Arrival Day. Lake Orta; 2 miles, easy, with an elevation gain of 300 ft

Upon meeting in Milan, you transfer by private coach to the idyllic medieval village of Orta San Giulio, nestled on the eastern shore of Lake Orta. At only eight miles long and two miles wide, Lake Orta—known for its serenity, simplicity, and religious devotion—is one of the smallest of Italian Lakes. You set off directly on foot following the lakeside promenade to explore the charming village and its rich architecture. From the town’s waterfront, Piazza Motta, you gently ascend the pilgrim’s way, a cobbled path that rises under the shade of pine, beech, and ash trees to the plateau of the Sacro Monte monastic complex, a UNESCO World Heritage site erected primarily in the 17th century. This unique site holds 20 Baroque chapels filled with life-sized terracotta statues and frescoes depicting the life of St. Francis of Assisi. From this tranquil vantage point, you survey the jewel-like lake and the islet of San Giulio, set against the striking backdrop of forests and granite outcroppings. Meandering back towards the village, the cobblestone paths lead to the lakeshore with its colorful fishing boats and narrow streets.

You arrive on foot at your delightful four-star lakeside hotel, set within the ancient walls of a 17th-century stone-cloistered convent. There is time to settle into your comfortable lake-view room before gathering in town at a cozy 16th-century wine bar for a welcome aperitivo—rich mountain cheeses, cured meats, and a sampling of several renowned wines from the neighboring Piedmont region will likely be offered. Dinner, perhaps beef carpaccio or smoked salmon, followed by a delicious lake fish or fillet of veal in white truffle sauce, is at your hotel’s restaurant—an enchanting setting with views of the dramatic medieval basilica of the Isola San Giulio illuminated against the night sky.

Orta to Pella to Isola San Giulio; 5 miles, moderate, with an elevation gain of 800 ft, and an initial 25-minute steep ascent

The day begins with a boat ride to the picturesque town of Pella, situated directly across the lake on the western shore of Lake Orta. From here, you wind up centuries-old stone pathways under a canopy of chestnut, oak, and large beech trees to a small collection of secluded villages and hamlets. In this mystical setting, you feel as though you have stepped back in time, when these pathways were main thoroughfares. Looping back down a cobblestone path through apple, pear, and persimmon trees, you arrive at the lakeside where a boat is waiting to return you to Orta San Giulio in time for an independent lunch in the town’s picturesque central square or along one of the many inviting alleyways—choices range from a lively, local trattoria to a simple pizzeria. Following lunch, there is time to explore the many delights of Orta San Giulio at your own pace.

In the late afternoon, a short boat crossing brings you to Isola San Giulio, named for the 4th-century Saint Julius who brought Christianity to the region after eradicating the island of a variety of snakes and monsters. Here on this tiny island, known as the “Island of Silence,” you visit the renowned and beautifully frescoed Basilica di San Giulio, originally founded by Saint Julius in 390 AD. From here you meander down a single footpath which encircles the island—La Via del Silenzio (The Way of Silence)—though if you follow it in the other direction it curiously becomes “The Way of Meditation.” As you walk past old greystone buildings clustered around the basilica and elegant villas framing the shoreline, you come across small plaques in several languages that remind you that you are in a place of reflection: “If you can be yourself, you are everything,” advises one. Dinner this evening is at a cozy trattoria, where you sample more regional specialties such as champagne risotto followed by a tender fillet of Fassone, Piedmont’s prized beef.

Orta to Armeno to Coiromonte to Gignese; 5.5 mile or 10 mile options, moderate to challenging, elevation gains range from 1000-2000 ft

Departing from Orta San Giulio by bus, your guide/s may choose one of two walk options, depending upon recent weather conditions. If conditions are dry, the first option begins at the village of Armeno, from where you begin a steady ascent alongside the Ondella River through beech and chestnut forest and across several small streams to the mountain village of Coiromonte. Alternatively, a short bus ride delivers you to the lakeside village of Pettenasco. Ascending through forests and tiered hillside pastures, the trail arrives in the village of Armeno in time for a late-morning coffee. From here you may opt to be driven to lunch or to continue on foot through this pastoral landscape, climbing up to Coiromonte. Here, you break for a lunch of local cheese and prosciutto crudo, caprese salad, and pizza.

