Your Perfect Capri Vacation Itinerary: Eat, Shop, and Explore

A Capri vacation is all about the finer things in life. How will you spend yours?

Only reachable by boat or helicopter, Capri is an Italian destination that dreams are made of. The island is tiny, only four miles long, and two miles wide, and boasts blue waters, rocky coastlines, and fragrant lemon groves.

Famous visitors of the past have included Jacqueline Kennedy Onassis, Grace Kelly, and Greta Garbo, while modern day stars include Oprah Winfrey, Mariah Carey, and luxury fashion designers like Valentino and Armani. Writers, filmmakers, and composers have created memorable works after finding inspiration everywhere they looked.

A Capri vacation is ideal for those who can appreciate the island’s rich history, while contributing to its understated elegance and fashionable ambiance. While one will always have time to relax and unwind in Capri, there are, of course, restaurants, shops, and attractions that are not to be missed. As you establish an itinerary for your trip to Capri, consider these iconic spots.

Where to eat on your Capri vacation

Capri Vacation Le Sirenuse

La Capannina

A meal at La Capannina represents the quintessential Capri dining experience. Since 1931, celebrities and other elite guests have always stopped into La Capannina, which serves fine, homemade local dishes. Owned by the same family since the very beginning, this restaurant is known for its unmatched hospitality, attention to detail, and signature pink tablecloths.

La Fontelina

La Fontelina only serves lunch, but it’s the type of prolonged lunch that you can make a whole day of if you choose. The restaurant is part of the La Fontelina Beach Club, where you can spend the better part of the day relaxing in the sun on the rocky shore. It’s only reachable by foot or water taxi (we recommend the water taxi), but this casual, no-frills beach lunch cooks up the freshest seafood you will ever taste.


Located in the Capri Palace Hotel & Spa, L’Olivo is the only restaurant on Capri to be honored with two Michelin stars. The dining experience is luxurious in every way — from the fine cashmere, linen, and cotton fabrics, to the handmade glassware, to the unobstructed views of the sea and pool area.

Where to shop on your Capri vacation

Capri Vacation Le Sirenuse

For the best selection of shops & boutiques…

If you want to do some serious window shopping and prefer to have shops within close proximity of each other, take a stroll down via Camerelle. This stretch features some of the major designers you’ll find at home, like Gucci and Fendi, but usually priced well below market value since you are on their home turf of Italy.

For custom-made pieces…

Capri is well-known for the cobblers that line the streets, making one-of-a-kind sandals from scratch. One of the best however, is da Costanzo on via Roma. Founded in the 1960s, the former owner’s son Antonio can make you a personalized pair of sandals in just a few hours.

For all types of custom-made clothing, stop by La Parisienne, the self-proclaimed inventor of Capri pants. Since 1906, shoppers have been able to share their vision, choose fabrics, and have clothing made especially for them in only one day.

For jewelry…

La Perla Gioielli is widely considered to be one of the finest jewelers on Capri. With a collection of both classic and statement pieces, you will undoubtedly find a beautiful token, reminiscent of your amazing Capri vacation.

Sites to explore on your Capri vacation

capri vacation

Blue Grotto

This is probably the most “touristy” activity on Capri, but it is simply one of those things you have to see to believe. “Grotto Azzura” is a natural sea cave with the bluest water you will ever encounter. The mouth of the cave is quite small, so visitors are brought in on small rowboats that hold a maximum of four people. The skipper will navigate through the small dark opening, into the sparkling cavern lit by blue light. The reflections are wonderful in the morning hours, and at their very best between noon and 2 p.m.

Villa San Michele

Villa San Michele was built by Swedish physician and author, Axel Munthe, around the turn of the 20th century. His dream home was erected on the ruins of an ancient chapel dedicated to San Michele – hence, the name of the villa. He wanted his home to be open to the sun and wind, with light everywhere. The result is a truly beautiful cliff top retreat that visitors to Capri flock to regularly. Villa San Michele is now a museum that features Munthe’s collection of art and archeological treasures, as well as hosts concerts and cultural events.

Piazza Umberto I (aka Piazzetta)

This small square is the center of life on the island of Capri, and it’s where you go to see and be seen. There are a handful of shops and restaurants, but mostly it’s just a bustling, busy square ripe for prime people-watching. Stop here when you arrive on the island to check out the scene and look for any familiar faces.

The Finishing Touch: Where to Stay

If you are planning a Capri vacation, you will undoubtedly need a place to stay and serve as home base. Browse WIMCO’s collection of private villas on Capri, or simply call our Villa Specialists and we will help you choose the perfect Italian island retreat.

You’ve been looking for this. Let us find you a villa on one of the most beautiful islands in the world. We love Capri, which features designer boutiques, picturesque scenery, and fashionable bistros and cafes, and we have villas right in the heart of it all.

Leave a comment: What time of year is your favorite to visit Capri? Where did you have your best Capri experience?


Interested in more Italian adventures? Explore everything from chocolate factories to underground tunnels in these three Umbrian hill towns: A Weekend in the Umbrian Hill Towns


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