experiences

4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€590

Per person

4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

5 departures available

October - November

Starting from

€1,420

Per person - min 2 pax

4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

October

Starting from

€950

Per person

4.6

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

Starting from

€300

€270

Per person

4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September - October

Starting from

€650

€585

Per person

4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

One departure available

September - October

Starting from

€420

€399

Per person

4.7

Weekend of sea and colors between Ischia, Procida and Vivara

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

€234

Per person

4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

October

Starting from

€230

Per person

4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

October

Starting from

€230

Per person

4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

Starting from

€600

€540

Per person

4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October

Starting from

€540

€513

Per person

4.8

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

October

Starting from

€242

€218

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

13880 reviews

June 2nd long weekend between Ponza, Palmarola, Zannone and Ventotene

06/10/2026

Donatella L.

Extraordinary, welcoming skippers and also creative cooks! Highly recommended!

In the blue of Capri and the infinity of the Amalfi Coast

06/10/2026

Antonio D.

We stayed on GEM for the weekend in Capri. Hospitality and Top Professionalism! The skipper is a prepared and kind person, the boat is very well maintained and with all the necessary comforts. Experience to be redone, congratulations to Spasso a Vela.

Weekend in Ischia and Ventotene: History and Nature

06/10/2026

Camilla P.

It was my first sailing holiday and I couldn't wish for a better experience! The skipper Umberto exceptional: helpful and attentive even before departure, he made us feel immediately at ease once on board. The group was created right away and the four days in those enchanting islands literally flew by. An unforgettable experience that I absolutely recommend!

Long weekend of June 2nd to discover the coves of the islands of Elba

06/10/2026

Riccardo C.

Great Marco and great Luciano. Always ready to raise the sails

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!