experiences

4.8

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

November

€299

Per person

4.2

Weekend of theoretical and practical course

Italy: Liguria

2 days - 1 night

7 departures available

October - November

€250

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 - Courses & regatta yacht sailing holidays & tours in Italy

563 reviews

Fantastic BARCOLANA: Racing in safety and joy!

10/15/2025

Giulia B.

Italy

Beautiful experience with nice and heterogeneous crew! Paolo is a professional person who guided and taught us, transmitting his passion for sailing. Advised!

Barcolana weekend in Trieste and surroundings.

10/15/2025

Barbara M.

Italy

MARINO fantastic skipper, he pampered us ( swim in the blue included), he was very helpful for all our whims. The Barcolana is a grandiose spectacle, seen from the sea it excites a lot, if you like sailing you can not avoid being there at least once. The kitten on board, Lightning is a very sweet travel companion. After the restyling in the shipyard, the catamaran will also be up to the task.

Barcolana 2025: experience the most beautiful regatta with me!

10/14/2025

Gabriele I.

Italy

Very good Gianni

Barcolana 57: a day at the most famous regatta in the world

10/13/2025

Alessandro Marco B.

Italy

All very nice. Antonio was an excellent skipper, very nice and helpful. Super crew! To be redone

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 2035144220

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 (360)Whole boat with skipper (285)Catamaran (45)Cooking service onboard (45)Sport & wellness (45)Family sailing cruises (35)Day trips (25)All inclusive (25)Courses & regatta (10)

Other travel ideas

Sailboat (130)Whole boat with skipper (98)Cooking service onboard (40)Catamaran (36)Exotic destinations (34)All inclusive (33)Sport & wellness (11)Family sailing cruises (10)Courses & regatta (7)Offshore (5)