The Top Reasons Why You Should Join a Group Sailing Vacation

idyllic tropical beach with white sand, palm trees and turquoise Caribbean sea water on exotic island in St Vincent and the Grenadines
idyllic tropical beach with white sand, palm trees and turquoise Caribbean sea water on exotic island in St Vincent and the Grenadines | © BlueOrangeStudio / Alamy
Lexi Fisher

Dreaming of a Caribbean holiday, but not sure where to start? A group sailing vacation could be your ticket to an off-the-beaten-track adventure without the cost of chartering your own boat, plus a skipper to show you the ropes – literally and figuratively. We’ve put together a handful of reasons that’ll make you want to cast off immediately.

Ready to set sail? Join a group sailing vacation with Culture Trip in exotic locations like Bora Bora, the Seychelles and the Caribbean.

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Uncover my top 3 recommended places from each continent on the map.
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CentralAmerica

GORGEOUS GUATEMALA

Gorgeous Guatemala

5 days . Mini
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1. Guatemala

An express adventure for those with limited time off. Prepare yourself incredible experiences. You will hike a volcano, visit mayan temples and witness a ceremony and take in beautiful colonial Antigua.

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CentralAmerica

BEACHY BELIZE

Beachy Belize

5 days . Mini
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2. Belize

A quick trip not too far away for those seeking a relaxing mini break. You will have plenty of free time to relax but also some awesome activities to experience the rainforest and the caribbean sea.
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CentralAmerica

COLONIAL MEXICO

Colonial Mexico

5 days . Mini
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3. Mexico

An exciting mini trip exploring the lesser known colonial towns of central Mexico. This is hte perfect trip for someone with limited time off and still wants to turn on explorer mode and do something different.
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SouthAmerica

ADVENTUROUS ECUADOR

Adventurous Ecuador

8 days . Epic
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1. Ecuador

A remarkable 8 days adventure through the Andes and the Amazon rainforest. The best choice for adventure seekers wishing to visit the 2 most iconic areas of South America, in only 1 week and no flights.

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SouthAmerica

ANCIENT PERU

Ancient Peru

9 days . Epic
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2. Peru

An alternative itinerary to classic Peru, from Cusco to Arequipa. This itinerary is great combination of highlights Cusco and Machu Picchu with the lesser known Arequipa and Colca Canyon.
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Europe

SEDUCTIVE SOUTHERN ITALY

Seductive Southern Italy

10 days . Epic
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1. Italy

The ultimate Italian experience from the vibrant streets of Naples to the breathtaking sceneries of the Amalfi Coast followed by Matera and down to Puglia with its golden beaches, intense flavours and fascinating destinations.

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Europe

EDINBURGH AND THE SCOTTISH HIGHLANDS BY TRAIN

Edinburgh And The Scottish Highlands By Train

7 days . Culture
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2. Scotland

Embark on this great adventure starting from London all the way to Scotland with a true Scottish experience made of breathtaking sceneries, whisky tasting and ..lots of fun! Ideal for train lovers and explorers.
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Europe

COMPLETE PORTUGAL BY TRAIN

Complete Portugal By Train

8 days . Culture
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3. Portugal

A wonderful train journey around Portugal, from the romantic city of Porto to the Douro Valley, to the beautiful Aveiro all the way to Lisbon and Sintra. The perfect trip to train, culinary and culture lovers.
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Asia

SOULFUL SOUTH KOREA

Soulful South Korea

10 days . Epic
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1. South Korea

Discover incredible temples, mountains and modern cities on this 10 day adventure. This trip is perfect for those seeking immersion in the cuisine, culture and natural wonders of South Korea.

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Asia

THAILAND, CAMBODIA & VIETNAM

Thailand, Cambodia & Vietnam

11 days . Epic
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2. Thailand

From Bankgok to Angkor Wat to Ho Chi Minh City and everything in between - adventure through the heart of South-East Asia. Taste the delights, see history brought to life and unwind on a Mekong River cruise.
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Asia

SECRETS OF SRI LANKA BY TRAIN

Secrets Of Sri Lanka By Train

10 days . Culture
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3. Sri Lanka

A fantastic adventure that showcases Sri Lanka's fantastic landscapes, wildlife and flavours. With 3 epic rail journeys, 3 UNESCO heritage sites and time to relax, this trip has loads to offer at a great price
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Africa

EPIC MOROCCO

Epic Morocco

11 days . Epic
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1. Morocco

An epic journey across Morocco: from Casablanca to Marrakech, through the blue city of Chefchaouen to the wonders of the desert and deep to the High Atlas Mountains - this trip has it all! Ideal for true explorers!

