Essential Experiences
Experience Italy beyond the ordinary with unforgettable food, wine, culture, and outdoor adventures.
Highlights
Venice • Winery Tour & Tasting • Republic of San Marino • Cooking Class • Barbecue Experience • Ravenna’s Mosaics • Truffle Hunting Experience • Canoe Journey • Gran Sasso Mountain Village Stay • Rome
We Handle the Bags, So You Can Explore!
Leave the luggage and logistics to us—your only job is to enjoy the journey.
Add Cancellation Waiver & Insurance
Recommended
Protect your travel investment with coverage for trip cancellation and interruption, medical emergencies, and baggage protection. For a small additional cost, enjoy peace of mind knowing you’re covered if the unexpected occurs during your travels.
+$599 per passenger
Tour Dates & Pricing
October 7 – 17, 2028
13 Days • 18 Meals • All-Inclusive Tour • Air Included
Double: $8,099 per person • Triple: $7,899 per person • Single: $9,799
*Please contact me soon if you’re interested. Most of our tours fill up a year in advance, so early booking is strongly recommended.
Day 1: Nashville to Venice – April 1, 2028
Hotel: Hotel Abbazia
Your Italian adventure begins with an overnight flight. Buongiorno and welcome to Italy! Upon arrival in Venice, we’ll board water taxis for a scenic ride across the Venetian Lagoon to our hotel. After settling in, enjoy your first afternoon exploring the canals, bridges, piazzas, and hidden corners of one of the world’s most magical cities.
I have personally written a Venice guide filled with my recommendations for shopping, local foods, drinks, museums, and more. Consider coming a day early with me—I’ll show you why there’s truly no end to the magic of Venice.
DAY 2: Welcome to Montecatini Terme, Italy
Today, our Tuscany adventure officially begins in beautiful Montecatini Terme, Italy, one of Tuscany’s most celebrated spa resort towns. Surrounded by rolling Tuscan hills, historic architecture, and charming streets, Montecatini Terme is the perfect place to settle in and experience the relaxed rhythm of Italian life.
Take time to get comfortable, explore the heart of town, and begin soaking up the sights and flavors of Tuscany. Tonight, we’ll gather with our fellow travelers for a special welcome dinner featuring regional Tuscan cuisine and Italian wines. It’s our first chance to share a meal, make new friends, and raise a glass to the unforgettable journey ahead. Dinner included.
Day 3: Venice – Gondola Boatyard
Includes: Breakfast
This morning, we’ll get a rare glimpse into Venice’s centuries-old gondola tradition with a visit to one of the city’s last two active boatyards. See firsthand the skill, precision, and artistry behind the crafting of Venice’s iconic gondolas and meet the traditions that have kept this remarkable craft alive for generations.
Afterward, we’ll enjoy a classic Venetian spritz and experience the Italian ritual of aperitivo. Then, the afternoon is yours to explore Venice at your own pace.
I’ll help you plan the perfect afternoon based on what interests you—hidden gems, shopping, famous landmarks, museums, or simply wandering the canals and enjoying the city. Maybe it’s time for your own gondola ride! Whatever suits your mood, I’ll help you make the most of your day in Venice.
Day 4: Venice – Dozza – Romagna Countryside
Hotel: Borgo Condé Wine Resort
Includes: Breakfast & Dinner
We say arrivederci to Venice and journey into the Romagna region, famous throughout Italy for its incredible food, wine, and relaxed way of life. Along the way, we’ll stop in the charming hilltop village of Dozza, known for its colorful murals, winding lanes, and impressive medieval castle.
Later this afternoon, we’ll arrive at one of my favorite hotels in all of Italy, Borgo Condé Wine Resort, our home for the next three nights. Nestled among the rolling vineyards of the Romagna countryside, this beautiful boutique resort blends modern comfort with timeless Italian scenery.
This evening, we’ll enjoy an exclusive tour of the resort’s winery followed by a wonderful dinner paired with expertly crafted wines. Surrounded by vineyards, rolling hills, and breathtaking countryside, this is the Italy people dream about.
Day 5: Romagna Countryside – San Marino
Includes: Breakfast & Dinner
After breakfast, we set out to explore San Marino, the tiny yet mighty republic nestled in the heart of Italy. As the fifth-smallest country in the world, San Marino is big on charm! Perched high atop Mount Titano, this UNESCO World Heritage site offers breathtaking views over the Adriatic Riviera and the rolling hills of Romagna.
We’ll wander the medieval streets and discover San Marino’s impressive fortress towers, ancient walls, gates, and bastions. Take time to soak up the views, grab a cappuccino, and enjoy a little people-watching while experiencing the unique atmosphere of this historic republic.
