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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!

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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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

5 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

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

October

€250

€238

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

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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!

COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

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

19099 reviews

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Discovering the Aeolian Islands Between Nature, Relaxation and Fun

09/11/2026

Andrea V.

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ES

Nice experience, fantastic places, I suffered perhaps more than I expected the heat especially at night. Davide is a very attentive and scrupulous captain and has often cooked excellent dishes.
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Seven days not only on the Amalfi Coast

09/10/2026

antonella a.

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IT

Lovely week on the boat. The organization was impeccable: every detail, from the timing to the activities, was carefully studied and with a professional and welcoming management. The proposed itinerary is exceptional: hidden bays, crystal clear waters, well-selected moorings even when the sea has forced us to change course. This is thanks to the skipper's extraordinary knowledge of the places, who guided us as only those who really live the sea can do. Each stage had a meaning, a rhythm, an emotion. The care for the crew was total, at 360 degrees. Comfort on the boat always at the top thanks to its large size, relaxed but also dynamic atmosphere, never boring. And when you went ashore, the entertainment was always calibrated: the right venue, the right time, the right mood. In short, I didn't take a boat holiday, but I did the boat holiday, the one that also changes the way you look at the sea and experience your land. An experience that stays with you, do it!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

09/10/2026

paola s.

I spent 7 wonderful and unforgettable days on the boat captained by Massimo, a correct, punctual and highly professional person. A great connoisseur of the sea and the winds, who, sailing under full sail, in preserves, was able to lead us to the most fascinating coves of the places included in the program (Sardinia-Corsica) with passion and competence. In addition, Massimo is an excellent cook and together with his skipper Vittoria, he has always delighted us with breakfasts, lunches and dinners, rich in flavors and imagination. The company (8 people in all) delicious and fun, and the memorable places, have made this holiday unique and exclusive, which I absolutely highly recommend!! Excellent verdict

Aeolian Islands on a sailboat: nature, sea and conviviality on Bavaria 46

09/10/2026

Fabio F.

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IT

With Rosario first of all you feel safe. Safety always comes first. In second place is a lot of sailing experience and knowledge of the islands from top to bottom. Rosario took us to fabulous spots for relaxation and snorkeling. Guaranteed fun.

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