215

experiences

4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

3 departures available

May - July

Starting from

€950

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

May - July

Starting from

€1,260

€1,197

Per person

4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

May - July

Starting from

€590

Per person

4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

June - July

Starting from

€680

Per person

4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

June - July

Starting from

€550

€523

Per person

4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

June - July

Starting from

€1,052

€999

Per person

5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

June - July

Starting from

€689

Per person

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

June - July

Starting from

€825

€743

Per person

4.6

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

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

May - July

Starting from

€650

€585

Per person

4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

One departure available

June

Starting from

€999

€949

Per person

4.7

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

Italy: Naples & Amalfi Coast

2 days - 2 nights

One departure available

June

Starting from

€320

€272

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

2 departures available

June

Starting from

€230

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

13782 reviews

May 1st long weekend between Elba and Capraia - 2 boats in company

05/6/2026

Massimo A.

Italy

Matteo is the most knowledgeable person on sailing I have ever met, and his boat has a comfort far superior to normal charters, having 18 meters in length. Perfect organization and reliability. The tour of Elba is easy but wonderful

May Day between Elba and Capraia

05/6/2026

Silvia V.

Italy

Very competent skipper, with a choice of stages always careful and well thought out to avoid possible inconveniences and please everyone. Thanks to the good weather and the favorable wind, it was the perfect combination of sailing and moments of relaxation and conviviality."

1st May: Whale watching expedition with WWF guide on an 18-meter schooner

05/5/2026

Patrizia A.

Everything was beautiful, except for the management of drinking water which seriously worried me.

Weekend in the Pontine Islands

05/5/2026

Antonella M.

Italy

We spent 3 beautiful days! Fabio is an attentive and nice skipper.

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!