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Sailing Holidays


Active Holidays
Our sailing holidays offer a huge range of awe-inspiring experiences across the world for travellers wanting to experience the beauty of their surroundings from the glistening sea waters.

If opting for a sailing holiday in Europe, you can look forward to admiring charming coastal villages, pristine beaches and ancient ruins from your serene sailing vessel. Further afield, Australia, the Indian Ocean and Belize are superb destinations for an unforgettable sailing holiday – each also renowned for their fantastic snorkelling and diving opportunities. Our sailing trips are led by expert skippers, so whether you want to help navigate, tack and steer, or simply kick back and relax on the deck with the cool sea breeze in your hair, the choice is yours.

A sailing holiday is a great way to encompass a variety of fantastic locations and experiences – each day discovering something entirely new. You could be gliding past the blissful beaches of Thailand, the breathtaking Whitsunday Islands in Australia’s Queensland, or the stunning atolls of the Maldives. Sailing holidays are capped at a low number of participants, making the group size ideal for fostering close and meaningful connections, with many travellers opting to keep in touch after the trip ends. In addition, our excellent range of hotels and local tours mean you can extend your sailing holiday and tailormake your own unique itinerary.

With more than 50 years’ experience, Trailfinders has developed the skills and expertise needed to put together all the pieces for a successful sailing holiday. Our expert travel consultants are mines of information, gathered from personal travel experience and are the best people to ask to create your perfect trip.
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OUR SAILING HOLIDAYS

Nobody offers more sailing holidays than Trailfinders.

To learn more about Seatrek Sailing holidays, check out our helpful guide here sharing what to expect on their one-of-a-kind sailing journeys through Indonesia.

Here's a snapshot of some our most popular sailing holidays. If you don’t see what you’re looking for, click on the link below them to see our complete range of trips or give us a call and speak to one of our travel experts.
Sail Maldives
Guided Small Group Sailing Tour
8 days / 7 nights

Take a trip to paradise and climb aboard a traditional dhoni boat for a sailing trip through the Maldives...

Guide Price: €2052 £1763 pp

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Sail Phuket to Ko Phi Phi
Guided Small Group Sailing Tour
4 days / 3 nights

Feel the wind in your hair as you set sail through the paradisical surroundings of Thailand's west coast...

Guide Price: €870 £750 pp

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Tropical North Queensland & Sailing the Whitsundays
Multi Centre Holiday
24 days / 23 nights

Immerse yourself in the endless beaches and lush landscapes of Tropical North Queensland, gateway to the Great Barrier Reef and home to the ancient Daintree Rainforest...

Guide Price: €4,399 £3,999 pp

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Sailing Greece - Mykonos to Santorini
Guided Small Group Sailing Tour
8 days / 7 nights

Sightseeing while surrounded by vivid turquoise waters and some of the southern Cyclade’s lesser-known islands doesn’t sound too shabby, does it? Let’s add filling up on flavourful Greek food and wine in local villages, exploring historic ruins, and relaxing on picturesque beaches into the mix — not to mention our all-new, state-of-the-art 57 ft yacht...

Guide Price: €1147 £974 pp

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Sailing Sri Lanka - South Coast
Guided Small Group Sailing Tour
7 days / 6 nights

Discover the culture and wild, natural beauty of Sri Lanka on a seven-day sailing with the perfect mix of chill-out time and exploration...

Guide Price: €1274 £1103 pp

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Jewels of Raja Ampat
Cruise Holiday
10 days / 9 nights

Glide through epic landscapes, caves, ancient rock paintings and coves filled with corals and fish of every colour...

Guide Price: €7,855 £6,525 pp

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WHERE TO GO ON A SAILING HOLIDAY

Our great range of sailing holidays across the world ensures you can find your perfect getaway. From drifting between the remote cayes and snorkelling hotspots of the Belizean coast, to sailing through the fabulous Canary Islands with on land hiking opportunities, to sailing through Greece’s breathtaking Cyclades islands, there is so much variety to choose from for your perfect sailing destination.

Choose from the below destinations to explore our range of sailing holidays in your desired location. Alternatively, if you are looking for some inspiration, give us a call and speak to one of our expert travel consultants.
Europe Sailing Holidays
Thailand Sailing Holidays
Indian Ocean Sailing Holidays
Australia Sailing Holidays

WHAT TO DO ON A SAILING HOLIDAY

If you want to experience the thrill of sailing through the beautiful blue waters, but don’t want to commit to a full-length sailing trip, why not opt for a day trip or an overnight sailing adventure? These local tours provide a taste of what it’s like to experience the freedom and excitement of life on board a sailing vessel, perfect for those new to sailing experiences.

One day you might be discovering Australia’s Whitsunday islands from an adults only yacht, soaking up the breathtaking views of the colourful reefs and glistening beaches that surround you, the next spotting dolphins as you gaze out from the deck of your catamaran in Mauritius.

Our collection of short sailing excursions will really help bring your holiday to life.
Whitsunday Islands Sailing Experience
9.5 hours
Departs: Queensland

For a touch of barefoot luxury, board a comfortable adults only boat for a cruise around the Whitsunday Islands and enjoy morning tea as you make your way to Whitehaven Beach.

Bay of Islands Catamaran Cruise
6 hours
Departs: Paihia

Hop aboard the only yacht licensed to view the resident dolphins of this subtropical island paradise!

Dolphin Coast Catamaran Cruise
8 hours
Departs: Mauritius

Grab your swimsuit and sun cream and set sail on a catamaran adventure in search of wild dolphins.

San Francisco Catamaran Cruise
1.5 hours
Departs: San Francisco

The beauty of San Francisco is best experienced from the water, so climb aboard a catamaran for a sightseeing adventure.

1 Night Whitsundays Siska Sailing
2 days / 1 night
Departs: Airlie Beach

Explore The Whitsunday Islands' top highlights aboard the classic ex-racing yacht Siska IV on this fun-filled sailing getaway.

Na Pali Coast Snorkel Cruise
5½ hours
Departs: Hawaii

Jagged spectacular sea cliffs, lava tubes and enchanting waterfalls – gaze upon all of this before you’ve even dived into the clear waters along Kauai’s Na Pali Coast!

OUR SAILING TOURING PARTNERS

Our carefully chosen sailing touring partners ensures that there is always a sailing holiday for you, no matter where you want to travel.

Both of our touring partners share our philosophy of delivering award-winning travel at the best value, making sure you’re in safe hands as you travel.
G Adventures

G Adventures has defined small group travel for over 30 years. Their sailing tours are an ideal style of travel for those looking to explore beyond the usual tourist trails, accessing secret lagoons, hidden coves and picturesque coastal towns. These aren't sailing courses - they are small group adventures on the water. No need for prior sailing knowledge, their skippers handle the ropes, so you can focus on the experience.

Intrepid Travel

For travellers yearning to get off the beaten track, Intrepid opens a whole new world. Explore your chosen destination via its waterways with the wind in your hair and the sun on your face with one of their sailing holidays. Perhaps opt to help navigate, tack and steer, or simply kick back with a glass of champagne, watching the world glide by.

Speak to a Travel Expert

We believe booking online is no substitute for one-on-one service. Between them our expert travel consultants have travelled to over 99% of the world's countries. As a result the service and advice they offer is second to none.

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The Middle East Africa New Zealand and the Pacific South and Central America South East Asia Australia India and Sri Lanka USA Islands of the Caribbean

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