Homepage cover
sailsquare logo

Log in

Gulet and sailing ship yacht sailing holidays & tours in Italy

Discover more than 1 opportunities to get on board a Gulet and sailing ship adventure in Italy. 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

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

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 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

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 - Gulet and sailing ship yacht sailing holidays & tours in Italy

102 reviews

avatar image

Elba, Corsica, Capraia: a traditional schooner walking the seas.

07/29/2025

Orazio B.

-

Italy

all very nice
avatar image

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

07/25/2025

Vivien L.

-

Switzerland

We had a brilliant first sailing experience on the main wwf boat mahayana. The trip was a perfect mix of whale/dolphin watching, snorkling and sailing. The crew was amazing with fransesco, melissa and lorenzo, they were very helpfull and did everything to make us feel great over the week. The wwf specific lessons in the evening + the boat history presentation made it even more special. We highly recommend the experience.
avatar image

Weekend on a beautiful traditional schooner in the Tuscan archipelago

07/2/2025

Daniela C.

-

Italy

The captain and crew made this weekend unforgettable with their professionalism, kindness, cheerfulness and humanity. It will remain an indelible memory in my memory and that of my son. Every expectation has gone. The Captain established an empathic relationship with us and guided us in a unique experience. The crew pampered and involved us. Absolutely recommended.
avatar placeholder

Weekend on a beautiful traditional schooner in the Tuscan archipelago

09/11/2024

Andrea F.

-

Italy

Beautiful experience on board the [hidden], the boat is wonderful, Francesco and Mela were very good in everything. Experience that I certainly recommend and that I also hope to repeat

Customer Support

nightLifeGeneralInfo

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!

search

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!

Italy: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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