Basil & Chocolate: Indulging in Italian Riviera and Umbrian Countryside Tour

A 8 day trip to Italy 
5 out of 5 stars
2 reviews

The charm of the Italian Riviera emanates from contemporary luxuries hidden within the serene seaside villages. The enchantment of Umbria rises from the medieval streets, bucolic hills, and overlooked towns that burst out of iconic vineyards. Your custom tailored tour combines the majesty of land and sea to take you on a remarkable journey through ancient city walls and continued traditions, tranquil hiking trails and opulent marinas. A statue of Neptune adorns the cliff that overlooks the Mediterranean as a powerful waterfall erupts from an emerald forest. Unwrap the wonder of the Riviera and Umbrian regions to enjoy pebbled beaches and perfect panoramas. 

Customize This Trip For Me
Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Levanto, Bonassola, Framura, Monterosso, Corniglia, Manarola, Riomaggiore, Vernazza, La Scarzuola, Bevagna, Marmore Falls, Assisi, Perugia, Pisa, the Gulf of Poets, Tellaro, Lerici 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Monterosso – Arrive at Pisa Airport and Transfer to Colorful Cinque Terre

The beauty of the five towns of Cinque Terre nears mythical proportions. Each town contains a distinctive culture and design, from nestling into the rocks of the Ligurian coastal mountains to forming a natural harbor overlooking the Mediterranean Sea. A series of trails connect the five towns together, strewn along the mountain ridges and over the plateaus and follows ancient goat herder paths and pilgrimage routes. Your flight will land at Galileo Galilei International Airport in Pisa where you will meet your private transfer. Venture first to the town of Levanto, located to the north of Monterosso and separated by a mountain promontory.

Next, board a local train for a brief, but scenic, ride through a tunnel to reach the station at Monterosso, the most northerly of the five towns of Cinque Terre. The city was first mentioned in documents written in the 11th century. Pebbles and white sand merge on the beach, set beneath the green hills that frame the town. Umbrellas shade the lounge chairs and fill with beachgoers. The Mediterranean Sea shimmers with sapphire hues that darken with the depths of the water. A hotel representative will meet you at the train station and escort you to the impressive hotel built on the terraces that overlook the Ligurian coast. Sheer cliffs turn the paradise into a stunning vista, and your private room will have a marvelous terrace that encompasses the beauty of the region, from the vineyards above to the splashing water below.

What’s Included: accommodation, transfer, dinner

Day 2: Monterosso – Trek the Splendor of the Church Trail Connecting the Towns

In the morning, you will catch a glimpse of the fascinating statue referred to as Neptune located at the end of the Fegina beach. Boats wade in the small harbor beneath the towering figure set in stone that reaches a height of more than 45 feet tall. The impressive ruins of the 16th-century castle prefigure the beauty and majesty of your day as you explore the trails above the five towns of Cinque Terre. Three of the original 13 towers remain and look out to the horizon. The trail referred to as Sanctuaries Way, travels for 12 miles but offers respite and easy access to the towns below for those not wanting to traverse the trail in its entirety. Each village erected their own personal sanctuary along the path in a show of their devotion.

Red and white stripes mark the trail as it meanders along the verdant vegetation that grows along the hillside. The views open to marvelous vistas of the mountain promontories and glistening Mediterranean as the calm water laps against the rugged shoreline. You will pass between the lush olive groves and vibrant vineyards and the aromas of sweet grapes and herbaceous olives add layers of welcomed complexity to the ambiance. The Sanctuary of the Madonna of Soviore rises above Monterosso at more than 1,520 feet above sea level, erected in the 13th century and features bright frescoes that decorate the vaulted ceilings. The trail leads you to the Sanctuary of Our Dame of Reggio, a 13th-century church that stands at nearly 1,150 feet above sea level. 

