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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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4.6

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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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

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

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4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

Per person

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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€845

€676

Per person - min 2 pax

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€325

€309

Per person

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4.9

Weekend sailing course from Bandol

France: French Riviera and Porquerolles

2 days - 1 night

6 departures available

September - November

€301

Per person

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

4 departures available

September - October

Starting from

€1,100

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

19092 reviews

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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/9/2026

Parmentier S.

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BE

We had a very pleasant time, a very nice captain and hostess, a super nice doggie, a very nice boat, wonderful weather and blue everywhere, the dream.
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Amazing Pontine Islands on a sailboat with private bathrooms

09/9/2026

Elena B.

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IT

A weekend dedicated to well-being and beauty. Comfortable boat (5 cabins with private bathrooms), clean, spacious and well maintained; skipper Dario and his right hand Enrica were helpful, kind and accommodating from the start. Perfect organization... it would take a thousand weekends like this! Thank you thank you

Ios, Sikinos, Folegandros and Anafi: the fantastic Cyclades of the South

09/9/2026

Elisabetta M.

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BE

WONDERFUL: this word can give you an idea of what awaits you on a holiday like this. It was an unforgettable week, in the middle of the sea, with fantastic people I didn't know and an absolutely unique skipper! Alessandro is the skipper that everyone would like, punctual, a profound connoisseur of the sea, an excellent cook and an unforgettable storyteller! We were lulled by the sea, we ate delicious food and, last but not least, the comets kept us company! I would leave immediately... thanks also to my extraordinary travel companions!
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Discovering the Aeolian Islands Between Nature, Relaxation and Fun

09/9/2026

Vincenzo R.

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IT

Good fifth ... sailing Eolie with Giovanni and his [hidden], a jewel of absolute comfort, was a once-in-a-lifetime experience, possible to replicate only with him. Because Giovanni spends himself to the maximum, all the time committed to introducing us to enchanted pieces of the Aeolian Islands, in-depth knowledge of the islands his... He knows everything about everything. Kindness, courtesy, understanding, management of unforeseen events, natural ability to make your guests feel at home, in your home, to make them feel like a group, Giovanni has a generous heart... and where there is heart there is everything. Be careful, however, there are fundamental rules, mandatory to be respected to close the circle of this unforgettable sailing. Seven days, each one different from the other, relaxation and fun at full speed, music, super-delicious aperitifs on absolute sunsets, flavors of an extraordinary cuisine prepared with care and passion that I would never have discovered if not spending all the time with him and his new adventure companions. Not just boating, an experience with high added value that after so much sailing with different skippers I didn't think could come true. Thank you very much Giovanni... you gave me a dream... Seeing is believing.

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