225

experiences

225

experiences

4.9

The Maddalena Archipelago by sail.

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

+35 travellers

have booked

Starting from

€650

Per person

4.5

1 Week Professional Catamaran Training - Cagliari Sardinia

Duration:

7 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€1,532

Per person

A week in the pristine waters of Lampedusa, Linosa and Lampione

Duration:

6 days - 7 nights

Italy:

Pantelleria and Lampedusa

Give this experience a try!

€800

Per person

4.8

Scopello, San Vito and Egadi: friends, good food sailing

Duration:

6 days - 7 nights

Italy:

Aegadian islands

+10 travellers

have booked

Starting from

€551

€580

Per person

4.6

Ponza and its wonders

Duration:

7 days - 6 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€665

€700

Per person

5.0

North/East Sardinia and South Corsica on a sailing boat with gourmet cuisine

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Katie H.

has booked

€1,000

Per person

5.0

Aeolian Islands on a sailing boat, an exaggerated holiday!

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

+6 travellers

have booked

Starting from

€425

Per person

4.8

ONE WAY Aeolian Islands by catamaran with hostess - from Palermo to Lipari

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

+2 travellers

have booked

€1,000

Per person

4.7

Cilento by Catamaran

Duration:

6 days - 7 nights

Italy:

Campania

+12 travellers

have booked

Starting from

€750

Per person

5.0

Exclusive itinerant route: Catania - Taormina - Tropea - Aeolian Islands

Duration:

8 days - 8 nights

Italy:

Sicily

Give this experience a try!

€799

Per person

4.8

The Egadi Islands as you've never seen them before on a 16-meter boat with hostess

Duration:

6 days - 7 nights

Italy:

Aegadian islands

+37 travellers

have booked

Starting from

€799

Per person

4.6

Sicily on a Sailing Boat in the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

+4 travellers

have booked

Starting from

€519

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

10893 reviews

Easter on the Island of Elba

04/22/2024

Antonios S.

Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza

Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!

Luxury sailing in the Gulf of Poets

04/15/2024

Antonio C.

Italy

Giornata splendida, mare e barca perfetti, altissimo valore aggiunto l’equipaggio, simpatico gentile preparato ma soprattutto disponibile, e Costanza ottima cuoca, esperienza fantastica, da ripetere!!

Veleggiata verso il farò di Cecina con Aperitivo a bordo

04/11/2024

maurizio r.

Italy

Grazie per la bella domenica di relax in barca Maurizio e Giuliana

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!