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Sailboat yacht sailing holidays & tours in Italy

Discover more than 43 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

43

experiences

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4.5

Isole Egadi, Riserva dello Zingaro, San Vito Lo Capo - Hostess a bordo

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

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Spring in the Cinque Terre

Duration:

3 days - 2 nights

Italy:

Liguria

Give this experience a try!

€189

€210

Per person

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5.0

Easter Sailing: Explore the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€495

€550

Per person

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5.0

April 25th and May 1st: sailing to the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€504

€560

Per person

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5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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56 travellers

Starting from

€675

€750

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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44 travellers

Starting from

€765

€850

Per person

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5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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11 travellers

Starting from

€379

€421

Per person

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4.8

Super!

Aeolian Islands on New Year's Eve: winter magic between sea, sky and land

Duration:

5 days - 4 nights

Italy:

Aeolian Islands

Give this experience a try!

€475

€500

Per person

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4.8

Super!

Aeolian Islands: sun, sport, music, good food... The rest is magic!

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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129 travellers

Starting from

€618

€650

Per person

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4.9

Super!

Weekend of relaxation and fun from Marina degli Aregai in Liguria

Duration:

2 days - 2 nights

Italy:

Liguria

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39 travellers

€285

€300

Per person

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4.5

Sailing holiday with maximum comfort

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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6 travellers

Starting from

€680

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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 yacht sailing holidays & tours in Italy

11190 reviews

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Capraia and Totani, let's go!

11/10/2024

Pablo C.

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Italy

Ci siamo trovati molto bene con Ivo: skipper professionale, cuoco provetto e persona gioviale con tanto da raccontare! La sua barca è in ottime condizioni e ben pulita. Torneremmo volentieri in barca con lui.
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Capraia: squid, walking and sailing!

11/4/2024

camilla t.

-

Italy

Alessandro è stato molto carino, gentile e disponibile ! Consigliatissimo :)
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Capraia and Totani, let's go!

11/4/2024

MATTEO R.

-

Italy

Skipper molto esperto, preciso e disponibile. Ottimo cuoco e pescatore!! Molto attento (anche troppo) alla cura della sua barca e alla sicurezza dell’equipaggio. Qualche costo extra (cambusa a forfait e tesseramento asd) da mettere in conto, ma nel complesso, consigliato!!
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Offshore and Night Navigation Course between Elba, Corsica and Capraia

10/22/2024

Marcello F.

-

Italy

Esperienza semplicemente fantastica e formativa!

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