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

Town of Positano on the Amalfi Coast, Italy

What to expect on this itinerary

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.

Countries Visited

Italy

Places Visited

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

Suggested Duration

8 Days

Customizable Itinerary

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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
Day 2

Monterosso – Trek the Splendor of the Church Trail Connecting the Towns

Day 3

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

Day 4

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

Day 5

Perugia – Explore the Delights of Tuscany en route to Gorgeous Perugia

Day 6

Perugia – Discover the Historical and Captivating Towns of Umbria

Day 7

Perugia – Visit Stunning La Scarzuola, Bevagna, and Marmore Falls

Day 8

Perugia – Depart for Home

Trip Highlights

  • Delight in an active exploration of the Italian Riviera north of Cinque Terre to enjoy the unhindered traditions and the gorgeous landscape
  • Wander along the Gulf of Poets to discover the small towns of the Italian Riviera before reaching the opulent Portofino
  • Walk the trails of Cinque Terre to connect the historical churches of each village while enjoying remarkable views of the landscape and coastline
  • Indulge in the bright flavors of the Ligurian coastline with a private cooking class in the heart of Monterosso al Mare
  • See the staggering and dramatic image of Marmore Falls in southern Umbria
  • Witness the elements of the Genoese and Pisan Republics that shaped the Ligurian coast as the two naval powerhouses fought for coastal supremacy
  • See the grandeur and charm of Pisa’s decadent past through its preserved architectural wonders dating back to the 12th century
  • Embrace the quality and unique characteristics of the chocolate crafted and sold in the city of Perugia
  • Sample the delicious qualities of the wines of Cinque Terre during a private wine tour led by a local guide
  • Wander through the distinctive treasures of La Scarzuola for an immersive experience in the creative mind of a celebrated 20th-century Italian Architect

Detailed Description

Your 8-day vacation will embody the enchantment of Italy to welcome you with a blend of history and beauty, tradition, and cuisine. Embrace the wonder of the seaside trails that connect the towns of Cinque Terre, and enjoy the marvelous cobblestone streets of Perugia, home to a medieval university and celebrated chocolate confections. Your Italian immersion will begin with your arrival at Galileo Galilei Airport in Pisa, and your private transfer will escort you to the seaside town of Levanto to meet your train to Monterosso al Mare. The short ride takes you through a tunnel of the Maritime Alps and opens to the bright light of the Mediterranean coast.

A representative from your hotel will meet you at the train station and lead you to your lavish accommodation located on the cliffs between gorgeous vineyards and magnificent water. You have the marvels of the land and the sea at your fingertips as you wake the next day to wander along the Sanctuary Trail to visit the towns and local churches of Cinque Terre from Monterosso to Riomaggiore. Next day, you will mount a bike and travel northbound along the Italian Riviera to visit Levanto, Bonassola, and Framura, known for its quiet beaches, serene landscape, and delicious focaccia bread.

Embrace the relaxed pace of the coastline as you continue to enjoy the Riviera at your leisure. You could wander the different trails along the hillside or venture to the secluded shore of Abbey San Fruttuoso. You could also visit the towns of Tellaro and Lerici, which have maintained their connection to their fishing village roots along the Gulf of Poets that leads to Portofino. Your private transfer will escort you to Pisa for an in-depth exploration of the former Republic’s grandeur and then continue southbound to the city of Perugia for an introductory tour of the medieval streets and ancient city walls.

Travel across the vale on the following day to visit the famous town of Assisi before returning to Perugia for a chocolate tour of the confectionaries and factories, including tasting the treasured sweet treat. Delve deeper as you move into the marvels of Umbria by visiting the distinctive towns of La Scarzuola and Bevagna, along with the dramatic Marmore Falls. Conclude as your private transfer will meet you at the hotel and lead you to Umbria International Airport for your flight home.  

Starting Price

$3,600 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

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Italy Tour Review: Vatican, Colosseum, Roman Forum, Pompeii, Tuscany, Venice, Cheese-Making Experience, Cooking Class, 13 Nights

Zicasso's travel agency far exceeded our expectations. We had our five-year-old and 11-year-old children with us, so the tour guides and walking needed to be kid-friendly.

Our hotel in Rome was wonderful, the location was perfect, and they had good A/C and a breakfast buffet. There were plenty of great restaurants within easy walking distance, as well as the Vatican.

Our tour guide for the Colosseum and Roman Forum was great. Pompeii was amazing. Our tour guide was basically a celebrity down there and knew exactly how to take us around the ruins without ever waiting.

Tuscany was our favorite by far. We did a cheese-making experience and lunch that was super-cool. The kids got to play with the farm animals and the owners were so attentive and interesting. We did a cooking class with a chef that was the kids' favorite thing on the entire trip. I would make a point to book this experience; the kids still talk about it and wear the aprons around the house. The resort in Tuscany was nice. We had our own private pool, plus the resort pool, and could easily walk to a small local town with some great food.

Venice was good, but probably our least favorite on the trip. You have to walk a ton, which was difficult for the kids, but it's still worth experiencing.

We travel a bunch and I would highly recommend using Zicasso's travel partner.

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Italy Tour Review: Monterosso al Mare, 10 Nights

We loved the hotels you selected. The drivers were prompt and the guides were good. We especially loved our guide in Florence. Monterosso al Mare was beautiful.

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Switzerland, Italy Solo Vacation Review: Zurich, Lucerne, Interlaken, Zermatt, Lake Como, Venice, Florence, Sorrento, Amalfi, Rome, Skydiving, Gondola Ride, Amalfi Coast Cruise, Scenery, Nature, Local Cuisine, 3 Weeks

My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.

Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.

Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.

Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.

What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.

Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.

As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.

Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.

The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.

This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.

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Italy Tour Review: Bologna, Parma, Modena, Balsamic Vinegar Factory, Wine Tasting, Cuisine, Cooking Class, 2 Weeks
"We set out to experience culture and food, and Zicasso’s travel agency did not disappoint."

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Italy Travel Review: Perugia, Orvieto, Rome, Cooking Class, Cuisine, 1 Week
"Zicasso’s travel company did an excellent job designing our trip and provided support when we needed to make last-minute modifications."

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Italy Family Vacation Review: Venice, Verona, Florence, Tuscany, Siena, Rome, Biking, Cooking, Wine Tasting, Olive Oil Experience, 10 Nights

Zicasso's travel company planned the most amazing trip to Venice, Verona, Florence, Tuscany, Siena, and Rome for our family of five. It was the best trip I've ever taken, and having all the details covered by them and plans and tickets sent to us via WhatsApp allowed us to really live in the moment and not have to think about what was next. I loved every second. I cannot wait to plan another trip to Italy to experience the southern half of the country.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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