experiences

5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

November

Starting from

€650

€585

Per person

4.8

Super!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

November

Starting from

€590

Per person

4.9

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

November

€299

Per person

4.9

Super!

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€420

Per person

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

One departure available

November

Starting from

€600

Per person

Daily sailing trip off the coast of beautiful Pisa

Italy: Tuscany

1 day - 0 nights

7 departures available

October - November

Starting from

€115

Per person

4.2

Weekend of theoretical and practical course

Italy: Liguria

2 days - 1 night

5 departures available

November

€250

Per person

4.0

East Coast of Sicily From Taormina to Portopalo. Cook on board

Italy: Sicily

6 days - 7 nights

5 departures available

November - December

€625

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

12350 reviews

Pontine Islands aboard a splendid 16-meter sailboat

06/20/2025

Francesco V.

Italy

Esperienza fantastica, ben organizzata. Sono veramente soddisfatto dell'itinerario e dell'equipaggio che si è creato. Coppia Skipper bellissima e super disponibile

Weekend of relaxation and fun from Genoa

06/20/2025

Cristina B.

Italy

Come prima esperienza in barca a vela direi super positiva

Sailing weekend in Liguria

06/18/2025

Giampietro D.

Italy

Barca confortevole, pulita e in ottime condizioni. Ottimo weekend anche se le condizioni meteo non erano delle migliori ed Alessandro ha sempre gestito ogni manovra con grande destrezza e sicurezza oltre a regalare momenti di ottima compagnia e simpatia. Consigliatissimo!!!

Aeolian Islands - Large and new catamaran equipped with every comfort

06/18/2025

Anton R.

Germany

Very nice boat, comfortable, own bathroom, nice bath. The islands, Volcano hike, Stromboli Lava seeing at night and the Island villages are all very beautiful. Maurizio is a nice, relaxed skipper. Can definitely recommend :)

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 2035144220

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!