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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

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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Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€585

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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4.9

Weekend of relaxation and fun to discover the Island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

Per person

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5.0

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

6 departures available

October

Starting from

€59

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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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

2 departures available

October

€320

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

€990

€891

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 o Capraia

Italy: Tuscany

2 days - 2 nights

38 departures available

January - December

Starting from

€275

€248

Per person

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4.7

Squid Festival- Capraia Island

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€250

Per person

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

2 departures available

October

€690

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.

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IT

A wonderful day Everything perfect and well organized Highly recommend

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