header cover
sailsquare logo

All inclusive yacht sailing holidays & tours in Italy

Discover more than 9 opportunities to get on board a All inclusive 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 - All inclusive yacht sailing holidays & tours in Italy

549 reviews

avatar placeholder

Gulf of Poets and Cinque Terre

09/15/2025

Mariangela C.

-

Italy

A perfect sailing weekend! Giorgio and Francesca made us feel at home right away, they wisely modified the itinerary based on the sea conditions, allowing us to fully enjoy the experience. Top boat! To be repeated
avatar image

A wonderful day.... on Lake Garda - ALL INCLUSIVE

09/12/2025

Giulia C.

-

Italy

Wonderful day, perfect organization, Emanuele was fantastic! Super recommended!!
avatar image

A wonderful day.... on Lake Garda - ALL INCLUSIVE

09/9/2025

Monica P.

-

Italy

Emanuele is an extremely kind, polite and helpful person. He told us many things about the lake, the surrounding villages, historical notes, navigation rules and answered all our questions. He let us steer the boat and gave us instructions on how to help him during the turns. In short, he made us part of the whole journey. And he's a great cook, too! Aperitif, spritz, lunch, coffee, fruit, desserts, there was everything! It was a beautiful day, relaxing and in good company.
avatar placeholder

Gulf of Poets and Cinque Terre

09/3/2025

Valentina G.

-

Italy

Giorgio and Francesca two excellent 'hosts': welcome, availability and kindness not for everyone. Serene seriousness at the helm of the boat and top aperitifs! P.s: we also saw dolphins!!!

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