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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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AMERICA'S CUP in pursuit of the AC40s!

Italy: Naples & Amalfi Coast

1 day - 0 nights

4 departures available

September

€180

Per person

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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

€350

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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4.5

Weekend on a sailing boat in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€380

€350

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

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

19196 reviews

North Corsica & Tuscan Archipelago: we love to travel a lot

09/23/2026

Lodovica G.

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IT

Wonderful experience! Thank you Marco until next time!

Wellness, sun, sea and adventure: a weekend full of sailing!

09/23/2026

Francesco G.

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IT

The 3 days of vacation we spent on the [hidden] were a wonderful experience. We saw beautiful places, and we had a very good time. The skippers Daniele and Maria Pia are delightful people, as well as very experienced and competent in the nautical field. And then, Maria Pia's cuisine was really excellent. Super recommended holiday!

Amazing Pontine Islands on a sailboat with private bathrooms

09/23/2026

Eleonora Santina Emma B.

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IT

Skipper and assistant skipper very friendly, pleasant and attentive both to the technique and to the atmosphere created in the group. Nice boat (maybe if there hadn't been a canoe on the deck we could have been wider in a higher number). Top destination!
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Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/23/2026

Miguel M.

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ES

[hidden] is a beautiful, safe, comfortable, and extremely well-maintained sailboat. Gianfranco loves sailing and a big smile appears on his face every time the sails are up and the engine is turned off.  No need to say that he is a skillful sailor, but apart from that, he is a fun and kind person, well-organized, and he made easy all the logistics about the trip. The crew was invited to participate in all maneuvers, and I enjoyed that a lot. I highly recommend the experience.

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