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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 26 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!

The Squid Festival in Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€320

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

16 departures available

May - September

Starting from

€430

€409

Per person

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4.9

Super!

Taste of the sea between the island of Capraia and Northern Corsica

Italy: Tuscany

7 days - 7 nights

9 departures available

July - September

Starting from

€700

Per person

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4.8

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

Italy: Tuscany

2 days - 2 nights

One departure available

October

€300

Per person

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4.9

Super!

The most important squid festival in the world - Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€310

Per person

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5.0

Super!

Squid Festival in Capraia!

Italy: Tuscany

2 days - 2 nights

One departure available

October

€290

€270

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

4 departures available

October - December

€190

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

12 departures available

June - September

Starting from

€793

€714

Per person

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4.9

Super!

Long weekend at the Capraia Squid Festival

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€350

Per person

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4.8

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

November

€299

Per person

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4.7

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

59 departures available

January - December

Starting from

€200

€180

Per person

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5.0

Weekend in Tuscany between Argentario and Giglio Island

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

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

3501 reviews

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Weekend in Capraia, the island with timeless sunsets

10/14/2025

Gloria G.

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Italy

Wonderful weekend. Super skipper! Very professional and helpful, he entertained us by telling us many curiosities about sailing and the places visited. The fantastic boat with ample space and equipped with everything you need! 100% recommended both the skipper and the destination!
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The sea and sailing in autumn: two days on Elba

10/13/2025

Roberto T.

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Italy

Ivo is a professional skipper. We had a technical outing that was very formative for me and we had fun.
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Weekend Elba o Capraia

10/8/2025

Massimiliano L.

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Italy

First time on a sailing boat, nice experience. Three stars because we could not follow the program due to the weather.
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Long weekend of whale watching with WWF guide on an 18-meter schooner

10/2/2025

Marco C.

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Italy

Unforgettable experience aboard the Schooner Mahayana. An essential and shared life on board. Thanks to Captain Francesco, his crew and WWF guide Ilaria, a serene and pleasant atmosphere was established with all guests from the beginning. Browsing great places. Educational experience on the marine environment with a focus on cetaceans and environmental impact. As a first experience we particularly appreciated the pace of navigation, the life on board and the company.

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