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Monohull yacht sailing holidays & tours in Italy

Discover more than 431 opportunities to get on board a Monohull adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

431

experiences

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5.0

Aperitif on a Sailing Boat and - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€90

Per person

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4.6

Educational weekends: manoeuvres and mooring in Tuscany 

Duration:

2 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€200

Per person

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5.0

Weekend in the coves of Ponza and Palmarola

Duration:

2 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€275

Per person

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4.7

Weekend sailing in the Gulf of Naples

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

Starting from

€260

Per person

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5.0

Weekend in Ponza, Palmarola, Ventotene

Duration:

2 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€250

Per person

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4.8

Seductive weekend on a sailing boat on the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+9 travellers

have booked

Starting from

€212

Per person

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4.5

In the blue of Capri and the infinity of the Amalfi Coast

Duration:

2 days - 2 nights

Italy:

Amalfi Coast

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+21 travellers

have booked

Starting from

€252

Per person

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5.0

Fantastic Weekend on Elba and Tuscan Archipelago

Duration:

2 days - 2 nights

Italy:

Tuscany

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+7 travellers

have booked

Starting from

€200

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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5.0

Weekend of Relaxation in the Argentario - Giglio - Uccellina

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€300

Per person

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5.0

Weekend of relaxation and fun

Duration:

2 days - 2 nights

Italy:

Liguria

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+23 travellers

have booked

Starting from

€261

€275

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

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

10021 reviews

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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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1st May - Whale watching cruise with WWF researcher between Elba and Capraia

05/6/2024

Francesca S.

-

Italy

Il meteo i giorni precedenti alla partenza era sfavorevole con molta pioggia, vento e onde alte, inoltre ho scoperto sul posto che il porto di Viareggio ha anche la problematica della secca. Lo skipper avrebbe dovuto cancellare la partenza, credo sia stato scorretto far presentare tutti i partecipanti e poi stare consapevolmente dal mercoledì al sabato pomeriggio in porto ad aspettare ed uscire solo dal sabato pomeriggio alla domenica pomeriggio. È vero che il tempo non si comanda, ma il giorno prima ormai già si sapeva che non ci sarebbero state le condizioni. Questa situazione mi è dispiaciuta molto, così come agli altri miei compagni, perché è un'esperienza molto dispendiosa ed è stato davvero spiacevole. Per fortuna ho trovato un bel gruppo e una brava e simpatica guida.
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April 25th long weekend in Bastia

05/6/2024

Lisa V.

-

Italy

Bellissima esperienza. Lo Skipper Enrico oltre ad essere un ottimo uomo di mare ci ha deliziati di ottimi pranzetti e cene in barca.
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25 April - 4 days sailing between La Maddalena and Bonifacio

05/3/2024

Bart S.

-

Spain

Excellent sailing trip in a comfortable boat with a great captain!! Grazie per tutto Leo & Crew!!!

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