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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!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

€300

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

3 departures available

October

€230

Per person

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4.9

Super!

Two days in Elba without worries with a professional skipper

Italy: Tuscany

2 days - 2 nights

One departure available

October

€315

Per person

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5.0

Super!

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

October

€275

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€750

€675

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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4.9

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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5.0

Super!

Squid Festival in Capraia with a professional skipper and chef

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

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

3 departures available

October

€230

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

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

19243 reviews

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Cast off for a week at sea, a thousand ways to experience it!

09/30/2026

Lauren W.

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AU

We had a wonderful time sailing with Alex on his boat Lady Sue. Alex is a very experienced Skipper and very attentive host who wanted to make sure we got the most from our trip. We were able to share stories and have a laugh with Alex. He is a fantastic cook if you are lucky enough for him to cook you a meal or two. On our first day, we had a coffee together and Alex made sure he understood what we wanted to experience so we could plan our week together. We then went food shopping together for the week and took off to our first spot to watch a beautiful sunset. We explored coves, visited islands, went paddle boarding, shared meals at little tavernas and connected with locals that our skipper knew. We had such beautiful days with perfect weather and some not so great weather days where we stayed docked at shore but we were able to adapt. Be flexible with expectations and keep ourselves entertained with exploring the port we were in, eating, resting and reading. We had some great sailing days with an opportunity to sail and skipper the boat and had other days where we just relaxed whilst Alex motored us to our next location. All up we had a great experience and would definitely do it again. It's a unique and special experience to be on a yacht travelling by water.

Sailing in the magical Sardinia of the South

09/30/2026

Moreno B.

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IT

The skippers Gianluca and Valeria are very prepared and professional, also good sailing instructors, nice and good cooks, a detail that should not be underestimated. A good friendship was immediately established. The itinerary to south-east Sardinia made us visit unforgettable bays and sea. I intend to have the same experience next year, perhaps on the west side.
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Sailing and Hiking in the Cyclades

09/30/2026

François-Gérald R.

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FR

Fantastic waters for wind sailing, Island knowledge well shared. Some inshore activities may last longer.
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AMERICA'S CUP in pursuit of the AC40s!

09/29/2026

Marzia B.

-

IT

A wonderful day Everything perfect and well organized Highly recommend

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