Homepage cover
logo

Log in

Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 33 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

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

3883 reviews

Weekend Elba or Capraia

09/16/2026

Mauro G.

-

IT

Fun boat in sailing. Too bad for the weather conditions of the previous days that made the sea not optimal. Still pleasant experience throughout. I recommend, for the optimal training of the guest crew, to plan the mood of the experience in advance. Thanks again to skipper Nicola who made us experience the thrill of upwind ⛵😊👍🏻

Week between the Tuscan Islands and Northern Corsica

09/16/2026

Rosanna B.

-

IT

Fantastic experience!! Splendid and very comfortable boat, wonderful itinerary!! Francesco is a very prepared, kind skipper, always present and attentive to any problem that may arise. He also knows the places on the itinerary very well and also provides very useful information on how to get around on land... I can only thank him!!
avatar image

Long weekend on Elba: 4 days of sun and sailing

09/16/2026

Arianna G.

-

IT

Four wonderful days, in which the wind and the sea were the setting for an experience that went far beyond the simple holiday. Paolo has been able to create a nice group, while respecting everyone's spaces and times. Always available, attentive to our needs and, above all... always proactive on aperitifs!! We were not looking for a sailing course, but a few days of sea, nature and freedom, and perhaps this is what I take home: the feeling that we too often live in a fast and constructed way, forgetting that sometimes the wind in our faces is enough, to raise our eyes to the sun or the moon and find some peace. Even if... you still haven't found what you are looking for. <3

Wellness, sun, sea and adventure: a weekend full of sailing!

09/15/2026

rosanna n.

-

IT

We had a beautiful we on a sailing boat. Daniele and Maria Pia are wonderful in putting everyone at ease. Excellent company, the itinerary and the food prepared by Pia who is a wonderful cook, able to find any variation she is asked for. Daniele gladly lent himself to a change of cove for an unforgettable swim, due to the headwind compared to the established itinerary. Everything perfect.

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