Trekking the Italian Riviera Tour: Treasured Trails of Cinque Terre

A 8 day trip to Italy 
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Redefine your ideas of comfort and luxury on the trails of the Italian Riviera as you relax in the natural landscape of the meandering cliffs and the stunning Mediterranean Sea. Your custom tailored tour will lead you along the ancient paths that connect medieval villages, secluded monasteries, and lush seaside towns. The scents of lemon trees and basil plants blend into the sea breeze as antique towers that have protected the coastline from pirates and maritime powers for centuries stand tall. Fishing boats return to the lively harbors with nets that burst with fresh fish. Indulge in the sun-soaked villages and the endless discovery of Ligurian splendor, from wine to frescoes, seafood to panoramic views. 

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Florence, Riomaggiore, Vernazza, Manarola, Corniglia, Monterosso, Levanto, Portofino, Portovenere, Santa Margherita 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Florence – Arrive in Florence for a Private Walking Tour of the Renaissance

Florence stands at the heart of Tuscany and fills the famous region with the luster of its Renaissance influence lining the Arno River. As your flight descends into the Florence airport, you will see the cypress trees and vineyards that rise along the rolling hills of the countryside. Your private transfer will meet you at the baggage claim and lead you along the cobblestones of Florence’s city center. The massive dome of the Florence Cathedral soars above the palaces and historical buildings of the city. Your guide will meet you in the hotel lobby to show you the wonders of Florence on an introductory walking tour to highlight the city’s open-air museum characteristics.

The Cathedral of Santa Maria del Fiore, Giotto’s Campanile, and the Baptistery rise from the heart of the Piazza del Duomo. The inlaid marble shines pink, white, and green in the passing sunlight. The Museo dell’Opera del Duomo hides in an antique palace that borders the square behind the Cathedral’s main entrance. The Cathedral is often considered the symbol of Florence, from its incredible dome designed by Brunelleschi to the sheer magnitude of the church, which reaches a length of nearly 500 feet long. The interior contains hints of frankincense that linger from mass earlier in the day.

The 44 stained glass windows from the 14th and 15th-century continue to glow with sharp hues that bring a rainbow of light into the nave. Lorenzo Ghiberti, who designed the bronze panels of the baptistery doors, also created the stunning Biblical depictions in the three rose windows. Your elaborate introductory tour of the city ends at the Church of San Miniato that overlooks the Tuscan countryside and Florence. The aroma of lush cypress trees overtakes the air outside of the entrance. You walked up the hill that bordered the city, which provides access to Piazza Michelangelo. Inside the church, the local monks still chant nightly, as they have since the church’s inception in the 11th-century.

What’s Included: accommodation, transfer, tour

Day 2: Santa Margherita – Transfer to Santa Margherita for an Introductory Hike

Florence returns to life in the morning with the aroma of freshly baked brioche that drifts along the cobblestone streets. The sunlight glistens off of the surface of the Arno River and ripples with the current. Your private transfer will meet you at the hotel and escort you to the city of Santa Margherita, located on the Ligurian Sea. Palm trees tower above the beachside promenade as boats sway in the gentle wake of the lapping water. You will have time to enjoy the tranquil seaside atmosphere of town before you meet your guide at the hotel.

Linger in the pleasant aroma of freshly grilled seafood accented with garlic and a squeeze of lemon. After you meet your guide,  step on the trail that leads you to the picturesque village of Portofino. The trail stretches for nearly four miles and includes stairs that lead to a top elevation of 1,100 feet above sea level. The Romans constructed the seaside colony, which the Genoese overtook around the 13th-century.

Various countries and cultures have added their unique mark to the town rich in pastel colored homes and lush trees that edge the Mediterranean Sea. Your guide will lead you up the pathway to Salita di San Giorgio and past the small yellow façade of the Church of San Giorgio.  The 16th-century Castle Brown was built to protect the city from rival city-states and navies. The neo-Gothic interior contains a remarkable tiled staircase as the lighthouse on the edge of the precipice offers unobstructed panoramas of the city below.

