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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 51 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

51

experiences

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4.9

Super!

2 June sailing on the island of Elba

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€315

€350

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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8 travellers

€297

€330

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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8 travellers

Starting from

€261

€290

Per person

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5.0

Island of Capraia sailing and wild nature

Duration:

4 days - 4 nights

Italy:

Tuscany

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4 travellers

€405

€450

Per person

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4.9

Super!

Easter sailing between the islands: Elba and Capraia

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€356

€395

Per person

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4.9

Super!

25 April between the island of Giglio and Elba

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€356

€395

Per person

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4.9

Super!

1st May of Gran Vela: Elba, Corsica and Capraia

Duration:

5 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€428

€475

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€324

€360

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

Give this experience a try!

€419

€465

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€630

€700

Per person

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4.9

Super!

Long weekend between Elba and Capraia, from Thursday to Sunday

Duration:

3 days - 3 nights

Italy:

Tuscany

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2 travellers

Starting from

€369

€410

Per person

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April 25 in the Tuscan Archipelago: between Elba, Giglio and Argentario

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€437

€460

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

3118 reviews

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Capraia and Totani, let's go!

11/10/2024

Pablo C.

-

Italy

Ci siamo trovati molto bene con Ivo: skipper professionale, cuoco provetto e persona gioviale con tanto da raccontare! La sua barca è in ottime condizioni e ben pulita. Torneremmo volentieri in barca con lui.
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Capraia: squid, walking and sailing!

11/4/2024

camilla t.

-

Italy

Alessandro è stato molto carino, gentile e disponibile ! Consigliatissimo :)
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Capraia and Totani, let's go!

11/4/2024

MATTEO R.

-

Italy

Skipper molto esperto, preciso e disponibile. Ottimo cuoco e pescatore!! Molto attento (anche troppo) alla cura della sua barca e alla sicurezza dell’equipaggio. Qualche costo extra (cambusa a forfait e tesseramento asd) da mettere in conto, ma nel complesso, consigliato!!
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Offshore and Night Navigation Course between Elba, Corsica and Capraia

10/22/2024

Marcello F.

-

Italy

Esperienza semplicemente fantastica e formativa!

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