There’s the Capri you daydream about: sunny piazzas, gelato in hand, the perfect Instagram snap. Then there’s the Capri that the brochures politely gloss over. It’s messier, louder, and a lot more real than the travel posters let on.
Trail of the Forts
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This six-kilometer hike between the Blue Grotto and Punta Carena follows the island’s western coast and travels past three historic military forts. They were built in the 1800s to protect Capri and now offer unmatched sea views, aromatic wild rosemary, and a rare pocket of solitude even in peak tourist season.
Punta Carena Lighthouse
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Capri’s southwestern point is crowned by a rust-red lighthouse that’s been guiding sailors since 1866. Punta Carena is also a go-to for cliffside swimming, rocky beaches, and aperitifs at sunset.
Scala Fenicia
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The 921 steps of this ancient Greek pathway climb steeply between Marina Grande and Anacapri. Once the main link between the two towns, the Scala Fenicia doubles as a heart-pounding workout and scenic marvel. Olive groves and lemon terraces reward climbers with panoramic sea views at the top.
Chiesa di San Michele Arcangelo
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Located in Anacapri’s center, this Baroque church is famous for its massive 18th-century hand-painted tile floor. The artwork illustrates the Garden of Eden in remarkable detail, best viewed from a raised balcony. Mythical animals, lush trees, and biblical drama stretch from altar to doorway in vivid blues and golds.
Gradola Swimming Terrace
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Skip the boatloads at the Blue Grotto and follow the signs to Gradola, a low-key local favorite. This rock terrace above crystal-clear waters has built-in ladders for swimmers and no sand in sight. There’s also a great seaside restaurant that offers fresh seafood and tranquil views.
Villa San Michele
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This villa was built by Swedish doctor Axel Munthe on ancient Roman ruins. Its gardens bloom year-round with cypress trees and wisteria, while the terrace reveals sweeping views of the Sorrentine Peninsula. Inside, you'll find Roman statues, Egyptian relics, and antique furnishings.
Monte Solaro Chairlift
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Capri’s highest point is best reached by a 13-minute chairlift from Anacapri. Monte Solaro rises to 589 meters and offers views of the Faraglioni, Mount Vesuvius, and even Calabria on clear days. It's a peaceful ride up and an even more striking panorama once you're at the summit.
Migliera Trail
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Unlike crowded coastal hikes, the Migliera cuts inland through Anacapri’s vineyards and wild groves. The trail ends at a dramatic cliff overlook, complete with a sculpture garden called the Philosophical Park.
La Casa Rossa
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This red-colored villa, built by American colonel John Clay MacKowen, stands out in Anacapri’s Boffe quarter. Inside, Roman statues pulled from the sea are displayed alongside 19th-century art. Architectural details borrow from Moorish and medieval styles.
Boffe Quarter
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The oldest part of Anacapri has narrow alleys, curved white rooftops, and lemon-scented air. Locals chat from balconies, and small bakeries serve warm pizzas and cherry pastries. It’s a peaceful contrast to Capri Town.
Orange Blossom Season
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Come spring, Anacapri’s streets are perfumed with the scent of blooming orange trees. The air becomes heady and floral, especially in quiet residential zones like Via La Vigna. The blossoms don’t last long, but they mark a moment when the town feels even more dreamlike than usual.
Lido del Faro
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One of Capri’s chicest beach clubs is located beside Punta Carena. Lido del Faro offers sunbeds, a sea-fed pool, and a full-service restaurant—all carved into the rock. It’s where locals and in-the-know travelers go to sip limoncello spritzes while watching swimmers leap from boulders into deep, clear water.
Il Riccio Sea Lounge
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Right above the Blue Grotto, Il Riccio has cliffside views and Mediterranean flavors. It’s Michelin-starred, but never stuffy. Expect fresh seafood, handmade pasta, and one of the most indulgent dessert rooms in Italy—all with a sea view that practically demands a long lunch.
Villa Damecuta
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This lesser-known Roman site offers a quieter, more mysterious experience than other island ruins. Believed to be one of Emperor Tiberius’s villas, Damecuta includes surviving archways and corridors set among pine woods. It’s easy to miss, but worth seeking out for the eerie calm and historical depth.
Anacapri’s Artisan Shops
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Behind the touristy storefronts are workshops still hand-crafting Capri’s iconic sandals, perfumes, and ceramics. Artisans here carry on traditions passed down through generations. These pieces tell a story that outlasts the vacation.