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

Verified Traveler Reviews

Based on 1250 reviews

Italy Tour Review: Abruzzo, Pescara, Chieti, Venice, Verona, Lake Como, Milan, Turin, Cooking Class, Opera, Boat Ride, Food Tour, 12 Days

This was my third customized trip with Zicasso. I previously worked with Zicasso to plan and take mother-daughter trips to Iceland and Croatia. They are the perfect company to help your dreams for a personally unique adventure come true!

This time, I traveled with my daughter, son, and daughter-in-law to Italy. My hope was for my daughter and son to see the towns where their great-grandfather and great-grandmother emigrated from in the Abruzzo region, in the towns of Roccamontepiano and Bugnara. My research had an address for where their great-grandfather was born. Our driver found the address and we took photos of us standing in front of the house, which could now be considered a real fixer-upper. Just the same, it was a moment never to be forgotten. Thank you to our driver and his wealth of information!

Our home base was in Pescara, where we enjoyed a walk on the beach, excellent local cuisine at a local restaurant, and seafood at another local restaurant. These were recommended by our local travel agent and were clearly favorites of the locals.

We had a wonderful tour in Chieti, an historic and cultural gem, with our guide. She too was a gem of a guide!

We then traveled to Venice, which was far less crowded with tourists than in the high season. Upon arrival, a private gondola ride during dusk and at sunset was a surreal way to be welcomed to this beautiful city.

The next day we had a magnificent tour of St. Mark's Basilica and Doge's Palace. Our guide was so engaging and knowledgeable, and eager to share ideas about other things to see while in Venice. We followed our tour with lunch at a historic restaurant, home to the invention of the Bellini. Yum! After lunch, we took the elevator to the top of the tower across from the basilica, with its spectacular panoramic view of the city and surrounding islands. Then our group splintered off—two of us did a Grand Canal boat ride and the other two headed to the isle of Murano to search for glass souvenir treasures.

Our next stop was Lake Como, with a one-hour unexpected stop in Verona. Thank you to our driver for suggesting the stop! Who knew there was a Roman arena and some to-die-for hot chocolate in Verona!

Then off to Lake Como. We had time before we could check in to our hotel, so we did a walkabout to acquaint ourselves with the city. We took a ride on the funicular for another delightful panoramic view and enjoyed cocktails while surveying the lake and city below. That evening, we traveled up into the mountains and had a marvelous meal at a mountain trattoria. We were just us and one other couple in the restaurant, and we watched the chef prepare our local food specialties from our table in front of the wood-burning fireplace. The mantel was adorned with trophies and photos of the local bocce teams over the decades. Again, if you want to travel for cibo delizioso, go to Italy!

The next day, we had a three-hour boat ride on Lake Como. Our skipper and guide made certain to point out and give some history on the villages dotting the coastline and the famous villas.

The following day we traveled north to Domaso for an afternoon at a family-run vineyard and restaurant with views of Lake Como and the Alps! Bellissimo! A family member gave us a wonderful tour of the history and the winemaking facility, as well as the many wines we sampled. We were treated to local charcuterie and ravioli that was made fresh while we were busy sampling. When we received the wine we ordered and shipped back home, they threw in extra gifts for us, with wishes for a Merry Christmas and Happy New Year!

Then we were off to Milan for a chance to try our luck at making our own pasta, sauces, and gelato at a cooking school. Our chef instructor guided us as we made tagliatelle with a pesto sauce and pumpkin ravioli with a cream sauce. Of course, there were wine pairings! He made certain our creations were delicious!

That evening, we donned our fancy apparel and headed to La Scala to take in the opera, "Così fan tutte." The modern take on the comedy was refreshing and the venue was a must-see!

The next day, we were met by our guide, who shared the history of the UNESCO site of Santa Maria delle Grazie and Leonardo da Vinci’s "Last Supper" with expertise and reverence, while keeping us engaged. She likewise inspired us as we toured the Duomo di Milano, San Maurizio al Monastero Maggiore, and the controversial Il Dito sculpture outside the city’s stock exchange.

That evening, we experienced a delightful meal at a Michelin-starred restaurant. The chef, from Naples, created and explained a never-to-be-forgotten bite-sized sampling plate highlighting the tastes of Naples on a plate shaped like the region, with its various borders.

