Distinct Trails of Italy Tour: An Active Exploration of Cinque Terre & Tuscany

Tuscany is famous for its lush rolling hills, vast vineyards, and towering cypress trees as country roads lead to enchanting preserved medieval towns. Your flight will arrive at Florence International Airport, and your private transfer will meet you at baggage claim to escort you into the Tuscan countryside. The sunlight spreads across the verdant olive trees as emerald vineyards blanket the hills as the scent of succulent oaks and herbaceous plains fill the air. Your guide will meet you at the head of a small trail that leads to Volterra as your transfer continues to town with your luggage. You will continue on the trail for an easy walk that will allow you to bask in the beauty of the landscape and stretch your legs after the flight.

Stone farmhouses rise out of the growing stalks, and your guide will have you grab a dangling olive to feel its plumpness and coarse texture. The town of Volterra rises above the cypress and oak trees on the hillside as you will reach the imposing walls that protect the medieval city, a structure matched in drama only by the remaining historical towers that create a stone skyline. Etruscans settled the province before the Romans overtook Tuscany in the 3rd century BC as the cobblestone lanes and studded walls were built between the 14th and 16th centuries. Wander through the Etruscan Museum for perspective on the 3,000-year-old history of settlements on the hillside with galleries that exhibit funerary urns, ceramics, and gold jewelry.

The sunlight washes over the three Etruscan heads that adorn the more than 2,000-year-old archway that leads into town. Cafes place tables and chairs along the narrow cobblestone streets that meander around the hillside as potted plants add lively greenery to the muddled stone and faded brickwork. Your guide will meet you after breakfast and will lead you out onto the trails that crisscross the Val di Cecina. Clay hillsides emerge from the manicured grass and vineyards inside a nature reserve that encompasses more than 29,600 acres. The peak of Monte Voltraio rises to a height of 1,502 feet above sea level, and the summit resembles a pyramid as it has been molded from sand and limestone.

Stone farmhouses and marvelous castles rise out of the plains alongside the trail. The water of the Cecina River spills over the pebbles and boulders on the banks and a quiet waterfall trickles down a pale, golden rock wall into a waiting pool framed by rustling reeds. Back in Volterra, you will have the remainder of the day at your leisure to enjoy the preserved history and marvelous charms of the rustic buildings and hidden avenues. Palazzo dei Priori was built in the 13th century and stands as the town hall. It remains the oldest seat of local government in all of Tuscany. The bell tower was constructed in the 19th century and offers an incredible vista for viewing the Tuscan countryside.

You will depart from Volterra early in the morning, and the aroma of fresh espresso will linger in your clothes. The rising sun will cast a brilliant light over the rolling hills and vivacious trees of Tuscany.  The scenery will shift as the hills rise into mountains and the cypress trees turn into holm trees. The aroma of the rich vineyards combines with the scent of the Mediterranean Sea in the refreshing breeze. You will reach the town of Riomaggiore, known as the southern gateway to Cinque Terre where the pastel painted tower-homes decorate the steep hillsides that lead to the water. The Mediterranean Sea curls against the sea break to separate the harbor from the open water. Narrow lanes connect to the single main street, which leads upwards to the 13th-century fortifications of Castle of Riomaggiore.

You will quickly discover the charms of the secluded fishing village in the forest that blankets the hillsides, the various shades of blue shining across the sea’s surface, and in the meandering narrow lanes that are lined with preserved medieval structures. The Church of St. Giovanni Battista was erected in the 14th century with a Gothic style visible in the two-sided aisle that leads to the nave. The coastal trail connects the five towns of Cinque Terre over the course of seven miles to reach an altitude of 656 feet above sea level. After you take some time to wander through Riomaggiore, your guide will lead you on a trail that connects to town to Manarola. The trail connects the hamlet churches at the tops of the hill before leading you to the streets of the cliff-side town.

Before you set out for the day, you can take a moment to enjoy the quiet mornings of Riomaggiore. Fishers return from the open sea with sea bass and mussels ready for market as the two narrow stretches of pebbled beaches remain empty before the sun has warmed the hillsides. You will look back to the terraced mountains to find the emerald glow of the olive trees and basil plants that thrive in the Mediterranean climate. You will meet your guide at the dock for a thrilling boat ride along the coastline.

Your guide will point out into the water near the coastline to show you a large statue of Jesus standing on the seabed. The crystalline water offers a perfect view down to the stone figure before the boat docks at San Fruttuoso. The medieval Abbey contains 8th-century foundations that once stood over the water with an arching base that allowed for ships to enter directly into the cellar. The water receded over the centuries to create a pristine, secluded beach in front of the Romanesque façade and dome of the preserved medieval structure.

