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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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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September - October

€680

Per person

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5.0

New

Cruise to the Golden Islands via the capes and bay of St Tropez

France: French Riviera and Porquerolles

5 days - 4 nights

27 departures available

February - October

Starting from

€595

Per person

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4.5

Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€290

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

2 departures available

October

€320

Per person

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New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€600

Per person

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4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

June

€625

Per person

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5.0

New

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

€590

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

€890

Per person

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4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Italy: Lake Garda

1 day - 0 nights

8 departures available

September - October

€150

Per person

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New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,645

Per person

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5.0

Capraia and Elba Island - Sun, Sea and Fun!

Italy: Tuscany

4 days - 3 nights

One departure available

October

€400

Per person

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5.0

New

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

19207 reviews

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

09/25/2026

Sina Melina B.

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DE

A reliable, welcoming skipper. He gives you free choice which time you want to wake up (he starts the trip in the morning and you can sleep longer if wanted) and how much you're interested in active participation of the sailing. The boot is very well equipped: three bathrooms, two SUPs, fins and snorqueling masks and everything you might need for cooking.
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Long Weekend Santa Candida - Ventotene

09/25/2026

Claudio Giuseppe L.

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IT

Super experience! Marco and Giada are fantastic! They know every corner of the Pontine Islands!

Sailing course in the Cyclades

09/24/2026

ruggero r.

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IT

Amazing experience!! The skipper followed me step by step, teaching me the basics of sailing with great professionalism and patience. We sailed with a perfect wind to have fun and learn and the nights spent in the roadstead were all in coves of fantastic islets. Highly recommended.

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/24/2026

Julie D.

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NL

I had such an amazing week sailing through the Sporades with Gianfranco. From the moment I arrived, I felt very welcome. The boat is absolutely beautiful, very well looked after and always incredibly clean. What I especially appreciated was how much effort Gianfranco puts into making everyone feel comfortable and at home on board. I really enjoyed learning more about sailing from him and getting some actual sailing experience along the way. And then there is the food! Gianfranco is an amazing cook and prepared some of the best lunches and dinners I’ve had in a long time. One of my favourites was a fish risotto with fresh prawns, squid and other freshly caught seafood for lunch. Eating something that fresh and delicious on the boat, surrounded by the beautiful Sporades, was definitely one of the highlights for me. I also feel very lucky with the people I shared this experience with. I came for a sailing trip and left with new friends, new sailing experience and so many beautiful memories. I had a truly wonderful time and will definitely look back on this trip with a big smile. Thank you Gianfranco for making it so special! ⛵️🇬🇷

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