Homepage cover
logo

Log in

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!

Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

6 departures available

October - November

€150

Per person

cover image
avatar image

4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€300

Per person

cover image
avatar image

4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

One departure available

October - November

€350

Per person

cover image
avatar image

4.5

Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€290

Per person

cover image
avatar image

4.1

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

November

Starting from

€275

€248

Per person

cover image
avatar image

4.7

Squid Festival 2023! - Capraia Isola

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€250

Per person

cover image
avatar image

5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

One departure available

October - November

Starting from

€430

Per person

cover image
avatar image

5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

One departure available

October

€215

Per person

cover image
avatar image

5.0

New

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€250

Per person

cover image
avatar image

5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

One departure available

October - November

€723

Per person

cover image
avatar image

5.0

New

Basic and advanced sailing courses

Italy: Liguria

2 days - 1 night

2 departures available

November

Starting from

€220

€198

Per person

cover image
avatar image

4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

5 departures available

November - December

€1,400

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

15136 reviews

avatar image

Sailing in the magical Sardinia of the South

10/8/2026

Sebastiano F.

-

IT

I was looking for a super sea to continue improving my sailing knowledge... With the staff of [hidden] I was able to find all this combined with irony and lightness that never hurt! P.S. Extremely recommended for sailing enthusiasts who want to grow Thank you very much to Gianluca, Valeria and Michela!
avatar image

Experience the sea in October!

10/6/2026

Luigi V.

-

IT

Super experienced and helpful skipper. He helped us learn the basics of sailing and life on a sailing boat. Great chef skills!

Aeolian Islands: between sea and authentic flavours

10/5/2026

Giorgia P.

-

IT

Wonderful experience!! Well maintained boat; very comfortable to have a bathroom available in each cabin. The tour allowed us to visit enchanting places, swim in crystal clear waters and enjoy excellent fish dishes and exquisite desserts. Carlo, our skipper (Merchant Marine Officer) has put his skills and abilities at our disposal. End of September was a good choice, always sunny without ever sultriness, the right water temperature for wonderful baths. Happy and fun company, with Lorenzo I was able to share culinary secrets in the kitchen. With a bit of luck, we sailed for a stretch in the company of a pod of dolphins. A holiday to be repeated and recommended. Giorgia P.
avatar image

Maddalena Archipelago, southern Corsica: wonderful Sardinia

10/5/2026

Michelle B.

-

US

Mossimo and Valentina were superb! Incredible sailing, delicious food, taking us to stunning locations it far exceeded my expectations! I highly recommend sailing with them. Cheers! Michelle

Customer Support

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!

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