Arrival in Florence. Transfer to Siena. City tour of Siena; 2 hours, easy (sneakers acceptable). Transfer to Montalcino

After meeting in Florence, you transfer to Siena. The week begins with a walking tour of the historic center of Siena, the atmospheric Tuscan city. With its mixture of Gothic and Romanesque architecture dramatically set on three hills, Siena rivals Florence not only in beauty but also in culture. Following a light lunch of Sienese specialties, you explore the world-famous Campo square, presided over by the impressive town hall and tower. The Campo is the setting of the celebrated Palio horse race. Your engaging guide leads you to the Duomo, the main cathedral, with its striking marble façade.

Later you transfer to Montalcino, your home for the next two nights. Unchanged since the 16th century, Montalcino is a charming walled hilltop town and the birthplace of Brunello, one of Italy’s finest wines. A magnificent fortress built in 1361 crowns its heights. Your family-run hotel is located at the edge of Montalcino’s medieval walls, in the town’s quiet pedestrian zone—ideally situated to explore the town’s cobblestone alleyways, stone houses, local shops, and cafés. You are welcomed with dinner in a warm, wood-beamed restaurant in the heart of town; a glass of Brunello may be paired with a tagliata fiorentina (local grilled beef), a perfect start to the week's culinary delights.

Torrenieri to Pienza; 6 miles, easy to moderate. Optional afternoon walk from Bagno Vignoni; 2-3 miles, easy to moderate

Today’s exploration begins in the outskirts of Montalcino. After an initial short drive to the village of Torrenieri, a dirt lane meanders along rolling terrain toward Pienza, the morning’s destination. Along a ridge between the Orcia Valley and the Crete Senesi (Sienese hills), you pay a visit to the 15th-century convent of Sant’Anna in Camprena, a breath-taking former Olivetan Benedictine monastery where “The English Patient” was filmed.

Lunch awaits at an old Tuscan farmhouse, where your hosts welcome you with an assortment of local pecorino (sheep cheese), cold cuts, homemade preserves and pickles, accompanied by their house wine. Following lunch you are driven a few minutes away to Pienza, the birthplace of Enea Silvio Piccolomini, elected Pope Pius II in 1458. Envisioning the creation of the “ideal Renaissance town,” Pius II had the village renamed and entirely redesigned by Florentine architect Bernardo Rossellino. While the village’s restructuring came to a halt following Pius II’s death, the vision of Humanist urban space and planning was superbly realized in the town center, Piazza Pio II, where the main monuments lie harmoniously along the town’s main axis, the town hall opposite the 15th-century cathedral.

An optional afternoon walk departs from the tiny spa town of Bagno Vignoni, where you can soak your feet in the warm waters flowing out of the town’s picturesque main square—the only one in Italy that is, in fact, a thermal pool. After returning to the hotel in Montalcino, there is time to relax before being driven to dinner overlooking the plains on the outskirts of town.

Montalcino to Sant’Antimo Abbey; 4-7 miles, easy to moderate. Transfer to Umbria; approximately 2 hours

Today you depart Montalcino on foot. You walk through gentle hills, in the shade of old-growth woods, and skirt vineyards where the famous Sangiovese Grosso grape is grown for Brunello wine. You might stop to visit an ancient Etruscan settlement, still under excavation, before continuing through farmland, ancient dwellings, wineries, and olive groves to make the dramatic descent to the isolated Romanesque Abbey of Sant’Antimo.

After a truly authentic lunch of pink risotto and wild boar stew, you leave southern Tuscany; the drive winds through the rolling hills and medieval hilltop villages of the Crete Senesi, then descends on the plains surrounding Lake Trasimeno and enters the main valley of Umbria, a region known as the “Green Heart of Italy.”

Your home for the next four nights—an elegant, historic property featuring a panoramic outdoor terrace and swimming pool—is in Spello, a walled Roman and medieval town. Time permitting upon check-in, a short introductory walking tour provides an orienteering overview. This evening an independent dinner awaits with your guides’ advice; perhaps a lively local trattoria or a glass of Sagrantino red wine, Umbria’s answer to Brunello, served al fresco on the terrace of your hotel.

