experiences

4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

4.8

Super!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

4.6

Cous Cous Fest: weekend of Sailing, Music and Cous Cous!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€350

€315

Per person

4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

Per person

4.8

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€430

Per person

4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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 - Sport & wellness yacht sailing holidays & tours in Italy

747 reviews

Magic of the Aeolian Islands: yoga and volcanic islands by catamaran

07/19/2026

Francesco R.

Beautiful islands, impossible to see them all in a week (you will have to come back); Simone, a young but experienced and capable skipper and extremely helpful. Boat with some flaws

Weekend a Capraia, trekking e natura

03/24/2026

Francesco V.

Francesco and Marco are two great professionals, but above all two great travel companions! Highly recommended experience

Weekend a Capraia, trekking e natura

03/23/2026

Niccolò S.

Francesco and Marco are two very prepared skippers and the perfect people with whom to embark on this type of adventure. Highly recommended.

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

11/10/2025

giulia f.

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

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!

Call us at

+44 20 3514 4220

Read our

Contact & Support

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

Sailboat (1250)Whole boat with skipper (1015)Cooking service onboard (195)Catamaran (140)All inclusive (95)Day trips (95)Family sailing cruises (90)Courses & regatta (45)Sport & wellness (40)WWF Sailing Cruises (30)

Other travel ideas

Sailboat (414)Whole boat with skipper (336)Cooking service onboard (107)Catamaran (75)All inclusive (51)Exotic destinations (29)Courses & regatta (21)Family sailing cruises (20)Day trips (19)Offshore (18)