Award Winning Ocean Sailing Expeditions, tailormade for everyone, led by world-class skippers.
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 adventures, and discover nearby sailing trips or explore world sailing destinations.
Join an unforgettable sailing adventure. Whether you’re an experienced sailor, or a complete beginner eager to learn to sail, we have a sailing trip for you.
Guided by world-class skippers, you'll join a crew of like-minded explorers and step outside your comfort zone. Our experienced and passionate skippers are dedicated to safe, sustainable travel and to helping you discover the thrill of life at sea.
WHAT MAKES US UNIQUE?
Our tailor-made sailing adventures blend hands-on learning, expert guidance, and a deep commitment to environmental conservation to craft fully immersive and unforgettable journeys.
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.
Wavysail’s skippered sailing adventures are led by some of the most experienced skippers in the world. Each of our leading skippers has been carefully selected for their extensive expedition experience as well as their leadership skills. 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.
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.
Hear from the people who joined our previous adventures
The skipper was excellent. So many adventures, amazing places. Highly recommended
SARA, UK
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
Not just an adventure. Truly, an accomplishment. A phenomenal experience
TRACEY, USA
Absolutely loved the trip. For a first time sailor it really was amazing.The skipper was ace, crew were fab and the sun shone - perfect!
MARC, UK
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
Take a look at our latest updates
· Fri 16 May 2025
Your opportunity to sail for free and help us bring Ocean adventure to life
· Wed 7 May 2025
Read why Wavysail Skipper, Jim Dobie thinks Scotland is one of the Best Sailing Adventures on Earth
· Sun 30 Mar 2025
Countdown to Summer sailing adventures has started!
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