Back at our wine resort this evening, we’ll end the day with a memorable wine-pairing dinner created to highlight the flavors of Romagna and the exceptional wines produced here. It’s the perfect way to toast our adventures in this beautiful region!
Day 6: Romagna Countryside – Choice on Tour
Includes: Breakfast & Dinner
Today, it’s your choice of adventure in the beautiful Romagna countryside! After breakfast, relax at our wine resort and soak up the peaceful surroundings. For a little extra indulgence, consider a luxurious spa treatment featuring an organic, wine-infused mud experience.
Or, head to Ravenna, a UNESCO World Heritage treasure and one of Italy’s most fascinating historic cities. Once a center of power during the final years of the Roman Empire, Ravenna is famous for its breathtaking churches and brilliant Byzantine mosaics. Our expert local guide will bring the city’s remarkable history and art to life.
Tonight, roll up your sleeves for a fun Romagna cooking class led by a local chef. Learn to make traditional pasta dishes such as garganelli and strozzapreti—yes, that really translates to “priest stranglers!” Then, we’ll sit down together and enjoy the delicious results of our work over a relaxed dinner. Another unforgettable day in Italy!
Day 7: Urbino – Pesaro, Marche Region
Hotel: Hotel Charlie
Includes: Breakfast
This morning, we’ll leave the vineyards of Romagna behind and journey into Italy’s beautiful Marche region, one of the country’s best-kept secrets. Along the way, we’ll visit the hilltop city of Urbino, a UNESCO World Heritage Site and the birthplace of the famous Renaissance painter Raphael.
Surrounded by ancient walls and rolling Italian countryside, Urbino feels like stepping back in time. We’ll explore the magnificent Ducal Palace, one of Italy’s most important Renaissance landmarks, and wander the historic streets that have inspired artists, scholars, and travelers for generations.
Later this afternoon, we’ll continue to Pesaro on the Adriatic Sea for a relaxing two-night stay. With its seaside promenade, welcoming atmosphere, and beautiful beaches, Pesaro offers the perfect blend of authentic Italian life and coastal charm.
Day 8: Pesaro, Marche Region – Truffle Hunting
Includes: Breakfast
Today, we’ll experience one of the Marche region’s most treasured culinary traditions—truffle hunting. We’ll head into the Italian countryside with a local truffle hunter and his specially trained dogs as they search the woods for these prized delicacies. It’s a chance to experience a side of Italy most visitors never see and meet the people preserving these traditions for generations.
After our truffle hunt, we’ll enjoy a farm-to-table lunch at the family’s organic farm, featuring fresh local ingredients and the authentic flavors that make the Marche region so special. These are the kinds of local Italian experiences that turn a great trip into an unforgettable one.
The afternoon is yours to enjoy back in the seaside town of Pesaro. Stroll along the Adriatic Sea, relax at a local café, browse the shops, or simply slow down and enjoy the relaxed coastal lifestyle that makes this part of Italy so appealing.
Day 9: Santo Stefano di Sessanio – Abruzzo Mountains
Hotel: Sextantio Albergo Diffuso
Includes: Breakfast & Dinner
Today, we travel deep into the Abruzzo Mountains, one of Italy’s most untouched and dramatic regions. As we leave the Adriatic coast behind, the scenery changes to rolling hills, rugged mountain peaks, and peaceful landscapes that feel a world away from Italy’s busy tourist cities.
We’ll arrive in the medieval village of Santo Stefano di Sessanio, a beautifully preserved, pedestrian-only hill town where time seems to slow down. Our hotel is part of the adventure as we settle into Sextantio Albergo Diffuso, a unique Italian hotel with guest rooms spread throughout carefully restored historic buildings within the village.
This evening, we’ll connect with local Abruzzo traditions during a hands-on experience making regional bread and cheese. Afterward, we’ll gather for dinner featuring the foods we’ve prepared and enjoy the simple, authentic flavors of Italian mountain life. This is the kind of unforgettable Italy most travelers never get to experience.
Day 10: Abruzzo Mountains – Campo Imperatore
Includes: Breakfast
Today, we’ll experience one of the most breathtaking landscapes in Italy as we travel across the Campo Imperatore plateau, more than 7,000 feet above sea level. Often called the “Little Tibet of Italy,” this vast mountain plateau offers incredible views of the Gran Sasso mountains, the highest peaks in central Italy.
Along the way, we’ll experience a true Abruzzo tradition—arrosticini, grill-it-yourself lamb skewers cooked over an open flame. Simple, rustic, and connected to the region’s shepherding heritage, this is one of those authentic Italian food experiences you won’t forget.
This afternoon, back in Santo Stefano di Sessanio, the choice is yours. Join a guided walking tour through the village’s stone alleyways and centuries-old buildings, or choose a guided hike to Rocca Calascio, one of Italy’s most dramatic mountaintop fortresses. History or adventure—either way, the views will be unforgettable.
