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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!

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

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

€980

Per person

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5.0

Super!

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

Greece: Cyclades

6 days - 6 nights

One departure available

September

€1,000

€750

Per person

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5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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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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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

4 departures available

August - September

€600

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

7 departures available

September - October

Starting from

€370

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

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

3 departures available

September - October

€650

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

Starting from

€1,000

€750

Per person

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4.9

Super!

7 giorni a vela alle Cicladi con gran finale a Santorini

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€790

Per person

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4.9

Super!

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

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

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

18895 reviews

A week in the Aeolian Islands - 6 islands in seven days

08/28/2026

Tiziana D.

"And you haven't seen anything yet..!" Our captain kept telling us. And so it was, in a crescendo of wonder and amazement: the long baths in ever-changing coves, the wait for the sciara and the wonder of the rain of drops of fire, the romantic sunsets every evening more spectacular, the warm nights under the shooting stars and the magic of the silent sunrises, the sailing in the safety of the port so as not to be reached by the incoming storm (we sleep with the air conditioning .. daje!!), the dancing aperitifs, the iridescent colors of the rocks, Bennato, Dalla and Queen in the background, the unbeatable dishes of the Bitta di Maria, the pane cunzato and the almond granita, the breathtaking beauty of Filicudi, the deep seabed in search of fish (look: two tuna, no they are amberjacks!!), the final surprise of the dolphins on the last day and the caves of ammmore ("so you just don't leave each other anymore!"). Thanks to [hidden] and Nicola, a brave but prudent captain, who pampered us all together with Ilaria and gave us unforgettable memories. Simone and Tiziana
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7 days of sailing between beautiful Croatian islands and crystal clear waters

08/28/2026

Fabio F.

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IT

Perfect boat, always clean and comfortable. The skipper is a real sailor, with him you will have a real sailing holiday. You always sail when you can and if you want to learn every question you will get an answer. All requests have been fulfilled and then the Kornati are spectacular. Sailing, breathtaking sea and pleasant company....this is the holiday with the [hidden]. Highly recommended!!

10-Day Cruise to the Sporades & Nature Park

08/28/2026

Claudia G.

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IT

Fabulous holiday. The itinerary traced by our skipper allowed us to mix time and experiences both at sea and on land very well. The stages he selected gave us immemorial baths in uncrowded coves characterized by very clean waters. Andrea was very professional, competent, public, and always attentive to the safety of the entire crew. Furthermore, with his calmness and infinite patience he managed to create a pleasant and convivial atmosphere among all his guests. We spent evenings in the roadstead under starry really difficult to forget. The management of the kitchen has never created disagreements as well as the management of the common fund. Claudia & Giuliana The roadsteads

Midweek on Elba, from Monday to Thursday

08/28/2026

Loriana V.

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IT

Wonderful experience. Paolo is not only an experienced commander, ready to manage, to "dive" into every new unforeseen event, but he is one of us and this makes the difference. When the goal becomes just a detail. Grating ❤️

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