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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!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€280

Per person

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5.0

Super!

From Skiathos to Athens

Greece: Sporades

7 days - 7 nights

One departure available

September

€620

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€700

Per person

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

€980

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

Per person

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3.8

Magical Pontine: full sail to discover the archipelago

Italy: Pontine Islands

3 days - 3 nights

2 departures available

August - September

Starting from

€499

Per person

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4.9

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€600

€540

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

4 departures available

September - October

€260

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

18645 reviews

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Island of Elba and South Corsica fantastic week

08/20/2026

Mirko G.

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IT

All great!!
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Learn to sail in a week in the Tuscan Archipelago

08/20/2026

cathy n.

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FR

First experience for us on a sailboat. We will keep wonderful memories of it. It was an incredible adventure! Thank you sincerely Marco for everything, we enjoyed it immensely.

Weekend Elba or Capraia

08/20/2026

Riccardo I.

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IT

A nice alternative weekend, especially for mid-August, with people we didn't know but we immediately got on well. Special mention for the skipper Sebastiano who in addition to sympathy also taught us something in terms of sailing. The only thing that my friends and I recommend to review to improve, is the departure time, since in the end we left on Saturday morning and we found it a bit useless to sleep the first night docked at the port.
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Whale watching cruise with WWF guide between Liguria and the French Riviera

08/20/2026

Giuseppe G.

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IT

Beautiful experience, I can only recommend it for those who want to experience the sailboat and experience the thrill of sightings as well as life on board. Andrea was very helpful and explained to us in an exhaustive way the life of cetaceans and the reason for this experience. Experienced skipper and help on sightings. The boat needs to be reviewed in general as maintenance and undersized for the number of crew on board, the only flaw (unfortunately)

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