Discover the Italy You’ve Always Dreamed Of
Experience the timeless beauty of Umbria and Tuscany as you explore medieval hill towns, historic castles, magnificent churches, rolling vineyards, and unforgettable Italian cuisine. Wander charming streets filled with local shops, breathtaking scenery, and centuries of history.
One of my favorite parts of this journey is the time we spend in Umbria—Italy’s hidden gem. With fewer crowds than Tuscany, it offers authentic culture, incredible food, world-class wines, and picturesque towns like Orvieto, Spoleto, Assisi, Montefalco, and Perugia.
Whether it’s your first visit to Italy or a return to experience its hidden treasures, I’ll be traveling alongside you to share my favorite places and make sure your vacation is everything you’ve imagined.
— Chuck Cinelli, Owner of Coco’s Italian Market
Essential Experiences
Enjoy three unforgettable nights in a restored Tuscan villa.
Discover the unique water-filled piazza of Bagno Vignoni in the heart of Tuscany.
Hunt for Italian truffles with a local expert and his truffle-sniffing dogs.
Highlights
Rome • Spoleto • Olive Oil Mill • Assisi • Home-Hosted Lunch • Truffle Hunting • Pecorino Cheese Farm • Pienza • Orcia Valley • Bagno Vignoni • Brunello Wine Tasting • Siena • Florence • San Gimignano
We Handle the Bags,
So You Can Explore!
Leave the luggage and logistics to us—your only job is to enjoy the journey.
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+$549 per passenger
Tour Dates
Thursday, April 22 – Tuesday, May 4, 2027
Pricing
Double Traveler
$5,999 per person
Single Traveler
$6,599 per person
Triple Traveler
$5,949 per person
What We’ve Included in This Price
Round Trip Air from Nashville Metro Airport
Air Taxes and Fees/Surcharges
Hotel Transfers
Day 1 Overnight Flight – Rome
I’ll meet you at the airport where our journey begins with an overnight flight. On board we have a cocktail, dinner then it’s lights out. Buongiorno, welcome to Italy, a land rich in history, culture, art and romance. Once settle in I will help you plan your fist afternoon in the Eternal City.
Day 2 Rome Dinner Kolbe Hotel
Our hotel is perched above the Palatine Hill, take a left from the main lobby and you will see the most important of the 7 hills of Rome. After stunning photos you can continue walking to the Coliseum but be back in time for our Welcome to Italy dinner. After dinner you can get more stunning photos of Rome at night.
Day 3 Rome – Spoleto – Umbria Breakfast, Dinner Hotel Antica Dimora Alla Rocca
After breakfast we head to Umbrian hill town of Spoleto to meet up with our local guide Romana. After our tour through the medieval historic streets, cathedral and aqueduct we have a free afternoon for more pictures and lunch. Someone always say to me, if we spend the rest of our time here I’ll be happy!” Spoleto is a quaint and charming town but the tour only gets better. Next we go see Carolos Carletti and his son Setimo to visit their olive oil farm and press. It has been in their family for over 500 years. The olives are crushed to a paste between rolling granite then pressed slowly as to not create any heat during the process for a superior olive oil. You’ll taste the difference and most everyone purchases a can or several to bring home. Next we get to our hotel for the next three nights . Our hotel is nestled in a picture perfect Umbrian hill town and launching point for our daily adventures. Click on the QR code for a short video I made on the Carletti oil.
DAY 4 Umbria Assisi – Home Hosted Lunch – Umbria Breakfast, Lunch
Today we travel to Assisi, the birthplace of St. Francis and visit the Basilica with Romana, learning about its history and importance in the art world too. If you want to venture up the hill with me I’ll show you St. Francis’s childhood home and where his father locked him in the pantry, then to the spot where he tells his father that he is giving up all worldly possessions. Next is an event and for most, the highlight of the tour. We visit the Albarello family in their farmhouse for lunch and unlimited wine! Of course made with local ingredients. Joe, along with his boys and wife Lucia treat us to several delicious courses (my mouth is watering as I write this) fun stories and a little entertainment in the parlor. You’ll love Lucia’s Tiramisu!
Day 5 Umbria – Truffle Hunting Breakfast lunch
When in the land of the best food in the world you have to experience Truffle Hunting with Lola the wonder dog. We take a nice, leisurely stroll through the fields and woods to learn about, seek and later enjoy truffles. It’s a lot of fun to watch the dogs scour the area sniffing out the prized truffles but it’s more fun to watch Monica’s reaction when the dogs find a truffle. She has a big personality and you will delight in her telling of the family stories of their hunting and selling truffles for several generations. Next we will head back to her home/store and sample the truffles in a variety of ways with their local wine. We return to the hotel and I’ll help you find a nice restaurant for dinner.
