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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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4.6

Relaxing weekend and sailing school

Italy: Tuscany

2 days - 1 night

2 departures available

October

€220

Per person

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5.0

Barcolana in the front row!

Italy: Venice and the Gulf of Trieste

3 days - 2 nights

One departure available

October

€250

Per person

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5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

4 departures available

October - November

Starting from

€430

Per person

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4.9

E-bike & Sailing Experience con degustazione vini all'Elba - 2 barche

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

€238

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

4 departures available

October

€215

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

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4.4

From Martinique to Guadeloupe riding the trade winds

Caribbean: Guadeloupe

10 days - 10 nights

One departure available

February

€1,250

€1,125

Per person

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5.0

Unspoilt Balearic Islands for max 4 guests: Mallorca and/or Menorca

Spain: The Balearic Islands

6 days - 6 nights

One departure available

October

€950

Per person

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5.0

New

Cruise to the Golden Islands via the capes and bay of St Tropez

France: French Riviera and Porquerolles

5 days - 4 nights

27 departures available

February - October

Starting from

€595

Per person

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4.1

Totano's cup 2027 weekend of sailing and party on the island

Italy: Tuscany

3 days - 2 nights

One departure available

October

€350

Per person

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New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€600

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

19244 reviews

Fast Sailing Experience between Authentic Islands and Good Food

10/1/2026

Alexandra C.

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CA

Great adventure, a mix of sailing, food and meeting new people! Usually, I get seasick but everything went well
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Cast off for a week at sea, a thousand ways to experience it!

09/30/2026

Lauren W.

-

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.

-

FR

Fantastic waters for wind sailing, Island knowledge well shared. Some inshore activities may last longer.

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