header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Italy

Discover more than 12 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

4.8

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

November

€299

Per person

cover image
avatar image

4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

November

€190

Per person

cover image
avatar image

4.8

Super!

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€420

Per person

cover image
avatar image

4.8

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€300

Per person

cover image
avatar image

3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

One departure available

November

Starting from

€600

Per person

cover image
avatar image
Day Cruise- Tour Golfo Dei Poeti

Italy: Liguria

1 day - 0 nights

18 departures available

October - November

€86

Per person

cover image
avatar image
A terrace overlooking the sea: a day to discover the Gulf of Naples

Italy: Naples & Amalfi Coast

1 day - 0 nights

3 departures available

October

Starting from

€110

€88

Per person

cover image
avatar image
Daily sailing trip off the coast of beautiful Pisa

Italy: Tuscany

1 day - 0 nights

7 departures available

October - November

Starting from

€115

Per person

cover image
avatar image

4.2

Weekend of theoretical and practical course

Italy: Liguria

2 days - 1 night

5 departures available

November

€250

Per person

cover image
avatar image
Week-end a Vela in Liguria

Italy: Liguria

3 days - 2 nights

5 departures available

October - November

€250

Per person

cover image
avatar image

4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

November

€650

€585

Per person

cover image
avatar image

4.1

East Coast of Sicily From Taormina to Portopalo. Cook on board

Italy: Sicily

6 days - 7 nights

5 departures available

November - December

€625

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

13632 reviews

avatar placeholder

Week-end all'Elba - Hostess a bordo

09/17/2025

Riccardo A.

-

Italy

I had a very good time and Vittorio is very nice
avatar image

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

09/17/2025

Sarah N.

-

Italy

I had an unforgettable sailing holiday thanks to our skipper! Always professional, helpful and attentive to everyone's needs, he made us feel safe at all times. He was able to combine competence and sympathy, making navigation relaxing and pleasant. He took us to wonderful bays, told us curiosities and made us experience the sea in an authentic way. The Aeolian Islands are a beautiful experience that I recommend to anyone who wants to discover sailing with the guidance of a reliable and passionate skipper. Thank you Nicola!!
avatar image

South Corsica: blue seen from a sailboat

09/17/2025

anna m.

-

France

Boarding Kalekoy means letting yourself be lulled by a hammock suspended in the blue, pampered by a crew that thinks of everything so that the journey is always pleasant and safe. There is meticulous attention to every detail, which, together with the incredible beauty of the places, makes this experience unforgettable and fosters the desire to leave, again and again ... The days are marked by delicious aperitifs, mouth-watering lunches and swims at breakneck speed (there is also the "tender" option, eh!) to reach beaches that have the unparalleled seduction of unspoiled places; In case of capricious weather, a walk on the cliffs overlooking the sea has the power to make you smile again and gives back to the eyes the enchantment of landscapes that even under a blanket of clouds have a charm of their own. Thanks to the "little" big Luigi: excellent steward. Alessandro, impeccable second on board, you are a very precious resource for Kalekoy and for all those who venture there: thank you and keep it up! Thanks for everything to Leonardo, an experienced captain, whose gaze and confident gestures immediately inspire blind trust. I would be delighted to be able to return to the waves aboard Kalekoy one day!
avatar placeholder

Egadi paradise for sailing and snorkeling

09/17/2025

MARYLENE E.

-

France

When we arrived in Marsala, we waited several hours on the dock before putting our luggage in the boat. Some went shopping. The next morning, a morning for the fishmonger. I would have preferred an organization that reduced the time of the races and a welcome drink at the finish (more friendly after hours of travel)more information on the organization of the trip and more communication from the skipper during the trip.

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