header cover

Yacht sailing holidays & skippered tours in Italy

Discover more than 41 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

41

experiences

cover image
avatar image

4.9

Super!

Wine Experience with Sommelier on the Island of Elba

Duration:

4 days - 3 nights

Italy:

Tuscany

avatar image
avatar placeholder

+2 travellers

have booked

€479

€599

Per person

cover image
avatar image
Portovenere - Ligurian and Tuscan Archipelago

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

€855

€950

Per person

cover image
avatar image

5.0

Summer in the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

avatar image
avatar placeholder
avatar placeholder

+9 travellers

have booked

Starting from

€531

€590

Per person

cover image
avatar image

4.7

Seductive weekend on a sailing boat on the island of Elba

Duration:

3 days - 2 nights

Italy:

Tuscany

avatar image
avatar image
avatar image

+50 travellers

have booked

Starting from

€239

€265

Per person

cover image
avatar image
Magical weekend on Giglio Island

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€252

€280

Per person

cover image
avatar image

4.9

Super!

A week in the Aeolian Islands - 6 islands in 7 days

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar image

+53 travellers

have booked

Starting from

€450

€500

Per person

cover image
avatar image
Experience among the Egadi Islands: a dream on a sailing boat

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€540

€600

Per person

cover image
avatar image

5.0

Free in the Wind... scents and wonders in the upper Adriatic

Duration:

2 days - 1 night

Italy:

Venice and the Gulf of Trieste

avatar image
avatar image
avatar placeholder

+8 travellers

have booked

Starting from

€171

€190

Per person

cover image
avatar image

4.8

A week in the Pontine Islands

Duration:

8 days - 7 nights

Italy:

Pontine Islands

avatar image
avatar image
avatar image

+12 travellers

have booked

Starting from

€585

€650

Per person

cover image
avatar image

4.8

Super!

Scopello, San Vito and Egadi: friends, good food sailing

Duration:

7 days - 7 nights

Italy:

Aegadian islands

avatar image
avatar image
avatar placeholder

+19 travellers

have booked

Starting from

€523

€550

Per person

cover image
avatar image

4.0

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

avatar image
avatar image
avatar image

+128 travellers

have booked

Starting from

€1,701

€1,790

Per person

cover image
avatar image

4.8

Lampedusa, Linosa and Lampione, islands on the high seas - all inclusive

Duration:

6 days - 7 nights

Italy:

Pantelleria and Lampedusa

avatar image
avatar image
avatar image

+23 travellers

have booked

Starting from

€713

€750

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

11321 reviews

avatar image

Discover the Aeolian Islands and their wonders

07/27/2024

edoardo c.

-

Italy

Indimenticabile, bellissime le isole Eolie! Grazie soprattutto a Rosario che ci ha fatto vivere a pieno i luoghi e la barca! Consiglierò questo tipo di esperienza a tutti, con l'augurio di trovare sempre uno skipper come Rosario.
avatar image

Enjoy sail: a Journey in the Aeolian Sea with Skipper and Sailor

07/27/2024

Micaela Z.

-

Italy

...altro che vacanza in barca a vela...una VERA ESPERIENZA di vita! Grazie al nostro comandante Andrea, abbiamo avuto una settimana per farci rapire dalle bellezze del mare, ci siamo fatti incantare dal mondo della barca e cadere innamorati delle fantastiche Eolie, una settimana per conoscere i membri dell'equipaggio e apprezzarci nelle nostre diversità saldando un legame unico, che solo una settimana prima sarebbe stato impensabile. una settimana per gustare del cibo delizioso e cucinato ad opera d'arte da Andrea che e' stato un cuoco ottimo, ma che ottimo...strepitoso, e sempre attento alle esigenze di ognuno. Esperienza indimenticabile, grazie comandante!! grazie ragazzi!!
avatar image

Enjoy sail: a Journey in the Aeolian Sea with Skipper and Sailor

07/26/2024

Katia P.

-

Italy

È stato il mio battesimo in barca, ne sono uscita assolutamente innamorata di questa esperienza…panorami fantastici, un grande senso di libertà, divertimento e attività a mare e a terra fantastiche… e poi che dire, il comandante è stato capace di far funzionare tutto alla meraviglia… oltre al fatto che sogno ancora la sua cucina…. Farei un’altro mese in barca solo per quello😅
avatar placeholder

4 days in the Pontine Islands (sailing school) 

07/26/2024

valentina P.

-

Luxembourg

Grazie Dario e Grazie Seneghe che ci avete regalato giorni di pura meraviglia, relax, buonissima compagnia e scarsa voglia di tornare in porto! Dario e’ un professionista, uno skipper talentuoso e con una vera passione per il mare, centrato, che sa trasmettere competenza e tranquillita’, il tutto condito da senso dell’umorismo, pazienza, grande umanita’ e ottimi gusti musicali 😊. Isole pontine come sempre splendide e Dario ha fatto di tutto per farci vedere il piu’ possibile in questi 4 giorni. Noi siamo stati benissimo e consigliamo al 100% questo viaggio. A presto Seneghe e a presto Dario!

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