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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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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€980

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

October

€250

€238

Per person

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4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

4 departures available

October

€200

Per person

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4.7

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

€600

€540

Per person

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4.3

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September - October

€890

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September - October

Starting from

€680

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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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

October

Starting from

€950

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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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

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

19104 reviews

Midweek getaway between Elba and Capraia

09/11/2026

Samanta B.

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IT

Fantastic experience on board! Edoardo is a competent skipper, a real sea dog who knows how to create a cozy atmosphere on the boat and patiently explained to us how to sail. He also recommended excellent trekking routes in Elba, an extra touch that made the cruise even more special, and the boat was very clean and well cared for
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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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