151

experiences

151

experiences

4.9

Between sunsets and aperitifs on a sailing boat

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

€400

Per person

4.9

Weekend at the Pontine Islands: Ponza and Palmarola

Duration:

3 days - 2 nights

Italy:

Pontine Islands

+3 travellers

have booked

Starting from

€240

Per person

5.0

Relaxing weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

+27 travellers

have booked

€265

Per person

4.9

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

+14 travellers

have booked

€269

Per person

4.5

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€269

Per person

5.0

Weekend at the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

+10 travellers

have booked

€313

Per person

Mini-cruise to the Aeolian Islands

Duration:

3 days - 2 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€219

€230

Per person

5.0

Weekend in the coves of Ponza and Palmarola

Duration:

2 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€275

Per person

5.0

Aperitif on a Sailing Boat and - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€90

Per person

5.0

Weekend in Ponza, Palmarola, Ventotene

Duration:

2 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€250

Per person

4.7

Weekend sailing in the Gulf of Naples

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

Starting from

€260

Per person

4.9

Sailing weekend on the Island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

+9 travellers

have booked

Starting from

€250

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

10894 reviews

A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

Italy

Bellissima esperienza, bella gente con uno skipper top!

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!!

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!