Day 11: Santo Stefano di Sessanio – Rome
Hotel: Ponte Sisto Hotel
Includes: Breakfast & Lunch
This morning, our first stop is the Tirino River, known for its crystal-clear blue-green water and some of the purest freshwater in Italy. Here, we’ll slow things down and take to the water by canoe, gently drifting through one of Abruzzo’s most peaceful river valleys.
Surrounded by reeds, open skies, and the quiet sounds of nature, this is an unexpected side of Italy that few travelers ever experience. It’s the perfect peaceful ending to our time in the Abruzzo Mountains.
After our time on the river, we continue to the Eternal City of Rome—because, as the saying goes, all roads lead to Rome! We’ll settle into the Ponte Sisto Hotel, ideally located near the trendy Trastevere neighborhood, with charming streets, local restaurants, and the energy of Rome right at our fingertips.
Day 12: Rome – The Eternal City
Includes: Breakfast & Dinner
This morning, we’ll set out on an immersive walking tour through Rome’s medieval district, a fascinating neighborhood built directly over the layers of ancient Rome. As we wander narrow cobblestone streets and pass dramatic stone buildings, you’ll see how thousands of years of history come together, with ancient ruins, historic churches, and everyday Roman life existing side by side.
One of today’s highlights is a visit to the panoramic terrace of the Vittoriano, where we’ll take in one of the most breathtaking views in Rome. From high above the city, look out across the Roman Forum, Colosseum, and the Eternal City and see the incredible layers of history that make Rome unlike anywhere else in the world.
Tonight, we’ll come together one last time for a special farewell dinner in Rome. We’ll share stories, laughter, and a toast to the unforgettable journey we’ve experienced together—from Venice and the vineyards of Romagna to the Adriatic coast, the Abruzzo Mountains, and finally Rome. Salute to an incredible Italian adventure!
Pre-Tour Venice Extension – Highly Recommended
Hotel: Hotel Abbazia – Venice
4 Days / 3 Nights • From $999 per person, double occupancy • 2 Breakfasts Included
If there is one upgrade I personally recommend on this entire journey, it’s arriving early in Venice. I do it myself every time I travel, and after leading dozens of Italy tours, I can tell you that beating the jet lag and giving yourself time to settle in completely changes your experience from the very first day.
This Venice pre-tour extension gives you extra time in one of the most beautiful cities in the world—the legendary Queen of the Adriatic. Instead of arriving tired and rushing into the itinerary, you’ll ease into Italy, explore the canals, enjoy a café along the water, and simply let the magic of Venice sink in.
You’ll also receive my 40-page Venice guide filled with recommendations for restaurants, drinks, shopping, museums, self-guided walking routes, and insider tips. Arrive a day early on your own to beat the jet lag, or join our guided pre-tour experience with the tour manager.
March 30: Overnight Flight to Italy
Your journey begins with an overnight flight to Italy. The adventure starts here—and you’re already giving yourself extra time to settle in and enjoy Venice the right way.
March 31: Welcome to Venice
Arrive in Venice, Italy, a floating city of palaces, canals, bridges, and timeless beauty. Today is yours to settle into Hotel Abbazia, relax, and begin discovering Venice at your own pace.
A local hospitality representative will be available in the evening with helpful suggestions for your first night. Enjoy a quiet dinner, wander along the canals, or sit with a glass of Italian wine and watch Venice come alive.
Why I Recommend This Extension
After all my years leading tours to Italy, I can say this is one of the smartest decisions you can make for your trip. You start rested instead of rushed, experience Venice without pressure, and begin your journey already in rhythm with Italy. For many of my travelers, this extra time in Venice becomes one of their favorite parts of the entire trip. I know it’s one of mine.
Rome Post-Night Extension – Highly Recommended
April 13, 2028
Hotel: Ponte Sisto Hotel – Rome • From $500 per room, per night
After an unforgettable journey through Italy, I strongly recommend adding one or two extra nights in Rome before heading home. You’re already in one of the most incredible cities in the world, so why rush to leave?
This is the perfect opportunity to experience more of the Eternal City. I can help arrange a private golf cart tour of Rome, one of my favorite ways to see the city without the long walks. Explore famous landmarks such as the Colosseum, Trevi Fountain, Piazza Navona, and Pantheon with ease and comfort.
Want to dive deeper into Rome’s history? Use your extra day to visit the Vatican Museums and Sistine Chapel, tour the Colosseum, or explore another landmark you’ve always dreamed of seeing. I’ll help point you in the right direction based on what interests you most.
This is one of the smartest upgrades you can make. It turns your final day in Italy from travel logistics into one more unforgettable experience before you say arrivederci to Italy.
