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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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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

€690

Per person

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4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

3 departures available

September - October

Starting from

€585

Per person

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4.6

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

One departure available

September

€345

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€1,100

€990

Per person

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4.0

European Mile Builder - Leg 6: Malta to Gibraltar

Spain: Andalusia

9 days - 9 nights

One departure available

October - November

€550

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

26 departures available

January - December

Starting from

€300

€270

Per person

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4.7

IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

Spain: The Balearic Islands

6 days - 7 nights

One departure available

October

€900

Per person

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4.0

European Mile Builder - Leg 2: Gibraltar to Las Palmas

Atlantic islands: Canary Islands

6 days - 6 nights

One departure available

November

€660

Per person

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5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

5 departures available

September - October

Starting from

€215

€194

Per person

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4.0

European Offshore Mile Builder - Leg 5: St Tropez to Malta

France: French Riviera and Porquerolles

6 days - 6 nights

One departure available

October

€550

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

19192 reviews

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Weekend in the Pontine Islands

09/22/2026

Alice P.

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IT

For me and my friend Pamela it was the first experience on a sailing boat, really amazing! The Pontine islands are a beautiful place to get to know and experience! The added element is definitely Fabio, who with his experience guides you in everything, including the appreciation of local food! As fate would have it, we found a great company to share this wonderful journey! So grateful!
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Gulf of Poets

09/22/2026

Paolo D.

Really pleasant weekend. Beautiful as a first experience of several days on a boat, thanks also to the nice companions on board. Giovanni nice, helpful, excellent *host". Nice boat. To be redone. I recommend it.

Amazing Pontine Islands on a sailboat with private bathrooms

09/22/2026

Roberta P.

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IT

We found malfunctions though, especially in the bathroom.

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/22/2026

Aida K.

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BA

I did the Sporades Experience tour and it was fantastic. What I liked the most was the mix of marina nights and sleeping at anchor. Every other night we stayed in a different marina, which gave us time to walk around and discover another island. The other nights we slept at anchor under the stars. Honestly, that was one of my favorite parts of the whole trip. Our captain, Gianfranco, was a great captain and an amazing cook. He enjoyed preparing delicious food for us, and we definitely ate very well. He may not always be the nicest person, but he is the best captain. He has a big heart, although he does get mad when I spill a drink or do not turn off the light. Maybe because he is a perfectionist! The boat was spotless, clean, well organized and very well maintained. You can tell Gianfranco takes a lot of pride in his boat and knows exactly what he is doing. He is well recognized in the sailing community, and after spending a week on his boat, I can understand why. Most importantly, I always felt safe with Gianfranco, and that means a lot to me. I joined this trip by myself, shared a cabin/bed with another female traveler, and ended up making great friends. Seven days later, I left with a lot of great memories, great food, beautiful islands and people I hope to meet again somewhere in the world. Getting on Gianfranco’s boat is a privilege — but don’t expect babysitting! He expects you to be part of the crew, not a passenger waiting to be served. And honestly, that made the experience even better.

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