Arrival in Santa Margherita Ligure. Nozarego to Portofino; 2 miles, easy to moderate, elevation gain of 385 ft and loss of 885 ft

After meeting at your charming in-town hotel, a brief public bus ride takes you to the village of Nozarego, the starting point for an approximate two-hour afternoon walk to the seaside resort of Portofino. From the charming sanctuary of the Madonna della Neve (situated at 500 feet above sea level), a 10-minute ascent over the luxuriant green hillside, followed by a short level stretch, brings you to the hamlet of Gave and its restored chapel, the Oratorio di San Gerolamo. From here you enjoy a wonderful view over the Abbey of Cervara, a national monument of Italy dating to the 14th century, before continuing on to Portofino in one of two directions—the route decided upon by your guide(s).

The first option rewards you with a less challenging walk along a shaded, cobbled path past farmhouses, through terraced olive groves, down to Paraggi, a tiny coastal town bordered by a beautiful sandy beach. An easy paved promenade, shaded beneath the canopy of a Holm oak forest, winds along the sea delivering you to the cobblestone streets of Portofino.

The alternative option departs the hamlet of Gave along an undulating path before reaching Acqua Morta and Acqua Viva, two small streams, the second so-called because it gave life to a series of 35 olive, chestnut, and wheat mills (one of which is now a visitor’s center), while the former did not have any mills along its course. Reaching Olmi, the highest point of today’s walk at 885 feet, you begin the long descent down a paved path into Portofino, passing by the chapel of San Sebastiano and enjoying splendid views along the way.

The picturesque village of Portofino, nestled into a cove between hills, was rediscovered by the jet set shortly after World War II and is considered to be among the most beautiful Mediterranean ports. Where once only fishing boats docked in the emerald-green inlet, now yachts arrive from around the world. You may choose to relax at an open-air café in the main piazza overlooking the colorful boats bobbing in the harbor, while indulging in a paciugo—a heavenly cup of strawberry and vanilla gelato (Italian ice cream) topped with fresh berries and cream. There is time to independently explore the small streets and browse the town’s boutiques and shops. For stunning views of the entire bay and the Tigullian gulf, you can walk from the famous village square, simply called La Piazzetta, up to the Church of San Giorgio. Perched high above the town, this church contains relics of St. George, Portofino’s patron saint. From here continue to another lookout point at the Castello Brown, a castle dating to the 16th century, before moving on to the very tip of the promontory and the Punto del Capo (Portofino lighthouse).

You return to Santa Margherita via a 20-minute ferry (time- and weather-dependent) or bus ride before gathering for a welcome aperitivo and orientation meeting at your hotel. Dinner tonight is a welcome feast at an inviting family-run restaurant in town. Bountiful seafood antipasti may be followed by the classical Ligurian primo, pansoti con salsa di noci (cheese-filled pasta topped with walnut sauce).

Ruta to San Fruttuoso; 3.5 miles, moderate to challenging, elevation gain of 750 ft and loss of 1,500 ft. Additional option of San Fruttuoso to Portofino; 3 miles, moderate to challenging

After a satisfying breakfast of coffee, bread, cheese, yogurt, and fruit, you transfer by public bus to the tiny and picturesque village of Ruta, at which point you enter the Regional Park of Portofino for an approximate four-hour morning walk. An initial 45-minute, 500-foot undulating yet steady ascent along a shady trail punctuated with a series of rough steps brings you to a spectacular ridgeline trail commanding an enchanting view of the Bay of Tigullio to the east and the Bay of Paradise and city of Genova to the west. Continuing beneath a canopy of chestnut, pine, and oak trees, you traverse the Portofino promontory—ascending 160 feet over a 40-minute period—and arrive at Semaforo Nuovo (“New Signal Station”). At 1,300 feet, you are rewarded with radiant coastal views.

Refueled with a snack and water break, you set off on a beautiful cliffside path overlooking the Cala dell’Oro Bay and the Bay of Fruttuoso. The dirt trail—bordered by fragrant Mediterranean macchia, myrtle, and berries—gently climbs and descends for just over an hour at which point you reach Pietre Strette (“Narrow Stones”), an area of narrow canyons surrounding the 1,500-foot summit of the forested ridge. Over the next hour you descend several stony switchbacks and old mule paths (elevation loss of 1,500 feet) to sea level and the hamlet of San Fruttuoso. This secluded haven, which can only be reached on foot or by boat, is picturesquely situated in a small, rocky cove. Under ownership and protection of the National Trust of Italy, procedures have recently been taken to recognize this hamlet as a UNESCO World Heritage site.

