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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!

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

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€441

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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5.0

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

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€700

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

4 departures available

July - September

Starting from

€200

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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4.9

Super!

Life Changing Experiences - Week in the Pontine Islands with photographer on board

Italy: Pontine Islands

6 days - 6 nights

2 departures available

August - September

€1,100

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

One departure available

August

€949

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

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

2 departures available

July - August

Starting from

€946

Per person

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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

One departure available

September

€300

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

18000 reviews

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Egadi Sail & Relax: the archipelago to experience

07/9/2026

Patrizia S.

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IT

Paolo is a competent, helpful and very nice guy! Wonderful boat equipped with all comforts. Thank you!

Four days in the Pontine Islands, just a stone's throw from Rome

07/8/2026

Francesco O.

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IT

A 360° experience: from the location to the skipper and his cuisine, from the beautiful group to the sailing between Palmarola and Ponza.
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Corfu between bays, taverns and myths.

07/8/2026

Farida B.

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IT

Fantastic experience! Traveling on a sailing boat is always a wonderful experience, if you do it with two captains like Léonore and Hansel, always professional, kind, helpful, attentive to safety and excellent cooks... becomes super awesome! They took us to discover wonderful bays and hidden corners, making us feel safe at all times. A journey dedicated to the sea, relaxation and good company that I will carry in my heart. Highly recommended!
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Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

07/8/2026

Fabio C.

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IT

Weekend on a sailing boat on the Island of Elba simply fantastic! Much of the credit goes to the skipper, an extremely professional, prepared and competent person, capable of transmitting safety and passion for the sea from the very first moment. In addition to his excellent sailing skills, he was always available, attentive to everyone's needs and good at creating a relaxed and pleasant atmosphere on board. Thanks to his knowledge of the island he took us to wonderful and uncrowded coves, making us experience places that we would hardly have discovered on our own. The boat was in perfect condition, well cared for and comfortable. It was a weekend of relaxation, fun and good company. An experience that I recommend without hesitation to anyone who wants to experience the sea in an authentic way. I would definitely do it again!

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