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How it works

Skippered sailing holidays for 20-35 year olds

Our trip style

Spend seven days sailing around the most breathtaking islands the Med has to offer. Explore historic towns, relax on board your own yacht and have the time of your life at the hottest local spots – the perfect balance for a memorable holiday.


Choose your MedSailors adventure from any of our destinations and get ready to embark on a trip with memories that'll last a lifetime. We've carefully tailored each route to give you a totally unique experience on a sailing adventure full of incredible sites and amazing people! Well, what are you waiting for?


Who travels with us

Every week we host a mix of guests from around the globe - solo travellers on the lookout for new travel buddies, couples keen for a getaway and groups of friends large and small making the best of summer sunshine. We make sure all guests are grouped with like minded travellers, so get ready to meet some awesome people.

Our yachts

All our boats are modern sailing yachts and catamarans, catering for every group size and budget. They accommodate 8-12 people and sail in flotillas of five to seven yachts, meaning there’s plenty of space for everyone, above and below deck.


What's included

  • 7 days on board accommodation
  • Breakfast and lunch freshly prepared every day
  • Your Yacht Master Qualified Skipper
  • A helpful Guest Experience Leader
  • Stand up paddle board, dinghy and snorkelling gear
  • Linen, towels and final cleaning
  • Tea, coffee and drinking water
  • BYO Alcohol & Snacks

Some routes also include transfers while on the islands, check your itinerary for specific details.

Our group sizes

We reckon our flotilla of five to seven yachts makes for the perfect sized group to get to know your fellow sailors. So, whether you want to explore in a small group, mingle with everyone at our MedSailors punch party, or take it easy with a laidback dinner for two, our group sizes mean you have the opportunity to do it all.


Keen to try your hand at quad-biking? Dying to become an expert in the local wines? Every route has a selection of amazing activities to give a go. Think every imaginable kind of water sport; exploring by scooter, bicycle, kayak or donkey; or grab your on-board paddleboard for a gander around the bays.



Below deck our yachts consist of four to five double cabins, with bunk rooms available for solo’s and sharing groups, and two to three shared bathrooms. You'll also find a large kitchen with a fridge to keep your drinks cold, a communal lounge and stereo system to get the tunes going on the top deck!

Your crew

Your skipper is your amazing guide around the islands and go-to for all things sailing. They'll help you discover hidden bays, prepare your delicious meals and teach you how to sail so that you can win the MedSailors Regatta! Each flotilla will also have a Guest Experience Leader who will help to organise your activities and recommend things to do on each island.

How much does it cost?

A sailing holiday is certainly not only for the rich and famous. You can spend a week sailing with us on your own yacht from as little as €540 per person plus local tax, including your skipper, breakfast and lunch every day. Budget a small bit more for dinners, drinks and activities so you can make the most of your holiday.

Travelling solo

Your MedSailors holiday comes packed with a bevy of mates, and we will make sure you are grouped with sociable, like-minded people. With cabin options to share a bunk room with another solo or upgrade to a single cabin you will fit right in on board. Prepare to have a lot of fun, make new friends and discover the best the islands have to offer.

Travelling with friends

Get away from the hustle and hop on-board one of our yachts for a week of relaxation, sunbathing and exploring the awesome local spots. There are plenty of like minded people to hang out with on your yacht or the flotilla. Whether you are a couple or a few friends, you will walk away with new friends for life and unforgettable memories.

Group bookings

Get the crew together for a memorable, envy inducing sailing holiday. With up to seven yachts sailing together you are guaranteed the trip of a lifetime on board your own dedicated boat with a Skipper on deck to help you and your mates navigate the islands.

Our travel experiences

We had the best skipper James Ellwood and Colm Pender organising a smooth operation, absolutely greatest team. This made the year special and has got me wanting more!!! Can’t wait for our next sailing trip with MedSailors!!

Nathan Thomas

I had one of the best weeks of my life with MedSailors! I had the best crew mates, skipper, cheeky adventures, and food. We have already talked about our next Med Sailor crew reunion! Just do won't regret it!

Alyson Erickson

MedSailors was above and beyond my expectations. A great mix of relaxing by the sea, touring the islands then eating, drinking and partying the night away.

Matthew Handy