Homepage cover
sailsquare logo

Sailboat yacht sailing holidays & tours in Italy

Discover more than 53 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

18 departures available

May - October

Starting from

€689

Per person

cover image
avatar image

4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€625

Per person

cover image
avatar image

4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

24 departures available

May - October

Starting from

€600

Per person

cover image
avatar image

4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

19 departures available

May - October

Starting from

€600

€540

Per person

cover image
avatar image

4.9

Super!

Traveling and Dreaming in the Gulf of Poets - All inclusive

Italy: Liguria

2 days - 2 nights

One departure available

May

€360

Per person

cover image
avatar image

4.9

Super!

"Nel blu dipinto di blu" - Sailing cruise in Northern Corsica

Italy: Tuscany

7 days - 7 nights

10 departures available

June - September

Starting from

€680

Per person

cover image
avatar image

4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

June

€360

Per person

cover image
avatar image

4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

16 departures available

May - September

Starting from

€430

€409

Per person

cover image
avatar image

5.0

Super!

Aeolian Islands and Egadi Islands in a week with chef on board

Italy: Sicily

7 days - 7 nights

One departure available

July - August

€950

Per person

cover image
avatar image

5.0

Super!

In the Aeolian Islands with chef on board

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July

€1,000

Per person

cover image
avatar image

4.8

Super!

Pontine Blue - Midweek Escape

Italy: Pontine Islands

4 days - 3 nights

17 departures available

April - July

Starting from

€210

Per person

cover image
avatar image

4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

5 days - 5 nights

4 departures available

June - September

€350

Per person

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 - Sailboat yacht sailing holidays & tours in Italy

12670 reviews

avatar placeholder

A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

-

Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%
avatar image

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

-

Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina
avatar image

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

-

Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.
avatar placeholder

LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

-

Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.

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