header cover

Yacht sailing holidays & skippered tours in Italy

Discover more than 60 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

60

experiences

cover image
avatar image

5.0

Spring on Lake Garda

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar placeholder
avatar placeholder
avatar placeholder

+25 travellers

have booked

€99

Per person

cover image
avatar image
Smart Working on a Sailing Boat: Adriatica is waiting for you on board!

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

€299

Per person

cover image
avatar image

5.0

Aeolian Islands - Volcanoes, Sail & Trekking

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

avatar placeholder
avatar placeholder
avatar placeholder

+4 travellers

have booked

€1,200

Per person

cover image
avatar image

4.8

May 1 BAREFOOT Bridge on a 17-meter boat

Duration:

3 days - 3 nights

Italy:

Tuscany

avatar image
avatar image
avatar placeholder

+7 travellers

have booked

€300

Per person

cover image
avatar image

5.0

Weekend of May 1st in Capraia

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€315

Per person

cover image
avatar image

4.3

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

Duration:

3 days - 3 nights

Italy:

Tuscany

avatar image

susanna s.

has booked

€399

Per person

cover image
avatar image

4.8

Vang Sheeting and TRIM on a state-of-the-art sailboat

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€140

Per person

cover image
avatar image
The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar placeholder

+4 travellers

have booked

€650

Per person

cover image
avatar image

4.9

May Day Sailing Bridge in Capraia

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€265

Per person

cover image
avatar image

4.5

Sailing on the Island of Elba

Duration:

3 days - 4 nights

Italy:

Tuscany

avatar placeholder

Elettra

has booked

€350

Per person

cover image
avatar image

4.9

May 1st long weekend sailing at the Pontine!

Duration:

5 days - 5 nights

Italy:

Pontine Islands

Give this experience a try!

€405

€450

Per person

cover image
avatar image

4.9

Trekking, E-bike & Sailing Experience, 1 May adventure on Elba.

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€618

€650

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

10894 reviews

avatar image

A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

-

Italy

Bellissima esperienza, bella gente con uno skipper top!
avatar image

Easter on the Island of Elba

04/22/2024

Antonios S.

-

Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza
avatar image

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!!
avatar placeholder

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!!

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