Following an optional swim in the inviting clear blue waters of the San Fruttuoso Bay, you sit down to a much-anticipated lunch—perhaps a fresh green salad along with the region’s signature dish, homemade pasta with pesto. Following lunch, you may accompany your guide(s) on a fascinating visit to the Abbazia di San Fruttuoso, a 10th-century medieval abbey.

This afternoon, you may choose to continue on a scenic two-hour walk to Portofino; otherwise opt to indulge in a bit of la dolce vita by taking a boat back to Santa Margherita (with a possible stop in Portofino). This evening you reunite at a fine seaside restaurant for a delectable dinner of typical Ligurian specialties, complemented by the region’s crisp white wine.

Levanto to Monterosso al Mare; 3.5 miles, moderate to challenging, elevation gain and loss of 1,300 ft

This morning a one-hour train ride brings you to the splendid seaside resort of Levanto, with breathtaking sea views along the way. Upon arrival at this ancient town, known as the “Gateway to the Cinque Terre,” you set off along its curved and colorful main street to visit its medieval frescoed loggia and Chiesa di Sant’Andrea (Church of Saint Andrew), exemplary of 13th-century Ligurian Gothic style with its façade decorated in black-and-white bands, and a magnificent rose window crowning the main door.

You may opt out of the day’s scheduled walk and enjoy an independent afternoon by taking a train directly to Monterosso al Mare, the first of the Cinque Terre villages and the day’s final destination. Alternatively, depart on the afternoon walk from Levanto’s medieval walls on a long, gradual climb along an ancient trade route passing through olive groves and terraced vineyards. The trail eventually levels off for an easy stretch with spectacular views before beginning another rigorous ascent over rough steps through oak woods. A much easier stretch of trail ensues through a pine forest culminating at the promontory of Punta Mesco. At 1,000 feet, your hard work is rewarded with an amazing bird’s-eye view of all five villages of the Cinque Terre. A final steep 45-minute descent down large stone steps delivers you to Monterosso al Mare and your family-run hotel set amidst a garden of towering palm trees, just around the corner from Fegina Bay and the best beach in the Cinque Terre.

After settling in to your new home for two nights, you stroll to dinner at Ristorante La Lampara, a lively, local restaurant where you are welcomed by the legendary and charismatic chef-owner Luigi Corciulo (“Ciak”) with a dazzling array of seafood antipasti—freshly-caught prawns, squid, sea snails, steamed mussels, and the highly-prized anchovies from Monterosso served fried, stuffed, marinated, or salted!

Cinque Terre: Monterosso to Vernazza; 2.5 miles, moderate with challenging sections, elevation gain and loss of approximately 700 ft

“The Five Lands” of the Cinque Terre are Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore: five small, remote villages strung along the coast northwest of La Spezia. They are linked by boat, rail, and footpath, allowing you to customize your walking experience over the next two days. Today’s scheduled walk, and arguably the most spectacular, begins in Monterosso, and continues for approximately two hours along a well-established footpath while offering views of the Ligurian Sea. After an initial lengthy climb up a steep cliffside stairway of several hundred steps, the trail winds up and down through groves of lemon, orange, and olive trees and beautifully terraced vineyards supported by hundreds of miles of hand-built dry stone walling. Known as mura a secco, these walls are a testament to the centuries of labor involved in shaping this fascinating landscape. Traversing extremely narrow trails—perched on terraces with a wall on one side and a drop of 10 to 15 feet on the other—you pass farmers at work using monorail systems to transport grapes and supplies up and down the steep hillsides. You reach Vernazza in time for lunch—likely a simple, authentic pizza or plate of homemade pasta—in the town’s colorful waterfront piazza.

This afternoon you are free to explore Vernazza or additional Cinque Terre villages by train, boat, or on foot. Dinner this evening is at your leisure; your guide(s) will provide suggestions from among the many dining experiences available in Monterosso al Mare.

Vernazza to Corniglia; 2.5 miles, moderate with challenging sections, elevation gain and loss of 700 ft. Corniglia to Manarola to Riomaggiore; 3.5 miles, easy to moderate. Transfer to Portovenere

Today’s exploration includes more of the picturesque “Five Lands” and culminates in the charming medieval town of Portovenere, situated at the mouth of the spectacular Golfo dei Poeti (Gulf of Poets). The gulf is so named because many poets, including Dante, Petrarch, Byron, and Shelley, have sung its praises—even the boats in the harbor sport romantic names inspired by these poets.

