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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!

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

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

6 departures available

June - September

Starting from

€650

€585

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

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

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

Why book a holiday with Sailsquare?

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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

17824 reviews

The wild south from Cagliari to CarloForte

06/21/2026

Danila G.

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SM

My experience has not ended, but only begun! GianRoberto, a compound name, a lot of stuff already, is a skipper with whom it is easy to share life stories and first of all a competent and sensible navigation. Sardinia is the backdrop without problems, beautiful even where it does not seem, but which explodes with poignant beauty if discovered with the eyes of those who have been able to choose "a little of the best and a little more" for the available days. Thank you very much for Gian's exquisite hospitality and the management of the whole experience made even more comfortable by Skyfall, an elegant and refined boat.
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The wild south from Cagliari to CarloForte

06/21/2026

Dario V.

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IT

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The wild south from Cagliari to CarloForte

06/21/2026

Giovanna P.

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IT

It was an experience above my expectations. The competent and kind skipper has been able to make this holiday one of the most beautiful ever done on a boat. The comfortable, clean and functional boat has been able to give each of us our own space.
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Three-Day Sailing Tour to the Pontine Islands

06/21/2026

NICOLA A.

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IT

Excellent experience with a very prepared skipper, no frills, excellent cook and maximum welcome and attention. We have just allowed the weather even sailed a little without an engine. We took the tender several times to better enjoy the islands. He tries to do everything possible to meet the scheduled times and succeeds. Recommended.

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