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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!

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!

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€600

Per person

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4.3

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€990

€842

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

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

€980

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

18851 reviews

Egadi Sail & Relax: the archipelago to experience

08/26/2026

SARA V.

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IT

Paolo and his [hidden] welcomed us perfectly in a beautiful week in the Egadi Islands! A dive to discover the real Sicily, thanks to the excellent pasta dishes prepared and recommended by Paolo, the sympathy of his cumpa skippers and the wind that gave us a little breather!! Paolo was attentive to our needs, always very helpful, sunny and welcoming; the [hidden] well organized, tidy and clean as a worthy travel companion of its commander! Good winds and see you soon!! ⛵️♥️

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

08/26/2026

Giovanni B.

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IT

A wonderful human experience... and boating. Marco and Britta make you feel at home both on board and in their wonderful cottage. [hidden] is a spartan boat, but it is an 'old lady', very suitable for navigating that cold, treacherous and fascinating sea.
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On board with the chef at the Egadi Islands

08/26/2026

Matteo Bruno S.

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IT

Max is an exceptional skipper: he was able to unite the group, entertain and fully immerse us in the local culture. It is difficult to make a review because everything was perfect: the places visited, the perceived safety on the boat, the sailing, the evenings with friends, the contact with nature and, as icing on top of all this, a cuisine of the highest level prepared every time with care and passion, to make us savor the flavors of the place. The energies and experiences experienced during such a week are rarely lived, and Max was able to encapsulate all this with a lot of heart. A word also for the crew who were unique! We will definitely do it again, thanks again! Alice and Matteo

Costa Smeralda and/or Gulf of Orosei on Maxi Yacht with hostess-cook

08/26/2026

Federico F.

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IT

Overall it was a good experience, especially thanks to the group that was created and the people on board. Marino and the hostess were friendly and pleasant, and we also ate well. As a starting point to make the experience even better, I would first suggest a greater sharing of the itinerary with the guests, of course always respecting the skipper's decisions related to weather and safety. It would also be nice to privilege, when possible, some coves or destinations less accessible by land, enhancing even more the beauty of a boat holiday. On the comfort front, considering the positioning of the experience, a few more attentions could make the difference: more comfortable cushions on deck, more efficient fans in the cabins, easier recharging of devices, a more functional aft shower and some extra care in daily cleaning and in the equipment for the table and aperitif. I would also suggest sharing more about the galley, common expenses and the week's program from the beginning, including the possible night in port. Finally, in the case of items lost due to bad weather or events not attributable to the guests, I would avoid including the cost in the common expenses, leaving the charge to the passengers only in cases of actual negligence. Overall it remains a good memory of the week and especially of the people I met. With a few small tricks, I believe that the experience aboard [hidden] can become even more pleasant and unforgettable. Greetings, Frederick

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