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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 111 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!

1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

Italy: Tuscany

3 days - 3 nights

One departure available

April - May

€430

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

One departure available

July

€590

Per person

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5.0

Super!

Discovering Elba... and maybe even Capraia!

Italy: Tuscany

3 days - 3 nights

One departure available

April

€390

€351

Per person

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5.0

Super!

Discovering the Island of Elba or Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

April - May

Starting from

€249

Per person

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4.9

Super!

A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

April

€220

Per person

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5.0

Super!

Long live Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

June

€400

€360

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

July

€230

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

4 departures available

May - June

Starting from

€250

€238

Per person

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4.9

Super!

Isola del Giglio - Festa dell'Uva e delle Cantine aperte

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

8 departures available

July - September

Starting from

€400

€360

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

3 departures available

June

Starting from

€567

€539

Per person

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4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

€999

€949

Per person

Why book a holiday with Sailsquare?

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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

3516 reviews

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Easter in Capraia and Corsica

04/14/2026

Giunio M.

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Italy

Wonderful days in the company of quiet people and lovers of the sea and sailing
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Offshore and night navigation course on cabin cruisers

04/13/2026

Marco B.

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Italy

Sailing course... but also a holiday. Navigation to Giglio and back via Elba with departure at night. Despite the little wind that blew in those days, Paolo was able to convey notions and make the students practice, all with the utmost sympathy ... Be prepared to be made fun of, especially if you're an engineer.
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Easter on the Island of Elba

04/9/2026

Miriam C.

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Italy

Very pleasant sailing experience. The boat was in good condition. Everything went according to expectations and the navigation was safe and relaxing. The only negative note concerns the owner, Enrico. During communications he was often grumpy, with a rather rigid attitude and not inclined to confrontation. This made the interaction less pleasant, especially at times when more availability and friendliness would have been useful. Overall, I recommend the experience for the quality of the boat and the service at sea, but I suggest the owner to improve the approach with customers to make everything really impeccable.
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Easter in Capraia and Corsica

04/9/2026

Monica L.

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Italy

Weekend absolutely up to expectations. Marco is a trained skipper, with great experience, very helpful, kind and caring towards his crew. His boat is hospitable and excellently cared for by him. All positive!!

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