Day 6 Umbria – Pienza Breakfast, Lunch Hotel Corsignano, Orcia Valley
After breakfast we leave Umbria to the center of Tuscany. Here you will see the iconic rolling hills and cypress trees of the Val d’Orcia region. This is the Tuscany you’ve seen in the movies, paintings and post cards. Today we stop to see our friend Enzo for lunch at his prized sheep farm. You will love their varieties of Pecorino cheeses and local meats. Afterwards i encourage you to visit his small shop to take some home to share with me when we all get back, LOL! Next we make our way to on your way to Pienza, a Renaissance village and summer residence of Pope Pius. The views were so stunning he was determined to make Pienza the most beautiful village in all of Italy. He hired architects and city planners to do just that and now we get to enjoy his vision. The evening is yours to eat, drink, and explore the local scene. You’ll love the views, cobblestone streets and little shops that adorn this town. When in Pienza I always visit my friend who owns La Mensa Del Conte because she makes the best homemade Pici, the local pasta cut. If you would like to join me for dinner I will make us reservations.
Day 7 Pienza Breakfast, Lite Lunch
Today we embark on a culinary journey through the undulating landscape of the Orcia Valley. We begin with a visit to an artisanal pasta factory, producing the local specialty – pici – with its organically-grown wheat. Next we make a stop to the unique hamlet of Bagno Vignoni, whose central piazza is filled with thermal water once used to cure pilgrims who stopped here on their way to Rome. You will love this cute village, stunning views, quaint shops and cafes. Next we explore one of the most famous wine towns in the world Montalcino. Every top-end wine list in the world serves a Brunello di Montalcino, made only from Sangiovese grapes grown in the surrounding hills. We tour a winery’s estate and cellar before indulging in a multi-sensory tasting of wine with music. Then back to beautiful Pienza for an afternoon on your own. By now you will be familiar enough with this small town to make some dinner plans. See me for some suggestions.
Day 8 Pienza – Siena – Chianti Region Breakfast Villa San Lucchese
On our way to our villa we stop in Siena to meet our guide and take a tour through Siena. Besides being an important medieval city Siena boasts the crazies horse race in the world, the Palio. Our guide will explain with passion how the 17 neighborhoods, or contrade all compete for the coveted banner and more importantly, bragging rights. Each cotrada has it’s own museum and chapel used for neighborhood events and of course blessing their race horse. Now we have free time in Siena where there is plenty of shopping, restaurants and photo opportunities. After we meet up at the Piazza it’s off through Tuscany’s Chianti Region to the restored Tuscan villa. You fall in love with the surrounding but more importantly the family that owns and runs it. They have a great breakfast and their restaurant is very good too.
DAY 9 Florence – Chianti Region Breakfast
Have a hearty breakfast for today we explore Florence, known as the Cradle of the Renaissance and where the Medici Family ruled for over 300 years and where patrons of so many greats including: Leonardo da Vinci, Michealangelo, Raphael, Donatello, Botticelli to name a few that we recognize. Florence is so rich in important history that there is too much to even mention here, as you can imagine. After we are done with our walking tour of this outdoor museum we are free to explore. Besides museums, obviously there is shopping as Florence is known for it’s gold jewelry and handcrafted leather. The restaurants are all fantastic too so let me help you plan your ideal day.
Day 10 Chianti Region – San Gimignano Breakfast Dinner
This is a beautiful way to end our tour, a visit to San Gimignano, “the Manhattan of the Middle Ages” whose 13th-century medieval towers stand tall over the surrounding vineyards. You will love taking photos of the towers and landscape against the rolling hills. While here we will have a few scoops of gelato from an award-winning ice cream maker Sergio Dandoli. You’ll taste why he’s won so many awards: all organic, with local and fresh seasonal ingredients. I always ask Sergio what he recommends and it’s always amazing. His gelato alone is worth the trip alone. You can’t get lost in this walled in town so wander the cobblestone street, peruse the shops and find the best perches to take landscape photos. There are several nice lunch spots in the main square. Once back to our villa it’s time to pack and get ready for our farewell dinner in the restaurant at Villa San Lucchese. We will laugh and toast a most memorable experience.
Day 11 Chianti Region – Tour Ends
Our journey through Tuscany and Umbria comes to a close today as after breakfast we will make our way to the airport, exchange phone numbers with our new friends and promise to come back to Italy sooner than later.
Optional Rome Pre-Tour Extension
Begin your Italian adventure with three unforgettable days exploring the Eternal City before traveling into Tuscany. Walk through ancient history, enjoy authentic Roman cuisine, and discover the landmarks that have made Rome one of the world’s most celebrated destinations.
Day 1: Overnight Flight
Depart for Italy as your unforgettable journey begins with an overnight flight to Rome.
Day 2: Welcome to Rome
Arrive in Rome and settle into your hotel before enjoying free time to explore at your own pace. Wander through charming neighborhoods like Trastevere, relax at a sidewalk café, or simply soak in your first taste of Italy. Dinner is on your own.
Day 3: Ancient Rome & Local Flavors
Discover the Colosseum and Roman Forum with an expert guide before enjoying free time to explore. This evening, sample authentic Roman pizza during a guided food tour through the lively Monti district. Breakfast and dinner included.
Day 4: Rome & Main Tour Begins
Stroll through Rome’s Renaissance and Baroque treasures, including the Spanish Steps, Trevi Fountain, and Piazza Navona. Enjoy free time before meeting your fellow travelers to begin your Tuscany and Umbria adventure. Breakfast included.
Accommodations: Kolbe Hotel Rome
Optional Additional Night: From $530 per room
