Homepage cover
logo

Log in

Sailboat yacht sailing holidays & tours in Italy

Discover more than 297 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€700

Per person

cover image
avatar image

4.5

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

Per person

cover image
avatar image

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€600

€570

Per person

cover image
avatar image

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

August - October

Starting from

€590

Per person

cover image
avatar image

4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€795

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

cover image
avatar image

5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€690

Per person

cover image
avatar image

4.7

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

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

Starting from

€1,041

Per person

cover image
avatar image

4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,000

Per person

cover image
avatar image

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

August - September

Starting from

€1,150

€1,035

Per person

cover image
avatar image

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,100

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€1,052

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 - Sailboat yacht sailing holidays & tours in Italy

12982 reviews

Sailing in the magical Sardinia of the South

07/8/2026

Cristina B.

-

US

This sailing trip was everything I dreamed it would be. Gianluca is an incredibly experienced Captain, who made us feel totally safe, and comfortable and he was so generous with his energy, to sail whenever possible and to create the most memorable experience for his guests. Every stop on our trip was beautiful and unique. I feel very lucky that my first sailboat experience was with this captain!
avatar image

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

07/7/2026

Giuseppe I.

-

GB

It was a fantastic weekend: super comfortable boat and skipper always attentive to the needs of the group, which allowed us to live a wonderful experience,

Weekend at the Marine Protected Area of the Tremiti Islands

07/7/2026

Giovanna N.

-

IT

It was our first experience on a sailing boat and, in addition to a nice and close-knit group of friends, we were lucky enough to meet an experienced and competent skipper. The outward crossing was completely under sail and, although the sea was a bit rough, he spent the best of his experience to make the navigation as stressful as possible for those of us who were at his first experience. Marco turned out to be a person attentive to our needs and every need and very pleasant entertaining us with his fascinating stories of the sea, the history of the Tremiti islands over the centuries and night observation of the constellations. A wonderful experience that we hope to repeat. See you soon and thank you again for everything Joan and Evelin

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

07/7/2026

Davide C.

Fantastic experience thank you 🙏

Customer Support

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!

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!

Italy: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964