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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

2 departures available

October

€1,300

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

2 departures available

October - November

€585

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October

€750

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

Per person

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5.0

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Barcolana Weekend: experience the largest regatta in the world

Italy: Venice and the Gulf of Trieste

3 days - 2 nights

One departure available

October

€420

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

2 departures available

October

€570

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

October

€370

Per person

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5.0

Super!

Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

29 departures available

October - November

€150

Per person

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5.0

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Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

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A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

€300

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

3 departures available

October

€230

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

4 departures available

October - November

€350

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

19257 reviews

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Saronic Islands and surroundings of Athens

10/5/2026

Erjon G.

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DE

Andrea is great Captain, we had amazing time even the weather was not our side still we enjoyed a lot.

Aeolian Islands: between sea and authentic flavours

10/5/2026

Giorgia P.

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IT

Wonderful experience!! Well maintained boat; very comfortable to have a bathroom available in each cabin. The tour allowed us to visit enchanting places, swim in crystal clear waters and enjoy excellent fish dishes and exquisite desserts. Carlo, our skipper (Merchant Marine Officer) has put his skills and abilities at our disposal. End of September was a good choice, always sunny without ever sultriness, the right water temperature for wonderful baths. Happy and fun company, with Lorenzo I was able to share culinary secrets in the kitchen. With a bit of luck, we sailed for a stretch in the company of a pod of dolphins. A holiday to be repeated and recommended. Giorgia P.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/5/2026

Aldo B.

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AT

My partner and I had an amazing week at sea, and a big part of that was our crew. Alessandro, our skipper, was highly professional and made us feel safe and well looked after at every moment. Carlo, our steward, was warm, attentive and always ready with a smile. The route between Corfu, Paxos and Antipaxos was stunning, with crystal-clear water and charming harbours. The crew went out of their way to make the trip special. We explored sea caves by dinghy, played an unforgettable volleyball match in the middle of the sea, and got great restaurant recommendations for our evenings ashore. Carlo's lunches on board were delicious, fresh and beautifully prepared. Alessandro and Carlo truly made this trip. We would happily sail with them again and recommend them to anyone looking for a relaxed, fun and well-organized holiday on the water. Thank you both!
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Maddalena Archipelago, southern Corsica: wonderful Sardinia

10/5/2026

Michelle B.

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US

Mossimo and Valentina were superb! Incredible sailing, delicious food, taking us to stunning locations it far exceeded my expectations! I highly recommend sailing with them. Cheers! Michelle

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