Homepage cover
sailsquare logo

Yacht sailing holidays & skippered tours in Italy

Discover more than 34 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!

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

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

May - July

Starting from

€689

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

3 departures available

June - July

Starting from

€625

Per person

cover image
avatar image

4.9

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

4 departures available

May - July

Starting from

€950

Per person

cover image
avatar image

4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

May - July

Starting from

€600

Per person

cover image
avatar image

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

€1,540

€1,463

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

5 departures available

May - July

Starting from

€600

€540

Per person

cover image
avatar image

4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

June

€360

Per person

cover image
avatar image

4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

4 departures available

June

Starting from

€430

€409

Per person

cover image
avatar image

5.0

Super!

Weekend Garda Lake 

Italy: Lake Garda

2 days - 2 nights

One departure available

May

€189

Per person

cover image
avatar image

5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

One departure available

June

€69

Per person

cover image
avatar image

4.8

Super!

Pontine Blue - Midweek Escape

Italy: Pontine Islands

4 days - 3 nights

5 departures available

June - July

Starting from

€210

Per person

cover image
avatar image

5.0

Super!

Afternoon sailing and barbecue evening

Italy: Lake Garda

1 day - 0 nights

One departure available

June

€135

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

13747 reviews

avatar placeholder

North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine

10/25/2025

Teresa B.

-

Germany

We were very lucky to spend 7 days with Bledar on his sailboat around Sardinia and Corsica and it was unforgettable! Every day, Bledar surprised us with new, freshly prepared culinary highlights - fresh, creative and prepared with a lot of love. He took care of us touchingly, left nothing to be desired and led us to the most beautiful bays, islands and snorkeling spots. We got to know wonderful people and thanks to his warm nature, everything felt like a vacation with friends. This week was the perfect mix of relaxation, adventure and enjoyment. It was the best holiday we have ever had. Thank you, dear Bledar, for this magical time! ❤️⛵️ Tuttepossible!
avatar placeholder

Barcolana weekend in Trieste and surroundings.

10/24/2025

Marilisa V.

-

Italy

Marino skipper of great experience and sympathy; Super event and experience just as much!
avatar image

Weekend in Capraia, the island with timeless sunsets

10/22/2025

Don D.

-

Italy

Great weekend !! Sailing until the last breath, all with a good skipper and also crew
avatar placeholder

Relaxing weekend between Portovenere and the 5 Terre

10/21/2025

Manuela S.

-

Italy

Fully satisfied Advice to live a unique experience.

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