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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!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

7 departures available

August - October

Starting from

€1,300

€780

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

3 departures available

September

Starting from

€441

€419

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€750

€675

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€690

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

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

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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