The center of Anacapri is rich in historic and cultural sights to visit. Most are located in the old town, which is primarily pedestrian-only.
This is the most historic neighborhood in Anacapri, a postcard-perfect district of flower-filled squares, whitewashed homes, and narrow, winding lanes. Many of the homes and buildings here still retain the traditional barrel vaults that were once common on the island.
One of the top sights in Anacapri is the Church of Santa Sofia, built in the 16th century and overlooking a pretty square with decorative benches. The Church of San Michele Arcangelo, a baroque masterpiece famous for its majolica floor created by the Neapolitan artist Leonardo Chiaiese that depicts Adam and Eve's banishment from the Garden of Eden.
One of the most unique museum collections on the island is located just a few steps from the Church of San Michele on Via Giuseppe Orlandi. The Casa Rossa, thus named because it is painted a deep shade of red, was the private residence of the American colonel John Clay MacKowen until the 1800s. The colonel amassed a large collection of archaeological artifacts during his years on the island, which he unearthed while adventuring along the walking trails that crisscross Capri. Together with this collection of ancient treasures, the Casa Rossa also houses statues found on the floor of the Blue Grotto and a number of 19th- and 20th-century paintings depicting the island and its lore.
If you continue walking towards Piazza Vittoria and take the flight of stairs up, you'll find a scenic path that leads to Villa San Michele and a panoramic overlook of the Bay of Naples. The villa is now a museum and was built by the Swedish physician and intellectual Axel Munthe when he lived on Capri. The villa and its idyllic garden and terraces offer dreamy views over the sea; the indoor rooms house a large collection of ancient artifacts and artworks amassed by Munthe during his time on the island.
The Ruins of Villa Damecuta
Villa Damecuta is one of the 12 Roman villas that the emperor Tiberius built on the island. Today, only ruins remain, surrounded by a cool pine wood.
The Blue Grotto
Not many visitors know that the most famous sights on the island of Capri – the beautiful Blue Grotto, named for the glowing blue light that filters into the cave from below the sea – is actually located within the confines of Anacapri. You can visit the grotto via a small rowboat; the line to board the rowboats is in the tiny harbor of Gradola, which you can reach by bus from Anacapri. You can also visit the Blue Grotto by sea from the Marina Grande port (large boats take passengers to the cave entrance, where you board the rowboats to enter the grotto).
The Blue Grotto on Capri
A Trip to the Peak of Mount Solaro
From Anacapri's main square, you can take the chairlift up to Mount Solaro. This lift fits one person per seat and makes the trip to the top in about 12 minutes. There are panoramic views over the island during the ascent to the peak, which is both the highest and most scenic spot on the island. From Mount Solaro, you can take in 360° views over Capri, Naples, and the entire bay, as well as walk and hike the trails that crisscross the mountain slopes (like the path that leads to the remote Santa Maria hermitage in Cetrella or the path that leads downhill all the way to the Piazzetta in Capri town). We highly recommend visiting the mountain peak, unless you are afraid of heights. If you don't want to take the chairlift, there are also trails that lead to the top of the mountain.