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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!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

9 departures available

July - October

Starting from

€570

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

5 departures available

August - 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

2 departures available

August - September

Starting from

€1,041

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

August - September

Starting from

€1,150

€1,035

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,100

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

13 departures available

July - October

Starting from

€570

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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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

4 departures available

August - September

Starting from

€950

Per person

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4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€800

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

9 departures available

July - September

Starting from

€730

€657

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

2 departures available

August - September

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

7 departures available

August - September

Starting from

€790

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

17998 reviews

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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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Long weekend between Ponza and Palmarola: adventure at the Pontine!

07/8/2026

ELISABETTA P.

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IT

boat not adequate as it is given and lacking in comfort, as well as sup, too high price for the one used. the fearful and unengaging skipper

Sailing in the magical Sardinia of the South

07/8/2026

Cristina B.

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US

This sailing trip was everything I dreamed it would be. Gianluca is an incredibly experienced Captain, who made us feel totally safe, and comfortable and he was so generous with his energy, to sail whenever possible and to create the most memorable experience for his guests. Every stop on our trip was beautiful and unique. I feel very lucky that my first sailboat experience was with this captain!

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