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Last summer, some friends of mine were getting married in Tuscany, so we decided to go somewhere somewhat conveniently located beforehand for a holiday. We toyed with a few locales: Sardinia, Elba, Portofino… ultimately opting to go in the other direction altogether, to Puglia. One overnight flight to Rome and one (thankfully, much shorter) flight to Brindisi later, we’d arrived. We spent six days in the southernmost part of Italy’s heel, ping-ponging around in a tiny rental car from Lecce to Castro to Otranto to Gallipoli to Tricase, with many stops along the way.
Our itinerary mostly consisted of long lunches, reading (ok—napping), and beach hopping. It was a much-needed recharge after months of work; plus, a good way to prep the social battery required for three days’ worth of destination wedding festivities. I learned that our visit happened to be during Ferragosto, which our hotel held a celebration for, and that my new favorite aperitivo snack is taralli, which I continue to keep stocked at home as a permanent souvenir from the trip. Talk about a peak Italian summer!
Ahead, everything I wore, ate, and snapped photos of during a relaxing trip to Puglia.
The Destination: Puglia
The Travel Outfit: Summer travel temperatures can be unpredictable, so I stick to comfortable separates that are light and layerable. You never know if the plane or rental cars are going to be well air conditioned, or well… not.
The Packing List: I’m big on accessorizing in the summer; you’ll find no shortage of shells and beaded baubles, sunglasses, and other joyful accoutrements in my suitcase. Otherwise, I keep to simple apparel: breezy trousers and plain tanks by day, white dresses and blouses by night. Then, I use the accessories to jazz things up. I never go anywhere in summer without Matteau’s white cotton pull-on pants or a pair of flip flops (or three).
Madewell
Faithfull
The Hotels: La Fiermontina Luxury Home Hotel is situated inside the 16th-century walls of old town Lecce. It was the perfect way begin our trip, just steps from the local restaurants and shops. With only 19 suites, our stay felt intimate despite being in the town center, whether we were enjoying breakfast or having a spritz by the pool. Sculpture works by Renè Letourneur and Jacques Zwobada are found throughout the properties grounds; though guests can also visit the Fiermonte Museum for more art—it’s a quick walk away.
After a few nights in Lecce we checked into the most traditional style of accommodation in the Apulia region—a masseria, or country estate. Masseria Montelauro was everything we needed. The quiet rural property is just outside the bustling coastal town of Otranto, and is run by a mother and her two daughters. We got the most out of our days relaxing and reading by their tranquil pool after exploring nearby beaches, before driving into Otranto for late dinners, gelato, and live music.
The Memorable Meals: On our first full day of the trip, we drove about an hour north of Lecce to have lunch at Il Principe del Mare, a place that came recommended by Catherine Saks (of the former beloved Danish label, Saks Potts). It’s a small spot perched right on the sea’s edge with open windows for walls, completely packed with locals—which is usually a good sign. I had a perfect plate of spaghetti alle vongole, a few servings of sea urchins (ricci di mare), tuna carpaccio, and gamberi. Both the food and views were divine. We wanted to go back every day for the rest of the trip—it set quite a high bar!
We started off our lunch at Taverna del Porto in Tricase by looking over a long list of natural wines and picking out our fish downstairs in their market. It was then prepared for us in a few delicious and beautiful ways, from crudo to pasta. We sat upstairs looking out over the sea and watched a bit of rain come down; luckily we were at lunch instead of on the beach when the weather turned. Funny enough, I ran into my colleague from British Vogue, Naomi Smart, after our meal. I guess we had the same idea!
The Swimming Stops: I stick to triangle bikinis and minimalist one-pieces for swim; my go-to labels are Tropic Of C, Jade, Eres, and Matteau. Sun protection is important to me, so you can usually find me sitting under an umbrella and with a hat on-hand—Janessa Leoné makes my favorite raffia topper.
On the days where we wanted to spend every hour seaside, Bagno Marino Archi was an easy choice. Built into the cliffs, the casual beach club had rows of umbrellas and chaises with plenty of places to swim. Spiaggia di Tricase Porto, on the other hand, was worth checking out for the scene and a quick swim to cool off, but it was quite busy. I wouldn’t set up there all day unless you had all the right equipment with you. My favorite spot was Lido La Sorgente in Castro. We arrived early and were lucky to secure two beach chairs and an umbrella, surrounded by local families. We picked up some fresh figs at a fruit stand nearby and took dips all day; it was the perfect place to read a book.
To me, there’s really nothing better than a beachside lunch—the kind you can stroll up to the table with your hair still damp from a dip and an easy coverup. Lido La Castellana was just that (just be sure to make a reservation). The outdoor eatery sits at the back of a tiny beach cove lined with beds and umbrellas on a patio under a shaded pergola. I shared a lobster spaghetti with fresh cherry tomatoes with my partner Adrian, and then took a nap on my chaise afterwards. An ice cream and a spritz (or two) followed suit once golden hour hit… what more can you ask for?
Jade Swim
Madewell
The Must-Buy Souvenir: My partner and I always buy olive oil when we travel; the greener the better! I became particularly obsessed with taralli, a ring-shaped cracker that comes from southern Italy. They were served at every aperitivo. We were headed to Tuscany after, and I got so nervous we wouldn’t be able to get them there, I purchased some to bring with us. If I’d checked luggage, I also would have brought home a few bottles of wine from Masseria Li Veli in Salento.
The Travel Bags: It’s much easier for me to work with carry-on luggage during summer trips, because beach clothes are way more packable. I have an old Vince carryall from 2019 that I plop on top of my suitcase, and it’s hands down the best oversized tote for travel. It fits so much but still manages to slide under the seat in front of you. I always have people asking me where I got it from. The brand doesn’t make my exact one anymore (the below is similar), but Vince team, if you’re reading this, let’s bring it back!
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