Kyle Dean Massey: My Italian Summer Vacation


As a working actor constantly moving between stage and screen, sometimes, it’s hard to find a moment to slow down. After joining the Pippin tour for a quick stint and filming the third season of Nashville, Kyle Dean Massey was ready for a break.

With Nashville shooting not picking up again for about a month, Massey packed his bags for Italy, where he stayed in Rome and took excursions around the country—one to the Amalfi Coast.

Broadway Style Guide recently caught up with Massey to discuss his summer travels.

How did you pick the Amalfi Coast?
All the locals in Rome said that getting down to the Amalfi Coast was a not-to-be-missed experience. I’ve always had a romantic idea of the Amalfi Coast from movies like The Talented Mister Ripley, so once the locals endorsed it, I was set on going.

Where did you stay?
I stayed in Positano at a lovely little pensione [boutique hotel] built into the cliffs overlooking the Mediterranean. The pensione was only accessible by a narrow foot path that zigzagged from the only road through the village. I woke up both mornings to a nice little balcony off my room with panoramic views, and breakfast was served on a terrace with coffee so good it makes you wonder why you ever settled for less.

What is your packing strategy when traveling?
Since I had an apartment in Rome, I was able to leave my large suitcase there for my weekend trip to the Amalfi Coast. I travel quite a bit for work, and I’ve learned to be more selective about what I bring with me. I’m not someone who can plan outfits ahead of time when I’m going to be gone for two or more weeks. Having a wardrobe where everything (for the most part) works together has helped make that easier for me.

What are your traveling essentials?
iPad for reading and the New York Times Crossword Puzzle app
One-Line-A-Day Journal
Leatherology Passport Cover

KDM Numbered

1. “Positano is crammed with shops, phenomenal restaurants and beautiful black rocky beaches.” 2. On the boat ride: “It’s the one thing I absolutely would not trade.” 3. The city at night. 4. “The walk to the inn on this winding walkway only added to the charm of the experience.” 5. “I feel like I never had a bad meal.” 6. The Amalfi Coast is a “not-to-be-missed experience”!

What are you summer product essentials?
I use a sea-salt spray and Bumble & Bumble Sumotech on my hair, Kiehl’s facial fuel with SPF 15, Immortal face cream at night, and my summer scent is Tom Ford’s Gray Vetiver.

What’s your go-to outfit while on the trip?
I’d say my go-to outfit in Italy was chinos, loafers, and some sort of t-shirt. Although it was really warm in Italy while I was there, I loved popping into nearly every old church I’d pass. Most churches enforce some sort of dress code, and shorts are usually not allowed.

What is your greatest extravagance when traveling?
I feel like an asshole for saying this, but it’s definitely flying first class. It obviously costs quite a bit more, but it’s worth it for me. The entire process: check-in, security, the lounges, boarding, and the flight itself become an enjoyable and comfortable part of the travel experience.

That boat ride looks pretty amazing…tell us about that!
I chartered a small boat with a captain who took us from Positano around Capri. It was a four-hour trip on a beautiful boat that was stocked with wine and Peroni. I stopped and swam in the beautiful grottos that surround Capri and took in the gorgeous scenery, and the captain drove the boat through Faraglioni, the giant rock formations just off the coast of the Island. It was spectacular.

What was the best meal you ate while you were there?
Oh gosh, it’s Italy! While I was in Positano, I had prawns the size of lobsters, the freshest burrata I’ve ever had, unreal gnocchi, and always locally made limoncello.

Best “you had to be there” travel moment?
The next weekend I was in Tuscany in a tiny village. A local that I had met for all of five minutes lent me his car, and I drove to the nearby town of Montepulciano where I had a great day and then proceeded to lose the keys. The local didn’t have an extra set. He was totally unfazed by it all. He picked me up on his motorcycle, and we drove in the night down dirt roads in Tuscany to a neighboring village where we had an unbelievable dinner. We never found the keys.