We may earn revenue from the products available on this page and participate in affiliate programs.

Picture this for a modern-day fairy tale: An American woman meets a handsome Italian man at a party in New York City, falls in love, then moves to Milan to eventually start La DoubleJ, the hot e-commerce business–turned–style bible. That woman-about-Milano, J.J. Martin, has designed a life spent hopping across Italian coastal towns and chic cities, searching for style inspiration and maximum dolce vita.

As Martin is in full swing of planning a pop-up series along the Italian coast—the first opens in Porto Ercole this coming weekend—and in the US this summer, we asked her to map out the ultimate guide to her favorite spots in the picturesque, cliff-faced towns of Capri, Positano, and Porto Ercole. In the tradition of her beloved Italian grand dames, Martin suggests the right outfits to dress the part for each spot. “Italians are more codified, sophisticated dressers,” she points out. “There’s a fundamental style chip they’re born with.”


Arguably one of the more recognizable and iconic spots of the Amalfi Coast, the island of Capri sits off the Neapolitan shoreline. Everywhere you look is like the Garden of Eden—wild and vibrant. Through the years, it has become a luxurious playground, boasting the finest in shopping, dine, and of course, sights. Getting to Capri is definitely a hassle but absolutely worth it!

Where to Stay

La Fontelina Beach Club Località Faraglioni
There are a few beach clubs in Capri, but this one is the best—an old-school place where you lounge on sun beds and eat delicious five-course meals with the glimmering sea in front of your eyes.

J.K. Place Via Marina Grande, 225
The owner, Ori, is a friend, and I always stay in his hotels in Florence and Rome, too, as they are all so chic. The Capri location is on a cliff far from the noise and bustle. Inside, the interiors by Michele Bönan are crisp and clean, and everything is just right. 

Where to Eat

Le Grottelle Restaurant Via Arco Naturale, 3
There are tons of great restaurants in the center of Capri, but I prefer the ones out of the limelight. Le Grottelle is on the far side of the island and you have to walk to get there, but then you sit outside and have a fantastic view of the Arco Naturale.

Lo Zodiaco Pizza in the Marina Grande Piazzetta Ferraro, 2/3
Sometimes you just want an easy pizza. And the good news is that a pizzeria in Italy always serves pasta, seafood, and salads, too. Everyone wins.

Where to Shop

Delfina Swimwear Shop Via Fuorlovado, 1/A
I have a thing about only shopping for swimwear when I’m actually on vacation. This little spot has great unexpected stuff—pieces from Laura Urbinati, whom I love, as well as some retro-shaped suits. Da Costanzo SandalsVia Roma 49There are great sandal makers all over Capri. You can’t go wrong. But I just happen to go to this guy the most. You can get them with a lot of bells and whistles or just super-simple. Lately I’ve been wanting to wear very plain flat sandals with everything.

Laboratorio Via Ignazio Cerio 6
Laboratorio is a local shop where you can find traditional pants and sweaters. It’s not “fashion”—just easy, beautiful clothes.

Eco Capri Shop Piazzetta Ignazio Cerio 11
Run by a local family, this historic shop is filled with lovely home objects and accessories. I’ve picked up needlepoint pillows, printed trays, and embroidered totes.


In Positano, you just take in the beauty of the scenery and go on hikes along winding roads.

Where to Stay

Villa Tre VilleVia Arienzo, 30
For me, Villa is absolute paradise. It’s a very small hotel with a sprawling property built into the side of a hill and submerged under a blanket of colorful flowers, trees, and exotic plants. There are special corners and nooks everywhere you look. I feel as if it’s an enchanted forest. My favorite room is entirely done in turquoise and white. 

Hotel Il San Pietro di Positano Via Laurito, 2 
If you want a more classic hotel experience, the San Pietro is fabulous. It’s one of those iconic Italian hotels with amazing views and an elevator that goes all the way up the cliff.

Where to Eat

Da Adolfo Via Laurito, 40
This is the quintessential Amalfi outdoor dining experience. You arrive by boat and then sit down to giant plates of seafood pasta right on the beach while the waiters break out Neapolitan songs. Everyone is in their swimsuits and caftans. It’s fabulous.  

Maria Grazia Via Marina del Cantone, 65, Massa Lubrense
Visit Nerano, another little town further out on the same peninsula as Positano, and eat here. The arancini is great and they do the best spaghetti with zucchini. The specialty is eggplant parmigiana.

Things to Do

Swim at Isola Dei Galli
Just in front of Positano is this beautiful small island that used to be owned by Russian dancer Rudolf Nureyev. It’s like a little sanctuary. There are only a few homes, and you can explore it quickly. But more fun is just to park the boat and swim around it. The water is sublime.


About four hours’ north from Naples, Porto Ercole is all about Hotel Il Pellicano—but the boat culture is also wonderful. Spending the whole day on the water is transportive. Rent a little boat and go explore.

Where to Stay

Hotel Il Pellicano Località Sbarcatello
This is one of my favorite hotels in the world. There’s a perfect mix of totally chic and yet totally laid-back in the way things feel. The owner, Marie Louise, fills the hotel with a whole cast of interesting characters, and she’s always on hand to orchestrate everything—including divine poolside cocktails and yoga. The boutique sells LaDoubleJ as well as other fun resort-y pieces. And the breakfast buffet is not to be missed! It’s almost worth not eating dinner—homemade zabaglione, special cakes, and great breads. You don’t ever need to leave this place, to be honest.”   

Where to Eat

Il Frantoio Via Renato Fucini, 10, Capalbio
This is a great restaurant to try about a half hour from Il Pellicano in Capalbio, a beautiful town where all of the Roman and Venetian aristocrats stay. It has a lovely outdoor garden and lots of typical dishes with wild boar. (The Tuscans love their wild boar!)

Where to Shop

Rasna Boutique Corso Italia, 17, Orbetello
In the neighboring town of Orbetello, Rasna is a very cute shop for both men and women. There’s not much good shopping around here, but this boutique is really nice! 

Day Trips

Giglio and Giannutri Islands
You must take a boat ride to these islands, which are part of the Tuscan archipelago. The water is gorgeous. There’s a town and vineyard with great wine in Giglio and a beautiful roman villa to visit at Giannutri.

Before you leave…

Visit Naples!

Most people land in the Naples airport or train station and hightail it to the beach spots, but the town itself is so gorgeous and filled with many special churches, hidden corners, and restaurants. I highly recommend spending an afternoon exploring there.

See more from the summer issue:
5 Up & Coming Charleston Designers You Need to Know
Twice as Nice: A Joint Bridal Shower for Creative Twin Sisters
16 Simple Swaps to Make in Time for Summer