Meet in Naples. Walking tour of Pompeii; 2 miles, easy (sneakers acceptable). Transfer to Ravello

Upon meeting in Naples, you drive a short distance to the archeological excavation site of Pompeii. A guided two-hour walking and historical tour provides a fascinating glimpse into the Roman town frozen in time in 79 A.D. by the eruption of nearby Mt. Vesuvius. In the early evening you arrive at the picturesque village of Ravello, perched high on a hilltop above the seaside town of Amalfi. Both Ravello and Amalfi, powerful towns in the Middle Ages, are rich with art and history. Ravello, the smaller and quieter of the two, has enchanted writers, artists, musicians, and travelers for centuries—Richard Wagner, D.H. Lawrence, and Virginia Woolf all spent time here. Its cobblestone ways are free of traffic and bordered by gardens and elegant villas, including the stunning 13th-century Villa Rufolo, famous for its spectacular gardens.

After checking into your hotel—a family-run, Old-World style property situated in the historic center of Ravello—an evening stroll in the lively main square, the Piazza Duomo, provides an opportunity to see the town’s 11th-century cathedral. From your hotel’s expansive terrace and dining room, where dinner is served, you are able to enjoy the breathtaking views of mountains plunging into the Tyrrhenian Sea.

Villa Cimbrone. Ravello to Torre dello Ziro to Valle dei Mulini to Amalfi; 5-7 miles, easy to moderate, several elevation gains and losses of 100-350 ft each

Today is spent in the valley between the towns of Ravello and Amalfi. First, a short walk brings you to the Villa Cimbrone, an original 19th-century estate where the splendid and slightly wild garden seems to literally hang on the cliff’s edge over the sea. Fragrant rose gardens, small temples, pavilions, and bronze and stone statues lead you to the Belvedere dell’Infinità (Belvedere of Infinity) to take in an awe-inspiring panorama, deemed by former Ravello resident Gore Vidal to be “the most beautiful in the world.” You then leave Ravello on foot for the tiny village of Pontone, the route weaving through cobbled ways and former mule paths, once the only roads connecting the network of hill farms and villages. From here you walk up a lengthy flight of steps and through an open pine forest to the Torre dello Ziro, a medieval tower perched on a crag with spectacular views over Amalfi and the waters below. Returning to Pontone, you are welcomed inside an inviting trattoria by Michele and Tina, a husband-and-wife team. A traditional lunch is prepared—perhaps risotto with wild mushrooms or homemade linguine puttanesca—from the fresh, seasonal ingredients of community farmers.

After lunch, a 15-minute and 150-foot ascent through terraced lemon groves and grape arbors leads to a saddle, the highest point of the afternoon’s walk, with views of the entire valley. You then descend a steep limestone-paved path to a brook rushing down from the mountain ridge, once a power source to the numerous paper mills for which Amalfi was famous. The trail descends stone steps through a shaded forest and follows contours of the hill into the Valle dei Mulini (Valley of the Mills). You walk past ruins of the mills into the heart of Amalfi, where you are free to explore the maze of whitewashed alleys, do a bit of window shopping along the Via Lorenzo d’Amalfi, or visit the stunning 11th-century landmark cathedral in the Piazza Duomo. Later, you return to the tranquility of Ravello via the tiny town of Atrani. Upon arrival at the hotel you may choose to relax, or browse the colorful ceramic shops in this delightful town before dinner on your own at one of Ravello’s many fine restaurants.

Bomerano to Sentiero degli Dei to Montepertuso to Positano; 6 miles, moderate, elevation gain of 300 ft and loss of 1,000 ft, possibility of vertigo in certain places. Transfer to Capri

Today’s walk begins on a southern slope above the Amalfi Drive, one of the most stunning coastal routes imaginable. The route today is the Sentiero degli Dei (Path of the Gods), one of the classic walks of the Amalfi Coast region. The path winds westward below the limestone ridge of the south-facing mountains with spectacular views of the sea and dramatic coastline. From grassy terraces ingeniously clinging to the hillsides, you walk past grazing sheep and goats, through bushes of heather, rosemary, and rock rose, and on to a mixed forest of oak and chestnut. You arrive in the enchanting hillside town of Montepertuso for a well-deserved lunch of local cheese, cold cuts, and grilled vegetables at a favorite family-run restaurant. The country restaurant is part of the Slow Food Movement, an international association promoting food and wine culture, while also protecting local food and agricultural biodiversity worldwide. Later you continue descending many ancient stone steps (elevation loss of approximately 1,000 feet) to Positano, where pastel-colored houses built into the steep hillside spiral down narrow streets to the café-lined beach. Once a small fishing village, Positano is now a chic seaside resort—thanks in part to John Steinbeck who, after a visit there in 1953, wrote: “Positano bites deep. It is a dream place that isn’t quite real when you are there and becomes beckoningly real after you have gone.”

