An Insider’s Guide To Capri, The Amalfi Coast’s Most Storied Island

The island of Capri on the Amalfi Coast is a storied destination the rich, famous, and fabulous often frequent, but what does it mean to truly experience and enjoy this mythical vacation spot in Italy? I have been lucky enough to visit Capri several times, and each time it feels like a place I both know and don’t know at all, which is part of its allure. This summer, I made my way back to the island with a group of friends, determined to experience Capri in a unique, non-tourist-y way — like a local or frequenter of the area.

In that pursuit, I sought out the advice of a friend of a friend who has spent several weeks in Capri the last 12 summers. Ilana Leighton is based between Nantucket and Boston, but she and her husband spend two weeks a summer in Capri, soaking in the lifestyle by renting an apartment and immersing themselves in the laid-back Italian culture. “Be prepared to walk a lot,” advises Leighton. “There are no cars in central Capri, and it’s amazingly beautiful. Explore the neighborhoods and smell the smells. The flowers are so beautiful, and the entire island smells of them.”

Luxury Travel Consultant for Atlanta-based Jetset World Travel Courtney Sheeley Wyckoff says that in order to really delve into what Capri is all about, you have to make some effort. “Capri is a very tourist-y island, so experiencing it in another way can be difficult,” she says. She agrees with Leighton that renting a home is a good start to having an authentic experience. “The best way would be to rent a house or villa and embed yourself with the locals. Go to the markets, ride the buses and taxis, and immerse yourself into everyday life. Capri is usually considered an overnight place or a place to visit for a day, especially during the summer. In order to experience Capri the right way, you must stay there for more than one day. Get off the beaten path and walk around. The best time to do that is June and October, because it is much less crowded. Also, the island is ideal for couples and groups — it is a little less ideal for families.”

Whether you’re solo or in a group, Capri is a bucket-list destination by all accounts, so here I round up some of the don’t miss spots to eat, shop, and explore.

Where To Shop

There is no debating that Capri is a luxury destination, so if you’re looking for high-end shopping you will find it. Dior, Chanel, Prada, Gucci, Hermes, Bottega? They are all there. The top designer shops range from spacious to highly curated and tiny, but they aren’t the only options if your bank account doesn’t allow for serious splurging.

Getting handmade leather sandals is a must on any visit to Capri. Make your way to Schettino Lella and choose from one of the many handcrafted sandals offered at this longtime family business. At 100% Capri, you’ll find the dreamiest selections of linen pieces you could ever imagine, perfect for Capri’s steamy summer temps. More airy, linen styles can be found at Ersilia Boutique, where you’ll find breezy button-downs, printed separates, adorable sets, and dresses. Take the time to wade through the jam-packed racks at Sud Capri where maxi dresses and brightly printed skirts abound — there are two locations on the island, and if you take the time, you can find some real treasures that will have people back home asking, “Where did you get that?”

Where To Eat

A trip to Capri — especially a first trip — is not complete without a visit to Da Paolino where you will dine among the island’s famous lemon trees. (Yes, you’ve probably seen this spot on your Instagram, but for good reason.) “You sit under a bed of lemon trees—it’s beautiful and smells incredible,” says Leighton.

Fresh fish, pizza, and — of course — an array of pastas are available at Villa Verde, located on a side street right in the middle of town. The huge outdoor terrace and fun vibe make this a lively spot that always translates to a good time, especially when dinner is capped off by their delicious frozen Limoncello cocktail. For an unforgettable thin-crust pizza, head to one of the oldest restaurants on the island Aurora, where yummy dishes are served at quaint tables set up in a pedestrian alley.

For Leighton, wandering around the island has also proved fruitful for finding lesser-known, delicious spots. “Lo Sfizio is a family-owned place about a 10-minute walk from the Piazzetta [the town square]. The food is amazing, and the people are wonderful. Also, make your way to La Cisterna, which you will never see in the tourist books. We stumbled upon it one night. We never order anything; the owner just brings us what he would eat!”

For prime people-watching, the deck at the five-star Quisisana — located steps from the central Piazzetta — has been welcoming royalty and rock stars since the mid-1800s. You’ll feel like a rock star sipping an Aperol spritz on the deck as you watch the people of Capri walk past. And, obviously, no trip to Capri is complete without the perfect gelato. You’ll know you’re in the right place when you see the line stretching down the street for a scoop or two at Buonocore. If you’re not in the mood for gelato, make your way to this pasticceria-slash-gelateria in the morning for their equally delicious almond croissants.

Leighton also says that sometimes keeping things simple is the best way to experience Capri. “Make sure to sit in the piazetta and have a drink or cappuccino and live like an Italian. No schedule and no rush,” she says. “Walk and explore. All the concierges and travel agents will send you to the same five restaurants — which are amazing — but if you just wander, you’ll find some of the best family-owned restaurants and people. “

What To Do

Beach clubs are the name of the game in Capri, and one of the most iconic (and Instagram-friendly, thanks to blue-and-white umbrellas) is La Fontelina. “Our customers have been returning for generations,” says co-owner and manager Gaetano Gargiulo. He attributes La Fontelina’s devoted customer base to the fact they try to make guests feel at home. That, and the fresh fish dishes and homemade pasta (don’t miss the local specialty, spaghetti with clams). “The secret is the simplicity of the dishes, cooked with love and always made with fresh ingredients,” he says. But La Fontelina is not only a restaurant, it’s also a beach club, complete with much-coveted beach chairs set up below the tables, along the sea. However, they are not first come, first served. Not in Capri. So what’s the secret? “Come to us every year and book a reservation and a beach chair for at least three consecutive days,” says Gargiulo. (Rumor has it that the more years you do that, the closer your beach chair gets to the water.)

Lido Del Faro is another exclusive, seaside spot accessed by a hidden footpath that winds through the countryside of the island. Tucked into cliffs that look out onto the spectacular Mediterranean, Lido’s setting makes the superb food and drinks taste even better.

As for what not to miss when you’re not at the beach clubs, Wycoff says to take to make sure you explore not only the main part of the island but also Anacapri, the sleepier little town located above Capri at the highest point of the island — known for beautiful hotels and spectacular views. “Capri is small,” says Wycoff. “I would recommend taking a boat tour and then a car tour, which allow you to see the entire island. Taxis (the special, convertible Capri kind) can take you to Anacapri for a nice hike and a visit to Villa San Michele, the former home of Swedish physician and author Axel Munthe, located on the ruins of an ancient chapel. And, take an island tour by boat, so you can see all the grottos and the beautiful water.” (Of course, the most famous among them would be the Blue Grotto, but the island actually has several.)

Once back on the main island, Wycoff says to make your way to the Piazzetta to soak in what Capri is all about. “Make sure to have an aperitif in the famous Piazzetta.” Leighton agrees the island’s town square is the center of the action. “Sit in the Piazzetta, sip an Aperol, and just take it all in,” she says. “There are so many different people and cultures in one spot.”