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The Best Sailing Vacations for Complete Beginners

From swimming with eagle rays to sipping cocktails on an island at sunset, there are amazing sailing vacations to be had
From swimming with eagle rays to sipping cocktails on an island at sunset, there are amazing sailing vacations to be had | © Jane Sweeney / Alamy

Looking for a yachting adventure but don’t know your stern from your bow? These high-end skippered trips require no sailing experience and will take you to some of the world’s most incredible destinations – from French Polynesia to the Caribbean.

If you’ve ever thought about learning to sail, these TRIPS by Culture Trip small-group adventures will introduce you to life on board a yacht, as well as the chance to swim with eagle rays, trek through tropical jungles and sip sunset cocktails on a deserted island. Here’s our pick of the best sailing holidays for total novices – all bookable with Culture Trip.

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Family playing on paddle boards in Cane Garden Bay, British Virgin Islands

Cruise between coral reefs and beach bars in the British Virgin Islands

No sailing expertise is required on this eight-day catamaran jaunt around the British Virgin Islands. Ask the crew for tips on sailing basics as you cruise around the islands, stopping to snorkel at the Sandy Cay coral reef and the sea caves of Normal Island. In between island hopping, relax on palm-fringed sands, tan on deck and visit the beach bar where the painkiller cocktail was invented in the 70s.

From US$1191.2 Next available from 12th Mar 2025 Secure your spot with a low deposit
Trip highlights and details
STARTS AT Bali, Indonesia
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ENDS AT Lombok Island, Indonesia
DURATION 12
GROUP SIZE 18
PHYSICAL RATING
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Idyllic tropical beach with white sand, palm trees and turquoise Caribbean sea water on Mayreau island in St Vincent and the Grenadines

Tour the Grenadines islands while learning your port from your starboard

Get a taste of life at sea on this excursion around the laid-back Grenadines islands in the Caribbean. In between sunny sessions on deck, you’ll go stand-up paddleboarding off empty beaches, swim with sea turtles or hike through the tropical forests of Mayreau – the smallest inhabited island in the Grenadines. Finish by crossing a bamboo bridge to swim under Saint Vincent’s Dark View waterfalls and detoxing in the geothermal springs and mud baths of Saint Lucia.

From US$4557.52 Next available from 2nd Mar 2025 Secure your spot with a low deposit
Trip highlights and details
STARTS AT Osaka, Japan
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ENDS AT Tokyo, Japan
DURATION 12
GROUP SIZE 16
PHYSICAL RATING
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