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
Mark Nayler

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.

Loved by over 40s

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.

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$

Next available from 1st Jan 1970

Secure your spot with a low deposit

Trip highlights and details

STARTS AT

Tortola, British Virgin Islands

arrow pointing to the right

ENDS AT

Tortola, British Virgin Islands

DURATION

8

GROUP SIZE

12

PHYSICAL RATING

Light

info icon

STYLE

Discovery

info icon
Woman snorkeling above stingrays in Bora Bora, French Polynesia

Swim with sharks and visit ancient temples on this expedition around French Polynesia

If you’re looking for a sailing holiday for beginners, this trip to the South Pacific is the one for you. Spend the first couple of days exploring the barrier reef and lagoon that surround the forested island of Bora Bora, swimming with rays, barracudas and blacktip reef sharks. On the smaller island of Raiatea, visit sacred temples and a black pearl farm – before winding up the white sands of Huahine to swim, paddle, snorkel and kayak.

From US$

Next available from 1st Jan 1970

Secure your spot with a low deposit

Trip highlights and details

STARTS AT

Uturoa, Raiatea

arrow pointing to the right

ENDS AT

Uturoa, Raiatea

DURATION

8

GROUP SIZE

12

PHYSICAL RATING

Light

info icon

STYLE

Discovery

info icon
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$

Next available from 1st Jan 1970

Secure your spot with a low deposit

Trip highlights and details

STARTS AT

Le Marin, Martinique

arrow pointing to the right

ENDS AT

Le Marin, Martinique

DURATION

8

GROUP SIZE

12

PHYSICAL RATING

Light

info icon

STYLE

Discovery

info icon
Woman enjoying the Anse Lazio beach on Praslin Island, the Seychelles

Snorkel with rays and sea turtles on this skippered voyage around the Seychelles

Sailing for beginners is rarely as relaxed as it is on this catamaran cruise around the Seychelles. You’ll be sailed to all the best spots, where you can snorkel with hawksbill sea turtles, manta and eagle rays and bottlenose dolphins – if you’re lucky. On land, stroll through the ancient, Unesco-listed palm forests of Praslin’s Vallee de Mai, where the world’s largest seeds (Coco de Mer) litter the ground.

From US$

Next available from 1st Jan 1970

Secure your spot with a low deposit

Trip highlights and details

STARTS AT

Seychelles, Africa

arrow pointing to the right

ENDS AT

Seychelles, Africa

DURATION

8

GROUP SIZE

12

PHYSICAL RATING

Light

info icon

STYLE

Discovery

info icon
In Big Major Cay, you can get very close to the famous swimming pigs in the Bahamas

Swim with pigs and meet endangered species in the Bahamas

Welcome aboard nautical novices, on this tour of the balmy Bahamas. Starting and finishing in Nassau’s Palm Cay Marina, you’ll hang out with critically-endangered rock iguanas on Allen Cay; swim with friendly, wild pigs off Big Major Cay; and meet the exotic finned residents of Thunderball Grotto – an underwater cave that appeared in the 1965 James Bond film. Other top snorkelling spots include the 30-plus beaches of Warderick Wells Cay and the submerged wreck of a World War II plane.

From US$

Next available from 1st Jan 1970

Secure your spot with a low deposit

Trip highlights and details

STARTS AT

Nassau, Bahamas

arrow pointing to the right

ENDS AT

Nassau, Bahamas

DURATION

8

GROUP SIZE

12

PHYSICAL RATING

Light

info icon

STYLE

Discovery

info icon
culture trip left arrow
 culture trip brand logo

Volcanic Iceland Epic Trip

meet our Local Insider

Hanna

women sitting on iceberg

HOW LONG HAVE YOU BEEN A GUIDE?

2 years.

WHAT DO YOU LOVE ABOUT YOUR JOB?

It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.

WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?

I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!

culture trip logo letter c
group posing for picture on iceberg
group posing for picture on iceberg

Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.

map of volcanic iceland trip destination points
culture trip brand logo
culture trip right arrow
landscape with balloons floating in the air

KEEN TO EXPLORE THE WORLD?

Connect with like-minded people on our premium trips curated by local insiders and with care for the world

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.

X

Keen to explore the world?

Our passionately curated premium small-group trips are an invitation to connect with like-minded people for once-in-a-lifetime experiences.