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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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4.8

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Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

5 departures available

September - October

Starting from

€1,300

€1,040

Per person

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

September - October

Starting from

€700

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€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

4 departures available

October

€570

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

€419

Per person

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5.0

Super!

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€490

€441

Per person

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4.8

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Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

3 departures available

September

Starting from

€490

€440

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

6 departures available

September - October

Starting from

€370

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€750

€675

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€570

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

19033 reviews

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Summer 2026 - Catamaran week in the Pontine Islands

09/6/2026

Maurizio M.

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IT

Cccvvbbbn

Midweek weekend in Elba: sea, scents, colors

09/6/2026

Mirko R.

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IT

Beautiful experience. Following Ivo s instructions, we sailed for two days, contributing personally to the management of the boat. But above all we found a familiar and very pleasant environment discovering wonderful corners of Elba. The dinner at anchor in Porto Azzurro was a dream. Thank you Ivo for sharing a little bit of your life with us.
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Egadi mon amour: seven days to fall in love, be amazed and relax.

09/6/2026

Lorenzo S.

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IT

Beautiful experience, competent and very helpful skipper.

North Sardinia and Corsica: blue seen from a sailboat

09/6/2026

deborah c.

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IT

We had a simply perfect sailing holiday. From the first day we felt at home: everything was organized down to the smallest detail and the attention to the guests was truly exceptional. Leo, the captain, has precise and impeccable handling of the boat and the trip in general, makes you feel safe at all times, conveys calmness and competence and is extremely professional. Luigi, the sailor, is an eclectic, funny, interesting person with his thousand stories to tell and has created a beautiful atmosphere on board. The dishes served at meals were exceptional, prepared with care and attention in the choice of ingredients that enhance the sea and the territory. In short, Leo and Luigi are fantastic and with them you have the desire that the journey never ends! If you have to board, you must have no doubts with them. Highly recommended!

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