Trails crisscross the hills and cliffs that surround the Abbey, which is situated in Portofino National Park. The beach fills with locals eager to enjoy the sun and the secluded stretch of beach. You will make your way along the steep path into the hills, finding historical mills at the eastern edge of the park. The mills were connected to the regional cultivation, processing figs, wheat, chestnuts, and olives. Vines dangle along the facades of older, abandoned mills. Strawberry trees grow wild along the heather that overlooks the Mediterranean Sea beside the delicate flowers and roses with roots growing beneath rocks.

In the morning, you will sip your espresso as you overlook the coastline. Locals enter the local cafés before they continue to work and the scent of savory focaccia emanates from the bakeries around town. After breakfast, your private transfer will escort you back to Tuscany, stopping in the town of San Gimignano.  The 14 towers that fill the skyline represent the wealth and prestige of the former noble families. Narrow medieval streets meander beneath the shadows of the towers, which once numbered 72 in total. The scent of creamy gelato and freshly baked brioche overtake the lingering aroma of stone. From the top of the 177-foot tall Torre Grossa, which was constructed in the 13th century, you will have a perfect view of the trees, vineyards, and saffron fields as they lead to the horizon.

After you enjoy the rich history and unique architecture of San Gimignano, your guide will take you along Via Francigena, an ancient pilgrimage road that leads from France to Rome, which also connects San Gimignano to Colle. The beauty of the vineyards and saffron fields, olive groves and oak trees remains captivating and urges you along the historical route before you reach the town. The mountain ridges run from east to west and hold the oldest neighborhoods of the town as some settled around the 10th century. The historical town center adorns the hill, built as a strategic point to view the surrounding countryside. The castle walls shape a dramatic figure on the outskirts of the town center as the circular towers and arching gate form a perfect picture of a fairytale structure.

In the morning, you will leave the defensive walls of Colle and make your way to the historical center of medieval Siena. Enter the walls of the city and follow the wide cobblestone boulevards of the enchanting city that leads to Piazza del Campo. The red and white 14th-century tower that is connected to the town hall reaches a height of 335 feet. Several hundred steps lead to the opening at the top of the tower to offer a view of the city’s red-tiled rooftops, labyrinthine streets, and the surrounding Tuscan hills.

Looking down on the piazza, you will see the unique curving shape of the palaces around the border. The Cathedral of Santa Maria Assunta was built in the 13th century and exhibits some of Italy’s finest Gothic design. Black and white horizontal stripes adorn the Campanile as a dramatic rose window adorns the center of the façade above the portico. The motif of stripes continues on the inside of the church, and the ceiling imitates the night sky with rich blues and gold stars.

Sections of the floor feature elaborate marble mosaics that number 56 panels in total, which were crafted between the 14th and 18th centuries. The most notable panel depicts the Wolf of Siena weaning Romulus and Remus beneath a tree, an allegory for the city’s beginnings. The library shines with pristine frescoes that depict scenes from the life of Pope Pius II as painted by Pinturicchio. The paths of the city lead to the vineyards around town where a local vintner will welcome you onto the grounds to explore the vines and sample the wine made on the property.

In the morning, the rustic and rosy hues of the Church of San Domenico shines against the emerald cypress trees that grow on the hillside. After breakfast, you will set out on Via Romea once again to follow the pilgrim’s trail around the hills outside of the city in view of the towering figure of the Basilica. The smooth hills glow green beneath the cloudless sky as red-dirt trails wind through vineyards and olive orchards. Yellow cereals offset the precious stone colors of the grass and sky as the town of Chiusi stops at the crown of a hill.

The aroma of cappuccino emanates from cafes between the museums and churches as a peppery note from traditional Tuscan pepe nero pasta fills the air. You can venture beneath the hilltop town through the network of tunnels once formed by the cisterns used to collect rainwater. The cool atmosphere will contrast with the warmth of the sun-soaked landscape. You will circle back to Siena to enjoy a gelato tour of the medieval city in the afternoon to sample a selection of traditional and creative flavors, each featuring the creamy texture and elaborate collection of ingredients in search of the perfect bite.

In the morning, you can take one last stroll along the cobblestone streets of Siena. The colorful facades of three separate palaces frame Piazza Salimbeni. The 14th-century Gothic Salimbeni Palace fills the center of the piazza and houses the office of Italy’s oldest bank. The 15th-century Buonsignori Palace holds the National Gallery, a museum that offers an overview of Siena’s artists between the 12th and 16th centuries. The majesty of the art and the splendor of the countryside urge you to stay longer in Italy, but your private transfer will meet you at the lobby ready to escort you to Florence for your flight home. You can always extend your stay and walk along the countryside outside of Rome to discover the villas and historical towns hidden by the regional hills, or you could travel north to Lake Como near the Swiss border.