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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 57 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

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5.0

Week end Elbani

Italy: Tuscany

3 days - 2 nights

7 departures available

May - June

Starting from

€251

Per person

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4.8

Weekend on the Island of Elba

Italy: Tuscany

3 days - 2 nights

3 departures available

April - June

Starting from

€260

€234

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

2 departures available

September

€260

€234

Per person

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4.8

Special May - Weekend on Elba

Italy: Tuscany

3 days - 2 nights

2 departures available

May

€220

€198

Per person

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4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

12 departures available

April - October

Starting from

€250

Per person

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4.7

Trekking & Sailing to discover Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

May

€299

€269

Per person

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4.8

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

4 departures available

June - August

Starting from

€395

€356

Per person

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4.8

25 April sailing in Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

April

€334

€284

Per person

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4.8

Vacanza a piedi nudi: Weekend tra Elba e Capraia su barca 15m

Italy: Tuscany

2 days - 2 nights

9 departures available

June - August

Starting from

€330

Per person

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5.0

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

12 departures available

May - July

Starting from

€670

Per person

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5.0

Wellness, sun, sea and adventure: a weekend full of sailing!

Italy: Tuscany

3 days - 2 nights

10 departures available

May - September

Starting from

€230

Per person

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

7 departures available

May - October

Starting from

€305

€275

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 Tuscany

3506 reviews

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Weekend on Elba "Only for four" for maximum comfort

11/25/2025

D. D.

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Italy

Great weekend! Impeccable welcome on Friday evening, really much appreciated. Very professional and prepared skipper (also the other crew members) - experienced hands-on in the challenging (but fun) crossing. I learned a lot (main objective - achieved). I hope to have the chance of another experience together soon.
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

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

11/5/2025

Marco F.

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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.
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LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

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Italy

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

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