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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 113 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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4.9

Super!

Sailing day in the Gulf of Follonica

Italy: Tuscany

1 day - 0 nights

One departure available

June

€100

Per person

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4.9

Super!

Easter between sun, sea, wind, sailing and relaxation

Italy: Tuscany

4 days - 4 nights

One departure available

April

€480

Per person

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5.0

Super!

A day of sun and swimming

Italy: Tuscany

1 day - 0 nights

One departure available

June

€70

Per person

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4.9

Super!

Christmas with your... Easter with whoever you want: get on board with us!

Italy: Tuscany

4 days - 4 nights

One departure available

April

€400

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

13 departures available

May - September

Starting from

€400

Per person

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4.9

Super!

Discovering the Island of Elba: 3 days of sea, wind and sun

Italy: Tuscany

3 days - 3 nights

8 departures available

April - June

Starting from

€400

€360

Per person

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4.8

Super!

May 1st long weekend between Elba and Capraia - 2 boats in company

Italy: Tuscany

3 days - 3 nights

One departure available

April - May

€350

Per person

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4.9

Super!

Weekend of relaxation and fun to discover the Island of Elba

Italy: Tuscany

3 days - 2 nights

4 departures available

June - September

Starting from

€380

€304

Per person

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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

€409

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

6 departures available

April - May

€390

€351

Per person

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4.9

Super!

A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

April

€220

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

3510 reviews

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Weekend a Capraia, trekking e natura

03/24/2026

Francesco V.

Francesco and Marco are two great professionals, but above all two great travel companions! Highly recommended experience
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Weekend a Capraia, trekking e natura

03/23/2026

Niccolò S.

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Italy

Francesco and Marco are two very prepared skippers and the perfect people with whom to embark on this type of adventure. Highly recommended.
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Midweek special on the island of Elba, 2 nights

01/24/2026

Sara M.

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Italy

I left with my brother: there were 7 of us, plus Marco. It was our first boat experience and we couldn't ask for anything better! Marco was extremely kind, helpful and attentive to every detail. The combination of the boat excursion and the trekking on the island was simply fantastic, everything impeccably organized. In addition, there was also the opportunity to enjoy free time in total relaxation. I absolutely recommend this experience with Marco!
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Experience the Befana as you have never seen it before... by boat!

01/14/2026

federico b.

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Italy

Beautiful 4 relaxing days despite the adverse weather, the legendary Francesco solved with trips to beautiful and really interesting places, excellent crew immediately close-knit.

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