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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!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€950

Per person

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4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

2 departures available

July - August

Starting from

€946

Per person

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4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August

Starting from

€850

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

5 departures available

August - October

€650

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€441

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€900

€855

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

2 departures available

July

Starting from

€590

€531

Per person

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5.0

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€700

Per person

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4.9

Super!

Weekend at the Pontine. Travel with photographer-Life changing experiences

Italy: Pontine Islands

3 days - 2 nights

3 departures available

September

Starting from

€370

€352

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€550

€495

Per person

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4.8

Super!

Let's enjoy the wonders of the Tyrrhenian Sea - Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

One departure available

August

€801

€761

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

17946 reviews

A full day on a sailing boat in the Gulf of ALASSIO

07/5/2026

Raffaella F.

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IT

Relaxing day!! Thank you Daniele and Edoardo
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Midweek sailing trip in the Gulf of Naples

07/4/2026

Andrea Z.

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IT

The skipper gennaro is a pleasant and helpful person, unfortunately the weather was not on our side, boat well maintained and tidy. Positive Opinion
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All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

07/4/2026

Erica M.

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IT

5 days of pure relaxation and fun! Despite the weather that was not always favorable, our skipper was able to make us sail in super safety, making the holiday unforgettable and full of emotions

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

07/4/2026

Maurizio N.

-

IT

The boat experience was wonderful thanks to the company and Matteo. He is a reliable and safe skipper but above all he is a welcoming and nice person. It is an experience that I recommend to everyone and that I will certainly repeat.

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