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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 76 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

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

Italy: Tuscany

6 days - 6 nights

2 departures available

August - 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

5 departures available

July - August

Starting from

€650

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

September

€293

€264

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

6 departures available

July - September

Starting from

€1,041

€989

Per person

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5.0

Capraia and northern Corsica sailing

Italy: Tuscany

6 days - 6 nights

6 departures available

August - September

Starting from

€750

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

€240

€228

Per person

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4.9

Super!

A week Sailing in Tuscany and Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

July

€870

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago

Italy: Tuscany

3 days - 2 nights

One departure available

September

€170

€153

Per person

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4.8

Corsica and Tuscany in flotilla, boats of 16 and 17 meters.

Italy: Tuscany

6 days - 7 nights

3 departures available

August

Starting from

€900

Per person

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4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July - August

Starting from

€1,052

€999

Per person

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4.8

Super!

Wandering in the Tuscan Archipelago on a comfortable 15-meter boat

Italy: Tuscany

6 days - 7 nights

One departure available

August

€990

Per person

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4.6

Week between the Tuscan Islands and North Corsica

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€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

3213 reviews

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

07/18/2025

Maurizio M.

-

Italy

Fabio and Angela are two excellent hosts. Of those who make the boat completely available to guests, to the point of making them the real owners by placing themselves at their complete disposal. Our desire - expressed from the beginning - was to "go sailing", carrying the boat and actively participating in the maneuvers. A will fully supported and guaranteed by Fabio, purist of sailing and good Master advocate of practice and putting himself to the test! We learned so much and had a lot of fun. Added to this is the good company, the beautiful (many) chats in the evening in the cockpit in the roadstead, with Angela's good food and a good glass of wine resulting from a careful and complete galley. We will definitely return to sail with them and [hidden], a boat that really knows how to give great emotions. Too bad only a day and a half lost for a great libecciata that forced us into port, ruining the initial intentions but allowing, thanks to Fabio, a nice complete circumnavigation of the island of Elba, wonderful even in its most hidden coves. Thanks guys.
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Set Sail with Family: 5 Days of Comfort & Adventure Around Elba Island

07/17/2025

LARA A.

-

Italy

An unforgettable experience. The holiday, although short, was really fun, relaxing, and above all it served to make us understand how much we love being on the boat, and therefore we will definitely do it again. The captain was fantastic, he always kept the whole crew happy, he proposed and shared with all the guests experiences and moments that we will not forget. Matteo is absolutely professional and attentive to everything, as well as nice. He also has a lot of patience with children, so I rate 5 stars! I recommend this experience to anyone who wants to try sailing with children. Thank you Matteo and thanks to Sailsquare for the professionalism and punctuality shown. Good bye Lara
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Long weekend among the queens of the archipelago - Elba and Capraia

07/16/2025

ALESSANDRO Z.

-

Italy

Edoardo, skipper, really smart person. Helpful, present, very professional, very discreet... everything you would expect from a real Skipper! We have a long way to Elba. Too bad that due to bad weather we were unable to go to Capraia. but the itinerary had been planned from the start. The return with full sails with fair wind made us have a lot of fun, excellent mixed and international company .. Top
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Weekend of sailing and relaxation on Elba

07/16/2025

Luca B.

-

Italy

Very positive experience, Josuah TOP skipper, comfortable boat and very well maintained. Definitely to be repeated 😊

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