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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 101 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

101

experiences

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5.0

Super!

May Day long weekend to discover the islands of Elba and Capraia

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€380

€460

Per person

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5.0

Super!

Settimana in barca a vela tra Toscana e Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€1,275

€1,500

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

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17 travellers

Starting from

€342

€380

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Duration:

3 days - 3 nights

Italy:

Tuscany

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19 travellers

€356

€395

Per person

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5.0

Talamone and Giglio Sailing Weekend with Geniale Vento, Mare, Libertà

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€405

€450

Per person

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4.8

Vacanza a piedi nudi: Weekend tra Elba e Capraia su barca 15m

Duration:

2 days - 2 nights

Italy:

Tuscany

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27 travellers

Starting from

€225

€250

Per person

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4.9

Super!

Sunny weekend on Elba from Friday to Sunday

Duration:

3 days - 2 nights

Italy:

Tuscany

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35 travellers

Starting from

€275

€305

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Duration:

7 days - 6 nights

Italy:

Tuscany

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9 travellers

Starting from

€630

€700

Per person

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5.0

Super!

Weekend Elba o Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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34 travellers

Starting from

€264

€293

Per person

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4.8

Let's enjoy the wonders of the Tyrrhenian Sea - Elba, Capraia and Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

€855

€950

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Duration:

6 days - 7 nights

Italy:

Tuscany

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115 travellers

Starting from

€714

€793

Per person

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Women's sailing

Duration:

2 days - 1 night

Italy:

Tuscany

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5 travellers

Starting from

€177

€197

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

3138 reviews

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25 April long weekend between Capraia and Northern Corsica

04/29/2025

VERONICA D.

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Italy

Un esperienza meravigliosa. Complimenti al capitano, bravissimo nel creare gruppo e un ottimo amico di bordo. A presto Francesco
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25 April long weekend between Capraia and Northern Corsica

04/28/2025

Luigi C.

-

Italy

Bellissimo weekend all'insegna del sole, del mare, della vela e della buona compagnia. Le mete della destinazione sono stupende, la barca é comodissima e Francesco é uno skipper esperto sempre attento alle esigenze dell'equipaggio. Ottimo cuoco, grande appassionato di vela e persona gradevolissima, ci ha fatto sentire a casa insegnandoci allo stesso tempo tante nozioni sulla vela, con passione e simpatia. Torneremo sicuramente a trovarlo!
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The sea and sailing in winter, 2 days on the island of Elba

01/1/2025

Alessio B.

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Germany

Ivo, il capitano, è un appassionato velista che ha saputo rendere molto dinamica la veleggiata. L‘ uscita è stata anche molto istruttiva grazie volontà di Ivo di trasmettere la sua conoscenza. Esperienza assolutamente da rifare.
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The sea and sailing in winter, 2 days on the island of Elba

12/31/2024

Enzo M.

-

Italy

Devo dare ragione a chi sostiene che navigare in inverno ha un fascino particolare. Siamo stati baciati dal un sole caldo per due giorni con un vento che ci ha permesso una navigazione top. Barca molto tecnica ideale per fare tanta esperienza. Con Ivo abbiamo trascorso dei giorni che portiamo nel cuore, tante emozioni, tante informazioni e la condivisione degli spazi quotidiani con un uomo davvero speciale che ci ha accolti a bordo come amici datati. Esperienza super positiva.

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