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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

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

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

7 departures available

September - October

Starting from

€230

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

€954

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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4.6

The Island of Elba, to make you live a special experience!

Italy: Tuscany

6 days - 5 nights

2 departures available

August

Starting from

€700

€650

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

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4.4

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

10 departures available

August - November

Starting from

€540

€513

Per person

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4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€280

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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

18469 reviews

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

08/12/2026

David B.

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IT

Everything was great, nice ride, lots of things to see, and great availability of Skipper and second. Maybe I would have preferred them to dedicate 1 more day to the most beautiful islands such as Antipaxos sacrificing a stop on the way back, and perhaps I would also recommend planning a dinner on board in the roadstead to also enjoy the boat for dinner, but these are details more to give some inspiration to the guys than for anything else. Generally you dine out and you still have the opportunity to see various villages, so even on this nothing to say, I visited beautiful places and also ate well. They also organized excursions and we had fun playing volleyball in the water in a particular place... Congratulations!
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/12/2026

Riccardo R.

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IT

Overall very nice and fun experience, made even more special by the sympathy of skipper Marco and co-skipper Luca. Definitely recommended
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Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/12/2026

Angela P.

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IT

The itinerary was confirmed as I had chosen. The experience was very positive (I had already taken a boat holiday years ago). Good harmony also with fellow travelers. Luca our skipper was very attentive, professional, but also very helpful to our needs. Overall satisfied

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/12/2026

Tommasina F.

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IT

A week of wonderful landscapes, special travel companions, parties everywhere, life at sea, all coordinated in the best possible way by the skipper and co skipper, Davide and Antonella, who made this week unique. Excellent organization, they follow you for any doubt or criticality. Definitely to be redone.

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