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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€935

€748

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

July - October

Starting from

€615

Per person

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4.8

Super!

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€820

Per person

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4.9

Super!

Tuscan Archipelago: An Oasis of Blue between Sea and Nature

Italy: Tuscany

6 days - 5 nights

5 departures available

July - August

Starting from

€650

Per person

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4.9

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

10 departures available

July - October

Starting from

€550

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

6 departures available

August - October

Starting from

€550

Per person

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4.8

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

10 departures available

July - October

Starting from

€530

€504

Per person

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4.9

Super!

Pontine Blue - Midweek Escape

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€300

Per person

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4.8

Super!

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

9 departures available

August - October

Starting from

€850

€808

Per person

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4.9

Week of sea, nature and fun in the Egadi Islands!

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€850

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

August - September

Starting from

€689

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

September

€293

€264

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 - Sailboat holidays & skippered tours

16268 reviews

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Pontine Islands aboard a splendid 16-meter sailboat

07/18/2025

Sabrina C.

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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 🥰
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Pontine Islands aboard a splendid 16-meter sailboat

07/18/2025

Laura D.

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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. 💙
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/18/2025

Nathalie B.

-

France

All the will Suddenly he leaves Faced with the obvious All this is immensity And work for 10 hours Always make choices of the heart Apologizing for a mistake This too is immensity All reality is immensity How the dream will then dissolve From tomorrow a new immensity will begin again From tomorrow From tomorrow From tomorrow •• Andrea Lazlo de Simone . Immensity And so, the mermaids disguised themselves as a birthday Elvis, the sea played at being the ocean and sailing did not challenge the fury of a capricious eole! New Odyssey, on a new parallel. For a parenthesis ... 'insolent'. And everything was ... immensity! Σας ευχαριστώ . Καλό ταξίδι …
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Pontine Islands aboard a splendid 16-meter sailboat

07/18/2025

Jennifer D.

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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!!

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