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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

New

Just relaxing while sailing on the Côte d'Azur

France: French Riviera and Porquerolles

2 days - 2 nights

One departure available

September

€450

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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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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4.8

EGADI AND COUSCOUS FEST of San Vito Lo Capo

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€630

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

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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€845

€676

Per person - min 2 pax

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4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

4 departures available

September - October

Starting from

€1,100

Per person

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4.7

IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

Spain: The Balearic Islands

6 days - 7 nights

One departure available

October

€900

Per person

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

5 departures available

September - October

Starting from

€690

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

19103 reviews

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Midweek relaxing in the Pontine Islands

09/11/2026

dario r.

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IT

A simply wonderful experience, one of those that are difficult to forget. We had a wonderful experience in the Pontine Islands aboard a sailboat and we can say with absolute sincerity that every single minute lived on that boat was special. Sea, landscapes, sunsets, relaxation and lots of fun: everything was just perfect. A special thanks goes to Mirko, our skipper, a truly fantastic person: very prepared, professional, attentive and always available. He was able to make the journey even more enjoyable, conveying safety and, at the same time, creating an atmosphere of great conviviality and fun. You can immediately perceive his experience, his passion for the sea and the great seriousness with which he carries out his work. With him we always felt in excellent hands and we were able to fully enjoy every moment, without worries. We absolutely recommend this experience, without any hesitation, to anyone who wants to experience the sea in an authentic and special way. Seriousness, professionalism, competence, fun and a beautiful atmosphere: we really couldn't ask for anything better. Thank you Mirko for making this trip to the Pontine Islands an unforgettable experience. We will definitely be back!
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South Sardinia - A Marine Paradise to Explore!

09/11/2026

Mariantonietta D.

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IT

Francesco pampered us throughout the trip with his attention to detail, with his cuisine and above all with his great experience at sea. Thank you Francesco
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Life Changing Experiences - Week in the Pontine Islands with photographer on board

09/11/2026

Leonardo S.

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IT

Fantastic experience, in addition to the splendid boat the difference is certainly made by Francesco who with his experience, sensitivity and respect manages to be an integral part of the experience, with his positive energy always ready to make you discover new places and tell you about them.
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Midweek on Elba, from Monday to Thursday

09/11/2026

Federica C.

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IT

A wonderful, intense and truly unforgettable experience. Three days lived on board, 24 hours a day, sharing spaces, laughter, stories, silences and pieces of life with people I didn't know until then. And perhaps this is the most beautiful gift of this experience: having started as strangers and having shared something that, in such a short time, has managed to leave a mark. A special thought goes to the captain. One of those people you don't meet every day. A man who has lived, who knows how to read people, listen to them and understand much more than what they say. Apparently a bit "bear", but with a huge heart. A person who, without wanting to, has left me something and that I will take with me. The sailboat was the perfect setting to slow down, breathe, look at the sea and really live in the moment. I go home with beautiful memories, new acquaintances and the feeling that certain encounters come into our lives for a reason. Thank you for these three days. Difficult to describe in words, impossible to forget. ❤️⛵️

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