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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.

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4.7

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

Italy: Tuscany

6 days - 5 nights

6 departures available

July - August

Starting from

€750

€638

Per person

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

Italy: Tuscany

6 days - 5 nights

4 departures available

July - September

Starting from

€1,000

€850

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

4 departures available

July - September

Starting from

€380

€342

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

3 departures available

July

Starting from

€395

€356

Per person

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4.8

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

Italy: Tuscany

2 days - 2 nights

5 departures available

May - June

Starting from

€250

€225

Per person

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4.9

Super!

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

May - September

Starting from

€305

€275

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

5 departures available

August - September

Starting from

€700

€630

Per person

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4.9

Unforgettable Catamaran Cruise in Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

11 departures available

June - August

Starting from

€1,093

€984

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

8 departures available

July - September

Starting from

€293

€264

Per person

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5.0

Sailing for a weekend at Elba Island - Spring/Summer

Italy: Tuscany

3 days - 2 nights

3 departures available

June

Starting from

€290

€261

Per person

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4.8

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

Italy: Tuscany

7 days - 6 nights

One departure available

August

€950

€855

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

11 departures available

June - September

Starting from

€793

€714

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

3363 reviews

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Weekend of relaxation and fun to discover the Island of Elba

05/14/2025

Claudia D.

-

Italy

Edoardo persona super disponibile e alla mano, esperienza in barca meravigliosa con panorami mozzafiato, super consigliato!
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Weekend in Capraia, the island with timeless sunsets

05/12/2025

Stefano F.

-

Italy

Marco è un vero appassionato di barche e, per questo, ti fa assaporare ogni momento che si trascorre a bordo
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1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

05/8/2025

Maria Pia D.

-

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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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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