header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Italy

Discover more than 19 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!

The Squid Festival in Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€320

Per person

cover image
avatar image

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

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

4.9

Super!

Long weekend at the Capraia Squid Festival

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€350

Per person

cover image
avatar image

4.8

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

5.0

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

One departure available

November

€99

Per person

cover image
avatar image

4.9

Weekend of relaxation and fun from Genoa

Italy: Liguria

2 days - 2 nights

4 departures available

October - November

Starting from

€260

€247

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

€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

4.0

Sagra del totano a Capraia 2025

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€390

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

€110

Per person

cover image
avatar image

5.0

Squid Festival 2025 on a sailing boat

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€390

€351

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

13745 reviews

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.
avatar placeholder

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
avatar placeholder

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

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