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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

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

7 departures available

August - October

Starting from

€1,300

€910

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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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

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

One departure available

August

€1,100

Per person

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

€378

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

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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

5 departures available

September - October

Starting from

€570

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

August - September

Starting from

€360

€300

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!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

6 departures available

September - October

Starting from

€570

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

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

18708 reviews

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Aeolian Islands: wellness, taste, fun with fabulous cook on board

08/23/2026

Pamela L.

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IT

We spent a very pleasant week in the company of Giacomo, the skipper, and Laura, his partner and queen of delicious first courses! The program included the visit of Lipari and Vulcano Panarea, Stromboli and Salina and what we appreciated most was the ability to reorganize the tour itinerary according to the weather conditions that also included a storm on the island of Lipari and even stronger on the nearby islands. The excursion that we enjoyed the most on the mainland were those to the crater of Vulcano which absolutely deserves the climb and the evening visit of Salina of which we savored the atmosphere that reigns in its narrow streets with elegant shops. The most exciting sea excursions were those to the Faraglioni, the Panarea bubbles and Strombolicchio. A big thank you to Giacomo, fabulous Cicero as well as an expert and prudent skipper and again thanks for the early morning that allowed us to admire the sciara of Stromboli in peace! And thanks to the kind Laura, tireless companion in our snorkels!
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/23/2026

Giulio R.

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IT

Beautiful experience! Heartfelt thanks to the skipper and co-skipper for their professionalism, passion and patience. Wonderful company and a great desire to share the sea and fun.
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The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/23/2026

Francesco D.

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IT

Unforgettable week. Sea, company and fun. Skipper Daniele always attentive and professional but also always ready to make a group! Crew Luna 10 cum laude. See you very soon for another adventure!

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/23/2026

Nicole L.

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IT

After my first sailing experience, I can only thank skipper Pietro and co-skipper Stefano who were fantastic. We created a unique atmosphere, which made the holiday pure fun while also discovering special islands such as the Aeolian Islands. Vote for this holiday 10+. Two notes for the Different team: the first, fewer people in the boats would make the environment a little more viable, the second a less tight schedule.

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