header cover

Yacht sailing holidays & skippered tours in Italy

Discover more than 200 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

200

experiences

cover image
avatar image

4.5

Classic is a chic ! Sailing between La Maddalena and Northern Sardinia

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€1,200

Per person

cover image
avatar image

5.0

Sea, sailing and relaxation in the beautiful Aeolian archipelago

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

avatar placeholder

Mauro

has booked

Starting from

€583

Per person

cover image
avatar image
The enchantment of the Egadi Islands: an unforgettable catamaran trip

Duration:

6 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€920

Per person

cover image
avatar image

4.4

Enjoy the Aeolian Islands with skipper and hostess

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

avatar placeholder
avatar placeholder
avatar placeholder

+8 travellers

have booked

Starting from

€1,040

Per person

cover image
avatar image
Discover the Egadi Islands on a Sailboat: Adventure and Fun

Duration:

6 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

€935

Per person

cover image
avatar image

4.0

Magical Amalfi Coast, Capri, Ischia and Procida by Catamaran

Duration:

6 days - 7 nights

Italy:

Amalfi Coast

avatar image
avatar placeholder
avatar placeholder

+6 travellers

have booked

Starting from

€1,350

Per person

cover image
avatar image

4.0

Sailing, Relaxation and Fun in the Pontine and Phlegraean Islands on a 15-meter Boat

Duration:

7 days - 7 nights

Italy:

Pontine Islands

avatar placeholder
avatar placeholder
avatar placeholder

+7 travellers

have booked

Starting from

€800

Per person

cover image
avatar image

3.5

Egadi Islands, Zingaro Nature Reserve, San Vito lo Capo

Duration:

6 days - 7 nights

Italy:

Aegadian islands

avatar placeholder
avatar placeholder
avatar placeholder

+4 travellers

have booked

Starting from

€675

€750

Per person

cover image
avatar image

4.5

1 Week Professional Catamaran Training - Cagliari Sardinia

Duration:

7 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

Starting from

€1,691

Per person

cover image
avatar image
Your Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar placeholder

+17 travellers

have booked

€903

€950

Per person

cover image
avatar image

4.6

Ponza and its wonders

Duration:

7 days - 6 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€855

€900

Per person

cover image
avatar image

5.0

Elba and Capraia - Sailing week among the Tuscan Islands

Duration:

6 days - 7 nights

Italy:

Tuscany

avatar placeholder
avatar placeholder
avatar placeholder

+13 travellers

have booked

Starting from

€830

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

avatar placeholder

25 April - Whale watching expedition with WWF researcher in Liguria

05/8/2024

Nicoletta S.

-

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!
avatar placeholder

Weekend with wine tasting between Santa Margherita Ligure and Portofino

05/7/2024

Valentina B.

-

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.
avatar image

Week End Basic and Advanced Sailing Course

05/7/2024

Antonio R.

-

Italy

Bellissima esperienza!!assolutamente da ripetere!!
avatar image

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

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964