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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

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 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€920

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!

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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4.8

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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4.7

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

Starting from

€1,100

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

7 departures available

August - October

Starting from

€570

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

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

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

18369 reviews

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

08/5/2026

Elena C.

-

IT

A wonderful experience, we collected beautiful memories thanks to Alberto who led us to truly magical places and gave us the first notions to understand the sailboat, also allowing us to try some maneuvers. The boat is very well organized, tidy and clean. A highly recommended experience!
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Ibiza & Formentera: an exclusive journey between sky and sea

08/5/2026

Giovanni M.

-

IT

The holiday was really exciting. My wife and I were lucky enough to find a fantastic crew. Angelo is experienced, helpful and passionate about the islands which are all lovely. He guided us in the management of the galley and recommended excellent restaurants and chiringuitos with fair prices. Captain Francesca's assistant is tireless and always ready to help. Together they managed to create an excellent group atmosphere that made the holiday unforgettable. Among the highly recommended activities is the rental of scooters to explore Formentera!

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

08/5/2026

Andrea B.

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IT

Beautiful experience. Initial fears of seasickness or the absence of a proper shower turned out to be excessive. Giovanni is a really competent and caring skipper, plus his passion for cooking also makes him an excellent chef! The Aeolian Islands are one more than the other and the coves where we stopped were amazing! The boat is super comfortable and the spaces more or less adequate to expectations.
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Aeolian Islands: between sea and authentic flavours

08/5/2026

Giovanna V.

-

IT

A fantastic experience thanks to the spectacle of the Aeolian Islands but also thanks to our skipper Carlo: a person who is helpful, attentive and always ready to satisfy our every request. Although he was reserved, he participated in our dinners, proving to be a pleasant, nice company and of great human value. Fair winds🤩🍸 ⛵️

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