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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!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

August

Starting from

€850

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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4.9

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

One departure available

August

€300

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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5.0

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

August - September

Starting from

€790

Per person

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4.9

Super!

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€990

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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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€700

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September

€790

Per person

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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

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

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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

18373 reviews

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

08/6/2026

Antonio C.

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IT

Competent, experienced and helpful skipper. Comfortable and spacious boat. Costa Smeralda even more beautiful by boat. Unforgettable experience
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Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

08/6/2026

Franka G.

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CH

With Laura, Enrico, Maura and Valentina.La explanation that the stop in Villefranche would have been made to help me and my mother is false: our flight was scheduled four days later. There has been a serious lack of attention to the safety of the crew, contrary to what is being made to believe. The most serious problem was the transfer from Plage du Grand Jardin to Villefranche-sur-Mer: about 75 miles covered in 12 hours under intense sunshine, with very few opportunities for swimming and, above all, no drinking water available from the previous evening. Most of the crew members were between 60 and 70 years old. Exposing people to these conditions for so many hours is a matter of safety, not simply a matter of unmet expectations. It is easy to continue to attribute everything to the wind and the sea conditions, which, contrary to what they try to present, were instead excellent. There were also concerns about the skipper's professionalism, particularly alcohol consumption and the fact that he smoked a significant number of cigarettes belonging to other crew members while they slept, without asking their permission.

Weekend on the island of Elba: among dolphins, enchanting bays and relaxation

08/6/2026

Daniela L.

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IT

Beautiful experience! A mini holiday full of unique landscapes, nature and new friendships. For most of the trips, the wind gave us the opportunity to use the sails. It takes a bit of adaptation to sharing spaces, but with a few tricks everything becomes manageable. A weekend to remember! Thank you Salvatore, you have passed on your passion for the sea and sailing.

Discover the Egadi Paradise by sailboat from San Vito Lo Capo

08/6/2026

Nadia C.

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IT

A bit disappointing experience. Somewhat restrictive rules on the boat (such as taking a shower before entering the cockpit after swimming), obligation to dine on land at least three evenings. The holiday begins on Sunday afternoon because on Saturday after boarding you are stopped, on Sunday you lose the morning shopping for the galley. It ends on Friday at lunchtime because we have to return to port, by motor, because we have to refuel. For the rest, a couple of evenings only in the roadstead and two beautiful sails. Extremely clean boat

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