header cover
sailsquare logo

Courses & regatta yacht sailing holidays & tours in Italy

Discover more than 16 opportunities to get on board a Courses & regatta adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

16

experiences

cover image
avatar image

4.3

Basic Sailing Course in Sanremo, enter the world of real sailing!

Duration:

4 days - 4 nights

Italy:

Liguria

Give this experience a try!

€405

€450

Per person

cover image
avatar image

5.0

Super!

Let's sail together in Southern Sardinia

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

avatar placeholder
avatar placeholder
avatar placeholder

12 travellers

Starting from

€618

€650

Per person

cover image
avatar image

5.0

Super!

School-holiday cruise from Marina di Pisa to Cagliari

Duration:

10 days - 10 nights

Italy:

Southern Sardinia

avatar image
avatar image
avatar placeholder

6 travellers

Starting from

€1,045

€1,100

Per person

cover image
avatar image
Regatta on a sailing boat - 100 of Montecristo

Duration:

2 days - 2 nights

Italy:

Tuscany

avatar placeholder
avatar placeholder
avatar placeholder

5 travellers

€499

Per person

cover image
avatar image

4.9

A weekend of offshore sailing

Duration:

2 days - 2 nights

Italy:

Tuscany

avatar image
avatar image
avatar placeholder

13 travellers

€210

Per person

cover image
avatar image
Minigiraglia May Day long weekend in Capraia

Duration:

4 days - 4 nights

Italy:

Tuscany

avatar placeholder
avatar placeholder

2 travellers

€499

Per person

cover image
avatar image

5.0

Super!

Sailing in southern Sardinia

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

avatar image
avatar placeholder
avatar placeholder

37 travellers

€1,000

Per person

cover image
avatar image
Approach to sailing - mini course

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€47

Per person

cover image
avatar image

4.3

Weekend of theoretical and practical course

Duration:

2 days - 1 night

Italy:

Liguria

avatar image
avatar image
avatar placeholder

6 travellers

€250

Per person

cover image
avatar image

5.0

Super!

Sailing Course Sailing for Your First Command

Duration:

6 days - 6 nights

Italy:

Tuscany

Give this experience a try!

€600

Per person

cover image
avatar image
Weekend between Versilia and the Gulf of Poets

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€250

Per person

cover image
avatar image

5.0

Capraia and Elba sailing course

Duration:

3 days - 2 nights

Italy:

Tuscany

avatar placeholder

Amedeo M.

€235

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 - Courses & regatta yacht sailing holidays & tours in Italy

546 reviews

avatar image

Weekend of theoretical and practical course

03/11/2025

Domenico B.

-

Italy

Corso efficace e a misura di studente: Giampaolo sa davvero tutto ed effettivamente se il vento fosse stato più intenso saremmo potuti uscire sapendo già come comandare una barca a vela. Fantastico!
avatar placeholder

Weekend of theoretical and practical course

12/8/2024

Fabio M.

-

Italy

Gianpaolo è un bravissimo skipper, ha saputo coinvolgere tutto l'equipaggio. Utilissimi i suoi consigli
avatar image

Weekend of theoretical and practical course

11/27/2024

Matteo S.

-

Italy

Gianpaolo è stato straordinario. Pozzo di conoscenza e di voglia (e pazienza) di condividerla in maniera efficace e pratica. Accogliente sia lui che la barca. Comodo anche arrivare al molo e parcheggiare eventuale mezzo di trasporto. La barca (per quella che è la mia poca esperienza in merito ancora) si è dimostrata molto adeguata alle applicazioni sia teoriche che pratiche e per imparare. Da rifare sicuramente, consiglio decisamente !!!
avatar image

Offshore and Night Navigation Course between Elba, Corsica and Capraia

10/22/2024

Marcello F.

-

Italy

Esperienza semplicemente fantastica e formativa!

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!

Italy: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964