Homepage cover
logo

Log in

Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 69 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

August

€510

Per person

cover image
avatar image

4.9

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€390

€351

Per person

cover image
avatar image

5.0

Sailing to discover the Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 7 nights

3 departures available

August

€1,250

Per person

cover image
avatar image

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

cover image
avatar image

4.0

An unforgettable week in the Tuscan Archipelago

Italy: Tuscany

7 days - 7 nights

3 departures available

August

€1,230

Per person

cover image
avatar image

New

Seven days of sailing and sea between Elba, Capraia and North Corsica

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

€1,230

Per person

cover image
avatar image

4.8

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

3 departures available

August - September

Starting from

€390

€371

Per person

cover image
avatar image

5.0

Between Capraia and Northern Corsica: sailing, crystal clear sea and freedom

Italy: Tuscany

7 days - 6 nights

2 departures available

August - September

€990

€891

Per person

cover image
avatar image

5.0

New

Island of Elba on a sailing boat: coves, crystal clear sea and relaxation

Italy: Tuscany

7 days - 7 nights

One departure available

August

€835

€752

Per person

cover image
avatar image

5.0

New

Educational cruise in the Tuscan archipelago and Cetacean sanctuary

Italy: Tuscany

7 days - 7 nights

One departure available

August

€865

Per person

cover image
avatar image

4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

2 departures available

September

€317

Per person

cover image
avatar image

4.5

Holiday - School between the Tuscan Archipelago and North Corsica

Italy: Tuscany

7 days - 7 nights

4 departures available

August

€900

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 - Sailboat yacht sailing holidays & tours in Tuscany

3676 reviews

avatar image

Midweek getaway between Elba and Capraia

07/25/2026

Maria V.

-

IT

Edoardo made me make peace with the sea! I was lucky enough to board his wonderful boat with my mom and I hope it will become an annual event :)
avatar image

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

07/25/2026

Michele G.

-

IT

Amazing holiday with a fantastic itinerary. A precise, prepared skipper who is very engaging in sailing manoeuvres. The boat is perfect.

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

07/24/2026

Eleonora F.

-

IT

We couldn't have wished for a better skipper! Very professional but easy-going, prepared, always kind and available for any need. The boat is very well equipped and well organized. He made us experience the real thrill of sailing by explaining all the details of sailing. Highly recommended, we will definitely return to the sea with him! We saw beautiful places, a variety of coves and a super blue sea! THANK YOU EDO!

The Island of Elba, to make you live a special experience!

07/24/2026

Filippo C.

Livio is an attentive and scrupulous skipper, a connoisseur of Elba, but also a nice and jovial person with whom to spend quality time. Highly recommended as a first experience.

Customer Support

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!

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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