header cover

Yacht sailing holidays & skippered tours in Italy

Discover more than 175 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

175

experiences

cover image
avatar image

4.5

North Sardinia and South Corsica by catamaran with flybridge

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

avatar image
avatar image
avatar image

87 travellers

Starting from

€799

€940

Per person

cover image
avatar image

4.2

Easter in Portofino - sailing between the Gulf of Poets and the Tiguillio

Duration:

3 days - 3 nights

Italy:

Liguria

Give this experience a try!

€332

€390

Per person

cover image
avatar image

5.0

Easter Sailing: Explore the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€495

€550

Per person

cover image
avatar image

5.0

April 25th and May 1st: sailing to the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€504

€560

Per person

cover image
avatar image

5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

cover image
avatar image

5.0

Super!

On board with the chef at the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

avatar image
avatar image
avatar image

56 travellers

Starting from

€675

€750

Per person

cover image
avatar image

3.7

Cruise course in Sardinia

Duration:

7 days - 6 nights

Italy:

Northern Sardinia

avatar image
avatar image

2 travellers

€630

€700

Per person

cover image
avatar image

5.0

Super!

Easter and Easter Monday with whoever you WANT! to the Pontine Comfortable max 4 pers

Duration:

5 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€590

€656

Per person

cover image
avatar image

5.0

Super!

Weekend SS. Peter and Paul at the Pontine

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€441

€490

Per person

cover image
avatar image

5.0

Super!

Famo Ponte on April 25th Palmarola Ponza ! COMODI MAX 4 Pers

Duration:

5 days - 5 nights

Italy:

Pontine Islands

Give this experience a try!

€585

€650

Per person

cover image
avatar image

5.0

Super!

Bridge on May 1, 2025 between Palmarola and Ponza: maximum comfort for 4 people

Duration:

4 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€522

€580

Per person

cover image
avatar image
Spring in the Cinque Terre

Duration:

2 days - 2 nights

Italy:

Liguria

avatar image
avatar placeholder

2 travellers

€189

€210

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

12187 reviews

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 placeholder

Capraia and Totani, let's go!

11/10/2024

Pablo C.

-

Italy

Ci siamo trovati molto bene con Ivo: skipper professionale, cuoco provetto e persona gioviale con tanto da raccontare! La sua barca è in ottime condizioni e ben pulita. Torneremmo volentieri in barca con lui.
avatar image

Capraia: squid, walking and sailing!

11/4/2024

camilla t.

-

Italy

Alessandro è stato molto carino, gentile e disponibile ! Consigliatissimo :)

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