What’s Included: accommodation, transfer, tour, breakfast, dinner

Day 3: Santa Margherita – Trek to San Fruttuoso and Continue along the Riviera

The morning air in Santa Margherita combines the delicate aroma of the sea with the sweet scent of the freshly baked bread that emanates from the cafes. Patrons linger in in the shade of the umbrellas as tables offer views to the water. Villa Durazzo stands on the hilltop overlooking the city with 16th-century grandeur. Lemon trees and hydrangeas grow in the elegant gardens as the interior houses a collection of 17th-century paintings. After breakfast, your guide will meet you at the hotel and lead you along the trails that wind up and around the seaside escarpments. From the town of Camogli, make your way to the secluded Abbey of San Fruttuoso, situated on a beach protected by the rocky outcroppings.

The water that once flowed beneath the archway of the abbey allowed transfer and cargo boats to weigh anchor beneath the structure. The shoreline receded and created a stretch of pebbled beach that locals enjoy visiting. The monastery was erected between the 10th and 13th-centuries and the Nolare Tower once acted as the center of the Abbey and faces out to sea. The lower cloister provides access to the burial chamber where the Doria family, the patrons of the monastery, rest. The history of the Chapel and the life of the monks are preserved in the main Abbey to reveal that the Romanesque church was constructed over an even older Chapel.

What’s Included: accommodation, tour, breakfast, dinner

Day 4: Monterosso – Visit Levanto and the Medieval Towns en route to Vernazza

In the morning, your guide will lead you to the town of Levanto, a region once overtaken and protected by the powerful Genoese navy. The 13th-century castle continues to dominate the hillside as the city walls wind along the borders and lead to the medieval castle in Celasco. The aroma of the sea blends perfectly with the slightly bitter scent of fresh-brewed espresso. Today, the trail will lead you across the Riviera to a maximum altitude of nearly 3,600 feet above sea level. The challenges of the steeper portions of the trail provide an unforgettable reward of the coastal views and secluded medieval churches adorning the mountaintops.

The trail leads you through the lush greenery of the hillsides that overlook the turquoise water and down into the stunning old town of Monterosso, the northernmost town of Cinque Terre. The scent of the herbaceous aroma of pesto emanates from the restaurants that line the cobbled streets. The small parish church of San Giovanni Battista stands near the train station as the old Genoese watchtower continues to look over the horizon from the promontory above the beach to look out for unfriendly visitors and pirates. On the trail that leads to the neighboring town of Vernazza, stop at the Madonna di Saviore, a church filled with spectacular baroque décor.

What’s Included: accommodation, transfer, tour, breakfast, dinner

Day 5: Monterosso – Explore Ancient Volastra and the Cinque Terre Trails

The beauty of the Ligurian coast and Cinque Terre is clearly seen from the unique perspective of every step. The seaside looks different from every angle, and the villages each contain a charm separate from their neighbors. After breakfast, you will return to the village of Vernazza, located on tiers that rise the hillside with a natural harbor that breaks the waves just below. The water crashes against the stones and mists into the air as the scent of grilled octopus with garlic and basil lingers in the sunlight. Your guide will lead you along the trail to Corniglia, the middle village of Cinque Terre. The ancient town of Volastra rises out of the vineyards and olive trees near the sanctuary of Manarola. The vines, basil plants, and lemon trees grow in abundance along the mountainside.

Olive orchards resemble forests as they decorate the terraced gardens. Corniglia is the only town of the five without a harbor as the town is situated nearly 600 feet above the sea. 300 steps lead up to the 13th-century Gothic church of San Pietro. You will linger in Corniglia for a bit longer to wander through one of the vineyards that overtake the landscape. The local winemaker will invite you in to see how the wine is made before pouring you a sample of a refreshing, crisp white wine that offers hints of lemon curd and melon. You will cross over an altitude of more than 2,920 feet between Corniglia and Manarola to enjoy the ever-changing view of the water and the refreshing sea breeze that sweeps across the trail.

