header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Italy

Discover more than 143 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

cover image
avatar image

5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

August - September

Starting from

€275

€248

Per person

cover image
avatar image

4.9

Super!

Egadi paradise for sailing and snorkeling

Italy: Aegadian islands

7 days - 7 nights

2 departures available

September

€600

Per person

cover image
avatar image

4.8

Super!

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

Starting from

€240

€228

Per person

cover image
avatar image

5.0

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€583

Per person

cover image
avatar image

4.8

Super!

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€590

Per person

cover image
avatar image

4.9

4 days in the Pontine Islands (sailing school)

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€270

Per person

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

One departure available

August - September

€750

Per person

cover image
avatar image

4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

September

Starting from

€220

Per person

cover image
avatar image

4.8

Super!

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

One departure available

September

€360

€342

Per person

cover image
avatar image

5.0

Super!

Midweek relaxing in the Pontine Mountains

Italy: Pontine Islands

4 days - 3 nights

4 departures available

September - October

Starting from

€337

Per person

cover image
avatar image

4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

€419

Per person

cover image
avatar image

4.6

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

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

September

Starting from

€750

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

13050 reviews

avatar placeholder

Four-day cruise to Elba or Capraia - Hostess on board

08/17/2025

Laura F.

-

Italy

Very nice boat, excellent organization, precise and safe skipper, Giulia great cook
avatar image

Southern Sardinia on a beautiful 16m boat with HOSTESS

08/17/2025

Giorgio D.

Fabio, the skipper, made us live a fantastic holiday by making us visit beautiful places. Fabio is a highly experienced [hidden] who knows how to combine the steering of the boat with grace and attention to guests. Last but not least, Claudia, a great hostess, pampered us by cooking delicious food, presented as you want to a master chef!!! To repeat and that I recommend to everyone! Ps. He also taught us the art of groundbait.
avatar image

A week of sailing and sea life on the island of Elba

08/17/2025

Valentina S.

-

Italy

Thanks to the seafaring experience and the adorable affability of the skipper Luca, we guests (3 strangers) felt at home from day one! It was a real pleasure to experience the sea as much as possible, spending almost always the night in the peaceful roadsteads of Elba. During the trip, Luca showed us the landscapes, history and peculiarities of his beautiful island. Thanks to a bit of favorable wind, we happily sailed during some trips. The best skipper and trump buddy ever! Thank you Luca and Buon Vento 🌬
avatar image

Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms

08/17/2025

Pablo P.

-

Italy

The skipper Fabio proved to be very competent in navigation, a great connoisseur of the winds, and an enthusiastic sailor who allowed us to enjoy the best sailing experience in total safety. The hostess Angela, as well as a talented vice skipper, proved to be kind and welcoming for the entire duration of the experience, making me feel always assisted. Both, in particular, did their utmost with kindness and courtesy to meet all my needs and it is not easy to impress me as positively as they managed to do. Let's say that if it were possible to put six stars... I would have put seven!! We will definitely see each other again!!

Customer Support

nightLifeGeneralInfo

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!

search

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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