Award Winning Ocean Sailing Expeditions, tailormade for everyone, led by world-class skippers.
Join a real adventure
Our sailing adventures range from one week to 50 days, with exciting expeditions worldwide. You'll join a small group, led by one of the world's most experienced skippers. Whether you're an experienced sailor looking to hone your skills, building miles, or have no prior sailing experience, you'll be equally welcomed.
Selected upcoming adventures
Scottish Isles, United Kingdom
02 - 11 August 2025
Sail Oban to Stornoway
Join Big Blue as we Sail the Northcoast 500 : Leg 1
$4,165.45
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.
Celebrating our journey
Latest Wavysail News
Take a look at our latest updates
· Fri 6 Jun 2025
Gill Open Oceans Scotland - Fully funded sailing adventures
Once again, Gill are supporting the Wavysail Open Oceans fund, giving four people the opportunity to join our Scottish adventures, fully funded.
· Fri 16 May 2025
Join our team - we're hiring a Content Creator
Your opportunity to sail for free and help us bring Ocean adventure to life
· Wed 7 May 2025
Explore Scotland under sail
Read why Wavysail Skipper, Jim Dobie thinks Scotland is one of the Best Sailing Adventures on Earth
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