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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

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

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

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

€585

€527

Per person

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5.0

Super!

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€600

€540

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

€300

€270

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

August - September

Starting from

€360

€300

Per person

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4.9

Super!

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!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

Starting from

€1,150

€1,035

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

2 departures available

September

€950

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

€600

Per person

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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September

€583

Per person

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5.0

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

4 departures available

August - September

Starting from

€700

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

18474 reviews

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Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea

08/12/2026

Eleonora B.

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IT

For our honeymoon we chose to visit the beautiful Aeolian Islands, and we couldn't have made a better choice. The most authentic way to experience them is from the sea, admiring breathtaking landscapes, enchanting bays and all the beauty that this corner of paradise can offer every day. We relied on Sailsquare for a private cruise and they introduced us to the [hidden] boat, captained by [hidden]: a young skipper, but with great experience and a contagious passion for the sea and for these islands. We spent an unforgettable week, feeling at home from the first day. Emanuele does not just take you to the most beautiful places, but really makes you experience the Aeolian Islands, telling its history, traditions and most authentic places. To make the experience even more special there are also his culinary skills: he is an exceptional chef and each dish is prepared with care, passion and love. What more can we say? Our honeymoon was simply perfect, an experience that we will always carry in our hearts. If you are looking for an authentic, exciting boat holiday full of unforgettable moments, Emanuele and [hidden] are the right choice. Eleonora and Guido
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Midweek sailing trip: two days at sea in Alassio

08/12/2026

Stephanie M.

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IT

Very well organized weekand Awesome experience
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The Mediterranean Mini-Flotilla: Capri, Ischia, and the Pontine Islands

08/12/2026

Alessandra P.

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IT

Very nice itinerary! Organization below my expectations: I had bought a mini flotilla and in the end only one boat left. The management of the relationship between participants and between participants and organization needs to be improved, especially in terms of timing and in the management of the galley.
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Amazing Pontine Islands on a sailing boat

08/12/2026

Fabia D.

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IT

Beautiful experience with a great crew! Barbara and Carlo were very helpful and attentive, the navigation was safe and pleasant and we visited beautiful places! Thanks to the next one!

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