Before leaving Milan, we had a tour of La Scala and its adjacent museum with our guide. She provided us with a history lesson that was quite interesting. That night, we dined at a local seafood restaurant, another treasure clearly favored by the locals. Our waiter was a gem and sent us off with the gift of a bottle of wine.

Our final stop was Turin. Once again, we divided—two of us visited the National Museum of Cinema and the panoramic lift housed in the museum. At the top, we gained a wonderful sense of the city,and the cinema museum was a fun surprise! Our other two toured the Juventus Museum and Stadium, and they thoroughly enjoyed their experience as well.

Our final day, we met our guide, who spent the entire day with us, with only a short break, beginning with a gourmet food tour of traditional Piedmont dishes. Along the way, she shared insights into the history and cultural significance of the foods. Later in the day, she guided us through the Royal Palace of Turin, including the Holy Shroud Chapel, Armory, and Museum. Once again, we were treated to a knowledgeable and entertaining guide.

We departed the next day, leaving with priceless memories of our Italy adventure.

Thank you so much to Zicasso’s travel agent. You helped make our trip come true with such care. Grazie mille!

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Italy Travel Review: Turin, Rome, Puglia, Florence, Food Tour, Winery, Museums, History, Art, Culture, 2 Weeks

Zicasso's travel specialist asked for our interests, to which we replied history, art, food, and wine. When queried about accommodations, our preferences were that they have character and be varied. Our expectations were exceeded.  

We were two couples who had a spectacular survey trip of Italy. Our agent addressed our request for history by arranging private tours with expert guides. We visited multiple eras: ancient times at the Egyptian Museum in Turin and the Colosseum in Rome; medieval times at the Medici palazzos; Byzantine times with views of the frescoes in Puglia; and modern history during a delightful food tour of Turin that featured historical cafés renowned for their political meetings and plotting. 

We indulged in a smorgasbord of art and history, as it is readily available wherever you journey in Italy. The guides and drivers were knowledgeable, pointing out treasures in the palazzos, the Vatican, the public squares, cafés, the cathedrals, and churches. Food tours featured cheese, capicola and truffle tasting. Multiple types of wines and vineyards were sampled, the settings varied and the offerings enjoyed.  

Accommodations could not have been better chosen. We enjoyed staying at a converted fortified monastery and a historic 16th-century palace. We appreciated the sunset over Turin from the upper deck of the hotel and enjoyed hidden privacy in Rome in our suites.  

During the trip, our guide shepherded this complex trip and promptly addressed any issues that occurred (delayed trains and coordinating tour guides). Unequivocally, each tour was unique and well picked by our agent. We strongly recommend this agency to help you have a fantastic trip to Italy! 

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Italy Tour Review: Sicily, Taormina, Agrigento, Palermo, Cefalu, Mount Etna, Erice, Castelbuono, Savoca, Valley of the Greek Temples, Wine Tour, Godfather Experience, Farm Cooking Class, Cheese and Pastry Tastings, 7 Nights

Zicasso’s travel professional crafted an unforgettable Sicily trip for our group of seven. After discussing our preferences, she designed a flawless itinerary, incorporating unique experiences that became trip highlights. Her communication was exceptional, with prompt responses to our questions before the trip and daily updates for the next day's activities, including driver and guide details, which were incredibly helpful.

We stayed at superb hotels in Taormina, Agrigento, Palermo, and Cefalù, each with stunning views and private tours. Sicily’s warm, hospitable people stood out compared to other European destinations. At our hotel on Via Leonardo da Vinci in Taormina, the staff greeted us warmly, setting a perfect tone. Other stops included Mount Etna, Erice, Castelbuono, and Savoca. All of these locations were great, but don't miss Castelbuono!

Two standout experiences were private meals with families. Near Erice, a chef and his family welcomed us into their sea-view home, preparing amazing Sicilian meals that felt like dining with family. In Palermo, another home chef and her husband created a similarly memorable evening, with lots of great conversation and stories.

Every driver was professional, friendly, and informative, while our guides — often archaeologists or historians — were engaging and knowledgeable.