Assisi city tour; 2 miles, easy. Countryside of Assisi; 3-4 miles, easy to moderate

The morning and early afternoon are devoted to an exploration of Assisi. This stunning town sits in a commanding position on the slopes of Mount Subasio and has retained its charming medieval qualities and strong associations with St. Francis. You tour its multifaceted historical center and the Basilica of St. Francis with a local guide. After lunch at a local pizzeria there is time for independent exploration of its narrow lanes and inviting shops.

The afternoon offers several options. You may choose to spend more time in Assisi on your own, return to the hotel and relax by the pool, or stroll the picturesque alleys of Spello. Alternatively, an easy walking option is offered—this time venturing out of town into the lush, surrounding countryside and olive groves, all the way back to Spello.

Dinner this evening is the fruit of your labor in an optional hands-on cooking class! You join Chef Marco Gubbiotti in the kitchen and help him prepare regional dishes while learning some of the many culinary traditions of the region.

Gubbio; 5-7 miles, easy to moderate

Gubbio, the medieval masterpiece of Umbria, charms with its intimate alleys and surprisingly spacious panoramic piazza, flanked by the stunning palazzo comunale. Following a scenic drive, the morning walk’s destination is the Church of Saint Ubaldo, perched high on the mountainside overlooking Gubbio. The church is the end point of the annual “Race of the Ceri,” a colorful historic festival where locals race ceri (giant heavy wooden structures that resemble candlesticks). The walking route passes by limestone outcrops and a tiny chapel, meandering through woods, along a creek, and up a narrow gorge. A lunch of regional specialties awaits at a local restaurant―perhaps suckling pig roasted over an open fire.

After lunch you are free to wander around the historic center and perhaps visit the stunning 14th-century town hall, the Palazzo dei Consoli, with its renowned art museum. Or you may choose to absorb the atmosphere of this Umbrian gem over a gelato or caffé before the return drive to Spello. Your guides provide ideas for dinner on your own in town; the restaurant or trattoria menu may offer chickpea soup drizzled with olive oil, bruschetta, or strangozzi, the regional square-shaped spaghetti.

Assisi to Spello via the Natural Park of Mount Subasio; 5-9 miles, easy to moderate

After breakfast there is a short transfer to the Natural Park of Mount Subasio, a protected area with serene paths meandering through open meadows and oak and pine woods. Mount Subasio is the sprawling mountain on whose flank Assisi is built. A haven of subtle beauty and spirituality, it was here that St. Francis preached to the birds, all gathered on tree branches. Hiking in the meadows along the summit of the mountain, you are likely to see grazing herds of sheep, white Chianina cows, and semi-wild horses before descending to lunch in the small, charming hamlet of Collepino. The table is waiting and spread with an ample antipasto of assorted bruschetta, followed by grilled meats and vegetables.

After lunch you may choose to return to Spello by van or to descend all the way on foot, continuing through olive groves and alongside the ancient Roman aqueduct that once brought drinking water into town along the eastern side of the mountain.

This evening’s farewell dinner is at an intimate restaurant, where you are welcomed with a glass of crisp prosecco on a panoramic terrace overlooking the Umbrian plain.

Easy city walking tour of Orvieto. Transition to Amalfi

You depart Spello for the picturesque city of Orvieto, situated atop a tufo (compacted volcanic ashes) outcrop. This final visit takes you to the main square and its magnificent Gothic cathedral, considered to be one of Italy’s most beautiful, with its intricate bas relief and mosaic-decorated façade. You depart from Orvieto’s train station for the connection via Rome to Naples, about a four-hour trip. Upon arrival in Naples, a short taxi ride takes you to your centrally located hotel. This evening, you can stroll nearby for dinner with the hotel’s recommendations, a first taste of delectable southern Italian cuisine.

Meet in Naples in the lobby of the NH Ambassador Hotel at 2:00 pm. Walking tour of Pompeii; 2 miles, easy (sneakers acceptable). Transfer to Ravello

You have time this morning for a short exploration of the fascinating city of Naples, perhaps even a visit to the National Archeological Museum, which houses a large collection from nearby Pompeii and Herculaneum.

Upon meeting your new group and guides at your hotel, 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—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.