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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!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

4 departures available

September - October

€260

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

2 departures available

September - October

Starting from

€860

Per person

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4.8

Super!

Summer is made for the Aeolian Islands! Weekly cruise

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€750

Per person

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

€950

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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4.2

New

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€990

€842

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

€690

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

€700

Per person

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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

Why book a holiday with Sailsquare?

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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

18659 reviews

Ibiza & Formentera: an exclusive journey between sky and sea

08/21/2026

Francesca G.

-

IT

Angelo very experienced and prepared skipper, gives safety. Francesca, the daughter, a very sweet helper. The boat is very large and beautiful, it would need a little more maintenance (especially in the bathrooms) and for example to replace the pillows of the beds!! From my personal experience, I think that 12 people on board are definitely too many... it becomes complicated to manage (independently) meals and maintain a good level of hygiene. I would suggest a light hostess service despite the fact that it involves a small increase in costs. Overall, positive experience that I would absolutely recommend.

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/21/2026

laura p.

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IT

Week in flotilla an experience to try! we had a great time with the crew and also with all the people at Different Sailing. On the boat with Eleonora and Marco we had fun and at the same time we always felt safe! Marco skipper highly recommended because he is resolute but always available and super calm.
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Quattro giorni all'Elba - Hostess a bordo

08/21/2026

Andrea M.

-

IT

It was a beautiful holiday. Comfortable boat with private bathroom for each cabin. Comfortable outdoor spaces considering the complexities of the sailboat. Vittorio and Giulia were excellent hosts. Vittorio's experience and Giulia's kindness pampered us for the entire holiday.

Sailing cruise in the Greek islands - The Saronic Islands

08/21/2026

francois Y.

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FR

Hello in fact we did not have Bertrand J. whom we had chosen because we missed the French we had kostis. After a few adjustments, we did a little less boating for 5 hours on the first day. And a little more sightseeing a little. He listened to our requests. We didn't do a bbq, he couldn't find a "spot". Too bad. The destination is good. August very busy, be careful.

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