What’s Included: accommodation, tour, breakfast

Day 3: Monterosso – Enjoy an Active Day Exploring the Ligurian Coast at your Pace

The morning in Monterosso rejuvenates you as the majesty of the landscape and seaside overwhelm your senses. Fishing boats set out in the early hours and return with the sun shining brightly in the sky upon the nets filled with octopus, prawn, and cod. At breakfast, you will sit on your terrace and enjoy a frothy cappuccino as the scent of the semi-sweet coffee blends with the salty aroma of the Mediterranean. After your meal, you will take your bicycle to traverse the paths that open up to sensational views of the landscape, the seaside, and the towns along the Italian Riviera.

A three-mile bike path travels northwest of Monterosso along a restored former railway tunnel. You will venture into the brick tunnels and glide through the mountains that border Levanto to arrive in the town of Bonassola. The authentic Italian town offers a smooth pebbled beach with the sapphire waters that splash against the shoreline. The bright colors of the nearby homes shine red, yellow, and orange and pleasant aroma of focaccia emanates from the celebrated bakeries sprinkled about town.

Locals from around the area visit Bonassola simply for a break from daily life, which you will find here as well. A coastal path leads to the serene 17th-century seaside chapel of La Madonna della Punta. With your bike you can continue northbound to the town of Framura, celebrated for its remarkable red marble rocks that frame the beach. The town is a collective of five hamlets with no town center, with each hamlet ascending the hillsides. Take the train back to Monterosso for your private cooking lesson and learn the traditions of Ligurian cuisine, which often consists of handmade fresh pasta, seafood, and pesto.

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

Day 4: Monterosso – Relax on the Ligurian Coast and in Cinque Terre at Leisure

In the morning, local beachgoers head to the secret beach of Guvano, a secluded stretch of sand between Corniglia and Vernazza. A hidden tunnel offers access to the shoreline and opens up to beams of soft light and emerald trees. Today you can bask in the entirety of the Italian Riviera at your leisure, from roaming along the trails that connect Cinque Terre to traveling by boat to the secluded Abbey of San Fruttuoso. For a unique experience, you could also venture to the town of Tellaro located on the Gulf of Poets.

The gulf was named after its allure to poets from around the world who embraced the natural beauty, including English Romantics such as Shelley and Byron. Boulders border the white sandy beach and draw your eyes to the indigo hues of the water. The town of Tellaro retains a strong connection to its fishing roots, and small fishing boats linger near the marina and along the narrow cobblestone lanes of town. Rose and yellow homes add brightness to the meandering passageways as hydrangeas blossom along the upper edges of town and bougainvillea drape across the stone structures.

The town of Lerici opens to a bustling marina watched over by a fairytale castle. The 12th-century construction has held a strategic position for the Republics of both Pisa and Genoa while footpaths connect Lerici to Tellaro. In the afternoon, after indulging in the beauty and enchantment of the gulf, you will return to Monterosso to meet your vineyard guide. Wander through the emerald colors and narrow trails of the vineyards terraced on the cliffs that overlook the shimmering sea. Your guide will explain the rich history of winemaking in the region, along with the unique properties of the grapes grown in the region’s particular climate.  

What’s Included: accommodation, tour, breakfast

Day 5: Perugia – Explore the Delights of Tuscany en route to Gorgeous Perugia

Since arriving in Monterosso, you have done more than see the beauty of the landscape and coastline of Liguria as you have also experienced the stories and culture of the people living along the Italian Riviera. Castles and towers offer insight into the decadent, but tumultuous, history of the Republic of Genoa that had overtaken the Pisan military to claim the towns along the shore, including the castle at Lerici. After breakfast, your hotel representative will guide you back to the train station for your quick journey to Levanto where you will meet your private transfer to Umbria.

En route to Umbria’s capital of Perugia, you will stop in the renowned city of Pisa for a look at the legendary might of the Republic’s former Navy. The power struggle between Genoa and Pisa shaped the Ligurian coastline for centuries, and the maritime victories helped fund the construction of Pisa’s gorgeous Cathedral, Baptistery, and the most iconic image of the city, the Leaning Tower. The city thrived under the patronage of the Medici in the 15th century long after Pisa’s Navy fell to the glory of the Genoese Republic and the city has a stunning design of small canals and arching bridges.

