experiences

4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

25 departures available

May - October

Starting from

€600

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

18 departures available

May - October

Starting from

€689

Per person

5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

2 departures available

October

€337

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

14 departures available

June - September

Starting from

€625

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

2 departures available

October - November

€583

Per person

5.0

Super!

The Squid Festival in Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€320

Per person

4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

June

€360

Per person

4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

5 departures available

October - December

€190

Per person

4.9

Super!

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

Italy: Tuscany

4 days - 3 nights

16 departures available

May - September

Starting from

€430

€409

Per person

4.9

Super!

Traveling and Dreaming in the Gulf of Poets - All inclusive

Italy: Liguria

2 days - 2 nights

One departure available

May

€360

Per person

4.9

Super!

Taste of the sea between the island of Capraia and Northern Corsica

Italy: Tuscany

7 days - 7 nights

9 departures available

July - September

Starting from

€700

Per person

5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

One departure available

October

€59

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

12654 reviews

Fantastic BARCOLANA: Racing in safety and joy!

10/15/2025

Giulia B.

Italy

Beautiful experience with nice and heterogeneous crew! Paolo is a professional person who guided and taught us, transmitting his passion for sailing. Advised!

Barcolana weekend in Trieste and surroundings.

10/15/2025

Barbara M.

Italy

MARINO fantastic skipper, he pampered us ( swim in the blue included), he was very helpful for all our whims. The Barcolana is a grandiose spectacle, seen from the sea it excites a lot, if you like sailing you can not avoid being there at least once. The kitten on board, Lightning is a very sweet travel companion. After the restyling in the shipyard, the catamaran will also be up to the task.

Weekend in Capraia, the island with timeless sunsets

10/14/2025

Gloria G.

Italy

Wonderful weekend. Super skipper! Very professional and helpful, he entertained us by telling us many curiosities about sailing and the places visited. The fantastic boat with ample space and equipped with everything you need! 100% recommended both the skipper and the destination!

Barcolana 2025: experience the most beautiful regatta with me!

10/14/2025

Gabriele I.

Italy

Very good Gianni

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!

Italy: the best travel ideas

Sailboat (340)Whole boat with skipper (275)Sport & wellness (45)Cooking service onboard (45)Family sailing cruises (40)Catamaran (40)Day trips (25)All inclusive (25)Courses & regatta (10)

Other travel ideas

Sailboat (126)Whole boat with skipper (95)Cooking service onboard (41)Catamaran (36)Exotic destinations (34)All inclusive (32)Family sailing cruises (11)Sport & wellness (10)Courses & regatta (7)Day trips (5)