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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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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

October

Starting from

€950

Per person

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4.8

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

Per person

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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€312

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

6 departures available

September - October

Starting from

€585

€527

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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4.6

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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5.0

New

Just relaxing while sailing on the Côte d'Azur

France: French Riviera and Porquerolles

2 days - 2 nights

One departure available

September

€450

Per person

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4.9

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

Greece: Sporades

6 days - 7 nights

2 departures available

September

Starting from

€750

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

€700

Per person

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5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

6 departures available

September - November

Starting from

€380

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

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

19025 reviews

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Four nights in the Pontine Islands - midweek

09/5/2026

Angela Chiara C.

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IT

A more than positive experience. Antonio is an experienced skipper who led us through the beautiful bridges despite difficult days due to too much wind. He is also a very good cook, which is not a given. Above all, it is not obvious that the skipper cooks as well, and this is undoubtedly an added value since it leaves you even more time to enjoy the sea. The boat is all made of wood, old style and this is its beauty; certainly small improvements can be made but at the end of the season I think it is more than understandable; The spaces are sufficient and essential as they must be on a sailboat. We were also lucky enough to catch a tuna and meet a dolphin along the way, what else could we wish for? For all of us it went very well. Thank you for everything, Antonio!
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Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

09/5/2026

Paolo F.

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IT

Responsible, precise and helpful: Josuah manages to put guests at ease by allowing them to fully enjoy their sailing holiday. The boat is meticulously maintained; The destination was modulated according to the weather, but still met expectations. Good winds.

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

09/5/2026

Aurelio C.

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IT

Beautiful destination and itinerary.
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Tuscany and Corsica: sailing sun adventure good food energy and well-being

09/5/2026

Valentina R.

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IT

Very nice boat, excellent skipper and owner, delicious food. Costs a little too high given the decidedly downsized changes of course.

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