experiences

4.8

Super!

Midweek holiday on Elba and basic sailing course.

Italy: Tuscany

2 days - 2 nights

3 departures available

August - September

Starting from

€220

Per person

5.0

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

July

€700

€665

Per person

4.9

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

October - November

€299

Per person

5.0

Sailing in southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

Weekend tra Versilia e Golfo dei Poeti

Italy: Tuscany

2 days - 2 nights

One departure available

July

€280

Per person

5.0

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

€795

Per person

4.5

Holiday - School between the Tuscan Archipelago and North Corsica

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€750

Per person

Approach to sailing - mini course

Italy: Tuscany

1 day - 0 nights

40 departures available

July - September

Starting from

€57

Per person

4.2

Weekend of theoretical and practical course

Italy: Liguria

2 days - 1 night

8 departures available

October - December

€250

Per person

5.0

Introductory sailing course

Italy: Liguria

2 days - 1 night

One departure available

September

€260

Per person

Approach to sailing: day on a boat with sailing lesson

Italy: Tuscany

1 day - 0 nights

80 departures available

July - October

Starting from

€77

Per person

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

544 reviews

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!

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

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 !!!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

10/22/2024

Marcello F.

Italy

Esperienza semplicemente fantastica e formativa!

Customer Support

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!

Call us at

+44 2035144220

Read our

Contact & Support

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

Sailboat (1530)Whole boat with skipper (1210)Cooking service onboard (200)Catamaran (140)Family sailing cruises (135)All inclusive (115)Day trips (115)Courses & regatta (55)WWF Sailing Cruises (45)Sport & wellness (30)

Other travel ideas

Sailboat (526)Whole boat with skipper (416)Cooking service onboard (102)Catamaran (70)All inclusive (59)Family sailing cruises (34)Courses & regatta (29)Day trips (28)Offshore (20)Sport & wellness (16)