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Monohull yacht sailing holidays & tours in Italy

Discover more than 432 opportunities to get on board a Monohull adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

432

experiences

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5.0

Weekend on the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+34 travellers

have booked

Starting from

€228

€240

Per person

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4.5

Weekend of sea and colors between Ischia, Procida and Vivara

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

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+13 travellers

have booked

Starting from

€237

€249

Per person

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4.8

Barefoot holiday: Weekend between Elba and Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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+15 travellers

have booked

Starting from

€260

Per person

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4.9

A weekend in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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cosetta

has booked

€265

Per person

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4.9

Between Western Liguria and Côte d'Azur from Imperia - Stewardess on board

Duration:

2 days - 2 nights

Italy:

Liguria

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+2 travellers

have booked

€275

Per person

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4.2

Relaxing weekend between Portovenere and the 5 Terre

Duration:

2 days - 2 nights

Italy:

Liguria

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+5 travellers

have booked

Starting from

€250

Per person

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4.4

Weekend Riviera Ligure di Ponente and Côte d'Azur - skipper and hostess

Duration:

2 days - 1 night

Italy:

Liguria

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+6 travellers

have booked

€200

Per person

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4.5

A week with YOGA and SAILING lessons in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€1,350

Per person

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Sailing weekend in Camogli and Portofino from Genoa

Duration:

2 days - 1 night

Italy:

Liguria

Give this experience a try!

€199

Per person

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5.0

The island of Ischia between sailing and trekking

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

€200

Per person

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4.7

Two hearts and a sailboat: discovering the Phlegrean Islands

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

Starting from

€225

Per person

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5.0

Weekend with wine tasting between Santa Margherita Ligure and Portofino

Duration:

2 days - 2 nights

Italy:

Liguria

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+18 travellers

have booked

Starting from

€289

€340

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 - Monohull yacht sailing holidays & tours in Italy

10008 reviews

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A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

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Italy

Bellissima esperienza, bella gente con uno skipper top!
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Easter on the Island of Elba

04/22/2024

Antonios S.

-

Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza
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Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

-

Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!
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Luxury sailing in the Gulf of Poets

04/15/2024

Antonio C.

-

Italy

Giornata splendida, mare e barca perfetti, altissimo valore aggiunto l’equipaggio, simpatico gentile preparato ma soprattutto disponibile, e Costanza ottima cuoca, esperienza fantastica, da ripetere!!

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