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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 62 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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4.8

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

27 departures available

March - October

Starting from

€230

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

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4.8

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€750

€675

Per person

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4.8

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

15 departures available

May - September

Starting from

€400

Per person

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4.8

Grand Tour of June 2nd: Elba, Corsica and Capraia

Italy: Tuscany

5 days - 4 nights

One departure available

May - June

€555

€472

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

6 departures available

July - August

Starting from

€1,052

€999

Per person

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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure - cook on board

Italy: Tuscany

6 days - 6 nights

3 departures available

August

Starting from

€1,600

Per person

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Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

11 departures available

May - October

Starting from

€275

€248

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

3 departures available

September

Starting from

€441

€419

Per person

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5.0

Weekend only four guests - Elba Island

Italy: Tuscany

2 days - 2 nights

3 departures available

March - April

Starting from

€260

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

3507 reviews

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Experience the Befana as you have never seen it before... by boat!

01/14/2026

federico b.

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Italy

Beautiful 4 relaxing days despite the adverse weather, the legendary Francesco solved with trips to beautiful and really interesting places, excellent crew immediately close-knit.
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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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