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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 92 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!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

June - September

Starting from

€793

€714

Per person

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4.9

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

Italy: Tuscany

7 days - 7 nights

3 departures available

July - August

Starting from

€700

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

7 departures available

July - September

Starting from

€293

€264

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

July

€395

€375

Per person

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4.8

Barefoot holiday: Weekend on Elba on a 17m boat

Italy: Tuscany

2 days - 2 nights

3 departures available

June - July

€330

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

€342

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€700

€665

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

July - September

Starting from

€1,041

€989

Per person

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4.9

Super!

Weekend on Elba Island

Italy: Tuscany

3 days - 2 nights

One departure available

July

€290

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

6 departures available

July - September

Starting from

€430

€409

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

10 departures available

June - October

Starting from

€260

€247

Per person

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4.9

Super!

A week Sailing in Tuscany and Corsica

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

Starting from

€870

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

3165 reviews

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Weekend a Capraia, trekking e natura

06/10/2025

Kristian G.

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Italy

Esperienza positiva e skipper disponibile
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Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

06/9/2025

Elisa P.

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Italy

Riccardo è uno skipper professionale e attento, cucina divinamente. La barca è ordinata e pulita e la compagnia è stata perfetta!
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Midweek special on the island of Elba, 2 nights

06/9/2025

Emilio B.

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Italy

Marco, valutazione da 1 a 10 gli do 11. Persona gentile, disponibilissimo, sempre pronto ad aprire le vele in tutte le condizioni. Barca non nuovissima, ma pulita ed ordinata. Mi è piaciuto molto e lo consiglio assolutamente a chi piace viaggiare in barca a vela.
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Weekend in the Wonderful Tuscan Archipelago

06/7/2025

Alessandro T.

Prima esperienza in barca a vela, è andata benissimo. Bello l’itinerario, barca splendida e in ottime condizioni, compagnia ottima. Un grazie speciale allo skipper Alberto per aver organizzato tutto alla perfezione.

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