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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

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€550

€495

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

4 departures available

July - September

Starting from

€200

Per person

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5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

7 departures available

July - September

Starting from

€1,450

Per person

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4.9

Super!

Life Changing Experiences - Week in the Pontine Islands with photographer on board

Italy: Pontine Islands

6 days - 6 nights

2 departures available

August - September

€1,100

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

One departure available

August

€949

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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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€950

Per person

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4.7

Amazing Pontine Islands in 4 days

Italy: Pontine Islands

4 days - 3 nights

2 departures available

July - August

Starting from

€437

Per person

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4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

2 departures available

July - August

Starting from

€946

Per person

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4.7

New

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

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - September

Starting from

€600

€540

Per person

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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

One departure available

September

€300

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

18026 reviews

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Midweek relaxing in the Pontine Islands

07/12/2026

Riccardo G.

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IT

Mirko is an excellent skipper with a lot of experience, very nice and helpful. The tour was beautiful. The only note to be made was the management of the galley: the skipper did not give clear instructions either for the initial expense or for the responsibility of preparing lunches and dinners, we did not know each other, the result was somewhat anarchic and improvised meals; In the end we did very well anyway.
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/12/2026

valentina t.

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IT

First (but I hope it won't be the last!) boat holiday experience. It lasted a week, but time seemed to dilate and flow slowly, in pleasant company. Seeing the islands from the sea offers another dimension, breathtaking places, views and colors. Too bad that the variety of species on the seabed appears "impoverished". We sailed little, almost always by motor, but certainly more easily.
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Mini whale watching cruise with WWF guide between Ponza and Palmarola

07/11/2026

beatrice c.

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IT

The trip exceeded my expectations thanks to Luca and Andrea. Andrea, our naturalist guide was always available at any time for any curiosity of the group, competent in the subject, generous, with remarkable soft skills, a serious young man, intelligent educated a reliable professional with great psychological balance. Luca, our skipper was a firm point, skilled, safe always attentive to our personal safety and to the boat, wise, polite, direct and directive the right: truly a great leader! Luca and Andrea are a couple that works very well, they know how to work in a synergistic, harmonious way, this makes them highly reliable, moreover excellent listeners and also funny!! With them I would go anywhere, relying on myself completely. I found the boat a bit too old and uncomfortable for 10 people, in my opinion Luca and Andrea and another person had to adapt a lot, even if I never heard a complaint from them. I thank you for all the welcome I received and for the joy I experienced.

4 Days Argentario-Giannutri-Giglio-Talamone

07/11/2026

Francesca M.

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IT

Tommy is a competent and easygoing skipper! He accompanied us on our first multi-day boat holiday with relaxation, irony and great availability. We met her wonderful family: Sofia and their magnificent "Leonidas"! Thank you for everything. See you next time!!

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