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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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4.9

Super!

Leave everything for the Island of Elba

Italy: Tuscany

2 days - 2 nights

4 departures available

June - July

Starting from

€280

Per person

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4.9

Super!

Weekend of relaxation and fun to discover the Island of Elba

Italy: Tuscany

3 days - 2 nights

4 departures available

June - September

Starting from

€380

€304

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

7 departures available

June - July

Starting from

€490

€466

Per person

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4.9

Super!

Magical night on the Island of Elba

Italy: Tuscany

1 day - 1 night

One departure available

June

€145

Per person

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5.0

Super!

Discovering Elba... and maybe even Capraia!

Italy: Tuscany

3 days - 3 nights

One departure available

July

€410

€369

Per person

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5.0

Super!

Long live Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

June

€400

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

6 departures available

July - September

Starting from

€200

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

2 departures available

June

Starting from

€380

€361

Per person

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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

6 departures available

July - September

Starting from

€400

€360

Per person

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4.7

Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

Italy: Tuscany

4 days - 4 nights

2 departures available

June - September

Starting from

€567

€539

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

4 departures available

June - August

Starting from

€700

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

3777 reviews

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Weekend Elba o Capraia

05/26/2026

Sabrina S.

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IT

Fantastic holiday with the guidance of Francesco who involved us a lot in managing the destination and the boat, taught us how the sea can create bonds.
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Weekend among the most beautiful coves of Elba

05/26/2026

Samantha G.

-

IT

We were literally welcomed by Marco and Carmen, it seemed to have known them for a lifetime. Evidently they attract beautiful people because the rest of the crew was also wonderful. Beautiful sailings (you can move as little as possible), but managed in full comfort. Finally, an excellent knowledge of the places that does not hurt and makes you enjoy unforgettable coves
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Tuscan archipelago between nature and relaxation

05/26/2026

Francesco D.

-

IT

Riccardo is a true professional, a reliable person and also an excellent travel companion. He was able to perfectly interpret our requests with availability and empathy, becoming in a few minutes a friend, an accomplice in adventures, a trusted person, as if we had always known each other ... Not just a skipper! Thanks to Riccardo and "[hidden]" for this wonderful experience!
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Weekend among the most beautiful coves of Elba

05/26/2026

Alessio B.

-

IT

It is difficult to put into words the beauty of the three days spent on the [hidden] with Marco and Carmen. I was with my girlfriend and together with 4 other girls met on the morning of boarding we created a beautiful close-knit group with whom it was wonderful to share laughter and moments that will remain in my heart. I can only spend wonderful words about Marco and Carmen, they are two people who immediately make you feel at home and are really professional and prepared in the maritime world and in sailing in general. I recommend everyone to try an experience with them because I assure you you will not regret it, on the contrary. The [hidden] (name of the sailboat) is comfortable and does not let you miss anything, it took us to wonderful coves and made us visit postcard ravines on the island of Elba. At the time of the final goodbyes we were all excited. I am sure of one thing, we will not lose sight of each other because you are 'magical' and pure people. Alex

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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 (545)Whole boat with skipper (385)Family sailing cruises (60)Cooking service onboard (60)Catamaran (35)WWF Sailing Cruises (35)Courses & regatta (30)Day trips (20)Sport & wellness (15)All inclusive (5)

Other travel ideas

Sailboat (620)Whole boat with skipper (482)Cooking service onboard (129)Catamaran (90)All inclusive (48)Family sailing cruises (33)Courses & regatta (32)Exotic destinations (28)Day trips (26)Offshore (20)

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