If there’s one place I return to in my work the way you return to a favorite café, it’s Italy. The truth is, Italy makes my job easy. The country does the composing, and I just try to keep up. The coastlines, colorful umbrellas, boats bobbing in the water, have all served as a muse to me over the years.
This is the story of how I learned to see Italy—trip by trip, beach by beach, vantage point by vantage point.
2013
I arrived in Sicily with a head full of maps and a camera that wouldn’t leave my hand. San Vito Lo Capo was my first immersion in true Italian beach culture—crowded in the best way, where beach days are a way of life. The Amalfi Coast introduced me to the art of mixing patience with elevation: drive the curves, climb where you can, then wait for the moment. In Positano, we met a local who casually solved my problem: “You need a boat.” The next morning, we had one. A day by boat changed everything, and I was on my way to Amalfi, Praiano, and Capri.
I crossed the country and learned “scale” in Rimini: miles of beach clubs, thousands of umbrellas, an entire visual grid humming in color. In Cinque Terre, Monterosso’s narrow strip of green-and-orange umbrellas tucked beneath the cliff was the image that had sent me to Italy in the first place. Seeing it in person felt like meeting a pen pal.
Read my travel journals from 2013 here: Part 1, Part 2, Part 3.
2015
Two years later, Jeff and I rented a car and gave ourselves permission to chase the coast. In Viareggio and Rimini, I brought a hardware-store ladder (the glamorous secret weapon) to earn cleaner lines and better height. It worked—and it reminded me that most “luck” is just effort with a good angle.
This was our first time visiting Italy together, and my first opportunity to take to the skies to photograph the coastline. Below are excerpts from the travel journal I kept throughout the journey. I hope you enjoy reading as much as I loved writing it.
I woke up and pulled back the curtains to see a beautiful blue sky- the perfect weather for my first ever aerial photo shoot over Italy! Jeff and I packed our bags and after a yummy breakfast set out on the road to the airport in Forte dei Marmi. Forte dei Marmi is a little bit like the Hamptons of Italy. Located not far from Rome and Florence, the elite circle of Italy tend to belong to one of the many gorgeous beach clubs that line the coast.
Our pilot and operating manager, Francesco and Antonio flew the helicopter in from Florence and were waiting for us upon our arrival at the “all grass” small airport.
After some security checks, they harnessed me in and we prepared ourselves to fly along the coast for about 40 kilometers ranging from Forte dei Marmi down to Viareggio. As we lifted off and came above the tree line, my little heart opened up and smiled - the sea of colorful umbrellas from above was even better than I could have ever imagined!
We took to the skies for the first time in Italy—Forte dei Marmi down to Viareggio, across the Adriatic beaches, and later over Amalfi and Capri. From above, the geometry clicked: boardwalks became rulers, umbrellas became pixels, and the sea read like negative space. On the ground, Puglia felt like a different country, white stucco, rocky coves, and locals turning tiny inlets into mosaics.
Read more about this special road trip here.
2017
We warmed up across the border in the South of France, then drove into Italy the cinematic way, out of a tunnel and straight into a gasp over Lake Como. To work the water properly, we teamed with Como Classic Boats for a two-boat day: I rode in a Riva Tritone with turquoise leather while a second boat let me photograph it against the shore. We traced the west bank in morning light—Villa del Balbianello, Villa Cassinella, the elegant lines of Villa d’Este—then crossed to Bellagio and Varenna as the sun pivoted.
The next morning I went up in the air to see what I could capture. A quick helicopter hour stitched together everything I love about Italy and aerials: geometry and grandeur, floating pools and cliff gardens, wooden runabouts threading a cobalt surface.
Venice was a fun lesson in art-history. It was a Biennale year, we drifted past monumental hands rising from a palazzo and ended the day with a spritz by the Cipriani pool. For a change of tempo, the Lido’s old-school cabanas (families keep the same ones for generations) brought back the joy of stripes. We closed the loop on the Ligurian coast—Santa Margherita, Portofino, Camogli, this time in full summer, when every umbrella is open. Everything looked like a moving postcard.
2019
After years of beaches, aerials, and small summer rituals, I gathered it all into ITALY—a love letter to the country’s coasts. Amalfi’s sun-soaked crescents, Sicily’s dramatic edges, wooden runabouts, cliffside clubs, and a few behind-the-scenes notes from the road—very much the spirit of La Dolce Vita: relaxed, patterned, irresistibly blue.
We marked the release with my biggest tour yet, visiting Eataly rooftops in LA and New York, Serena & Lily stops across the country, plus favorites in Boston, Chicago, Dallas, Houston, San Francisco, Philly, D.C., Atlanta, the Palisades, Newport Beach, and more. Meeting so many of you, hearing your Italy stories and seeing where the pictures live in your homes was the true highlight!
2024
This most recent chapter returns to Lake Como with Passalacqua—an 18th-century villa created as a “place of the heart” for friends, long tables, and the fine art of dolce far niente. That spirit is what I tried to bottle: glassy morning water traced by wooden boats and terraced gardens slipping toward the lake.
This is such a special destination if you ever get to visit, and I put together this Travel Guide to share with you my favorite ways to enjoy Lake Como!
Italy has given me so much—beautiful images, but also a way of savoring a place I cherish. If any of these destinations live in your memories too, I hope the work takes you right back!
Cheers,
Gray