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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

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

Per person

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4.7

Flotilla Marmaglia Sun & Fun - Croatia - WOMEN SEATS ONLY - BUS INCLUDED!

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

Starting from

€1,180

€800

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,290

€1,190

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August

Starting from

€920

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€795

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

August - September

Starting from

€600

Per person

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4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

August - October

Starting from

€590

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

Starting from

€900

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

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

18292 reviews

Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

08/2/2026

Beppe l.

Hello we had a really good time we didn't know what to expect since it was the first experience of its kind, Mirko is a multifaceted skipper capable of operating at his best in different situations

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

08/2/2026

enrico c.

-

IT

I will write that with a group of nice travel companions I accompanied a presumptuous skipper on a trip, almost exclusively by motor, between Sanremo and the Porquerolles, with stops chosen according to his tastes, without the slightest respect for the program or the requests of cruise passengers. 1/3 of the crew even disembarked before the end of the trip. I was about to do it, annoyed by this unusual behavior for trips of this type. I just want to thank my fellow travelers. The review also applies to my wife who wanted to have her first sailing experience and does not motorboat. Destination too far to reach by sail, so said the skipper.
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On board with the chef at the Egadi Islands

08/2/2026

Sara M.

-

IT

All very well! Bad weather blocked us for a day in port and despite this Max managed to make us do what was planned in the program. He always advised us on what to visit on land and complied with our requests. He cooked us fabulous dishes!! Traveling with him was really a pleasure. Egadi what can I say... Go and see them for yourself!!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

08/2/2026

Sabine M.

-

CH

We had an unforgettable sailing trip. Huge kudos to our skipper, Paolo; in addition to his excellent navigation skills, he made us feel completely safe at all times. Paolo put together a fantastic sailing itinerary, taking us to beautiful coves and beaches where we could snorkel and watch fish in the crystal-clear, wonderfully warm water. Dario was an excellent and very nice cook, who spoiled us with truly wonderful meals. He even showed me how to cook a proper carbonara sauce. Whenever we had questions about the marine life, he was more than happy to explain things to us. When we anchored in the harbor, the crew made a reservation at an authentic and delicious restaurant. The atmosphere on board was fantastic, thanks to the really lovely people in the group. It was the perfect blend of adventure, safety, enjoyment, and great company! We would love to come back!

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