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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 86 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

A week Sailing in Tuscany and Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€995

Per person

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4.8

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

One departure available

August

€780

€741

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

One departure available

September

€567

Per person

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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure - cook on board

Italy: Tuscany

6 days - 6 nights

3 departures available

July - August

Starting from

€950

Per person

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4.7

Your office with sea view: midweek between Capraia and Elba

Italy: Tuscany

2 days - 3 nights

One departure available

July

€390

Per person

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5.0

Tuscan Archipelago: night and day sailing

Italy: Tuscany

4 days - 3 nights

2 departures available

August

Starting from

€320

€288

Per person

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4.9

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

Italy: Tuscany

4 days - 3 nights

One departure available

August

€510

€459

Per person

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4.8

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

2 departures available

August - September

Starting from

€410

€369

Per person

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4.0

July... what an Elba! Three days on a sailing boat

Italy: Tuscany

3 days - 3 nights

6 departures available

July - August

Starting from

€349

Per person

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4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

August

€510

Per person

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4.9

Quattro giorni all'Elba - Hostess a bordo

Italy: Tuscany

4 days - 5 nights

One departure available

August

€800

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

Why book a holiday with Sailsquare?

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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

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

3630 reviews

4 Days Argentario-Giannutri-Giglio-Talamone

07/11/2026

Francesca M.

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IT

Tommy is a competent and easygoing skipper! He accompanied us on our first multi-day boat holiday with relaxation, irony and great availability. We met her wonderful family: Sofia and their magnificent "Leonidas"! Thank you for everything. See you next time!!

Midweek getaway between Elba and Capraia

07/11/2026

Simona S.

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IT

Beautiful and highly recommended experience. A real escape from everyday life, to rediscover beauty and slow rhythms. Marco welcoming, nice and safe. Top.

Midweek getaway between Elba and Capraia

07/11/2026

Stefania B.

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IT

Marco was a perfect skipper! For us it was the first time on a sailing boat and he was able to convey his passion as well as the values of this type of holiday to us in an excellent way. He created an ideal atmosphere within the group with particular attention to ensuring every balance always with good humor and sympathy. His exemplary professionalism and great experience as a skipper are indisputable and he gave us confidence and led us to discover unknown coves. Thank you Marco who made us fall in love with sailing!

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

07/11/2026

Debora G.

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IT

Beautiful experience, Luca an excellent skipper who together with Matteo made us discover the most beautiful beaches up to Capraia!

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