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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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4.7

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

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

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

13 departures available

June - October

Starting from

€570

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

June - September

Starting from

€950

€855

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

June - October

Starting from

€690

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€1,041

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€1,052

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

34 departures available

January - December

Starting from

€300

€270

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

6 departures available

July - September

Starting from

€900

Per person

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4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

11 departures available

June - September

Starting from

€730

€657

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

July - October

Starting from

€650

€585

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

10 departures available

June - September

Starting from

€790

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€650

€585

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

17875 reviews

Four days in the Aeolian Islands from Capo D'Orlando

06/25/2026

Edoardo A.

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IT

Let's start by saying that Vittorio has an extreme knowledge of the boat he steers (being his property) which immediately puts you at ease and makes you feel calm. If we combine this with the deep knowledge of the sea and the islands that it proposes as a destination... We get a fabulous holiday! He was able to bring us and recommend (never impose) beautiful places, both at sea and on land. It was an experience of absolute relaxation, without missing the educational and sailing part. (optional) In short, what can I say, super recommended!! Thank you Vittorio! Ours is a goodbye Fair winds
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Midweek relaxing in the Pontine Islands

06/25/2026

marcella c.

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IT

Great experience. Very good skipper from all points of view, always ready to add his experience and knowledge. New and well maintained boat.
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Long weekend between Elba and Capraia, from Thursday to Sunday

06/25/2026

Nicola A.

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IT

Really great experience. The boat is as it appears in the photos, no strange or unpleasant surprises. The places visited were lovely and the experience really great. Victor accompanied us on this trip, instead of Paolo, and he was a really great skipper, very helpful, company and very easy-going. Very very recommended

Short Week at the Egadi Islands between Nature, Relaxation and Fun

06/25/2026

RICCARDO D.

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IT

An experience that to define excellent would be an understatement. The sailing experience was splendid, with wonderful views, crystal clear sea and the priceless feeling of freedom. But what made this experience truly unique was the human factor. The skipper proved to be an exceptional person in every respect: professional, prepared, attentive to safety, impeccable in organization and endowed with rare relational qualities. He managed to create an atmosphere of serenity, conviviality and sharing that made everyone feel at ease from the first moment, transforming a simple trip into an authentic and memorable experience. The cuisine deserves a special mention. Although meals are not a due or obvious service in this type of experience, the skipper wanted to offer much more than could be expected. And what a surprise! These were not simple meals, but real gastronomic moments. Each dish was prepared with care, passion and great attention to the quality of the ingredients. Honestly, the meals were beyond all expectations: delicious, tasty, irresistible. The kind you look forward to and that, jokingly, can be addictive. Each course was a confirmation of the talent and generosity of the skipper, who also proved to be exceptional in the kitchen, managing to constantly amaze everyone on board. In a world where we often limit ourselves to providing the expected service, here we clearly perceive the desire to offer much more: passion, attention, hospitality and a genuine care for the well-being of guests. It was not only a fantastic sailing experience, but an extraordinary human experience made up of sea, friendship, professionalism and unforgettable flavors. Five stars are not enough. An experience that I would recommend without any hesitation and that I will take with me as one of the best memories of recent years. Congratulations to the skipper: exceptional at sea, exceptional with people and exceptional also in the kitchen.⭐⭐⭐⭐⭐+∞.

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