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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 42 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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4.7

Week between the Tuscan Islands and North Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

Starting from

€600

Per person

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4.9

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

7 departures available

September - October

Starting from

€275

€248

Per person

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4.6

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

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

€419

Per person

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4.9

Super!

6 days of Elba, Capraia and Corsica

Italy: Tuscany

6 days - 5 nights

One departure available

August - September

€750

Per person

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4.9

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

October - November

€299

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

September

€280

Per person

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4.9

Super!

Weekend on a sailing boat between Capraia and Elba

Italy: Tuscany

2 days - 2 nights

One departure available

September

€350

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 - October

Starting from

€240

€228

Per person

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4.9

Super!

Trekking weekend on the Island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

September

€340

€323

Per person

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4.9

Super!

Weekend on a sailing boat between Capraia and Elba

Italy: Tuscany

2 days - 2 nights

One departure available

August

€500

Per person

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4.9

Super!

A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

September - October

€220

Per person

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4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

8 departures available

September - December

€190

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

3411 reviews

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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

08/27/2025

Ilaria D.

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Italy

The sailing trip between the Island of Elba, Capraia and northern Corsica was extraordinary. Sailing between these islands is an experience that combines the charm of unspoiled nature, breathtaking landscapes, the intense colors of the sea and sky, the silences interrupted by the sound of the sea and the wind and the pleasure of discovering something new every day. The people on board were the element that made this holiday special. Living in small spaces was an experience that further enriched the group: the restricted sharing of environments and the need to collaborate created a special bond between all of us, transforming every moment into an opportunity for discussion, friendship and lots of laughter. The skill of the skipper Alessandro was essential to make this adventure even more pleasant and safe, allowing us to relax and fully enjoy the trip. I recommend this experience to anyone who wants to experience the sea in an authentic way! A trip that will remain in the heart!
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Weekend Elba o Capraia

08/27/2025

Chiara B.

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Italy

Excellent first experience for me, who had never traveled on a sailboat: the boat beautiful and in perfect condition - also thanks to the precision of the skipper Nicola, always careful that everything was in order and working; the company really excellent; Nicola a true professional and excellent company.
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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

08/27/2025

Davide R.

-

Italy

Beautiful holiday despite the weather conditions were not the best. As soon as the weather permitted, we sailed great thanks to the skill of our skipper Fabio, very prepared.
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Sailing in the enchanting scenery of Elba, Giglio and Giannutri

08/26/2025

Arianna D.

-

Italy

A spectacular week in wonderful company. Despite the bad weather a couple of days Marco took us to special places, [hidden] entered my heart! Definitely to be redone :)) Fair winds!

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