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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 43 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 Northern Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

€700

Per person

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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

Per person

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4.9

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

2 departures available

August - September

Starting from

€650

Per person

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4.8

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

€361

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

Starting from

€300

€270

Per person

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4.8

Super!

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

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

3 departures available

September - October

€650

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

September

€250

€238

Per person

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4.7

Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

Italy: Tuscany

4 days - 4 nights

One departure available

September

€567

Per person

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5.0

Midweek Tuscan archipelago

Italy: Tuscany

4 days - 4 nights

3 departures available

August - September

€500

Per person

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4.9

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€390

€351

Per person

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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.

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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

3787 reviews

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Weekend Elba or Capraia

08/22/2026

Sara S.

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IT

Perfect weekend, Sebastiano skipper super helpful. Beautiful experience!
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Quattro giorni all'Elba - Hostess a bordo

08/21/2026

Andrea M.

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IT

It was a beautiful holiday. Comfortable boat with private bathroom for each cabin. Comfortable outdoor spaces considering the complexities of the sailboat. Vittorio and Giulia were excellent hosts. Vittorio's experience and Giulia's kindness pampered us for the entire holiday.
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Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

08/21/2026

Barbara R.

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IT

Jo is a fantastic commander, capable, helpful and great company. I had a lot of fun, lots of swimming in wonderful places, starry nights, laughter, good food and even some nice upwinds. I recommend to everyone and fair winds!
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The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/21/2026

Arturo M.

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IT

Everything perfect. I recommend everyone to try this experience. I will definitely stay here again

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