header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Italy

Discover more than 43 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

4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

October

Starting from

€200

Per person

cover image
avatar image

4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€751

Per person

cover image
avatar image

4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€615

Per person

cover image
avatar image

4.8

Super!

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

2 departures available

October

Starting from

€850

€808

Per person

cover image
avatar image

5.0

Super!

Experience in the Egadi Islands: A Dream on a Sailing Boat

Italy: Aegadian islands

7 days - 7 nights

3 departures available

October

Starting from

€400

€360

Per person

cover image
avatar image

4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

One departure available

September - October

Starting from

€240

€228

Per person

cover image
avatar image

5.0

Midweek relaxing in the Pontine Mountains

Italy: Pontine Islands

4 days - 3 nights

5 departures available

September - October

Starting from

€337

Per person

cover image
avatar image

4.2

Stuffed anchovies: magical weekend from Genoa

Italy: Liguria

2 days - 2 nights

2 departures available

October

Starting from

€265

Per person

cover image
avatar image

4.7

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

October - November

Starting from

€1,455

€1,382

Per person

cover image
avatar image

5.0

Super!

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

One departure available

September

Starting from

€99

Per person

cover image
avatar image

5.0

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

4 departures available

October

Starting from

€337

Per person

cover image
avatar image

4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

October

Starting from

€294

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

12599 reviews

avatar image

Pontine Islands aboard a splendid 16-meter sailboat

07/18/2025

Sabrina C.

-

Italy

First time on a sailboat, first time in Ponza, they were 4 days that I will remember and they will have a special place in my heart. Thanks to Leonardo and Elena for the perfect organization, and availability.. The navigation was perfect, despite the rough sea, I never had any doubts about the skipper's skills who showed confidence and experience. The destination and the surrounding areas that we visited with the tender are magnificent,.. I highly recommend this experience , the boat is very nice, clean and comfortable. We shared our holiday with unknown people but with the same desire to spend unforgettable days. Thank you all 🥰
avatar image

Pontine Islands aboard a splendid 16-meter sailboat

07/18/2025

Laura D.

-

Italy

It was my first experience on a sailing boat, I was inspired to be able to travel by sea from cove to cove, but I was full of doubts, I was afraid of being sick. And instead I was practically always fine. I arrived at the port and the departure was unfortunately with very rough seas. Instead, I discovered that with the necessary precautions, i.e. the classic pill, I could feel good and enjoy the sea and navigation! We immediately sailed for five hours, the wind was blowing very strongly, the black waves pushed us and we arrived in Ponza at sunset fiery red. This was just the beginning, I then saw wonders, one after the other coves, rock cathedrals, natural arches, emerald green sea, I do not deny that I was unexpectedly moved by such a wonder .. I was lucky with the group that was bubbly and close-knit. I really appreciated Leonardo's ability to steer the boat with seriousness and palpable experience, he also took us with the tender everywhere, it was an exploration that I appreciated very much. During the day we also had fins, masks and sups available. Elena the wife was always present, very friendly and attentive with all of us. I also loved being able to cook for everyone, I wished I could have done so much more to be honest 😅 I was lucky to do my first sailing with them and I will certainly repeat a new experience shortly. Thanks for everything. 💙
avatar image

Pontine Islands aboard a splendid 16-meter sailboat

07/18/2025

Jennifer D.

-

Italy

I put myself to the test because for me, it was my first experience on a sailing boat. Leonardo is a Captain who has been able, with his experience, to guide the whole group on this beautiful holiday, he has made us discover places of extraordinary beauty, willing to comply with our requests. Elena entertains the bench, helps her husband and takes care of all the guests. I feel lucky to have chosen this route and these people. The boat is beautiful, kept in impeccable condition, my cabin was delightful. On a boat there are many rules: you have to understand and respect them! This experience is for you if you're open, ready to share fun moments with a group of strangers. keyword: SHARING! A varied and bubbly group, I immediately empathized with most of them. I relaxed, tanned, explored with Sup, snorkeled etc. Beautiful location, the surreal sea! Things I didn't like: the sailor's 😅 shower and the rough sea, for the rest: I can't wait to do it again!!
avatar image

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

07/18/2025

Dag Petter H.

-

Norway

Seven days of pure magic in the Aeolian Islands – an unforgettable experience thanks to Nicola We have just finished a week on a sailing boat among the beautiful Aeolian Islands and we cannot find the words to describe how extraordinary this experience was. The credit for this perfect trip goes above all to our skipper, Nicola, an impeccable, experienced and passionate guide, who turned every day into something special. From the first moment on board, Nicola made us feel safe and comfortable. His knowledge of the sea, the islands and the winds is impressive: he took us to hidden coves and dreamy bays, away from the most crowded tourist routes, making us experience the most authentic and wild Aeolian Islands. He was able to read the weather and adapt the itinerary with intelligence and flexibility, always ensuring maximum comfort and beauty. In addition to being an excellent skipper, Nicola is a sunny, hilarious, kind and always helpful person. He was able to create a relaxed and convivial atmosphere on board, bringing the group together naturally and making every moment – from sailing at sunset to aperitifs at anchor – unique and unforgettable. The nights under the stars, the crystal clear water of Panarea, the fumaroles of Vulcano and the fiery sunsets seen from Filicudi deserve a separate chapter... each island gave us different emotions, but all with a common denominator: the feeling of being in excellent hands thanks to Nicola. If you are thinking of a sailing holiday in the Aeolian Islands, do it – and if you can, choose Nicola as your skipper. He is not only an experienced captain, he is a true lover of the sea who will make you experience the islands with new eyes. Thank you very much, Nicola, from Greta and Petter. See you on the next adventure!

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