Marbled structures tell stories of the rich history, including the establishment of the University in the 14th century. In the Piazza dei Miracoli, you will find the leaning tower reaching a height of 186 feet, with a tilt of nearly four degrees. The foundations were laid in the 12th century with marble, and each tier contains encircling pillars that resemble a wedding cake. The wonder of the structure, and the attention to detail in the architecture of the Cathedral and Baptistery, create a lavish display of the city’s former grandeur.

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

Day 6: Perugia – Discover the Historical and Captivating Towns of Umbria

The medieval streets of Perugia meander along the hilltop lined by antique buildings. The ancient settlement was once 12 separate Etruscan cities protected by walls that continue to wrap around the historical center extending more than 9,000 feet around town. In the morning, the streets fill with the pleasant aromas of confections, from freshly baked brioche to decadent chocolates. Assisi, the most famous town in the Umbrian region stands across the vale and rises along the opposite hillside of Monte Subasio before reaching the edge of the woods.

The rosy hue of the historical walls glows as your private transfer will lead you across the valley to the entrance of the birthplace of St. Francis. The dominant figure of the 14th century, Rocca Maggiore adorns the top of town and offers a panoramic view of Perugia and the surrounding valleys. The Basilica di San Francesco draws most people to the city, whether religious pilgrims or visitors eager to view the elaborate display of devotion to the saint after which the current pope took his name.

The main structure was erected in the 13th century after the construction of the lower church. A series of 28 frescoes offers an interpretation of the life of St. Francis in vibrant, colorful detail. The frescoes have been attributed to the celebrated artist Giotto while the lower Romanesque structure reflects the simplicity of St. Francis. When you return to Perugia, your guide will meet you at your hotel ready to uncover the sweet secrets of the city beginning with a fantastic demonstration of chocolate creation as the nearby factory fills with the scent of rich, dark chocolate that overflows into the streets.

What’s Included: accommodation, tour, breakfast

Day 7: Perugia – Visit Stunning La Scarzuola, Bevagna, and Marmore Falls

The medieval houses and ancient walls of Perugia feature a golden hue in the morning light. The youthful ambiance of the city derives from the students who attend a university established in the early 14th-century. Your guide will meet you after breakfast and lead you into the golden hills of Umbria at the town of La Scarzuola. Milanese architect Tomaso Buzzi attempted to construct the ideal 20th-century city to connect the existential and the physical components. The original city was erected in the 13th century on the remote hillside following the pathway of St. Francis as the pilgrim had planted a rose and laurel bush near his shelter, around which a Franciscan community grew in the early 15th century.

Buzzi transformed the existing monastery in the 1950s and turned the convent gardens into an intricate hedge maze accentuated with fountains and exotic plants. After wandering along the mystical structures of La Scarzuola, you will continue southbound to Marmore Falls. The natural emerald forests frame the falls, which reach a total height of more than 540 feet along the Nera River. The powerful cascade has inspired poets for two millennia, including Nero and Lord Byron. Mist spouts upward from the falls along the various tiers as the thundering sound echoes through the expanse of trees.  

What’s Included: accommodation, tour, breakfast

Day 8: Perugia – Depart for Home

The Arco d’Augusto is one of seven gates that allow access to the city of Perugia and was originally constructed by the Etruscans in the 3rd century BC. An inscription on the gate praising Roman Emperor Augustus dates from the 1st century BC, after which a seven-month siege led the Romans to victory over the city. Two trapezoidal towers flank the elegant arches, and the aroma of fresh brioche and cakes emanate from the antique display case found in a café in the heart of Perugia that has done business for more than 150 years. The splendor of the city comes as much from the cuisine as from the rich history, and this last morning gives you one last chance to enjoy it. After breakfast, your private transfer will meet you in the lobby of your hotel and escort you to Umbria International Airport for your flight home.

What’s Included: breakfast, transfer 



Please inquire for a custom quote. The price is customized based on final accommodation choices, travel dates, and other custom preferences.