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Crewed yacht sailing holidays & tours in Tuscany

Get on board on a crewed sailing holiday in Tuscany for the most relaxed time ever.

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

June - September

Starting from

€793

€714

Per person

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5.0

Super!

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

4 departures available

July - August

Starting from

€1,100

Per person

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5.0

Super!

A fantastic day on a boat in the blue sea of Tuscany

Italy: Tuscany

1 day - 0 nights

38 departures available

June - August

Starting from

€125

Per person

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5.0

Super!

Tuscany & Corsica in the program pure energy on 18 meters of splendor !!

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€990

€891

Per person

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5.0

Super!

Week in Corsica with wellness programme

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,559

Per person

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4.3

Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms

Italy: Tuscany

5 days - 6 nights

10 departures available

June - September

Starting from

€750

Per person

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4.9

Argentario, Giglio and Giannutri Week - Hostess on board

Italy: Tuscany

6 days - 7 nights

One departure available

July

€1,060

Per person

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5.0

Sailing adventures: summer sailing camps IN ENGLISH - for children 10-14 years old

Italy: Tuscany

5 days - 5 nights

2 departures available

June - July

€800

Per person

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5.0

Overwhelmed by an unusual destiny in the blue sea of Corsica

Italy: Tuscany

6 days - 7 nights

One departure available

August - September

€700

Per person

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4.3

Elba a sea of Izola - Hostess on board (3Cab/3Bagni) - ALL INCLUSIVE

Italy: Tuscany

3 days - 3 nights

One departure available

June

€450

Per person

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5.0

Sailing to discover the Tuscan Archipelago

Italy: Tuscany

7 days - 7 nights

One departure available

July - August

€1,150

€1,035

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 - Crewed yacht sailing holidays & tours in Tuscany

157 reviews

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Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

06/9/2025

Elisa P.

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Italy

Riccardo è uno skipper professionale e attento, cucina divinamente. La barca è ordinata e pulita e la compagnia è stata perfetta!
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June 2nd long weekend in the Tuscan Archipelago with PROFESSIONAL CHEF SKIPPER

06/4/2025

Angelo V.

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Italy

Riccardo è stato favoloso: skipper molto abile, simpatico e socievole, ti mette subito a tuo agio. E' cuoco e si occupa sempre lui di cucinare e gestire la cucina (spesa, sistemazione, pulizia): cucina molto bene, è stato un plus notevole nella vacanza! Inoltre preferisce andare sempre a vela ed usare pochissimo il motore, è stata una magnifica esperienza!
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June 2nd long weekend in the Tuscan Archipelago with PROFESSIONAL CHEF SKIPPER

06/3/2025

Gabriele R.

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Italy

Avventura unica! Davvero un'esperienza molto bella. Abbiamo trovato un bel gruppo e ci siamo divertiti. Lo skipper, Riccardo, è una persona super disponibile, super piacevole e un gran cuoco 😉 Voto 10
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Weekend gourmet con chef e degustazione di vini all'Isola d'Elba

05/28/2025

Laura B.

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Italy

Bellissimo fine settimana, Lorenzo è uno skipper molto competente e affidabile, cosa da non sottovalutare quando si va per mare, barca pulitissima, menù molto curati e vari, consiglio caldamente questa esperienza.

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