s your holiday, so you choose.

From Dragon Bay you could head west to Sandy Island, venturing to the centre of this tropical paradise to discover its secluded freshwater pool shaded by swaying palms.

Paddleboarding and catamaran

Further along the coast is St George’s, the capital of Grenada. Be sure to tour the Belmond Estate, a cocoa and spice plantation where you can even make your own chocolate. Or stroll Grand Anse Beach, lined with charming bars and restaurants.

Embark next on a leisurely cruise to St Vincent and the Grenadines. Known for their pristine beaches and mouth-watering cuisine, why not enjoy these beautiful islands from the deck of your luxury yacht while your skipper serves up fresh-caught seafood?

If you fancy something more active, hike to the summit of La Soufriere Volcano for spectacular views, or ask your skipper to sail to Anchor Reef where you can explore a staggering variety of marine life.

East Winds Hotel in St Lucia

Finally, combine your luxury cruise with a stay at the East Winds Hotel in St Lucia situated on one of the island’s finest beaches, for the ultimate indulgence.

Sail the British Virgin Islands - stay at Peter Island.

Experience the natural and cultural treasures of the British Virgin Islands. Your adventure begins as you set sail for Cooper Island, with its secluded bays that are a mecca for divers, exploring ancient shipwrecks and watching turtles glide through the warm waters. In the British Virgin Islands it is said that more than two people on a beach is busy; ask your private chef to pack you a champagne picnic and have your skipper drop you off at a deserted beach for a romantic date with difference.

Then it’s off to Virgin Gorda to explore Spanish Town and Savannah Bay, perfect for island culture, souvenir shopping and a spot of snorkelling. On dry land hike across Gorda Peak National Park for panoramic views, before heading to Marina Cay to unwind in laidback bars and restaurants.  Cane Garden Bay beckons, a voyage to discover Tortola’s western coast of palm-clad hills and the Callwood Rum Distillery for tastings of white and gold rums.

Anchored catamaran in the Caribbean

To the west, you’ll encounter the vibrant nightlife of Jost Van Dyke and the Great Harbour. For a pirate’s adventure your catamaran will also journey to Norman Island, said to have inspired Robert Louis Stevenson’s Treasure Island. Perhaps you’ll find pieces of eight overlooked for centuries.

Peter Island in the British Virgin Islands

Finally, dock at Wickham’s Cay and stroll through the J.R. Botanical Gardens for beautiful wildlife and tropical scenery while also enjoying the sultry spell of Tortola. After your stunning adventure on the high seas we suggest you rest and reflect at the private island resort and spa, Peter Island, once home to Christopher Columbus, Sir Francis Drake and Blackbeard the pirate.  

Visit our sailing holiday pages for inspiration and more reasons why you should consider an exciting Caribbean cruise or read our FAQs

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