Diary of Capri

Setting down on Italy’s crown jewel of an island – synonymous with vintage glamour – remains a thrill of people-watching and aperitivo, with the essence of Ancient Rome always just footsteps away

By Cheryl Caira

Marina Grande

Image: Ellena McGuinness on Unsplash

The ancient fishing port of Marina Grande is the landing point and first glimpse of the island for many visitors, with its line-up of boats, bustling waterfront and colourful houses peeking out from the famous cliffs.

The Blue Grotto

The magically shimmering waters of the Grotta Azzurra seem chaotic at first, as people crouch down in little boats steered by local fisherman to enter the narrow-mouthed sea cave, but once inside, the blue reflection illuminating the cavern is mesmerising. If you’re lucky, your sailor might break into operatic song as you glide along.

Faraglione di Mezzo

Word has it that if you take a boat ride with your paramour beneath Capri’s “arch of love”, the centre of three dramatic sea stacks on the island’s southern coast, Cupid’s arrow is sure to strike for eternity. Opt for one of the two-hour private boat tours of the island so you’ve got time to fully survey its craggy magnificence.

 Chiesa San Michele

The charmingly miniature San Michele church is a unique find on one of the more tranquil streets in the picturesque, whitewashed town of Anacapri. The ceramic tile floor is entirely hand painted, dating from 1761, and masterfully depicts Adam and Eve ultimately departing the Garden of Eden.

Scoglio delle Sirene


The striking outcrop of Sirens’ Rock (so-called because the Latin King Ulysses was, according to legend, seduced to the area by the dangerous song of the Sirens) is more celebrated these days for its atmospheric restaurants looking out onto the crashing waves. The restaurant of the same name serves beautiful seafood and Caprese ravioli filled with caciotta and parmesan cheese.

 La Piazzetta

It may be petite as squares go, but it’s Capri’s central point for glamorous yet laid-back socialising. Climb the stairs leading to the church of Santo Stefano and survey the action (you might catch a stylish Italian wedding filling the square on a weekend) then descend and sip on a potent espresso or a traditional Aperol Spritz, before wandering the tiny nearby streets filled with designer and independent boutiques.

Da Paolino


As serene atmospheres go, having dinner on a beautiful terrace beneath the lush greenery of a lemon grove is hard to beat. Da Paolino has seen a host of famous names dine amongst its fruit-laden trees over the years, and its signature dish – perfectly al dente rigatoni with zucchini flowers – is absolutely delicious.

Monte Solaro

Boasting Capri’s most handsome panorama, the island’s highest point is reached by scenic chairlift or by walking up an equally enjoyable mountain path for around an hour. The views at the top extend to the Bay of Naples, the surrounding island of Ischia and the tips of the Faraglione rocks, pointed out by the statue of Emperor Augustus, who landed on the island and fell for its charms in 29 BC.

Certosa di San Giacomo 

The oldest historic building on Capri, the Carthusian monastery and charterhouse of San Giacomo is an arresting sight, with its main Renaissance cloister – Chiostro Grande – set around a grassy geometrical centre, with grounds sometimes used for cultural exhibits. The views out to sea from the gardens are also well worth perusing.

Eco Capri


Everything on display in the effortlessly chic Eco Capri is based around the innovative design of Italian fashion legend and artist Laetitia Cerio, with the concept store established by the designer’s grandson. Much of the creations feature the enduring symbol of the “Capri lovers”, with the theme of the Caprese sea (and its emblematic octopus) embroidered and printed on hats, scarves, clutch bags, and voguish items for the home.