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Featured sailing holidays

Our sailing adventure trips range from one week to 50 days, offering exciting destinations worldwide. Whether you're an experienced yachts-person looking to hone your skills, a coastal sailor building miles, or have no prior sailing experience, you'll be equally welcomed. Join us to learn to sail a yacht, embark on thrilling adventure sailing, and discover nearby sailing trips or explore world sailing destinations.

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Featured 2025 Adventures

epic adventure

Cape Town, South Africa

24 March - 10 May 2025

South Atlantic Expedition

An epic crossing of the South Atlantic Ocean from Cape Town, including five days exploring Saint Helena Island

$9,198.42/pp

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relaxing adventure

Split, Croatia

23 - 30 August 2025

Croatia sailing adventure

A week of hands-on sailing with one of our world leading skippers, exploring the beautiful Croatian Coastline

$3,280.92/pp

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stretching adventure

Scottish Isles, United Kingdom

02 August - 05 September 2025

Sail the Northcoast 500 - Tour of Scotland

A new twist on a classic Tour of Scotland as we sail the Northcoast 500

$7,883.42/pp

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Featured 2026 adventures

epic adventure

Greenland, Greenland

10 August - 28 September 2026

North West Passage

Take on the "Everest" of Sailing and prepare to be part of something amazing.

$64,435.00/pp

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Experience a journey of discovery with Wayvsail

Join an unforgettable sailing adventure. Guided by world-class skippers, we’ll encourage you to leave your comfort zone whether you’re an experienced sailor already, or just starting out and want to learn to sail, we have a sailing trip for you. You will sail with like-minded people, led by experienced skippers who are passionate about exploring the world sustainably and safely.

WHAT MAKES US UNIQUE?

Unique for our tailor-made sailing adventures that blend hands-on learning, expert guidance, and a deep commitment to environmental conservation you’ll embark in the journey of a lifetime.

Tailor-made experiences

With a maximum group size of six people, our sailing adventures are uniquely personalised and flexible. We connect with you beforehand to understand your sailing experience and aspirations for the trip. Whether you wish to learn celestial navigation, build miles, or simply experience the majesty of an ocean voyage, we tailor each journey to ensure you have an amazing time. It’s all about creating an adventure that adapts to your desires and ensures a truly unforgettable experience.

World-class sailing skippers

Wavysail’s skippered sailing vacations are led by some of the most experienced skippers in the world. Each of our leading skippers boasts a minimum of half a million miles of sailing experience—equivalent to sailing around the world ten times! Our team includes explorers, world record holders, and above all, passionate sailors. Rest assured, you are in safe, capable hands, ensuring an incredible and enriching learning experience on every sailing expedition.

Active participation and learning

Our trips are immersive sailing adventures where you actively participate in every aspect of the journey. Learn to menu plan for an Atlantic crossing, master reefing sails, and navigate by the stars—you’ll do it all. While some parts will be exhilarating and others challenging, our experienced skippers will guide you through every step. Together, we’ll create lifelong friendships through shared adventure and discovery.


What our clients are saying

Hear from the people who joined our previous adventures

Woman sailing with Wavysail

The skipper was excellent.  So many adventures, amazing places.  Highly recommended

SARA, UK

Cape Town, Africa sailing trip

Awesome trip from Cape Town to St Helena. An adventure I will never forget. I made life long friends and experienced the thrill of blue water sailing. St Helena is totally unique. Highly recommend this trip for your next adventure.

MIKE, USA

Sailing boat

Not just an adventure. Truly, an accomplishment. A phenomenal experience

TRACEY, USA

A boat sailing in the ocean with an amazing sunset

Absolutely loved the trip. For a first time sailor it really was amazing.Th Skipper was ace, crew were fab and the sun shone - perfect!

MARC, UK

A boat sailing in the ocean

Having returned from our mile building trip to St Helena I would like to thank Wavysail for organizing a once in a lifetime experience. It was one of the most incredible experiences of my life and so many life lessons learnt apart from the actual sailing experience gained. 

BYRON, SOUTH AFRICA


The Daily Journal

Take a look at our latest updates when we’re at sea

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WAVYSAILEMAILBLOGAWARD

Wavysail named 2024 Global Champion for Sustainable & Inclusive sailing

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Meet the Open Oceans Crew - Amber and Alfie

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Tincturemainimage

CUSTOMER NOTICE : Wavysail and Tincture London

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FEATURED IN

Trustpilot
Ultimate Travel Club
Sail Scotland
Adaptive Adventurers
The Times
St Helena Tourism