header cover
logo

Log in

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.

cover image
avatar image

4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

Per person

cover image
avatar image

4.9

Super!

Sailing day in the Gulf of Follonica

Italy: Tuscany

1 day - 0 nights

One departure available

June

€100

Per person

cover image
avatar image

4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

4 departures available

June - September

Starting from

€300

Per person

cover image
avatar image

4.8

Super!

Capraia and northern Corsica: sailing in the sea of cetaceans

Italy: Tuscany

7 days - 7 nights

One departure available

July - August

€600

Per person

cover image
avatar image

4.7

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

Italy: Tuscany

4 days - 4 nights

One departure available

September

€567

€539

Per person

cover image
avatar image

4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

Per person

cover image
avatar image

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

€342

Per person

cover image
avatar image

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

cover image
avatar image

4.8

Super!

Cruise course Pisa-Naples navigation

Italy: Tuscany

10 days - 10 nights

One departure available

June - July

€1,200

Per person

cover image
avatar image

5.0

Super!

Argentario, Giannutri and Giglio Island on wooden schooner

Italy: Tuscany

3 days - 2 nights

One departure available

June

€300

Per person

cover image
avatar image

4.9

Super!

Magical night on the Island of Elba

Italy: Tuscany

1 day - 1 night

One departure available

June

€145

Per person

cover image
avatar image

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

Why book a holiday with Sailsquare?

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

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

3780 reviews

avatar image

Weekend among the most beautiful coves of Elba

06/2/2026

Gianmario B.

-

IT

We spent the weekend with two professional, attentive and caring people towards guests. Carmen and Marco are people who enter into symbiosis right away, giving full availability to make you feel at ease and as if you have always known them. Boat in excellent condition, nothing is missing, you obviously need a spirit of adaptation not being in your bathroom at home. The relationship that is created during the experience with all the guests is also beautiful, in this experience we met wonderful people. We recommend everyone and Fair Winds

Weekend among the most beautiful coves of Elba

06/1/2026

Francesca C.

-

IT

I had never had a multi-day experience on a boat, let alone on a sailboat, but I couldn't imagine a better experience than the one Marco and Carmen offered me. The [hidden] is comfortable and equipped and Marco and Carmen make it a home for the time of the experience, managing to create cohesion and participation in the group. On the [hidden] you are a crew, you learn, you collaborate and you get to know each other. The itinerary is beautiful, with crystal clear water and incredible views. I saw dolphins for the first time up close, very close. I saw fish and birds whose names I knew and for the first time I slept lulled by the waves. I really spent three beautiful days, with a nice crew that immediately, thanks above all to the energy transmitted by Carmen and Marco, cohesive and collaborated for the success of the trip. So what can I say, fair winds! I really think I will make it again and I will certainly recommend it to everyone!
avatar image

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

06/1/2026

Luca N.

-

IT

Very nice experience! The boat, Princess [hidden], spacious and also comfortable, with everything we needed. Matteo super available to any request. Luca, the skipper who accompanied us, very prepared, great enthusiast explained the sailboat and its secrets, patient and great company made us feel at home. We sailed in the southern part of the Elba coast, with various stops for swimming and in the evening we slept at anchor in the Gulf of Laconella. Nice experience!
avatar image

Weekend Elba o Capraia

05/26/2026

Sabrina S.

-

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.

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Call us at

+44 20 3514 4220

Read our

Contact & Support

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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 (550)Whole boat with skipper (380)Family sailing cruises (60)Cooking service onboard (60)WWF Sailing Cruises (35)Courses & regatta (30)Catamaran (30)Day trips (20)Sport & wellness (15)All inclusive (5)

Other travel ideas

Sailboat (599)Whole boat with skipper (467)Cooking service onboard (123)Catamaran (91)All inclusive (46)Courses & regatta (30)Family sailing cruises (30)Exotic destinations (26)Day trips (23)Offshore (20)

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Sailsquare

Travellers

Providers

Follow us on

FB IconIG IconYT Icon

Secure payments

MastercardVisaGoogle PayApple Pay

Top Destinations

Top Travel Ideas

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964