Chase the Sun: Ultimate Winter Sailing Adventures Await
Escape the chill for some warmth and adventure with our Winter Sun Adventure Sailing Holidays. Designed for those who need some sun, sailing, and fun during the colder months, we have a superb selection of offshore and coastal Caribbean sailing trips, as well as captivating voyages through Europe’s sunniest spots, including Spain, Portugal, the Canaries, and Morocco. Whether you’re navigating the turquoise waters of the Caribbean, exploring the rich cultures and coastlines of Southern Europe, or setting sail across the Atlantic for a blend of both worlds, our winter sun adventures provide the perfect getaway from the winter blues.
17 Items
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Coastal
1 Week Sailing Vacation in the Bahamas
34 Days from £10
Experience paradise with a week-long Bahamas sailing adventure. Sail in crystal-clear waters, wander sun-kissed beaches, dive on coral reefs, and discover paradise islands. 1 week of tropical bliss and unforgettable sailing.
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Offshore
Adventure 1000: Sail Bahamas to New York City
13 Days from £2,399
Sail 1,000 nautical miles from the Bahamas to New York City, mastering offshore skills with expert training. Experience breathtaking ocean vistas and a magical arrival into New York Harbor past the Statue of Liberty.
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Antigua 5 day Explorer
Experience paradise with a 5 day Antigua sailing adventure. Sail in crystal-clear waters, wander sun-kissed beaches, dive on coral reefs, and discover this paradise island. 5 days of tropical bliss and unforgettable sailing.
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Caribbean Christmas & New Year Sailing: The Grenadines
12 Days from £2,499
Celebrate Christmas and New Year sailing the Grenadines. Join a hands-on adventure from St Lucia, exploring Bequia, Canouan, the Tobago Cays, Union Island and more. Swim with turtles, wander colourful island markets, and anchor beneath leaning coconut palms. Spend Christmas in tropical calm, then ring in the New Year anchored beneath Caribbean stars. No experience needed. Solo travellers welcome. A unique way to escape winter and welcome the New Year on warm trade winds and open sea.
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Offshore
Caribbean Offshore 1000: Antigua to Jamaica
Embark on a truly exhilarating offshore sailing passage across the Caribbean, with 1000 miles of adventure sailing across the Caribbean Sea from Antigua to Jamaica
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Offshore
Caribbean Offshore 1000: St Lucia - Dominican Republic
12 Days from £2,399
Spectacular offshore and coastal sailing in the warm Caribbean trade winds from St Lucia to the Dominican Republic, where humpback whales gather in their stunning breeding grounds - an unforgettable sailing adventure
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Coastal
Grenada Sailing Week
10 Days from £2,199
Grenada Sailing Week is racing without the bluster. Set deep in the southern Caribbean, between the islands of Grenada and Carriacou, it’s low-pressure, high-fun sailing at its best. Expect white sand beaches, jungle-covered hills, turquoise water, and a welcoming crowd. Each day ends with a party or beach BBQ, and the atmosphere is pure Caribbean charm. This is one of our most loved events—and easily the friendliest regatta out there.
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Offshore
Offshore Passage: Atlantic Spain to the Canaries
12 Days from £2,199
A wonderful offshore passage in the warm lower latitudes, sailing from Spain's Atlantic coast to the Canary Islands and warm Atlantic trade winds
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Offshore
RORC Caribbean 600
10 Days from £2,499
Race in the RORC Caribbean 600: Six hundred miles of exhilarating offshore racing, weaving through Caribbean islands.
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Offshore
Sail Across the Atlantic Using Celestial Navigation
36 Days from £5,999
Once-in-a-lifetime Atlantic sailing adventure from the Caribbean to the United Kingdom, navigated by celestial navigation rather than GPS. Learn ancient techniques, sail the open ocean, and reconnect with nature on this unique adventure.
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Offshore
Sail the Atlantic: New York - Newfoundland - UK
The ultimate Atlantic sailing adventure, starting in New York City and sailing north Nova Scotia and on to Newfoundland, before crossing the Atlantic Ocean and arriving into the beautiful west coast of Scotland.
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Offshore
South to the trade winds: Celestial Navigation Voyage - Spain to the Canaries
14 Days from £2,499
Learn to use celestial navigation on a spectacular offshore passage from Spain's Atlantic coast to the Canaries. Starting with a two day theory course, you sail 1000 miles south without using GPS!
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Coastal
St Maarten Regatta
11 Days from £2,499
Join this exhilarating, week-long regatta, mixing none-too-serious but competitive yacht racing with wonderful Caribbean culture and events ashore.
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Offshore
The Bay of Biscay: Passage Making Masterclass
13 Days from £2,499
Join an intensive sailing course crossing the Bay of Biscay, focusing on more advanced navigation, seamanship, and handling challenging offshore conditions. Initial shore based training day before sailing.
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Coastal
The Leewards: Emerald Islands Of The Caribbean
Up to 11 Days from £2,299
Sail through the Leeward Islands and explore the best of the Caribbean. Begin in St Lucia, anchoring beneath its towering volcanic peaks. In Martinique, soak up the island’s unique blend of French sophistication and Caribbean soul. Head to Dominica to paddle the winding Indian River and hike into thick rainforest. Sail on to Guadeloupe, with its mix of blissful anchorages, white sand beaches, and sleepy offshore islands. Conclude your journey in the sailing mecca of Antigua.
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Coastal
The Mystery Islands of the Caribbean
10 Days from £2,299
Explore the unspoiled Caribbean on this sailing trip, as the boat tours islands few sailors ever reach. Experience raw, off-the-beaten-track sailing as the Caribbean once was: untouched, adventurous, and unforgettable.
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Coastal
The Windwards Islands: Exploring the Grenadines
10 Days from £2,299
Sail the Windward Islands on a hands-on Caribbean sailing adventure. Starting in St Lucia, we island-hop south through the Grenadines, navigating crystal-clear waters, coral reefs, and secluded anchorages. Explore Bequia’s boatbuilding heritage, snorkel with turtles in the Tobago Cays, wander Union Island’s colourful markets, and anchor beneath leaning coconut palms in Salt Whistle Bay. Short distances and plenty of time ashore mean a new destination to explore each day, combining relaxed sailing with real discovery.
