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 adventure sailing, and discover nearby sailing trips or explore world sailing destinations.
Cape Town, South Africa
07 October - 23 November 2024
An epic crossing of the South Atlantic Ocean from Cape Town, including five days exploring Saint Helena Island
$4,994.25/pp
Split, Croatia
24 - 31 August 2024
LAST MINUTE due to late drop-out, come sailing with one of our world leading skippers, exploring the beautiful Croatian Coastline
$1,991.04/pp
$3,322.84/pp
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.
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 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.
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.Th 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 when we’re at sea
· Sat 25 May 2024
The AHOY Centre joins Open Oceans fund to make Ocean sailing accessible to dis-advantaged young people
· Fri 19 Apr 2024
We are pleased to announce Gill as the latest partner of the Open Oceans fund
· Mon 15 Apr 2024
Booking protection now available on Wavysail bookings made on our site
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