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Yacht sailing holidays & skippered tours in Tuscany

Discover the magic of sailing holidays in Tuscany! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

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New

Day trip to the island of Elba - Porto Azzurro

Italy: Tuscany

1 day - 0 nights

One departure available

August

€80

Per person

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New

Slow sailing in Portoferraio - daily trimaran trip

Italy: Tuscany

1 day - 0 nights

2 departures available

August

€80

Per person

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4.7

The Island of Elba, to make you live a special experience!

Italy: Tuscany

6 days - 5 nights

5 departures available

July - August

Starting from

€700

Per person

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4.9

Leave everything for the Island of Elba

Italy: Tuscany

2 days - 2 nights

One departure available

July

€320

Per person

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4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

August

€510

Per person

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4.9

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€390

€351

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

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4.0

An unforgettable week in the Tuscan Archipelago

Italy: Tuscany

7 days - 7 nights

3 departures available

August

€1,230

Per person

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4.9

Face to face with the Archipelago(s)

Italy: Tuscany

2 days - 2 nights

One departure available

July - August

€279

Per person

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4.8

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

3 departures available

August - September

Starting from

€390

€371

Per person

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5.0

Between Capraia and Northern Corsica: sailing, crystal clear sea and freedom

Italy: Tuscany

7 days - 6 nights

2 departures available

August - September

€990

€891

Per person

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5.0

New

Island of Elba on a sailing boat: coves, crystal clear sea and relaxation

Italy: Tuscany

7 days - 7 nights

One departure available

August

€835

€752

Per person

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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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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 - Yacht sailing holidays & skippered tours in Tuscany

3939 reviews

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Long weekend among the wonders of Elba and Capraia

07/28/2026

Luca C.

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IT

Very pleasant experience indeed! I spent a wonderful sailing holiday on the Island of Elba with skipper Marco. Right from the start he proved to be competent, helpful and always attentive to the needs of the crew. The atmosphere on board was relaxed and fun, and we visited beautiful places. It was an experience

Skipper e Hostess - Weekend full comfort isola d'Elba

07/28/2026

umberto c.

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IT

We spent a wonderful weekend on board the [hidden] in the company of Francesco and Valeria, a super crew! They took us to some of the most beautiful coves and beaches on the Island of Elba weather permitting. In fact, the weekend was not accompanied by perfect weather but, thanks to their experience and attention to safety and our comfort, they gave us great tranquility and we were able to enjoy the sea, the boat and sailing. Francesco, an experienced skipper, always has everything under control. Both then welcomed us with a hospitality and sympathy that made us feel as if we were friends. The menu proposed and then prepared by Valeria is really good. We hope to repeat the experience soon!
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Weekend on the Island of Elba

07/28/2026

Mattia B.

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IT

Vittorio is a very prepared skipper on the Island of Elba. We appreciated him both for the human side and for his culinary skills: it is not easy to find a skipper who is passionate about cooking. Despite the less than perfect weather, he managed to accommodate almost all our wishes. The boat has a wide stern and is therefore spacious and welcoming.
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Weekend on the island of Elba: among dolphins, enchanting bays and relaxation

07/28/2026

alfredo v.

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IT

The experience overall was pleasant from the point of view of the company: The captain is an experienced, sociable and definitely very talkative person, able to entertain the group with continuous stories and conversations. That said, expectations were different. In two nights and half a day of navigation we visited only two beaches on Elba, both easily accessible by land. I expected that a sailing experience would offer the opportunity to discover more hidden coves and places that are difficult to access, which represent the real added value of this type of holiday. Also considering that the island has two sides and that it is also possible to adapt the itinerary according to the wind, I think there was room to explore different areas and make the most of the time spent sailing. Overall, it is an experience that I would recommend especially to those looking for a convivial experience, with aperitifs, chats and moments of sociality on board, more than to those who want to experience sailing as an opportunity to contemplate authentic and less frequented places, for those who love the sea at 360 degrees.

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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
uide to sailing vacations with children

Tuscany: the best travel ideas

Sailboat (345)Whole boat with skipper (230)Cooking service onboard (50)Family sailing cruises (35)Sport & wellness (25)Catamaran (20)Day trips (20)WWF Sailing Cruises (20)Courses & regatta (15)

Other travel ideas

Sailboat (392)Whole boat with skipper (318)Cooking service onboard (98)Catamaran (72)All inclusive (49)Exotic destinations (25)Family sailing cruises (19)Courses & regatta (19)Offshore (17)Sport & wellness (17)

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