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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 27 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

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4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

3 departures available

October

€200

Per person

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4.8

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

63 departures available

January - December

Starting from

€200

€180

Per person

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4.8

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

October - November

€299

Per person

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4.8

Super!

Weekend - Elba... the scents, the sea and its colors!

Italy: Tuscany

2 days - 2 nights

One departure available

September

€230

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

September

€280

Per person

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5.0

Super!

Weekend of fun and relaxation on a sailing boat on the island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€250

Per person

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5.0

Super!

Transfer to the Island of Elba

Italy: Tuscany

1 day - 0 nights

One departure available

September

€60

Per person

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4.9

Super!

A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

October

€220

Per person

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4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

7 departures available

October - December

€190

Per person

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4.9

Super!

Trekking & Sailing Experience-Weekend lungo a Capraia in compagnia

Italy: Tuscany

4 days - 3 nights

One departure available

September

€440

Per person

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4.8

Super!

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€420

Per person

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4.8

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

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€300

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

3477 reviews

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Trekking and sailing weekend on the island of Elba

09/16/2025

Fabio B.

-

Italy

Ok
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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

09/15/2025

Giulia P.

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Italy

Four boats, two islands, a family: a few points to sum up one of the most beautiful holidays ever. Dinners at anchor under the stars, aperitifs at sunset, naps under the sun. But also coves and wild beaches, sperm whales and unexpected "wild". On board, a lot of sharing that, from the beginning, led us to bond with each other and to make us feel, right from the start, friends since always. A unique experience to experience the sea in a memorable way.
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Weekend on a sailing boat between Capraia and Elba

09/15/2025

Tamara V.

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Italy

Nice very new boat but some amenities were missing. I thought better destinations Good skipper
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Weekend Elba o Capraia

09/15/2025

Valentina N.

-

Italy

Very prepared skipper, fun crew so overall an excellent experience definitely to be repeated.

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