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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!

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

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

5 departures available

September - November

€250

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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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

10 departures available

July - November

Starting from

€500

€425

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

Per person

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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

8 departures available

August - October

€650

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

2 departures available

July - September

Starting from

€200

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

14 departures available

July - November

Starting from

€600

€540

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

9 departures available

July - September

Starting from

€700

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

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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