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Yacht sailing holidays & skippered tours in Tuscany

Discover the magic of sailing holidays in Tuscany! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

51

experiences

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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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4.8

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!

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!

Sunny weekend on Elba from Friday to Sunday

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€261

€290

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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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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4.6

Whale watching cruise with WWF guide between Tuscany and North Corsica

Duration:

6 days - 7 nights

Italy:

Tuscany

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37 travellers

Starting from

€989

€1,041

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 - Yacht sailing holidays & skippered tours in Tuscany

3347 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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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
uide to sailing vacations with children

Tuscany: the best travel ideas

Other travel ideas

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