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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 78 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!

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!

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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4.9

Super!

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

July

€395

€375

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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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

September

Starting from

€430

€409

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

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€420

€399

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

3198 reviews

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Weekend on Elba Island

07/8/2025

Giovanna B.

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Italy

Weekend in barca a vela splendido! Tempo ottimo, vele spiegate e piacevoli compagnie . Anthony è skipper molto capace e sempre attivo oltre ad avere un sense of humour vincente!!! Ha cercato sempre di soddisfare ogni richiesta , ha dato indicazioni sui luoghi visti e sulla vita di barca, E' simpaticissimo e .... non ultimo.... un ottimo chef! Ha sempre cucinato piatti gustosi e vari, curandone anche la presentazione !!! E pensare che si i è trovato a bordo vegani , intolleranti al pesce e altro!
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Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

07/8/2025

sonia s.

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Italy

-ho trascorso con Paolo e Bianca una vacanza stupenda . Loro sono gentilissimi simpaticissimi Bianca è una cuoca bravissima. Sono molto disponibili . La mia prima esperienza in barca a vela è stata piacevolissima. Ho visto posti stupendi, calette che altrimenti non avrei potuto vedere se non in barca . Consiglio vivamente una vacanza con Paolo e Bianca
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Weekend of sailing and relaxation on Elba

07/8/2025

Andrea P.

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Italy

Complimenti a Jo …. preparato, disponibile e cordiale. Solo due giorni ma sufficienti per staccare la spina! Consigliato !
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Weekend of sailing and relaxation on Elba

07/7/2025

Carlo R.

-

Italy

Esperienza fantastica, ottima compagnia, bella barca, skipper eccezionale sempre gentilissimo e disponibile. TOP

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