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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

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

4 departures available

August - October

Starting from

€860

€774

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

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

2 departures available

August

€990

Per person

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4.9

Super!

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€990

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€716

Per person

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New

Corsica Sailing Experience for only 4 people

France: Corsica

7 days - 6 nights

One departure available

August

€900

Per person

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5.0

Super!

ONE WAY Marina River - Porto Vecchio

France: Corsica

3 days - 3 nights

One departure available

August

€290

Per person

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4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

One departure available

August

€749

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

September

€790

Per person

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4.7

La Dolce Vita on a sailboat: discovering the Côte d'Azur

France: French Riviera and Porquerolles

7 days - 6 nights

One departure available

August

€649

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

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

18261 reviews

Trip with photographer to the Pontine - Life changing experiences

07/31/2026

Silvia A.

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IT

They were wonderful days, between dream places, a lot of relaxation and moments that we will carry in our hearts. The boat is really well maintained, very clean and cared for in every detail. But what really made the difference was Francesco: a special person, always available, attentive and able to make you feel at home from the first moment. He pampered us throughout the experience, always making us feel at ease and transmitting his passion for the sea. Thank you so much Francesco, for making these days so beautiful. If we had to do a sailing experience again, we would choose you again without a second thought!

Whale watching cruise with WWF guide in the Corfu archipelago

07/31/2026

Elisabetta R.

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IT

Super reliable skipper, Fantastic WWF guide: an extraordinary mix of competence, sympathy and sensitivity. The atmosphere on board absolutely positive and in harmony despite the fact that we did not know each other. Beautiful experience, too bad we couldn't spot more animals but the weather was not perfect. You can't have everything... 😊

Midweek getaway between Elba and Capraia

07/31/2026

Francesca G.

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IT

Marco is very competent and knows how to put every person at ease, even those like me who were at their first experience on a sailing boat. The perfect company I found then made the holiday even more beautiful

Corsica & Capraia - only 4 guests - sun adventure & relaxation!

07/31/2026

David C.

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DE

An unforgettable holiday in all respects. The skipper is well trained in the area since he has always frequented it, the boat is well maintained and very comfortable. Luca is always available and attentive to everyone's needs and always makes you feel at ease. Even northern Corsica in July does not have many tourists so you can have a quiet holiday and this is not possible elsewhere. Even with the other passengers I was really lucky.

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