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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.

86

experiences

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4.7

Two boats walking on the island of Elba: the magic of the roadstead!

Duration:

6 days - 5 nights

Italy:

Tuscany

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Lorena L.

Starting from

€638

€750

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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18 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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23 travellers

Starting from

€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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29 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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32 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

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5.0

Weekend gourmet con chef e degustazione di vini all'Isola d'Elba

Duration:

3 days - 2 nights

Italy:

Tuscany

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valerio p.

Starting from

€315

€350

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

3144 reviews

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1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

05/8/2025

Maria Pia D.

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Italy

TOP
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A long weekend of sea and freedom from Argentario to Elba

05/7/2025

RAFFAELE L.

-

Italy

Per il ponte del 1 maggio 2025 siamo stati a bordo di OTHELLO per una minicrociera di 4 giorni. La barca è molto bella, elegante ma estremamente funzionale e curata, comoda e con molte dotazioni. I bagni riservati nelle singole cabine sono stati per noi un dettaglio importante, come gli ampi spazi anche all’interno. L’atmosfera da subito è stata accogliente e simpatica grazie ad Enrico che si è dimostrato per tutta la vacanza uno skipper straordinario sia per le sue doti tecniche che come persona. Tonia, la compagna di Enrico, ha completato la splendida atmosfera respirata sulla barca con la sua simpatia, empatia e accoglienza. Il gruppo quindi si è amalgamato in modo molto speciale. Un meteo favorevole ci ha permesso di svolgere il programma previsto: Argentario, isola del Giglio ed Isola D’Elba. Enrico, con la sua esperienza ha organizzato le tratte in modo sicuro, considerando venti e correnti. E’ stato molto bravo a coinvolgerci in tutte le fasi della navigazione, a secondo dei livelli di conoscenza e di interesse individuali. Mia moglie ed io consigliamo vivamente un’esperienza con Enrico e Tonia, che con tutti i loro racconti ci hanno lasciato una grande voglia di tornare su OTHELLO e di visitare tanti altri luoghi.
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Weekend in Capraia, the island with timeless sunsets

05/7/2025

Leonardo R.

-

Italy

Marco è un grande appassionato di vela ed un professionista del settore della nautica. Lo capisci subito perché ti coinvolge nel suo mondo sin dal primo minuto e condivide con gli ospiti le sue esperienze e le attività di bordo, sempre e solo in piena sicurezza. Sono stati due giorni divertenti; lo consiglio a chi ha voglia anche di imparare e di rilassarsi allo stesso tempo!
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Weekend in Capraia, the island with timeless sunsets

05/7/2025

Simone S.

-

Italy

Un’ottima esperienza, Marco un grande skipper appassionato del mare!

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