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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!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

3 departures available

September

€200

Per person

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5.0

Super!

Wandering between Tigullio and Cinque Terre

Italy: Liguria

7 days - 7 nights

One departure available

September

€700

Per person

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5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

7 departures available

July - September

Starting from

€1,450

Per person

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4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

One departure available

July - August

€946

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

One departure available

July - August

€890

€680

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

3 departures available

August

Starting from

€850

Per person

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5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

4 departures available

August - September

€649

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

4 departures available

July - August

Starting from

€250

Per person

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4.9

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

7 departures available

July - September

Starting from

€550

€495

Per person

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4.7

Kornati: the pearl of Croatia

Croatia: Kornati Islands

6 days - 7 nights

3 departures available

August

Starting from

€800

€760

Per person

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4.9

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

7 departures available

August - September

Starting from

€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

18110 reviews

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

07/19/2026

Mauro C.

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IT

On the board with Luca and Tommaso you can fully appreciate the beauty of those who do their job out of passion and not out of duty, together with the generous joy of their young age. Splendid places, chosen with the care of those who know them deeply and love them with equal depth. Thank you guys.

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

07/19/2026

Valentina B.

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IT

I signed my daughter up for this cruise with the confidence that it would be a great experience. Reality exceeded expectations. My daughter came back enthusiastic about everything. Nature, the baths, the navigation and tracking and the crew the stars..... Everything lived intensely

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

07/19/2026

Viviana M.

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IT

I had a fantastic sailing holiday in the Egadi Islands. Alessandro guided us to discover these wonderful places and a sea of infinite shades of blue, always with great professionalism, competence and attention to safety. What made this experience really special was his way of letting us experience the boat: not as simple guests, but as real sailors. He taught us many technical aspects of navigation, transmitting respect for the sea, for nature, for the rules of the boat and for life on board. A sailing holiday can be done with many captains or skippers, but not everyone knows how to teach you how to really live it. With Alessandro you not only take home the memory of wonderful places, but also an authentic experience that makes you appreciate sailing and the sea in a completely different way. Congratulations to its background music from a fine palate. W Sicily. Wherever you go you will be thrilled

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/19/2026

Chiara A.

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IT

A splendid week from all points of view, the Pontine were a wonderful discovery, the companions of adventure and the captain as well. Antonio is very knowledgeable and professional, but also super helpful for laughter and fun (... five stars also as a chef!!)

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