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Yacht sailing holidays & skippered tours in Italy

Discover more than 236 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

236

experiences

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5.0

4 days relaxing in the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€480

Per person

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5.0

Crazy Ogliastra, mini-cruise through the wonders of Sardinia

Duration:

3 days - 3 nights

Italy:

Southern Sardinia

Give this experience a try!

€780

Per person

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4.3

July, how good I want you! - Stewardess on board - 3 Cab/ 3 Bathrooms

Duration:

4 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€429

Per person

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5.0

3 DAYS 2 NIGHTS Sailing the Ligurian Coast from GENOVA

Duration:

3 days - 2 nights

Italy:

Liguria

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+7 travellers

have booked

€342

€380

Per person

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5.0

AEOLIAN ISLANDS with hostess/cook BOAT 16.5 mt exclusive x6 people

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+21 travellers

have booked

Starting from

€998

Per person

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4.8

Discovering Elba and its beauty

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€497

€552

Per person

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Mini cruise Syracuse - Marzamemi

Duration:

3 days - 2 nights

Italy:

Sicily

Give this experience a try!

€801

€890

Per person

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5.0

Sailing, swimming and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+6 travellers

have booked

Starting from

€85

Per person

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5.0

Four days in the Pontine archipelago

Duration:

4 days - 3 nights

Italy:

Pontine Islands

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+5 travellers

have booked

€460

Per person

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5.0

5 days sailing the Tuscan Archipelago

Duration:

5 days - 4 nights

Italy:

Tuscany

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+2 travellers

have booked

€550

Per person

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4.9

Sails into Infinity: 3-Day Adventure in the Pontine Islands

Duration:

3 days - 3 nights

Italy:

Pontine Islands

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+20 travellers

have booked

€371

€390

Per person

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4.8

Weekend on the Island of Elba

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€290

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

10917 reviews

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25 April - Whale watching expedition with WWF researcher in Liguria

05/8/2024

Nicoletta S.

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Italy

Sabrina e Silvia due Guide appassionate e competenti, super disponibili per tutte le necessità delle persone a bordo. In quattro giorni si é creato un clima di amicizia e un affiatamento tra l’equipaggio che non avrei mai sperato! Nonostante le condizioni meteo marine non sempre ideali siamo usciti sempre in sicurezza e abbiamo fatto avvistamenti ogni giorno. Nicola lo skipper ha fatto sempre il possibile per assicurare la nostra permanenza sulla barca confortevole, come se fossimo a casa nostra. Esperienza che consiglierei a tutti, tornerò sicuramente!
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Weekend with wine tasting between Santa Margherita Ligure and Portofino

05/7/2024

Valentina B.

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Italy

Siamo stati fortunati ad avere Giorgio come skipper durante il nostro weekend in barca a vela. La sua gentilezza e professionalità hanno reso l'intero viaggio un’esperienza straordinaria. Giorgio ha mostrato una grande attenzione per la sicurezza e il comfort a bordo. La sua personalità amichevole e la sua capacità di mettere a proprio agio le persone hanno reso il viaggio ancora più piacevole. Giorgio è stato un ottimo skipper ma anche un provetto chef: grazie alla conoscenza dei vini e alla passione per la cucina ha creato un aperitivo stuzzicante e una cena, a base di pesce, davvero deliziosa. La barca è molto bella, confortevole e pulita. Consiglio vivamente Giorgio a chiunque cerchi un'esperienza di vela emozionante, in un contesto amichevole.
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Week End Basic and Advanced Sailing Course

05/7/2024

Antonio R.

-

Italy

Bellissima esperienza!!assolutamente da ripetere!!
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Weekend in Capraia, the island with timeless sunsets

05/7/2024

enrico g.

-

Italy

ottimi compagni di viaggio , marco m disponibilissimo e molto preparato grazie a tutti

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