experiences

5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

October

€337

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

One departure available

October - November

€583

Per person

5.0

Super!

The Squid Festival in Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€350

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

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

€300

Per person

4.9

Super!

The most important squid festival in the world - Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€310

Per person

4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

One departure available

October

€190

Per person

4.9

Super!

Long weekend at the Capraia Squid Festival

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€350

Per person

4.7

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

October

Starting from

€200

€180

Per person

4.9

Weekend of relaxation and fun from Genoa

Italy: Liguria

2 days - 2 nights

3 departures available

October - November

Starting from

€260

€247

Per person

5.0

Weekend in Tuscany between Argentario and Giglio Island

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

4.8

Feast of the squid island of Capraia.

Italy: Tuscany

3 days - 2 nights

One departure available

October

€300

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 - Yacht sailing holidays & skippered tours in Italy

13745 reviews

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

Relaxing weekend between Portovenere and the 5 Terre

10/21/2025

Manuela S.

Italy

Fully satisfied Advice to live a unique experience.

A day sailing in the fantastic Gulf of Trieste

10/20/2025

Monica C.

Italy

The skipper Paolo simply fabulous. The super cozy and high-performance boat. We had a beautiful, immersive experience and learned even a minimum basis of sailing concepts

We have known the Aeolian Islands for 20 years. - Live them with us.

10/20/2025

Marco F.

Italy

Pasquale is a profound lover and connoisseur of the Aeolian Islands. Beyond the experience at sea, it also suggests excursions and places to visit on land

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!