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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 81 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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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

Starting from

€793

€714

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

July - September

Starting from

€293

€264

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

4 departures available

July - September

Starting from

€1,041

€989

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

2 departures available

July

Starting from

€395

€375

Per person

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4.9

Super!

Tuscan Archipelago: An Oasis of Blue between Sea and Nature

Italy: Tuscany

6 days - 5 nights

6 departures available

July - August

Starting from

€650

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

5 departures available

July - October

Starting from

€260

€247

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€700

€665

Per person

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4.7

Whale watching cruise with WWF guide between Tuscany and Northern Corse

Italy: Tuscany

6 days - 7 nights

7 departures available

July - September

Starting from

€1,041

€989

Per person

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5.0

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

July - August

Starting from

€430

Per person

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4.9

Super!

A week Sailing in Tuscany and Corsica

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

Starting from

€870

Per person

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4.6

Week between the Tuscan Islands and North Corsica

Italy: Tuscany

7 days - 6 nights

6 departures available

July - September

Starting from

€600

Per person

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4.8

Super!

Elba, Capraia, Corsica and basic sailing course

Italy: Tuscany

6 days - 6 nights

One departure available

August

€600

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

3191 reviews

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Weekend a Capraia, trekking e natura

07/5/2025

Sonia G.

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Italy

Non ero mai salita su una barca... e stata la mia prima volta... devi dure che è stata un esperienza bellissima... un weekend indimenticabile.. che porterò sempre nel mio cuore.... lo skipper Francesco una persona formidabile....simpatico...gentile.... ..disponibile... e soprattutto molto bravo anche in cucina... ci ha sorpreso con i suoi primi veramente molto buoni... Sicuramente un esperienza da ripetere...
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Midweek special between Capraia and Northern Corsica

07/5/2025

PASQUALE L.

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Italy

Professionalità, sicurezza, adattabilità.
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Midweek special between Capraia and Northern Corsica

07/4/2025

Daniela M.

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Italy

Una crociera bellissima in un mare meraviglioso, equipaggio simpaticissimo e uno skipper eccezionale.: Marco è un esperto di mare e di vela, ma anche una persona attenta alle esigenze degli ospiti a bordo e.... (ciliegina) sempre pronto ad issare le vele!!! Grazie Marco, vacanza da 10 cum laude!
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Whale watching cruise with WWF guide between Elba, Pianosa and the canyons of Corsica

07/2/2025

Veronica S.

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Italy

Era proprio quello di cui avevi bisogno! Tanto mare, nuove esperienze e persone meravigliose! Silvia,Paolo e Dario, che ci hanno accompagnato in questo viaggio, si sono dimostrati super prepararti, professionali e hanno fatto di tutto per rendere questa esperienza perfetta! C'è stata tanta collaborazione tra di noi, dal tenere in ordine la barca, al cucinare tutti insieme, al decidere giorno per giorno quello che sarebbe stato il programma della giornata. Non mi sono sentita semplice una cliente ma parte integrante dell'equipaggio, il che ha reso tutto ancora più autentico! Abbiamo anche avuto molta fortuna con il meteo e abbiamo fatto un sacco di avvistamenti di vario tipo :) consiglio questa esperienza a tutti quelli che amano il mare, che hanno voglia di imparare e esplorare 😍

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