Following lunch, a beautiful trail through pine and birch forests leads to the open meadows of the Tre Montagnette, which marks the highest point of the day’s walk (45-minute/1,000-foot ascent). The view is superb from this point at 3,600 feet, with Lakes Orta and Maggiore framed below by soaring mountain chains—the most remarkable being the distant snow-covered peak of Monte Rosa. With a summit just over the border in Switzerland of 15,203 feet, it is the second highest in the Alps and Western Europe. Following a descent in the direction of the town of Gignese on the watershed separating Lake Maggiore and Lake Orta, a short coach transfer then brings you to the resort town of Stresa on the shores of Lake Maggiore. The setting of Hemingway’s “A Farewell to Arms,” Lake Maggiore is a captivating 40-mile-long lake whose western shore is in Piedmont, eastern shore in Lombardy, and whose northern shoreline borders the Swiss canton of Ticino. From Stresa you board a boat to Isola dei Pescatori (Fishermen’s Island), where you receive a warm welcome at your charming hotel, spectacularly situated in the middle of the lake. Each of the 12 rooms of this historic, green-shuttered hotel is named after a local flower and features views of the Borromean Gulf and flower-filled balconies. Inhabited since the 16th century, this tiny island still retains its original fishing village atmosphere. There is time to relax, have a swim in the lake, or to explore the quiet alleyways of this romantic isle. Weather permitting, a dinner featuring fresh lake fish, perhaps delicately flavored perch, the symbol of Lake Maggiore, is served al fresco on the hotel’s terrace overlooking the sparkling lights of nearby islands and passing ferry boats.

Lake Maggiore and Isola Bella exploration; 1 mile, easy. Transfer to Bellagio. Villa Melzi; 1 mile or 2.5 mile options, easy

After breakfast the morning is spent exploring the Borromean Isles—specifically the tiny Isola Bella, which is entirely occupied by the Palazzo Borromeo and its Italian garden. Built in the 17th century for the Borromeo family, this splendid summer palace features a wealth of paintings by Lombard artists, sculptures by Canova, and Flemish tapestries. Mussolini attempted to ward off WWII here at the Conference of Stresa in April of 1935. Following a guided tour of the palace, wander the opulently sculpted gardens rising from the water’s edge—a pyramidal succession of ten terraces culminating in a square. Gravel walkways, shaded by orange and lemon trees, meander past 17th-century statues, pebble-studded grottoes, and luxuriant vegetation—laurels, cedars, magnolias, cork oaks, sago palms, heliotrope, camellias, and oleanders.

Nearing lunchtime, you boat back to the mainland and the lakeshore town of Stresa. Following time for an independent lunch and exploration, you are picked up by a private boat to cross the lake to the town of Laveno, from where you embark on an approximate two-hour coach transfer to the tiny town of Cadenabbia, situated on the western shore of Lake Como. From here you board a ferry to the picturesque town of Bellagio, “the pearl of Lake Como,” and your home for the next three nights. Set magnificently on the promontory where Lake Como and Lake Lecco meet, you are positioned to experience the best these elegant lakes have to offer. Setting off directly from the ferry dock, a short stroll down a scenic waterfront path brings you to the magnificent Villa Melzi, built in 1808 for the Duke Francesco Melzi d’Eril, assistant to Napoleon, and now home to a distinguished Lombardian family. Following a visit to the manicured lawns and luxuriant gardens of this heavenly white villa, you make your way to your hotel via a shorter 20-minute walk, or a longer 2½-mile option, exploring some of Bellagio’s hamlets.

The elegant Hotel Belvedere, owned and run by five generations of women from the same family since 1880, is tranquilly located a few minutes' walk above the shops, restaurants, and traffic-free waterfront of Bellagio, and overlooks the crystal blue waters of Lake Como and surrounding mountains. The hotel’s private gardens, with a heated outdoor swimming pool, large panoramic Jacuzzi and spa, are yours to enjoy over the next few days. Dinner, at your resort hotel, rounds off an inspiring day.

