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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 33 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!

Midweek Tuscan archipelago

Italy: Tuscany

4 days - 4 nights

One departure available

September

€500

Per person

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4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€280

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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5.0

Super!

Squid Festival in Capraia with a professional skipper and chef

Italy: Tuscany

2 days - 2 nights

One departure available

October

€250

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

One departure available

September

€317

Per person

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4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

June

€625

Per person

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5.0

Capraia and Elba Island - Sun, Sea and Fun!

Italy: Tuscany

4 days - 3 nights

2 departures available

September - October

€400

Per person

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

€325

€309

Per person

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4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€299

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

27 departures available

January - December

Starting from

€300

€270

Per person

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4.7

Squid Festival- Capraia Island

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€250

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

3886 reviews

North Corsica & Tuscan Archipelago: we love to travel a lot

09/19/2026

francesca vera p.

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IT

Beautiful holiday, lovely places. Thanks to Marco and his travel companions!
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Five days barefoot between Tuscany and Corsica

09/19/2026

Mariella D.

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IT

The holiday went well. Matteo was helpful. For 4 nights, arriving in Corsica becomes very long the navigation and inevitably the possibilities of swimming are reduced. Then the cost of fuel can affect a lot

Five days barefoot between Tuscany and Corsica

09/18/2026

daniela s.

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IT

It was an unforgettable experience, the travel companions were delightful, efficient and fun. Lorenzo, the captain was splendid in managing the crew lightly and equally splendid in managing the storm while sailing

Weekend Elba or Capraia

09/16/2026

Mauro G.

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IT

Fun boat in sailing. Too bad for the weather conditions of the previous days that made the sea not optimal. Still pleasant experience throughout. I recommend, for the optimal training of the guest crew, to plan the mood of the experience in advance. Thanks again to skipper Nicola who made us experience the thrill of upwind ⛵😊👍🏻

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