experiences

4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

December

Starting from

€300

€270

Per person

4.8

Super!

Relax alle Eolie con stile - Hostess Inclusa!

Italy: Aeolian Islands

7 days - 7 nights

One departure available

December

Starting from

€525

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 Italy

13857 reviews

2 June: Whale watching expedition with WWF guide on an 18-meter schooner

06/8/2026

Giovanna G.

A fantastic experience for anyone who loves the sea and wants to discover more about its marine life.

Midweek special between Capraia and Northern Corsica

06/7/2026

DANIELA C.

Thank you very much, Marco! You are an attentive, kind and always available skipper. From the first moment you manage to make everyone feel welcomed and at ease, sharing your beautiful boat with great generosity. Your experience and expertise convey safety and serenity, allowing everyone to fully enjoy every moment of navigation. The boat is perfect, spotless and equipped with every comfort. You know how to choose the best routes and spectacular destinations. Thanks also to my travel companions for the pleasant company.

June 2 long weekend on a catamaran in the Cinque Terre

06/7/2026

LUCA M.

what can I say ... formally it was only 96 hours along the Ligurian Levante ... but on the sea time passes along like the waves and on board Cassiopeia navigation envelops you as gently as the wind towards the coast ... But what turned a long weekend into a special experience was a set of ingredients... a nice crew with intelligent children attracted more by the sea than by a tablet ... A comfortable and spacious catamaran ... but above all Antonio, a captain who makes the difference by pampering the crew, preparing delicious food and always sailing in total safety: absolutely recommended!

Midweek special between Capraia and Northern Corsica

06/7/2026

Silvia G.

Thank you Marco, you were an excellent skipper, you told us so many interesting things, you led us safely to beautiful places.,Waking up in the morning and swimming in an emerald bay, all for us, is an unforgettable experience! Thanks also to all the travel companions who helped make this trip magical.....and thanks especially to [hidden]!

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!