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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 63 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

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

8 departures available

August - October

Starting from

€230

Per person

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5.0

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

Italy: Tuscany

3 days - 2 nights

One departure available

September

€230

Per person

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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

One departure available

September

€300

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

2 departures available

September

€280

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

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

Super!

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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4.9

Super!

Squid Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October

€280

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

3707 reviews

Midweek getaway between Elba and Capraia

07/31/2026

Francesca G.

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IT

Marco is very competent and knows how to put every person at ease, even those like me who were at their first experience on a sailing boat. The perfect company I found then made the holiday even more beautiful

Corsica & Capraia - only 4 guests - sun adventure & relaxation!

07/31/2026

David C.

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DE

An unforgettable holiday in all respects. The skipper is well trained in the area since he has always frequented it, the boat is well maintained and very comfortable. Luca is always available and attentive to everyone's needs and always makes you feel at ease. Even northern Corsica in July does not have many tourists so you can have a quiet holiday and this is not possible elsewhere. Even with the other passengers I was really lucky.

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

07/30/2026

Giovanna F.

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IT

Beautiful first experience on a sailing boat, with a skipper attentive to the needs of his guests and scrupulous. Livio, known (for me) as "Lucio", in addition to sailing, with his infinite stories makes you fly to spaces and places of other times ... But be careful not to take away the cookies for breakfast, he could get very angry!! Joke: peaceful and very discreet person. See you soon!
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Midweek getaway between Elba and Capraia

07/30/2026

Giulia G.

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IT

This boat experience was positive. Everything was handled well, even the small unforeseen events. Marco was just amazing. Kind, caring and super nice. Also thanks to him we were able to make a super close-knit group.

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