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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

New

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

€590

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

€890

Per person

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4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Italy: Lake Garda

1 day - 0 nights

6 departures available

October

€150

Per person

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5.0

Capraia and Elba Island - Sun, Sea and Fun!

Italy: Tuscany

4 days - 3 nights

One departure available

October

€400

Per person

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4.4

The unspoiled paradise of the BVI

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

Per person

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5.0

New

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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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

One departure available

October

€607

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

4 departures available

October

€320

Per person

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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

Starting from

€845

€676

Per person - min 2 pax

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

One departure available

October

€325

Per person

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

One departure available

October

€1,100

Per person

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5.0

Raja Ampat: New Year's Eve in the last paradise

Indian Ocean: Indonesia

12 days - 12 nights

One departure available

December - January

€2,070

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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