Homepage cover
logo

Log in

Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 39 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

Per person

cover image
avatar image

4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

3 departures available

September - October

€650

Per person

cover image
avatar image

5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

September

€250

Per person

cover image
avatar image

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

cover image
avatar image

5.0

Midweek Tuscan archipelago

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€500

Per person

cover image
avatar image

4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

Starting from

€300

€270

Per person

cover image
avatar image

4.9

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

2 departures available

August - September

Starting from

€650

Per person

cover image
avatar image

4.9

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

September

€390

Per person

cover image
avatar image

4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

cover image
avatar image

4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

€700

Per person

cover image
avatar image

4.8

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

€361

Per person

cover image
avatar image

4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€325

€309

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 - Sailboat yacht sailing holidays & tours in Tuscany

3831 reviews

avatar image

Midweek on Elba, from Monday to Thursday

08/29/2026

Nicoletta G.

-

IT

Moments of pure happiness and lightheartedness with the sea in their eyes. [hidden] is not only a cozy and comfortable boat, it is much more than that. Paolo turned out to be an experienced, ironic, brilliant Commander, with a contagious laugh, able to handle any situation in the best way and who faces the worst storms with lucidity and cold blood. With him and [hidden] you get on great! Thank you [hidden], thank you Commander and thank you to the amazing SDV crew, who helped make these days superb! ⛵️❤️

Midweek on Elba, from Monday to Thursday

08/29/2026

Katia F.

-

IT

From strangers to crew we set off for a wonderful day in the middle of the sea, guided by a special Komandante. Uncorking bottles of Bubbles at sunset and sing at the top of their lungs with the bow towards the sea shouting to the world that they want a reckless Life. I'm back home and the first thing I want to do is press Rewind to relive every single moment of this Wonderful because even among strangers, as in fairy tales, music and the sea are enough to feel good⛵️🎶❤️ Brava Katia, great choice 🥰

Midweek on Elba, from Monday to Thursday

08/28/2026

Loriana V.

-

IT

Wonderful experience. Paolo is not only an experienced commander, ready to manage, to "dive" into every new unforeseen event, but he is one of us and this makes the difference. When the goal becomes just a detail. Grating ❤️

Midweek on Elba, from Monday to Thursday

08/28/2026

Luca C.

-

IT

Captain Paul V. made the experience unique! Professional, experienced.

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!

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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