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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!

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

Per person

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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

8 departures available

July - November

Starting from

€500

€425

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€750

€675

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€600

Per person

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5.0

Super!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€650

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

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

5 departures available

September - October

Starting from

€275

Per person

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4.8

Super!

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

Italy: Tuscany

6 days - 6 nights

9 departures available

July - September

Starting from

€980

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

Per person

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5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

5 departures available

July - August

Starting from

€425

€383

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

5 departures available

August - October

€650

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

18017 reviews

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Kornati: the pearl of Croatia

07/11/2026

Silvia M.

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IT

Wonderful week with good winds, beautiful coves, the company and guidance of Marco!
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Let's discover the Aeolian Islands together by sailing

07/10/2026

Davide R.

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IT

Unforgettable holiday! Mario is the skipper everyone wants. He knows Aeolian Islands inside out, and everyone knows him there. Thank you for everything. I hope to see you again soon! :)
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Midweek sailing trip in the Gulf of Naples

07/10/2026

Raquel Leonor C.

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ES

Best of all, Sandro the Skipper 🇮🇹 Amazing 👌 ⭐️⭐️⭐️⭐️

Mini whale watching cruise with WWF guide between Ponza and Palmarola

07/10/2026

Anna D.

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IT

It was my first experience on a sailing boat and I can only say that I can't wait to repeat! Andrea, our guide, was very good: prepared and able to create a good atmosphere - as well as giving very interesting information. Our commander Luca was also very good. I also and above all thank the wonderful travel companions. Excellent balance between navigation, swimming in the sea, visits to the islands, studying cetaceans. Nice project!

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