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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

3 departures available

October

€1,300

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September - October

€700

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

4 departures available

September - November

Starting from

€585

€527

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

4 departures available

September - October

€370

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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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

3 departures available

October

€570

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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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

September - October

Starting from

€230

Per person

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4.9

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The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

Per person

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5.0

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

One departure available

September

€490

€440

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€750

€675

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

19170 reviews

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

09/20/2026

Paola E.

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IT

Francesco is a super skipper: with great experience, attentive to everyone's needs, ready to welcome requests when possible and to suggest proposals to enjoy the holiday to the fullest! Always safe, he chose the best landings to make us feel good even when the weather did not seem favorable. The destination is a succession of bays, green, azure and blue seas, picturesque villages with taverns by the sea. Clean and comfortable boat with everything you need. Highly recommended!
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We have known the Aeolian Islands for 20 years, live them with us!

09/20/2026

Antonio G.

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GB

The Aeolian Islands are a wonderful archipelago and Pasquale, the skipper, is an extremely prepared person with social projects outside sailing worthy of praise. Couldn't recommend skipper and better holiday

Palma de Mallorca All Inclusive on 18m Ketch

09/20/2026

Matteo E.

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IT

This was a really good sailing trip. It was well organized, relaxed, and enjoyable. A special mention goes to Filippo, our skipper. He is not only a highly capable and experienced sailor but also a genuinely kind and welcoming person. He was always happy to listen to everyone’s ideas, adapt the itinerary when possible, and make sure everyone felt comfortable and involved. One of the biggest surprises of the trip was his cooking! Every day he prepared delicious meals and snacks that went far beyond what we expected on a sailing holiday. He is truly an amazing chef, and every meal became another highlight of the experience. We visited beautiful coves and stunning spots around Mallorca, enjoyed great sailing conditions, and shared unforgettable moments together. The atmosphere on board was always friendly, relaxed, and fun. And of course, Noa was the real star of the trip! She won everyone’s heart, and we all had so much fun playing with her throughout the week.

Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/20/2026

Emma Angela M.

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FR

A wonderful holiday, I can only recommend it! The boat was very comfortable and you felt comfortable right away. Great excursions with crystal blue water and beautiful bays. Alessandro and Carlo were very attentive and made for a particularly pleasant stay. So we had a great atmosphere in the group with the other travelers and a great time together. This holiday was a special experience, thank you for that!

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