What is Vagabond Sailing?

We believe that life is too short to be just another tourist. Vagabond Sailing is a diverse global community for all who love authentic travel adventures on the seas. Join the facebook group at http://www.facebook.com/groups/vagabondsailing to stay updated on upcoming voyages and events. Membership is free.


Vagabond Sailing is about much more than sailing it’s about making connections with other travelers, it's about going with the flow and letting a place reveal its hidden beauty to us that can't be seen or experienced in any other way. We go off the well trodden tourist track and experience local life and authentic cultural experiences. We indulge in the local fare and have the time of our lives. 

Eat delicious new foods, see awe inspiring historical sites, sip cocktails while watching the sun set. Sailing holiday's with us can be as relaxed or as intense as we want it to be!


Not only are we flexible, but also we cater to various themed activities such as yoga weeks, water sport weeks, art weeks, silent meditation weeks and more.  All of our sailing adventure weeks are open to anyone between the age of 18 and 80. We also run trips for families that want to book the entire boat.


What we do

We have extensive knowledge of cruising areas around the world with hidden bays, idyllic beaches and beautiful destinations. We use this knowledge to co-create with each group the best sailing adventure possible.

You can learn to sail or just relax on the deck soaking in the sun and scenery. The perfect environment to read a captivating novel or chill out to the tunes of your choice. There are many opportunities to swim and snorkel in crystal clear waters and time to explore white sand beaches. We might BBQ fresh caught fish on uninhabited islands and you'll be able to sleep under the stars in hammocks on the deck or the beach if you choose. We run specialised yoga and meditation weeks with qualified instructors. If you enjoy adventure sports you'll be able to throw yourself from coastal cliffs, explore caves and coves and perhaps try your hand at windsurfing, kite surfing water skiing or scuba diving. This really is your sailing adventure, and can be tailored to be as energetic or as relaxing as you want it to be. 

You can join as a group of up to 10 friends, a family, as a solo traveller or any combination! It’s an awesome way to meet new people, make new connections and for old friendships to flourish.

Other than start and finish ports we have no fixed itinerary - we literally sail where the wind takes us. The night before, your skipper will assess the weather and, depending on wind conditions, suggest a plan for the next day. Every day can be different from the last.


In general, our voyages are usually 1-2 weeks in duration. We typically sail 52 foot monohull sailboats with 5 cabins and 3 bathrooms, but we can take out smaller boats as well for smaller groups. Members usually bring at least one friend along with them to bunk with. Voyage costs are intentionally kept low and shared family style. The total cost per person ranges anywhere from $600-$1,000+ USD per person depending on seasonality, location, and trip duration. Scholarships are sometimes available.


Who we are

Vagabond Sailing was started by friends and couchsurfing enthusiasts, Captain Rob Patrick Lyón and Marco Grasso. Rob is a commercially licensed RYA Yachtmaster sailboat captain and PADI divemaster living in Bali, Indonesia. Marco is an Italian skipper and entrepreneur currently living in beautiful Rome, Italy.



If you have any questions at all, just ask.