Day 1

Meet your Backroads Trip Leaders (the folks wearing Backroads T-shirts) at 10 a.m. at Hotel Excelsior in Naples. Please arrive dressed in your walking clothes, and have a daypack and your rain gear handy.

Shuttle to Sant’Agata 2 Hours
Colli delle Fontanelle Route 4.8 Miles (490-foot elevation gain)
Ferry to Capri 45 Minutes

After meeting in Naples we shuttle to our picnic spot in the hills above the vibrant port town of Sorrento. Here we get acquainted over a lunch of local specialties, including fior di latte, a mozzarella-like cheese produced in the nearby Monti Lattari (or ―Milk Mountains).

Our first hike leads along the edge of Colli delle Fontanelle, past pine trees, Mediterranean flora and olive groves, with commanding views of the expansive Amalfi Coast. You’ll get accustomed to the cobblestone paths and rugged steps that make this area so charming—as well as challenging to hike!

After you make your way down to the Sorrento dock, we ferry across the deep blue waters of the Bay of Naples to the island of Capri, whose limestone peaks, narrow twisting streets and delightful gardens have charmed visitors for centuries. In 29 B.C. Emperor Augustus visited the island and was so struck by its beauty that he nicknamed it Apragopolis, meaning ―land of sweet idleness,‖ and acquired it from Naples in exchange for larger wealthier Ischia. Later, between A.D. 27 and 37, Emperor Tiberius ruled the Roman Empire from his private home at Villa Jovis, the largest of 12 villas he built on the island.

Take the funicular (cableway) to Capri Town, perched 450 feet above the harbor, and stroll to our abode for the night, Hotel Mamela. It’s ideally located just steps from the celebrated Piazzetta, nicknamed ―the world’s living room. This lively square has been attracting the rich and famous—including Frank Sinatra, Rita Hayworth and Brigitte Bardot—for decades.

Spend the afternoon hobnobbing in town while enjoying a cappuccino or relax poolside at the hotel. This evening your leaders host a reception followed by a dinner of delicious Caprese delicacies at a local restaurant.

Lodging: Hotel Mamela

Day 2

Monte Solaro Hike 1.4 Miles (1,000-foot elevation gain)
Shorter Option: 1.1 Miles with Chairlift (990-foot elevation gain)
Optional Capri Coastal Loop 3.5 Miles (340-foot elevation gain)
Ferry to Amalfi 1 Hours

Embark on a morning hike along stone paths to Monte Solaro, the island’s highest point. Feast your eyes on awe-inspiring views of the sea and the famous Faraglioni, the rock formations that many people consider the symbols of this rugged island. (The term faraglioni describes a geological formation in which sea and wind erode high sheer cliffs to such a point that sections remain isolated from the mainland.) Walk or take the chairlift down to chic Anacapri, the only other hamlet on the island, where you can enjoy lunch on your own. Then stroll through town or head back to Capri Town to explore its sophisticated shopping district. It’s a perfect time to pick up some lemon-infused perfume, soap or the locally made liqueur, limoncello.

If you’d prefer to keep hiking, head out on a heart-pumping coastal loop leading to Capri’s rocky edges. After taking in the amazing vistas, check out the Grotta di Matermania, believed to have been a shrine for ancient pagan rituals of self-castration, animal sacrifice and hypnotism. Don’t miss l’Arco Naturale, an enormous natural rock arch rising several hundred feet above the sea.

Reconvening at the harbor, we catch a ferry to Amalfi and our home for the next two nights, Hotel Luna Convento. Tonight’s dinner is at a nearby trattoria.

Lodging: Hotel Luna Convento

Day 3

Valley of the Mills to Ravello Route 4.5 Miles (1,200-foot elevation gain)
Longer Option: Ravello Loop 7 Miles (1,200-foot elevation gain)
Amalfi Guided Walk 1 Hour

This morning we set out from the hotel, stopping en route at Museo della Carta, a former paper mill and small museum dedicated to the venerable tradition of handmade paper. Amalfi is one of two cities vying for primacy in the production of paper in Italy, and you’ll learn about the history during a short guided tour.

Afterward, enter the lush green Valle dei Mulini (or ―Valley of the Mills‖), passing centuries-old paper mills and bubbling streams lined with wildflowers. A challenging ascent brings you to the medieval village of Pontone, where we pause for a rest in the main piazza. Then we hit the trail again and continue up cliff-hugging stairs to the beautiful hilltop hamlet of Ravello, affectionately known as the ―aristocrat of the Amalfi Coast.

After having lunch on your own, meet up with the group for a tour of the gardens at one of Ravello’s jewels, Villa Rufolo. If you have extra energy, make the steep descent along manmade stairs, first to sleepy Atrani and then to Amalfi, or hop in the van for a lift down the hill.

This evening a local guide leads us on a walking tour of Amalfi before our dinner at a seaside restaurant in the neighboring town of Atrani.

Lodging: Hotel Luna Convento

Day 4

Shuttle to Bomerano 45 Minutes
Sentiero degli Dei Route 4.5 Miles with Shuttle (120-foot elevation gain)
Longer Option: Positano 8 Miles (140-foot elevation gain)

After breakfast we shuttle to quiet Bomerano for today’s spectacular and demanding hike. Probably the best-known hike in the area, Sentiero degli Dei translates to ―Path of the Gods‖—you’ll soon understand why. Climb the famous trail, which includes several short steep ascents, before arriving at a vantage point hundreds of feet above the sea. Beneath a pure blue sky, you’ll marvel at the colorful towns scattered along this magnificent stretch of coastline. We meet Maurizio, our local guide, who brings the region’s rich past to life as he leads us to the small village of Nocelle.

After a well-deserved lunch break, we shuttle to Hotel Savoia in Positano. If you’d rather continue on foot, pass through the hamlet of Montepertuso on your way down to Positano and our hotel.

Tonight you’re on your own for dinner, with time to explore this famed coastal town, known for its cliffside villas, the dome of Santa Maria Assunta church, and inviting shops and cafés.

Lodging: Hotel Savoia

Day 5

Santa Maria del Castello Loop 4.5 Miles (1,300-foot elevation gain)
Shorter Option: Santa Maria del Castello 3 Miles with Shuttle (1,300-foot elevation gain)
Longer Option: I Trasiti Viewpoint 5.5 Miles (1,700-foot elevation gain)

We fuel up with a delicious buffet breakfast before shuttling to Montepertuso for the week’s most vigorous hike. Begin with a tough ascent under the welcome shade of cypress, pine and myrtle trees. The terrain levels out at Caserma Forestale, an old stone structure in the woods. Here you’re rewarded with outstanding views of the coast and a glimpse of the highest peaks of the Monti Lattari. If you’re in the mood for more climbing, branch off on the longer option to the I Trasiti viewpoint—a great spot for photos! Otherwise, continue along the level path to Santa Maria del Castello for an ample lunch at a favorite family-run restaurant. Then it’s all downhill to Positano (feel free to hop in the shuttle).

For our final evening together we enjoy a feast of traditional Mediterranean cuisine at Ristorante al Palazzo, one of Positano’s most beloved restaurants. Raise your glass to a magical week spent on the Amalfi Coast. Salute!

Lodging: Hotel Savoia

Day 6

Positano Loop 1.4 Miles (300-foot elevation gain)
Shuttle to Naples 1½ Hours

If you’d like one more opportunity to dip your toes in the Mediterranean, head out on a short walk to Fornillo Beach for a refreshing swim in the sea. Or enjoy a leisurely breakfast and perhaps a final stroll through town. Later this morning we shuttle to Naples, where we say our goodbyes.