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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

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€312

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

Per person

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4.9

New

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

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€600

€540

Per person

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

€950

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

Per person

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4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

September

€400

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€760

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

September

€1,150

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

18916 reviews

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Different flotilla in Ionian Greece: nature, new friends and fun

08/29/2026

Lucian Alexandru L.

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IT

A memorable experience.
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/29/2026

Alberto Z.

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IT

Beautiful experience, excellent organization, thanks go to Simone for his commitment and dedication, as well as to the staff, the skippers and with praise for our Pablito, good both at sea and in the console. A holiday not so suitable for those seeking relaxation 😎
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Sailing to discover the Egadi Islands

08/29/2026

Francesca B.

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IT

Fantastic week, ema and Irene are experienced, competent, kind and super nice. They welcome you as if you were at home. They know the sea and sudden changes and this made me feel very safe: how can a storm come if the sky is completely starry and the sea is a table?!? And instead, just as they had predicted, it was better not to leave😅 ready to advise alternatives and support in activities if you cannot navigate, kind mediators in the dynamics of unknown people. Their route, outside the classic Egadi tour, allowed us to see dolphins, turtles, the coast of Scopello, the zingaro reserve and San Vito. With the "good" wind on the way back we also did a wonderful 3-hour🥰🥰🥰 sail Thank you thank you Ema and Ire... fair winds and I hope our routes will re-meet soon ❤️❤️❤️❤️

A sailing holiday: discovering the Pontine Islands

08/29/2026

PAOLO S.

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IT

Marco is a capable and responsible skipper. I would have liked to go ashore a few more times to visit the islands.

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