Homepage cover
logo

Log in

Sailboat yacht sailing holidays & tours in Ionian Islands

Discover more than 5 opportunities to get on board a Sailboat adventure in Ionian Islands. A unique experience with a local skipper, starting at €350 a week.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat yacht sailing holidays & tours in Ionian Islands

995 reviews

avatar image

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

11/3/2026

Alvise V.

-

IT

Great!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/15/2026

Lara R.

-

CH

We had a wonderful time and the crew took good care of everything we could have wished for. Thank you very much for the great experience!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/12/2026

Fiona B.

-

AU

Andrea was a fantastic skipper and Carol was a great hostess. The week was filled with beautiful beaches, delicious lunches and great conversations and was a perfect way to relax for a week. It was fun sailing along with the second yacht, and we had a great time playing volleyball together. The boat was comfortable and plenty of spots to relax above deck in the sunshine. I highly recommend this trip. Andrea and Alessandro are expert sailors who take the very best care of their customers and always put safety first - but maximize fun and stunning scenery throughout. The hosts on board (Carol and Carlo) were exceptional - making delicious and varied food each day. And little Mattias - the best boat poodle there ever was! What are you waiting for - book this adventure. Thank you Andrea, Carol and Marta for an unforgettable week.

Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/12/2026

Lee T.

-

GB

Wow I had a fantastic week with Alessandro and Carlo, they both were so kind and caring and went out of their way to ensure we had a fantastic trip, even when the weather on the last 2 days meant we had to change the itinerary Ale found a way to ensure we didn’t miss out on visiting new places. Carlo was a fantastic host, his cooking was amazing and so much to eat every day as well as his friendly smile and always there to help. Alessandro, what a great guy, a great skipper, always ensuring we were happy and safe and would go out of his way to take us ashore and find the best restaurants. I have made a new friend for life and will be back next year 🤣 Thanks to you both for a memorable holiday

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964