What’s Included: accommodation, tour, breakfast

Day 6: Portovenere – Travel from Riomaggiore to Portovenere by the Coastal Path

Wake up to the beauty of the Ligurian Sea, which refreshes its majestic appearance daily to show you a newfound trait you hadn’t previously noticed. After breakfast, you will take a quick, scenic train ride to Riomaggiore. The pastel homes rise from the water as if built into the cliffs as the promontories narrow and connect over the pebbled beach. Your guide will lead you through the cobbled streets en route to the trail to Portovenere. The meandering path takes you along the pine trees that blanket the hills as the herbaceous scent gives way to the sweet aroma of the chestnut trees and the greenery stands out from the clear blue sky.

At the church of the Madonna della Monteneri, look back at the water for a quiet view of the horizon as it reaches the edge of the cliffs in the distance. The hills reach a height of more than 1,500 feet along the trail before they fall to the Peninsula of Poets. You have a perfect view of the 16th-century Castello Doria as it rises above a rocky outcrop extending away from the town. The trailhead leads to a vista of the harbor and the sea, crowned by the subtle mixture of the sea breeze and small orchard. The colorful homes on the seaside are up to eight stories tall and were originally constructed in the 12th-century, conceived as defensive towers for the harbor.

What’s Included: accommodation, tour, breakfast, dinner

Day 7: Florence – Enjoy a Scenic Cruise to La Spezia and Return to Florence

The sunlight washes over the limestone rocks and turquoise waters of the Gulf of Poets. Linger in the morning breeze and bask in the fresh scent of the sea as the gulf was named after the famous writers that revered the landscape of the region, from Lord Byron to Percy Shelley, along with Gabriele D’Annunzio. The Tinetto Islands rise out of the La Spezia archipelago 55 feet above sea level. The islands housed a 6th-century monastery settled by the Saracens, which contained two naves and monk cells each linked to one another. After breakfast, board the ferry to La Spezia and pass the by the walls of the islands, which shine gray and gold with their unique Triassic carbonate rocks formations.

Your private transfer will meet you in La Spezia and escorts you back to Florence. The remainder of the day is at your leisure to relax in the majesty of the Renaissance city. For a unique experience, you can visit the Officina Profumo Farmaceutica di Santa Maria Novella, nestled into a side street near the Santa Maria Novella Church. The perfume emanates from the discreet doors and drifts down the street as the office is the world’s oldest perfume maker started by Dominican friars in the 13th-century. The former chapel maintains the religious frescoes that decorate the walls.

The ancient workshop contains antique equipment once used by the monks to procure the sought after aromas. 17th-century vases and jugs from Montelupo add to the illustrious charms of the exhibits inside the perfume museum. You can even find the Medici coat of arms adorned with a painting of St. Peter. The fragrances are almost overwhelming and span centuries of work and understanding and the sales room still have carafes once used to contain the various aromas produced inside the perfumed walls.

What’s Included: accommodation, transfer, tour, breakfast

Day 8: Florence – Depart for Home

You could spend all of your days walking the trails in and around Italy, enjoying the refreshing breeze of Tuscany and the cool sea air of the Mediterranean. Vineyards span the rolling hills outside of Florence while in the city itself the Renaissance palaces frame the cobblestone streets. You have walked along the seaside cliffs and medieval towns of the Italian Riviera; you have strolled along the hills of Florence’s borders and listened to monks harmonize with Gregorian chants. After breakfast, your private transfer meets you at the hotel and escorts you to the Florence airport for your flight home. You could extend your vacation to experience other regions of Italy to enjoy the walkways of Rome or the labyrinthine canals of Venice, each providing unique paths and inspiring charm.

What’s Included: breakfast, transfer 


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.