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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

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

Starting from

€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!

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

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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

€550

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

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

18482 reviews

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Midweek sailing trip: two days at sea in Alassio

08/13/2026

Alvaro B.

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IT

skipper Daniele with hospitable sailing experience Very nice and comfortable boat, great decision to sleep in the air-conditioned harbor A tip: for lunch on the boat I recommend agreeing on the menu beforehand otherwise you run the risk of having two identical lunches For the rest it was a really good experience

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

08/13/2026

Aurora G.

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IT

It was the first experience on a boat... unique and spectacular! Annalisa and Emanuel were able to make us feel immediately at ease. Both, experienced and close-knit sailors, emanate an immense passion for what they do, able to transmit it to all their companions. Two sunny, kind, helpful and knowledgeable people who take you to discover fantastic and exclusive places; deserted beaches and islands, far from the chaos, where it is possible to admire all the beauty of the Greek islands both during the day and during the night with breathtaking starry skies. The boat is well organized, allowing you to move freely and safely even in small spaces. Moreover, Annalisa and Emanuel are also fantastic cooks, capable of preparing exquisite delicacies with local flavors and in great abundance! Also thanks to our travel companions, we can say that we embarked as perfect strangers and then disembarked feeling part of a group of friends. Thank you very much Emanuel and Annalisa for this unforgettable experience... See you soon!
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Two days at the Tremiti Marine Protected Area

08/13/2026

Anna M.

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IT

The boat and the service could be improved.... The tremors are much more than what we have seen, the sail is something else. High cost to experience. Skipper too apprehensive and not very empathetic puts you a little anxious puts you in awe and you don't enjoy your holiday Despite some very welcome gestures of courtesy, the feeling of unease prevailed. Would not recommend

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/13/2026

francesco b.

-

IT

The trip was unique in its kind for the good relationship that was created between the crew of the boat. For me it was an authentic and fun experience that for a week makes you think of nothing else

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