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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

Super!

Premium

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

One departure available

September - October

€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

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

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4.7

Super!

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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4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

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

19077 reviews

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Sailing weekend with skipper cook

09/8/2026

Flavia G.

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IT

Weekend with perfect conditions to relax! Flavio was discreet but of company and cooks in an excellent way!! The Trieste and Slovenian coasts are beautiful and we found beautiful water!! We also loved the boat!
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Five days at the Pontine from Ostia - Sailing course and more!

09/8/2026

Giuseppe G.

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IT

This experience also included a sailing course. The skipper Enzo is an excellent instructor, competent, patient and always ready to involve the crew in steering the boat. We sailed a lot. The boat is well maintained, comfortable and clean. The dolphins also noticed it and accompanied us both in the navigation to Palmarola and in the one for the return to Ostia. Enzo knows the Pontine very well, we enjoyed the most beautiful coves without haste and always in safety. Also thanks to the favorable weather that gave us a beautiful relaxing but also active holiday for those who wanted to participate in the management of the boat during the numerous sailings.
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Five days at the Pontine from Ostia - Sailing course and more!

09/8/2026

Coretta P.

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IT

Beautiful holiday that I recommend to anyone who wants to experience the sea in the most intense and authentic way, with a discreet spirit of adaptation and a great desire to sail, learn and regenerate. Enzo proved to be a particularly professional, patient and prepared skipper, able to convey his experience by enriching every moment with many ideas and interesting topics. I sincerely thank all the crew for the fun and the many laughs shared!

Gulf of Poets

09/8/2026

Silvia M.

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IT

Giovanni super skipper, kind, helpful is a super pleasant company! Very nice destination, especially on the first day of sailing. Definitely recommended experience!

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