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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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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September - October

€680

Per person

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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€690

Per person

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€325

€309

Per person

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4.9

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

Greece: Sporades

6 days - 7 nights

2 departures available

September

Starting from

€750

Per person

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5.0

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

Italy: Liguria

2 days - 2 nights

6 departures available

September - November

Starting from

€380

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

5 departures available

September - October

Starting from

€585

€527

Per person

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4.6

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€700

€630

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

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4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

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 - Sailboat holidays & skippered tours

19108 reviews

Unforgettable adventure in the Aeolian Islands

09/12/2026

Andrea M.

The holiday was a really nice experience, wonderful places visited in the best possible way for an island: the boat. Gaetano was a professional skipper, doing everything he could to make the holiday enjoyable, despite some breakdowns or malfunctions of the boat, which would need more maintenance as it is an old boat. The departure (and return) from Santa Flavia is a bit penalizing for the distance, which involves, especially on the way back, a long day of navigation. The small port of Santa Flavia is not touristy and therefore not very comfortable, especially for the night of return. It would be better to find a solution that is a little more comfortable and perhaps less distant from the islands. Overall we had a great time!
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Midweek getaway between Elba and Capraia

09/12/2026

Nikhita R.

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IT

Unforgettable experience and even better to have made a friend discover this reality. We both fell in love with it. Thanks to Edoardo who had the patience and the right spirit of adaptation in managing several generations of women! We can't wait to set sail again.
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Midweek relaxing in the Pontine Islands

09/12/2026

Giovanni F.

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IT

The boat is large, new and equipped with all comforts, but the highlight is certainly Mirko who in addition to being an excellent skipper also managed to make us feel comfortable and safe when we encountered a lucky man on the return trip. The islands are very beautiful and being able to enjoy them from the sea makes the experience top!
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Summer 2026 - Catamaran week in the Pontine Islands

09/12/2026

Maverick R.

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IT

It took me a week to decide what to write and how to describe this wonderful holiday spent on board with a formidable captain like Marco and a splendid Giulia who pampered us for a week. It is also difficult to express the sensations felt in seeing those wonderful places that Marco himself, with great will and I imagine also effort, has led us to see, and experience. A real merit also to his professionalism in managing every situation, in wanting to be the right detached but with a chat that is never denied. I feel I want to recommend this experience to those who will read this review of mine, as I will also recommend to those I know and ask me where to go, to take a holiday by the sea, to try this experience. Really, really good and both good! A heartfelt thank you ☺️

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