Villa Carlotta and Villa del Balbianello; 4.5 miles, moderate with a 30-minute ascent. Additional option: Madonna del Soccorso; 2 miles, moderate with a 25-minute steep ascent, elevation gains range from 300-800 ft

The day begins with a ferry ride to the resort town of Tremezzo, situated on the stunning western side of Lake Como. Here you tour the 17th-century Villa Carlotta, whose famous works of art and terraced gardens of rhododendrons, azaleas, and camellias have inspired poets and travelers for centuries. Ascending the gentle hills above the lake, you walk through ancient villages and along terraced footpaths that seem a world away from the elegant lifestyle of the lakeside resort towns. Following a short break, you have the option to descend to the quaint fishing village of Lenno where, after some time to explore the town’s narrow, cobblestone streets, you enjoy a leisurely lunch at one of the many fine restaurants or cafés gracing the waterfront promenade. Alternatively, those inspired to walk a little farther, by way of a cobblestone pilgrimage pathway marked with chapels symbolizing the Mysteries of the Rosary, will be graced with a magnificent view of the lake from the vantage point of the Madonna del Soccorso sanctuary. If choosing the latter option, a light lunch, perhaps a tasty panino, is served at the sanctuary before you descend to Lenno, where you reunite as a group.

This afternoon, you embark on a private boat ride to the striking Villa del Balbianello, situated at the tip of a small wooded peninsula overlooking Lake Como, almost opposite Bellagio. Built for Cardinal Angelo Maria Durini in 1787, the villa now belongs to the National Trust of Italy. It was here that one of the recent “Star Wars” films was shot, as well as a number of other feature films including “A Month by the Lake” and “Casino Royale.” Following a guided visit to the villa’s elegant gardens and interior, you return to Bellagio with time to enjoy your hotel’s amenities and appreciate the late afternoon sun as it casts shadows on the hills over the lake. This evening, your guides provide ideas for dinner on your own in town; the restaurant or trattoria menu may offer traditional polenta or pasta with porcini mushrooms and the fresh catch of the day—likely the local lake fish, lavarello or missoltin.

Varenna to Vezio; 5 miles, moderate with a 30-minute steep ascent

Following an enticing breakfast of homemade baked goods and preserves, eggs, cured meats and cheeses, you board a local ferry to Varenna, an attractive village on a small promontory. Considered by many to be the most picturesque town on Lake Como, Varenna boasts charming rustic houses, flower-filled balconies, winding alleyways, and a lovely lakeside promenade. The Sentiero del Viandante (Wayfarer trail) takes you through the rugged hills above Lake Lecco, passing the Fiumelatte, a unique stream that (seasonally) is “the color of milk” as it froths over rocks and descends to the lake. Ascending through the forest, the trail traverses northward and enters the hamlet of Vezio, whose collection of ancient stone homes is inhabited by just twenty families. Cobblestone pathways lead to the ruins of the Castle of Vezio, perched high above the lake in a strategic position, providing views of the lake and the distant Alpine ranges, “one last time.” Descending the steep, cobblestone pathway to Varenna, you arrive at a charming lakeside restaurant in time for a lunch of local delights.

Following a mid-afternoon ferry ride back to Bellagio, there is time for some last-minute shopping, exploration, or relaxing poolside before gathering again for an aperitivo on the panoramic terrace of your hotel; peanuts, olives, caper fruit, and savory puff pastries are accompanied by a selection of sparkling, white, and red regional wines. This evening’s farewell feast is on the cozy outdoor terrace of an award-winning restaurant tucked away up one of Bellagio’s many steeply stepped cobblestone lanes; the menu, based on innovative variations of traditional specialties, features delicious homemade pasta and lake delicacies finished off with creatively presented sumptuous desserts.

Arrivederci!

After enjoying a final group breakfast, a private coach brings you to the train station in Milan for connections to your next destination.