Similar to yesterday’s walk from Monterosso to Vernazza (but with fewer steps!), the trail from Vernazza to Corniglia begins with a steep ascent up a set of stone steps before leveling off through terraced vineyards clinging to seaside cliffs. The narrow trail continues for approximately two hours before reaching Corniglia, the most untouched of the Cinque Terre villages. Unlike the other villages of the Cinque Terre, Corniglia is not directly adjacent to the sea. Instead, it is on the top of a promontory more than 300 feet above the sea, surrounded on three sides by vineyards and terraces, while the fourth side descends steeply into the sea. From Corniglia, you set off on your next leg: a 45-minute walk to the cozy, classic seaside town of Manarola and the center of Cinque Terre’s wine production. Comparatively easy, the route winds down a lovely little road through vegetable gardens and terraced vineyards. After a slight ascent, you are rewarded with a final cliffside stretch rich in panoramic views. Leaving the pink-colored houses of Manarola behind, your exploration of the Cinque Terre concludes with a 20-minute stroll along the Via dell’Amore (Road of Love), a scenic paved waterfront promenade leading to Riomaggiore, the southernmost of the five villages known for its historic character and colorful tower houses.

A ferry ride (weather dependent) brings you to your final destination: the Roman-Byzantine town of Portovenere, a UNESCO World Heritage site, where you view both the sea and the nearby Apuan Mountains. The captivating town paints a colorful canvas against the azure sea with its tall and narrow pastel-colored houses lining the waterfront promenade. Perched high on a rocky cape overlooking the sea is San Pietro, a 13th-century Gothic church. Its black-and-white-striped exterior has made it a landmark recognizable from far out at sea. After settling in to your seaside hotel, you embark on a short boat ride to the island of Palmaria—just off the coast of Portovenere—for a magical al fresco dinner, overlooking the waters below.

Isola Palmaria; 2.5 miles, easy to moderate, elevation gain and loss of 1,200 ft

Following breakfast on the terrace overlooking the sea, you begin the day’s adventure with a return boat trip across the bay to Palmaria. This beautiful island, declared a Natural Regional Park, boasts a network of walking paths with stunning viewpoints of its dramatic cliffs and nearby Tino Island. Disembarking in the small harbor of Terrizzo, home to the island’s few homes and a restaurant, an easy 20-minute walk leads you to the meticulously restored 19th-century fortress of Umberto I, which now houses a museum dedicated to the oceanography and undersea archeology of the Mediterranean. From this spectacular viewpoint, the trail gently ascends into a sea of terraced olive groves before leveling off through a forest of Holm oak and pinewood. The air is perfumed by sage, broom, and myrtle underfoot as you approach the southern tip of the island. Here lush Mediterranean vegetation is replaced by steep rocky cliffs, deep ravines, and abandoned quarries of the black and golden-veined Portoro marble—now home to wild goats and an extensive colony of Herring Gulls. A challenging, yet short (20-minute) climb leads to the summit where you are rewarded with unsurpassed 360-degree views.

After a snack and water break, a 45-minute descent by way of an asphalt road or more challenging dirt trail returns you to the hamlet of Terrizzo, where your boat is waiting. Time and weather permitting, you boat around the island to explore several wonderful grottoes—the famous Grotta Azzurra (Blue Grotto), the Grotta Vulcanica, a volcanic grotto housing an ancient freshwater spring, and the Grotta dei Colombi, where Paleolithic evidence was discovered in the 19th century—before returning to Portovenere for lunch at a seaside trattoria.

Following lunch you may accompany your guide(s) on an optional walking tour of Portovenere, whose highlights include the churches of San Pietro and San Lorenzo and the Genovese Doria Castle. This evening a stroll along the waterfront leads to an elegant restaurant for a sumptuous farewell feast of seafood from surrounding waters—sea bass grilled to perfection or tuna in a fresh anchovy and caper sauce. Ideally positioned at the mouth of the harbor, you are afforded breathtaking views of the gulf and fishing boats returning home from sea—a perfect venue for toasting your Ligurian adventure and new friends.

Arrivederci!

After a bountiful breakfast, you are driven to La Spezia train station where you continue home or on to your next destination.