header cover

Yacht sailing holidays & skippered tours in Italy

Discover more than 197 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

197

experiences

cover image
avatar image

4.9

Sailing & Adventure in the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar image

+34 travellers

have booked

Starting from

€713

€750

Per person

cover image
avatar image

4.9

Adventure Flotilla in Costa Smeralda and Corsica

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

avatar image
avatar placeholder
avatar placeholder

+3 travellers

have booked

€799

€999

Per person

cover image
avatar image

4.9

Beautiful bays between North Sardinia and South Corsica on a catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

avatar image
avatar image
avatar image

+33 travellers

have booked

Starting from

€945

€1,050

Per person

cover image
avatar image

5.0

Tour of Elba and Capraia

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€1,300

Per person

cover image
avatar image

4.2

La Maddalena and its archipelago up to the south of Corsica.

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€600

Per person

cover image
avatar image

4.9

Sun & Sea Sailing in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€836

€880

Per person

cover image
avatar image

5.0

Gulf of Naples, Pontine, Amalfi Coast... Sailing in comfort!

Duration:

7 days - 7 nights

Italy:

Gulf of Naples

avatar placeholder
avatar placeholder
avatar placeholder

+10 travellers

have booked

€1,490

Per person

cover image
avatar image

4.7

Discovering the most beautiful corners of Sardinia

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

avatar image
avatar placeholder

+2 travellers

have booked

Starting from

€998

€1,050

Per person

cover image
avatar image

5.0

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

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar image
avatar placeholder
avatar placeholder

+6 travellers

have booked

Starting from

€79

Per person

cover image
avatar image

4.8

Let's discover the Aeolian Islands together by sailing

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar placeholder

+23 travellers

have booked

Starting from

€740

Per person

cover image
avatar image

4.5

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Duration:

6 days - 7 nights

Italy:

Pontine Islands

avatar image
avatar image
avatar placeholder

+9 travellers

have booked

Starting from

€664

€699

Per person

cover image
avatar image

4.0

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

avatar image
avatar image
avatar image

+108 travellers

have booked

Starting from

€1,986

€2,090

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

10907 reviews

avatar image

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!!!
avatar image

Sailing, early sun and aperitif at sunset ... What else?

05/3/2024

Cristiana L.

-

Italy

Giornata stupenda! lo skipper Emanuele molto simpatico, alla mano e soprattutto molto preparato e affidabile. Abbiamo veleggiato con un bel vento, io sono interessata alla vela ed Emanuele mi ha spiegato tante cose, fatto fare delle manovre e riposto pazientemente a tutte le mie tante domande. Abbiamo anche fatto un bellissimo aperitivo all'ancora. Non posso che consigliare vivamente questa esperienza!
avatar image

May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms

05/2/2024

susanna s.

-

Italy

una splendida vacanza . Fabio e Angela gentilissimi mi hanno offerto ogni confort a bordo e insegnato i primi rudimenti della vela .
avatar image

25 April - Whale watching expedition with WWF researcher in Liguria

05/2/2024

Rossella D.

-

Italy

Esperienza complessivamente decisamente positiva, nonostante le importanti difficoltà causate dalle pessime condizioni meteorologiche. L'estrema professionalità dello skipper e delle guide di whale watching, insieme al grande affiatamento e collaborazione che si è creato con tutto l'equipaggio, hanno fatto in modo che l'intera esperienza si vivesse nel migliore dei modi, in totale armonia, portando a casa anche grandi soddisfazioni di avvistamento di delfini, balenottere e tartarughe! Un'esperienza davvero indimenticabile, grazie di cuore!

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