Italy | Isola di Capri: The Jewel of Southern Italy

Picturesque Capri and secluded Anacapri, on the beautiful Mediterranean Sea.

Italy flag
  • peninsula surrounded by blue waters
  • Isola di Capri
  • Pennisula at night with a sea view

Trip Highlights:

  • Hike to the top of the highest peak on the island: Monte Solaro.
  • Experience the coastal Faraglioni Rocks, home to a diversity of maritime birds.
  • Feast on authentic Mediterranean cuisine.

Inviting villages, towering limestone cliffs, a rich history, and the tranquil water of the Tyrrhenian Sea – all of this and more awaits you on the Italian island of Capri! The colorful isle sits off the western coast of southern Italy, its shores visited for millennia by Greek and Roman sailors. Originally established as a Roman resort the Isle of Capri has a deep history of tourism and relaxation – it is easy to see why! Here the people are welcoming, the culture draws from Roman, Greek, Norman, and Arabic-Sicilian influences, and the towns are marked by old bohemian villas set against the Tyrrhenian’s cobalt water. 

The journey to Capri begins by ferry from the Italian city of Naples, which deserves an extra night’s stay if time allows. Naples has made an international name for itself through its Roman history, lively nightlife, and many UNESCO world heritage sites. Equally deserving of your time is a visit to the top of the nearby volcano Mount Vesuvius. 

Our trek begins in the city of Capri and takes us through villas and villages, into the “Grotta Azurra”, or Blue Grotto, and to the top of the highest peak on the island. Monte Solaro. On this trek, we stay in the island villages of Capri and Anacapri. Capri rests on a plateau above the island’s main port, the Mariana Grande. The town’s tiered stone buildings rise up above the rocky coast and the view down towards the harbor is akin to something out of The Odyssey.

From Capri, we set out on adventures to three separate destinations. The first is to Villa Jovis – the historic home of the grim Roman emperor Tiberius, and then onward to the Faraglioni Rocks, a set of hulking coastal rocks that offer a refuge to a diversity of maritime birds. The second trip from Capri takes us by boat to the famous Blue Grotto, a seaside cave illuminated by an underwater channel which creates a magical sapphire color in the water. The final hike from Capri takes us over the summit of the Monte Solaro and to our next hotel in Anacapri. Anacapri is a peaceful village that is considered the most authentic cultural destination on the island. Our last day takes us on a hike out of Anacapri to the Lighthouse of Faro. This lighthouse sits on the island’s westernmost point and is a favorite destination for locals who enjoy swimming on the rugged and isolated peninsula. 

The hiking in Capri often follows ancient paths. On our journey, we travel along ancient trade routes, cobbled Roman roads, and seaside trails which run above the limestone cliffs that line the coast. The hiking here is pleasant, traveling through lemon and olive groves, with some hearty but manageable ascents. One of the great charms of the region is that all the full days of hiking enjoy views of the Tyrrhenian Sea and its stone beaches.  

In Capri, the food is much of what you would expect from the Mediterranean fare, with cheeses and dried meats, olives, and local olive oil, as well as fresh seafood all prepared with true Italian love of cooking. Unique to the culture of Capri is the tradition of “peasant fare” characterized by local ingredients, including the cornucopia of fresh produce made available by the island’s verdant gardens. Dining itself is a unique experience on this trip, as the setting always feels like an adventure backward in time, whether above the historic Mariana Grande, or among the colorful coastal buildings of Anacapri. 

The history of Capri dates back to the Neolithic Period, with a well-preserved Greek and Roman history as well. The Greeks first settled Capri around what is now the Mariana Grande, which still has Greek era steps leading to it from the town. The island was subsequently claimed by Naples until the Roman emperor Augustus secured it in a land trade. The Roman era led to the major development of the island, constructing all of the major villas around the town of Capri as well as a series of watchtowers along the western coast. During the medieval period, the island was largely left to the whims of pirates, until the first tourists returned to the island after the Renaissance, leading to the modern tourist and fishing economy that defines the island today. 

This tour takes us through locations of stunning natural beauty and history. The ferry to Capri as well as our journey through the Blue Grotto puts us right on the cobalt waters of the Tyrrhenian Sea. The formations of the limestone cliffs along the coast pose a dramatic landscape for hiking, while the pastel buildings of its villages provide a relaxing and charming home after a long day’s walk through the sunny hills of Capri.  

Trip Itinerary

You will first arrive at Naples airport to catch a bus or taxi to the harbor and continue to the Isle of Capri by ferry. Transfer to our intimate, boutique hotel walking distance from the center of Capri town with breathtaking views of the sea. Meet the group and your guide for welcome drinks and dinner at 7 pm.

We picked a stunning and serene coastal hike as a warm-up on your first day on Capri. Familiarize yourself with the island as we walk to Villa Jovis, Tiberius’ home, and on to Arco Naturale, to reach ‘belvederes’ of the Faraglioni Rocks. Along the way enjoy views towards the Amalfi Coast and get a glimpse of Villa Malaparte, one of Capri’s most famous modern structures.

Distance: 5.5 miles. Elevation gain/loss: 920 ft.

This classic day trip begins with a ride on the famous Capri funicular to the Marina Grande. Here we meet our captain and set off to the otherworldly Blue Grotto. Our ship takes us around the western tip of the island and then crosses under the Faraglioni natural arch. After lunch at Marina Piccola, we embark on a short but beautiful hike back to Capri and our hotel.

Distance: 3 miles. Elevation gain: 500 ft.

One of the best island day hikes in the Mediterranean awaits. We hike direct from our Capri hotel up through the wonderfully shady beech forest following a well-made, historic path. The trail brings us ever higher winding through limestone crags before breaking out into unforgettable open views of the Marina Piccola and the Faraglioni rock. We picnic on the summit of Monte Solaro before descending to our 4-star hotel in Anacapri.

Distance: 7 miles. Elevation gain/loss: 1900/700 ft.

Today we embark on a spectacular outing along the rugged western tip of the island that connects traditional farming paths and historic watchtowers before looping back toward the incredible lighthouse of Faro. The path finishes with a final climb past the Migliera viewpoint before returning to our hotel.

Distance: 6 miles. Elevation gain/loss: 1700/500 ft.

Isola di Capri: The Jewel of Southern Italy | Italy

Similar Trips

You Might Also Like...