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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!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

5 departures available

June - July

Starting from

€490

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

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4.8

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September - October

€242

€218

Per person

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5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

2 departures available

July - September

€740

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

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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4.8

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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5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

8 departures available

July - September

€1,600

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

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

2 departures available

August

Starting from

€849

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

17815 reviews

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4 weekdays in the Pontine Islands

06/20/2026

simona s.

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IT

Stefano is an excellent captain. Admired the mooring maneuver in Nettuno, not very easy. Also always calm, kind, nice. Even with the crew it went quite well. The only regret is almost always the engine, but it's no one's fault, especially if you have a busy schedule to respect because those who signed up want to do that. I need experience to understand that in the next short period I will look for only one Ponza, so you can choose the coves where to go according to where the wind blows and really sail. Until next time, Stefano

Three days on Elba for just four guests on board

06/20/2026

luca c.

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IT

Wonderful experience on Elba. The skipper Pier is very prepared and willing to pass on his experience in sailing. The boat is well maintained and the right space to enjoy a weekend at sea with friends. We highly recommend a weekend aboard the Kinky to those who want to experience the sea in peace, learn more about sailing and rely on a competent, passionate and attentive skipper.

Midweek relaxing in the Pontine Islands

06/19/2026

roberta r.

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IT

Beautiful ride. Mirko was great at 360 degrees, the best skipper I have ever had to deal with! Experienced, kind, nice and very proactive. He made us see very beautiful things and stop in beautiful bays. He is also a good cook. Bravo Mirko super skipper!
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Midweek in the Pontine Islands. Between Ponza, Palmarola and Zannone

06/19/2026

Silvia C.

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IT

Really enjoyable experience. Marco and Giada accompanied us on a beautiful tour of the Pontine Islands making us discover beautiful bays also preparing excellent dishes. Marco is a very attentive and experienced skipper. Comfortable boat, a plus definitely the two sups at our disposal.

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