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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 24 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

24

experiences

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Magical weekend on Giglio Island

Duration:

2 days - 2 nights

Italy:

Tuscany

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5 travellers

have left

€252

€280

Per person

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5.0

Long weekend at the Capraia Squid Festival

Duration:

3 days - 3 nights

Italy:

Tuscany

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2 travellers

have left

€371

€390

Per person

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4.6

Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

Duration:

3 days - 2 nights

Italy:

Tuscany

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7 travellers

have left

€275

€290

Per person

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4.9

Capraia Squid Festival - Hostess on board

Duration:

2 days - 2 nights

Italy:

Tuscany

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Manuel

has left

€250

Per person

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4.8

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Duration:

3 days - 3 nights

Italy:

Tuscany

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4 travellers

have left

€361

Per person

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4.9

Three days at the Capraia Squid Festival - Hostess on board

Duration:

3 days - 3 nights

Italy:

Tuscany

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2 travellers

have left

€375

Per person

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3.7

Squid Festival in Capraia 2024

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€480

Per person

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3.7

Four days of sailing school in Punta Ala

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€580

Per person

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4.9

Week-end all'Elba - Hostess a bordo

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€250

Per person

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Portovenere - Ligurian and Tuscan Archipelago

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€350

Per person

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4.9

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

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8 travellers

have left

€290

Per person

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4.8

Super!

Weekend - L’Elba... i profumi, il mare e i suoi colori!

Duration:

2 days - 2 nights

Italy:

Tuscany

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28 travellers

have left

€180

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

3115 reviews

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On board a classic sailing ship between Elba-Capraia-Corsica

09/30/2024

Simone B.

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Italy

La settimana è andata benissimo, gli Skipper Paolo e Tommaso sono stati fenomenali, ci hanno coinvolto nelle manovre di vela ⛵️ed è stato interessante ascoltare le loro storie di mare! La barca è ben tenuta e le cabine sono confortevoli. Per ultimo ma non meno importante Tommaso ci ha cucinato da 5 stelle 😋
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Barefoot holiday: Weekend on Elba

09/30/2024

Carlotta G.

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Italy

La vacanza è andata bene, una bella esperienza. Lo skipper molto cordiale e competente. Le uniche note sono: il check in era entro le 20, mentre un gruppo si è presentato con 2 ore di ritardo. L'altra è che mi aspettavo visite a più cale, mentre sono state visitate 2 cale sconosciute e ne primo giorno siamo stati fermi 8 ore, con clima a favore.
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Last sun on Elba - Sailing weekend

09/30/2024

Nadia S.

-

Italy

Paolo....persona squisita e molto professionale, con lui ti senti tranquilla! Grazie della bellissima esperienza! Da rifare molto volentieri!
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Seductive weekend on a sailing boat on the island of Elba

09/30/2024

Francesca M.

Il mio primo weekend in barca a vela è coinciso con l'ultimo giro di boa della MobyDick all'Isola dell'Elba. Grazie all'equipaggio ben assortito e con un ottimo spirito di adattamento, unitamente all'esperienza e all'estro del nostro skipper Luca, posso dire di aver condiviso una bellissima esperienza! Pronta a salpare di nuovo ;)

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