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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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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

9 departures available

July - October

Starting from

€230

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

5 departures available

June - August

Starting from

€900

€765

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€650

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

13 departures available

July - November

Starting from

€540

€513

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

Per person

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4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

One departure available

August

€800

Per person

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5.0

Super!

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

Per person

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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

9 departures available

July - November

Starting from

€500

€425

Per person

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5.0

New

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

Italy: Aegadian islands

7 days - 7 nights

6 departures available

June - September

Starting from

€600

€540

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

13 departures available

July - November

Starting from

€600

€540

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

3 departures available

July

€590

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

17877 reviews

Three-Day Sailing Tour to the Pontine Islands

06/26/2026

Ylenia M.

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IT

Three-day tour of the Pontine Islands with skipper Antonio Sánchez... Simply fantastic! Three days of pure relaxation, laughter and excellent food, immersed in wonderful places. Antonio welcomes you as an old friend: a humble, genuine and always available person. In addition to being an exceptional cook, he is a true sea dog who knows how to fascinate with his stories and knows the island in every corner. He is attentive to every detail and always ready to satisfy any need, qualities that really make the difference. An experience that I recommend without hesitation. See you on the next adventure... fair winds, Captain! ⛵️
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Midweek getaway between Elba and Capraia

06/26/2026

Stefano S.

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IT

Unforgettable holiday... I had already had an experience and even this time I was not disappointed... mentally I'm still in the boat 👏👏

Four days in the Aeolian Islands from Capo D'Orlando

06/25/2026

Edoardo A.

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IT

Let's start by saying that Vittorio has an extreme knowledge of the boat he steers (being his property) which immediately puts you at ease and makes you feel calm. If we combine this with the deep knowledge of the sea and the islands that it proposes as a destination... We get a fabulous holiday! He was able to bring us and recommend (never impose) beautiful places, both at sea and on land. It was an experience of absolute relaxation, without missing the educational and sailing part. (optional) In short, what can I say, super recommended!! Thank you Vittorio! Ours is a goodbye Fair winds
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Midweek relaxing in the Pontine Islands

06/25/2026

marcella c.

-

IT

Great experience. Very good skipper from all points of view, always ready to add his experience and knowledge. New and well maintained boat.

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