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Yacht sailing holidays & skippered tours in Italy

Discover more than 138 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

138

experiences

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5.0

Spring on Lake Garda

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+27 travellers

have booked

€99

Per person

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4.4

Sailing Excursion Alghero ( Skipper + Hostess )

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€90

Per person

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5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+48 travellers

have booked

Starting from

€99

Per person

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5.0

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

€130

Per person

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4.6

Meditation & Sailing

Duration:

5 days - 5 nights

Italy:

Tuscany

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+3 travellers

have booked

€480

Per person

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5.0

Trekking & Sailing Experience-Weekend lungo a Capraia in compagnia

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€361

€380

Per person

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5.0

Weekend in Capraia, the island with timeless sunsets

Duration:

2 days - 2 nights

Italy:

Tuscany

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+18 travellers

have booked

€225

Per person

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5.0

Weekend sailing among the Pontine Islands

Duration:

3 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€360

Per person

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4.3

Elba a sea of emotions - Stewardess on board - 3Cab/3Bagni

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€399

Per person

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4.9

Vela Trekking e Mountain Bike

Duration:

3 days - 3 nights

Italy:

Aeolian Islands

Give this experience a try!

€265

Per person

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5.0

Il tuo weekend in barca tra Relax e divertimento

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€356

€375

Per person

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4.8

Sailing on Elba

Duration:

3 days - 3 nights

Italy:

Tuscany

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+2 travellers

have booked

Starting from

€324

€360

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 - Yacht sailing holidays & skippered tours in Italy

10913 reviews

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Weekend in Capraia, the island with timeless sunsets

05/7/2024

Irene T.

-

Italy

Marco è un gran marinaio, super esperienza!
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Week End Basic and Advanced Sailing Course

05/7/2024

Federico B.

-

Italy

Skipper molto preparato, ha messo tutti a proprio agio. Barca confortevole, una giusta via di mezzo tra creciera e regata. Comoda e spaziosa per la crociera ma anche con la possibilità di molte regolazioni più caratteristiche della regata. Esperienza positiva! Assolutamente da ripetere!
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1st May - Whale watching cruise with WWF researcher between Elba and Capraia

05/6/2024

Elettra B.

-

Italy

Esperienza ottima. Immersione totale nella vita da barca con una parte di spiegazioni sulla vita del mare e dei nostri stupendi mammiferi marini. Organizzato con cura, attenzione e andando incontro ai bisogni delle persone presente dove possibile. Barca stupenda, tenuta bene, cibo in abbondanza, persone speciali con cui condividere spazi e tempo. Silvia molto attenta, veloce e simpatica, con una conoscenza approfondita della vita marina e non solo che trasmette senza fatica. Giulia super preparata e ottima relatrice. Anche se il tempo ci è stato avverso è stata un'esperienza unica di cui sono molto soddisfatta. Consigliata. Il capitano della vela è stato il top. Elettra .
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Catamaran weekend: La Spezia, Portovevere, Lerici and Cinque Terre

05/6/2024

Paola d.

-

Italy

Esperienza superpositiva. Catamarano comodissimo e nuovissimo.. Molto gradita la prenotazione delle cene a terra da parte dello skipper Maurizio sempre disponibile e discreto. Grazie 😀

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