Highlights included a welcome dinner in Taormina, a farm cooking class, two wine tours with lunch, a Mount Etna hike, a Valley of the Greek Temples tour, town and village tours, cheese and pastry tastings near Cefalù, and a farewell dinner. The Godfather tour in Savoca was special, with our guide introducing us to a local who played Apollonia’s mother, waving from her balcony.

Our travel professional's meticulous planning and personal touches made this trip extraordinary. Thanks to Zicasso for matching us with the tour company and we highly recommend them for a perfect Sicilian/Italian adventure!

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Italy Tour Review: Tuscany, Florence, Montalcino, Castellina, Chianti, Wine Tasting, Cheese Experience, Local Cuisine, Walking Tour, 9-Day Trip

We loved everything about our trip to Tuscany. We had great, comfortable hotels as bases to explore the beautiful countryside and towns. Our hotels had kind, welcoming staff. Zicasso's travel company provided helpful suggestions and reserved non-touristy restaurants and enjoyable, interesting activities: eating in Florence, wine tasting in Montalcino, and cheese making in Pienza.

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Italy Vacation Review: Taormina, Cefalu, Palermo, Ortigia Island, Catania, Mount Etna, Cooking Class, Winery Visit, 9 Nights

I was connected with the travel company through Zicasso. What an amazing trip! Many thanks to our travel designer of the travel company!!!

Our travel designer and her expert team planned a trip to Sicily for my husband and I, my siblings, and my sister-in-law. We were six and everything about the trip was executed beautifully and with great attention to every detail.

We chose to go to Taormina, Cefalù, Palermo, and Ortigia Island, flying direct in and out of Catania. Our travel designer arranged all transfers by private van for the six of us and we never had to worry where or when we were going anywhere. She was able to make changes on the spot and accommodate our every wish.

Planning the trip was so easy, as she was available to chat with me on the weekends to answer questions and clarify details. She even made dinner reservations in every city. I cannot say enough about her willingness to be available and the choices she helped us make. From the terrific winery near Mount Etna to a drive up Etna, guided tours (we had an incredibly fabulous art historian showing us the churches of Palermo), a day at leisure on the beaches of Cefalù, and an amazing cooking class in Palermo, where we learned about and visited the markets, and made pasta and cannoli, every experience was better than the one before it.

We definitely recommend, with five stars, the travel company. Have them plan your trip to Italy! This was my first time back to Europe since 2004 and it was stellar!

I surely will use this company when I plan new trips to Italy, and Zicasso as well!

When we were trying to decide where to go, we chatted with travel partners in several European destinations. Zicasso chooses the best of the best and our experiences with each of them was exceptional!

We will be back to Zicasso when we travel to other destinations!!

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Italy Trip Review: Rome, Venice, Florence, Opera, Walking Tours, 10 Nights

We had a fantastic experience for a first-time trip to Italy. I wasn't sure how this would be, considering I learned about Zicasso while trying to plan the trip myself. Zicasso put me in touch with a travel specialist and the whole team was incredibly responsive to my many, many questions. If they were ever annoyed, it didn’t show.

I really wanted a smooth experience for my family of five, including three teens, one of whom has Celiac. Our agent was great in helping plan out the experience we wanted. As you may know, it is challenging to find rooms for five in Europe, but the travel company found apartments (usually two bedrooms with a pull-out couch) in the heart of town. You can really customize what you do, but we elected to plan our own meals and handle some of our own transport. We did have one issue where the van driver taking us to the train failed to show. I got one with Uber and the travel company quickly (I mean before we got home quickly!) refunded that amount.

Our contact in Italy was amazing and patient. I can’t give her enough credit. Any time I was unsure of something, she was there. The tours were great, especially Florence and Rome. You may be able to find the companies online, but ours seems to have the connections to get the best guides.

As for meals, we didn’t have any issues. We used an app and got a few recommendations from the travel company and local guides. Even our wine-tasting tour out in Tuscany was accommodating.

I would use our travel company and Zicasso again. I think the only downside is we tried to cram a lot in and it was hot. I probably should have asked for one to two fewer or shorter walking tours, especially on days we switched cities. Otherwise, it was excellent.

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Customizable Itinerary

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

28,000+ Verified Traveler Reviews