Homepage cover
logo

Log in

Yacht sailing holidays & skippered tours in Italy

Discover more than 42 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

4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

5 departures available

October - November

Starting from

€1,640

€1,558

Per person - min 2 pax

cover image
avatar image

4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€590

Per person

cover image
avatar image

4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

October

Starting from

€950

€855

Per person

cover image
avatar image

4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

cover image
avatar image

5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

2 departures available

October

€220

Per person

cover image
avatar image

4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

Starting from

€300

€270

Per person

cover image
avatar image

4.4

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October

Starting from

€540

€513

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

October

Starting from

€230

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

October

Starting from

€230

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

One departure available

September - October

Starting from

€650

€585

Per person

cover image
avatar image

4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

Starting from

€750

€675

Per person

cover image
avatar image

New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

4 departures available

October - November

Starting from

€500

€348

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

14253 reviews

A week in the Aeolian Islands - 6 islands in seven days

07/23/2026

Deborah T.

-

IT

Unforgettable holiday! We managed to tour all the islands included in the itinerary, discovering wonderful corners. Nicola was fantastic: he understood our tastes on the fly, guiding us to magical coves and uncrowded places, away from the chaos. Five well-deserved stars, highly recommended!
avatar image

Week end in Costa Azzurra

07/23/2026

Isabella R.

-

IT

Beautiful experience. Alessandro turned out to be a skipper with a lot of experience, always attentive to the needs of the participants and available to rediscuss the plans depending on our preferences or weather conditions. The boat is impeccably maintained and is perfect for a weekend of freedom.
avatar image

The magic of the Egadi Islands aboard a brand new catamaran

07/23/2026

Maurizio D.

-

IT

Giuseppe was an excellent commander, a great connoisseur of the territory and, above all, of the local realities, which allowed us to live decidedly rewarding experiences on his advice. I add the sympathy and humanity of the character who, among other things, had his birthday during our vacation :-) . Thank you for everything!!

Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea

07/22/2026

chiara a.

-

IT

I had contacted the skipper beforehand to warn him that I did not eat fish and he had told me that there were no problems. It was not made WhatApp group before and no one was asked for preferences on breakfast, food, alcohol etc etc. We found ourselves with a galley made without sharing with a charge of 320 of wine, spirits well hidden in the shopping at the supermarket and about 500 euros of fish. I have never been offered any alternative but an egg omelette (with 50 euros spent on eggs) and twice a participant friend of the skipper made me a sauce with great controversy because the skipper imposed himself as a cook denying us to be able to cook. When I represented my need, I was literally pilloried and forced to eat salad that others ate as a side dish after succulent fish dishes. Now I'm wondering if I could get a refund??!! I had already used your platform and I had found it well, this is the reason why I used it again. I represent that we did not have the skipper indicated but there was a switch with his father Andrea who imposed the presence of his partner for two days (I do not know if he contributed to the galley). criticized me continuously because I did not eat fish and in general everyone for everything and in particular those who did not drink as much as he did. The whole group had difficulty communicating with the latter and in the last few days the situation has worsened. If you want further details write to me

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