header cover

Yacht sailing holidays & skippered tours in Italy

Discover the beauty of Italy and treat yourself to a sailing holiday of relaxation, fun, and unique landscapes. Sail around the beautiful islands of Sicily and Sardinia, discover the Lipari, Pontine and Aegadian Islands by boat or anchor in the romantic bays of Tuscany or Cinque Terres.

331

experiences

cover image
avatar image

4.9

Between Western Liguria and Côte d'Azur from Imperia - Stewardess on board

Duration:

2 days - 2 nights

Italy:

Liguria

Be the first one to book!

€190

Per person

cover image
avatar placeholder
A weekend in Liguria between Genoa and Portofino

Duration:

2 days - 2 nights

Italy:

Liguria

Be the first one to book!

Starting from

€180

€200

Per person

cover image
avatar image

4.9

SUSHI SU UNA LUSSUOSA BARCA A VELA

Duration:

1 day - 0 nights

Italy:

Lazio

Be the first one to book!

€70

Per person

cover image
avatar image

4.8

An unforgettable sail to discover the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

avatar placeholder
avatar placeholder
avatar placeholder

+14 travellers

Have booked

Starting from

€298

€350

Per person

cover image
avatar image

4.9

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

Be the first one to book!

€290

Per person

cover image
avatar image

5.0

Trekking weekend on the Island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

avatar placeholder
avatar placeholder
avatar placeholder

+12 travellers

Have booked

Starting from

€228

€240

Per person

cover image
avatar image

4.5

Spinnaker and Gennaker course: hoisting/lowering manoeuvres and adjustments

Duration:

2 days - 2 nights

Italy:

Liguria

avatar placeholder
avatar placeholder

+2 travellers

Have booked

€280

Per person

cover image
avatar image

4.9

A weekend of sailing between Capraia and the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

avatar image
avatar placeholder
avatar placeholder

+6 travellers

Have booked

€212

Per person

cover image
avatar image
Weekend between Genoa and Portofino: experience the sea, the food, the emotions

Duration:

2 days - 2 nights

Italy:

Liguria

Be the first one to book!

Starting from

€204

€240

Per person

cover image
avatar image

5.0

Tartare, prawns and bubbles in Santa Margherita Ligure - ALL INCLUSIVE

Duration:

2 days - 2 nights

Italy:

Liguria

avatar image

Claudia undefined.

Has booked

Starting from

€224

€249

Per person

cover image
avatar image

4.9

Weekend on Elba between Sailing, E-bike and Tasting in a farmhouse

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

€390

Per person

cover image
avatar image

4.9

E-bike & Sailing Experience with wine tasting on Elba - 2 boats

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

€314

€330

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

10887 reviews

avatar placeholder

Ventotene by sailing boat from Naples

10/16/2023

Manuela M.

Come chiudere “l’estate” in bellezza? Con un week da sogno a Ventotene con Gennaro ed Emiliano! Le aspettative non vengono mai disattese …e ci salutiamo sperando nella benevolenza del meteo per poter dire la settimana prossima… noi siamo ancora qui! L’estate non è finita! Incrociamo le dita!
avatar placeholder

Weekend of sea and colors between Ischia, Procida, Vivara and the Phlegraean fields

10/16/2023

Manuela M.

Quando vuoi avere la certezza di passare un eccellente week and a vela …..non puoi che scegliere Gennaro ed Emilano! Compagni di viaggio ke diventano amici, cibo eccellente preparato con amore dalla ormai carissima Raffaella, richieste improbabili tutte accontentate, barca sempre al top ma soprattutto loro, Gennaro ed Emiliano che fanno la differenza!
avatar placeholder

Aeolian Islands in Blue between sea and sky: Sun, sport, music, good food ... The rest is magic!

10/16/2023

Damien B.

-

Switzerland

It was my first excursion by boat and it was an incredible experience! I can only recommend it! The landscapes are beautiful and the boat is well-maintained with enough space and a nice Skipper. ++ Dario knows a lot about the sea and his boat! He likes to share what he knows about it. He knows also when to integrate the group and when to let things happen. He likes humans and is very kind. During, before and after he was also very reachable. -- I would have appreciated more information and clarity about excursions. I added them below to help the comments readers. ?? Be aware of taking good shoes, warm clothes and a torch if you want to climb the Stromboli (which I highly recommend) There is the possibility of eating in restaurants on different islands. Being barefoot is recommended on the boat. Bring your eco-shampoo with you. The bedsheets were furnished. Hope that's help and that you will enjoy the tour!
avatar image

Aeolian Islands in Blue between sea and sky: Sun, sport, music, good food ... The rest is magic!

10/16/2023

Davide P.

-

Italy

Bella Vacanza, lo Skipper Dario è molto competente la sua passione per il mare è trasmessa con amore a tutti i membri dell' equipaggio, conosce benissimo le isole e sa come muoversi.

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!

Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

Aeolian Islands

Stromboli, Vulcano and Lipari are just some of the best destinations for a sailing or catamaran vacation in Sardinia.
Guide to the Aeolian Islands on a sailing boat

Sardinia

Costa Smeralda, Maddalena Archipelago and San Pietro Island are just some of the best destinations for a sailing or catamaran holiday in Sardinia.
Guide to the Sardinia on a sailing boat

Capri, Ischia and Procida

Enchanted landscapes and elegant haunts, thermal springs and seabeds full of surprises, simplicity and glamour: there is more than one reason to choose these timeless islands as a destination for a yachting holiday in stages.
Guide to Capri, Ischia and Procida on a sailing boat

Amalfi Coast

Positano, Amalfi and Cetara are just some of the best destinations for a sailing or catamaran holiday in the Gulf of Naples.
Guide to the Amalfi Coast on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
Guide to sailing vacations with children

Italy: the most beautiful places to sail

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964