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Africa

ULTIMATE EGYPT

Ultimate Egypt

9 days . Epic
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2. Egypt

From Cairo to Aswan, this trip brings the land of the pharaohs to life. You'll visit the Pyramids, Valley of the Kings and Luxor Temple and cruise down the Nile in style. This is the perfect way to explore Egypt.
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Africa

IMMERSIVE KENYA

Immersive Kenya

8 days . Epic
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3. Kenya

An immersive blend of culture and wildlife for first time travelers to Africa. Learn about Nairobi, sample local coffee in the Aberdares and finish up with a fantastic safari stay in the Masai Mara.
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Learn about life on the high seas

If you’ve ever wanted to learn to sail, this is the best way to get a taster. A group sailing holiday means you have the comfort of a skipper and crew taking charge, so you can relax on deck with a margarita and a book. However, if you’re keen to understand the sailing basics, there will certainly be opportunities for you to trim the sheets – that doesn’t involve bed linen, by the way – and take the helm if you like.

Live your best life on a chartere yacht with new friends

It’s surprisingly affordable

A boat charter might sound like something that only celebrities can afford, but splitting the cost with others makes a sailing holiday much more affordable. Instead of spending money on luxury resorts and individual activities, everything is included on a group trip – aside from your flights – so you save your hard-earned money for an extra cocktail on the beach or souvenirs to take home.

Get off the beaten track

Over 70 percent of our planet is covered in water, which means that many of the world’s most beautiful and undiscovered destinations are only accessible by boat. This is especially true in the Caribbean, where most islands don’t have airports and many are uninhabited. With a boat, the possibilities for adventure are endless.

Visit St Vincent and the Grenadines for the day

Escape the crowds

One of the great things about a sailing holiday is the ability to, well, sail away. We all know what it’s like to look forward to a relaxing getaway, only to have a mass of tourists descend on your carefully chosen destination. When the crowds become too much, weigh anchor and sail off to find your own private escape.

Visit more than a single destination

When the only limit to your freedom to roam is the depth of the water, the possibilities are thrown wide open. Instead of being stuck on a single island, a sailing holiday gives you the chance to explore dozens, each unique in its own way. Plus, you’ll get the most out of your vacation time by combining your accommodation and means of transportation into one.

Explore Carriacou Island on your sailing vacation

Make new friends

Booking a cabin on a shared boat means you’ll get to meet other like-minded people. You all share the sense of adventure that brought you there in the first place, so why not take the opportunity to connect with people you wouldn’t have met otherwise? Strangers are friends you just haven’t met yet, after all.

Immerse yourself in nature

You can’t get any closer to nature than living on a sailboat. When reef-lined bays and sheltered mangrove lagoons are literally your back garden, you’ll experience the best that nature has to offer. Whether it’s snorkelling with turtles and eagle rays, watching herons hop between mangrove roots, or the gentle flight of frigatebirds gliding gracefully above your head, wildlife is all around you.

Go snorkelling with stingrays in Bora Bora

Soak up the sensational views

And who can forget the spectacular Caribbean sunsets? From a sailboat, you’ll have uninterrupted views of the horizon as the sun sets the sky ablaze and cotton-candy clouds melt into the cerulean sea. If you’re lucky enough to have a cloudless horizon, you might even see the green flash – a spark of emerald light emitted by the sun the moment it finally sinks beyond view below the horizon. Blink – and you’ll miss it.

Enjoy a unique adventure

Each sailing holiday is a new and exciting adventure. Whether you’re keen to learn to sail, spend as much time in the water with colourful reef fish as possible, or visit endless white sand beaches, raise the sails and head off into the horizon – who knows what awaits you?

Discover unique sealife in the Caribbean waters
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Volcanic Iceland Epic Trip

meet our Local Insider

Hanna

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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!

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

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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.

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