Capri is most often associated with glitz and glamour, home to elegant designer boutiques and surrounded by luxurious yachts moored just offshore. But there is another side of the island, with a slower pace and calmer atmosphere, that offers the possibility of discovering the island from a more laidback, authentic point of view. For hiking enthusiasts or fans of history and art—or simply those looking for a quiet spot to spend a holiday relaxing—Anacapri and the surrounding countryside is ideal.

The town of Anacapri, in particular, is a sleepy, timeless that spot sits on the highest point of the island, thus its name. The municipality is set on the slopes of Mount Solaro, the peak of which offers spectacular views across the island and can be reached on foot via a moderately challenging hiking trail or simply with the chairlift (not recommended for those who suffer from fear of heights!)

Less expensive than the town of Capri, Anacapri is perfect for those who want a casual holiday far from the chaos of the crowds and nightlife for which Capri is famous. There is a wide variety of restaurants and artisan workshops in town making everything from leather sandals and fabric to ceramics, coral jewelry, and other local crafts.

There are a number of walking and hiking trails for every skill level that set off from Anacapri, in including the path to the Migliera Scenic Overlook and the Trail of the Forts.

A Thousand Steps to the Port

The famed Scala Fenicia (Phoenician Steps...though they were actually built by the Greeks!) sets off from Anacapri, running from the town center to the Marina Grande port below. There are 921 steep steps covering a staircase that stretches 1.7 kilometers (1 mile). We suggest taking on the steps only for those who are particularly fit, as they can be a challenge even if you are headed downhill.

Fans of art and culture will find plenty of treasures to explore in Anacapri. Take in the sweeping views from the house-museum of Axel Munthe, the eccentric and captivating Villa San Michele; as well as Casa Rossa, one of the most unique and fascinating buildings on the island. The monumental churches of Santa Sofia and San Michele Arcangelo are also worth a visit. The latter is known for its stunning historic majolica ceramic floor that depicts the Garden of Eden and "original sin."

A number of Capri's most iconic sights are located in the municipality of Anacapri. The most famous, of course, is the Blue Grotto (Grotta Azzurra), followed by the picturesque Punta Carena Lighthouse, one of the oldest in Europe and the second-largest in Italy after the Lanterna Lighthouse of Genoa.

Both these sights can be easily reached by bus from the center of Anacapri via two different bus routes, each of which takes about 10 minutes to reach its destination. Both the Faro-lighthouse and Gradola, the location of the Blue Grotto, can also be reached by taxi, scooter, or private car service directly from either the port of Marina Grande or the Piazzetta in Capri Town, as well as other locations across the island.

Anacapri is also an excellent choice for families with children, as the town has a nice playground, the shady Damecuta pine grove (where the remains of an ancient Roman villa are also located), outdoor play spaces on Mount Solaro, and a number of pedestrian-only areas in the town center where kids can walk without the danger of traffic.

Lively and elegant, Capri is ideal for those looking for a glamorous vacation destination with a VIP atmosphere and plenty of nightlife. Capri Town and the surrounding areas are generally more crowded as most clubs, restaurants, and luxury hotels are located here, as well as designer boutiques sporting the most famous names in Italian and international fashion.

Capri is also home to the island's only port and the iconic Piazzetta, the focal point of the island's social life set beneath the picturesque clock tower. Here, café tables are crowded with Hollywood stars, famous athletes, and other celebrities drawn to the island for its “La Dolce Vita” and paparazzi cachet.

You can also explore the island via a number of scenic trails from Capri, from the easy walk to the Tragara scenic overlook or the longer hike to Pizzolungo.

Beaches in Capri

Unlike Anacapri, which only has rocky coves and beach clubs set up on platforms above the water, Capri is home to the few true beaches on the island, including Marina Grande, Marina Piccola, and Palazzo a Mare. Keep in mind, however, that even these beaches are quite small and lined with pebbles and stones, not sand.

In addition to the glitterati draw of the local clubs, Capri hosts a number of must-see sights and attractions for those visiting the island, including the panoramic Gardens of Augustus; the Charterhouse of San Giacomo; and the Roman ruins of Villa Jovis, the largest of 12 pleasure palaces that Emperor Tiberius had built on Capri. We also suggest a stop to take in the lovely Villa Lysis, an Art Nouveau residence built in 1904 by the Parisian nobleman Jacques Fersen.

Capri is also where you can admire the island's most well-known feature, the towering Faraglioni sea rock formations. And what's the best way to take them in? A boat tour with a Prosecco toast on board!

Anacapri is best if you:

• Prefer a quieter destination with fewer crowds

• Love walking and hiking

• Enjoy artisan workshops more than fashion boutiques

• Are traveling on a budget

Capri is best if you:

• Love a glamorous atmosphere and want to party until dawn

• Plan on spending a significant amount of time on the beach

• Are a shopaholic, especially high fashion

• Can splurge on a luxury break