Following a visit in Positano, you shuttle to Sorrento’s port to board a ferry for the short ride to the Isle of Capri (between 25 and 40 minutes). This nautical approach provides excellent views of the Sorrentine Peninsula and the striking “teeth” of Capri, the Faraglioni cliffs. Upon arrival at Capri’s Marina Grande, you board the funicular and ascend to the island’s elegant main square, Piazza Umberto I, or as the locals simply call it, La Piazzetta. After checking in to your cliffside hotel, you may enjoy an aperitivo on the terrace overlooking the waters below or among the citrus trees of your hotel’s garden. Dinner, likely the fresh catch from the waters below, is served at the hotel’s restaurant.

Anacapri to Belvedere Migliera to Monte Solaro to Anacapri. Moderate to challenging option is 6 miles with an elevation gain of 1,300 ft and possibility of vertigo. Easier option is 4 miles with an elevation gain of 400 ft and a chairlift ride. Additional afternoon option of Belvedere delle Noci or Arco Naturale; 3 miles, easy to moderate

Capri’s early-morning light invites exploration as you drive up the winding road via public bus to Anacapri, a small town of 5,000 residents, formerly connected to the Marina Grande only by the Phoenician Steps—a flight of 800 stone steps reputed to have been built by the Greeks. The morning’s walk brings you to the Belvedere della Migliera viewpoint with vistas of neighboring Ischia and Procida islands, and the Punta Carena lighthouse. Some may choose the challenging option—to reach Capri’s highest point, Monte Solaro (1,926 feet above sea level), on foot; the less strenuous ascent is by the 12-minute seggiova (chairlift)! After enjoying a refreshment and stunning view over the Bay of Naples and the Amalfi Coast, you return to the base of Monte Solaro—again, either on foot or by chairlift—and are free to enjoy lunch on your own in the village of Anacapri. Regrouping after lunch, your guides lead you to the Church of San Michele, an 18th-century gem whose majolica tiles of Adam and Eve are one of the finest examples of Neapolitan Baroque artwork.

In the later part of the afternoon you have several options for exploring Capri at your own pace. You may choose to browse in the island’s chic and inviting shops, enjoy a swim in the hotel’s outdoor pool, or take an easy walk to the Arco Naturale, or Belvedere delle Noci, permitting a close-up look at the island’s limestone rock formations carved by the sea. For dinner on your own, you can venture into one of Capri’s numerous restaurants to enjoy, perhaps, a signature insalata caprese followed by perfectly grilled fish or scampi.

Transfer to Sorrento. Afternoon option of Monte San Costanzo to Termini; 4 miles, easy to moderate

Catching a late-morning ferry to Sorrento, you arrive in time for an excellent lunch and some free time for browsing. The afternoon walking option is at the tip of the Sorrentine Peninsula, where from the chapel atop Monte San Costanzo there are outstanding views of the entire region; the Bay of Naples laid out on the right and Capri rising starkly from a glistening blue sea straight ahead. You descend from the summit across the grassy hillside, rich with Mediterranean scrub (macchia) and sprinkled with orchids and various types of broom, and continue on to the small village of Termini. Returning to Sorrento and checking into your historic seaside hotel—a luxurious property with an expansive terrace and swimming pool—you soon depart for a group dinner at a nearby restaurant for a taste of traditional Sorrentine cooking.

Colli di San Pietro to Monte Vico Alvano to Arola; 5 miles, moderate, elevation gain of 1,000 ft and elevation loss of 230 ft

A splendid view of Mount Vesuvius and the Bay of Naples greets you at breakfast. Today’s walk begins at the estate of Colonna Castle in Colli di San Pietro, a short coach transfer from Sorrento. A few long switchbacks on a sustained ascent lead to a small plateau at the center of Monte Vico Alvano. From here you may ascend another 95 feet to reach the peak and a large iron cross from where there are fantastic views over the Bay of Naples and the Gulf of Salerno. As you descend through a chestnut forest to the saddle between Monte Vico Alvano and Monte Comune, wonderful views of the Amalfi Drive and the Sentiero degli Dei (Path of the Gods) open before you. This saddle is the watershed between the Gulfs of Naples and Salerno, and in the springtime is filled with wild asphodels, rock roses, and orchids. You continue the descent to Arola where our friends Tony and Camillo welcome you for a spectacular lunch on the terrace of their family-run osteria overlooking the sea. The Slow Food restaurant features traditional Sorrentine recipes made with farm-fresh produce, including homemade ricotta and provolone cheeses. Soon after you return to Sorrento for some last-minute shopping or exploration, or join your guides for an easy walk nearby.

This evening you enjoy a farewell dinner, feasting on freshly caught seafood, locally produced vegetables, olive oil, wine, and limoncello.

Departure from Sorrento

After enjoying a copious breakfast, your guides assist your departure at your leisure from Sorrento.