ETW #2 Travel to Italy | Interview with Stephen Oddo

Rome Italy

From to Naples to Milan and everywhere in-between, learn how to plan the perfect trip to Italy with top travel tips provided by Stephen Oddo, co-founder of Walks of Italy.

Episode #2 is all about how to plan the best trip to Italy, whether it’s your first time or one of many. Italy is one of those rare destinations around the world that has captured the imaginations of almost every tourist. Either you want to visit or you have already visited, Italy is one of the most popular countries in the world. Due to its size and history, each region is incredibly different from one another and the experiences to enjoy in Naples will be in stark contrast to those found in Milan. To help us navigate what to see, do and eat in Italy, Italian travel expert and co-founder of Stephen Oddo joins us to share some of his top recommendations.

Florence Italy

In the interest of full disclosure, in 2012 I joined a few different walking tours in Venice, Milan and Florence and that experience helped prove to me the importance of a good guide, even if it’s just for a few hours.

To learn more about those travel experience please check out these posts I wrote after the tours:

Foggy Walk Through Milan

Lost and Found in Venice

A Walk Through Florence, Italy

Stephen Oddo co-founded, an online travel company for visitors to Italy offering sightseeing tours, in 2009. Walks became  one of the largest suppliers of FIT travel services in Italy, a success he attributes largely to social media and content marketing strategies. Walks has since launched tours in New York, Istanbul, Paris, Barcelona, Madrid, London, Athens, New Orleans, and San Francisco, rebranding as in late 2017. Their newest product, Walks On Walk Off™, is an innovative walking tour pass available in 5 cities, defining a new category of sightseeing. Walks is now one of the largest wholly-owned suppliers of sightseeing tours in the world, handling hundreds of thousands of passengers annually. Stephen oversees 10 global offices, is an expert in technology and digital strategy, and speaks at numerous industry events. You can also find Stephen on Twitter and Take Walks on Twitter, Facebook as well as Instagram.

In the episode Stephen and I discussed a number of topics from the best time of year to visit the Amalfi Coast to under-the-radar spots in Rome and the advantages of staying on a working farm in Tuscany. For more information on Stephen and his company,, please visit their web site. To learn more about the specific tours we mentioned, please visit the excursion pages below:

Venice ItalyVenice Full Day Lagoon Tour

Caesar’s Palace Tour (special access to closed sites on the Palatine Hill)

Pompeii, Positano and Amalfi Coast Drive tour from Rome

Amalfi Coast Day Trip From Rome by High-Speed Train


By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

1 thought on “ETW #2 Travel to Italy | Interview with Stephen Oddo”

  1. Great podcast, especially liked this episode. We used Walks when we visited Italy in 2017, both in Rome for a Vatican/Sistine Chapel tour and also did their Tuscany day-trip from Florence which was wonderful. Curious that Cinque Terre didn’t get a mention. It was, for us, a splendid highlight — we are both hikers spent two nights there exploring. I take your point about Florence. I liked it and I was glad to have gone, but I don’t need to go there again. Whereas with Venice and Rome — I would go back in a heartbeat! Super fun to hear a great discussion and I made some notes for our next Italian trip!

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