header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Italy

Discover more than 28 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

4 departures available

July - August

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

5 departures available

July - August

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

July - August

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

4 departures available

July - August

Starting from

€600

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

4 departures available

July - August

Starting from

€600

€540

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

5 departures available

July - August

Starting from

€430

€409

Per person

cover image
avatar image

4.9

Super!

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

Italy: Tuscany

7 days - 7 nights

4 departures available

July - August

Starting from

€700

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!

A bordo con lo chef alle Egadi

Italy: Aegadian islands

7 days - 7 nights

3 departures available

July

Starting from

€800

€720

Per person

cover image
avatar image

4.9

Super!

Life-changing experiences: Four days in the Pontine Islands with photographer on board

Italy: Pontine Islands

4 days - 3 nights

5 departures available

June - July

Starting from

€450

€428

Per person

cover image
avatar image

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

July - August

Starting from

€793

€714

Per person

cover image
avatar image

4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

July

Starting from

€272

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