An Epic Italian Adventure: From Winnipeg to Florence, to Chianti, to Tuscany to Rome to the Amalfi Coast and Beyond

Day 1: From Winnipeg to Florence

Our journey began with an overnight flight from Winnipeg to Montreal, then onward to Frankfurt. After a quick one-hour flight, we finally landed in Florence. Unfortunately, our luggage didn’t make the trip with us, but that didn’t dampen our spirits. We purchased a few necessities and began our adventure.

Florence: After a much-needed pizza break, we checked into our charming Airbnb, which was in the perfect location right in the heart of the main area. Eager to explore, we strolled along the Arno River, taking in the breathtaking views from the iconic Ponte Vecchio. The statues lining the bridge were captivating, each telling its own story. We took some time explore, stumbled upon a quaint wine window, and savored a delightful dinner in one of Florence’s bustling squares. The highlight of the evening was a golf cart ride to Piazzale Michelangelo for the sunset. The view was spectacular, though it was quite crowded—next time, we’ll arrive earlier. We ended the night with a cab ride back to our Airbnb, exhausted but exhilarated. Once our child and my mother went to bed, we ventured back out to enjoy some live music and a night cap of, you guessed it, wine.

Day 2: Exploring Florence and Chianti

We started the day with breakfast at a cute little restaurant nearby. Our first stop was the Galileo Museum, where we marveled at the incredible collection of scientific instruments and learned about Galileo’s groundbreaking work. More statues and historical sites beckoned as we wandered through Florence, culminating in a visit to the magnificent Duomo.

After lunch at a cozy diner, we finally got our car—and our suitcases! We hit the road towards Chianti, where we visited a local winery called Terre di Perseto. Tasting the regional wines was an experience in itself. We checked into our VRBO in the quant village of Badia a Passignano, which resembled a medevil castle. We played a game of soccer with epic views, and wrapped up the day with another wine tasting session at Osteria di Passignano.

Day 3: The Charm of Tuscany

Our third day began with a visit to the prestigious Antinori Winery. The architecture alone was worth the trip, and the wines were simply divine. Next, we headed to San Gimignano, famous for its medieval towers and beautiful landscapes. After a delightful lunch, we continued to Siena, stopping for groceries before checking into our VRBO. The day concluded with a visit to Siena’s historic center, Il Campo, a vibrant square perfect for people-watching and soaking in the local culture.

Day 4: Castles and Countryside

We embarked on a day of exploration, starting with a visit to Monteggiori. The history and architecture were fascinating, transporting us back in time. Our family enjoyed the props in the museum and our time spent in the village. We then visited another castle, each with its unique charm. The Siena Circuit was another highlight, offering a unique go karting experience that our son loved. After a visit to Orsta de Pecci, a serene park, we enjoyed dinner and a wine tasting in Monteriggioni, known for its exquisite wines and picturesque views.

Day 5: Val d’Orcia and Montepulciano

Driving through the scenic Val d’Orcia was a delight for the eyes, with rolling hills and picturesque landscapes at every turn. We even encountered part of the one of Gladiator’s filming location in Pieve di Corsignano. Our destination was Montepulciano, where we explored the intriguing underground city. Later, we relaxed at our hotel’s pool and spa, a perfect end to a day of sightseeing.

Day 6: From Castles to the Eternal City

We set off for Civita for a quick visit and enjoyed walking across the bridge to get to the village. Our son was especially excited to enter the castle-like town and let his imagination soar. Next we embraced the saying, “all roads lead to Rome”, as we made our way to our Airbnb near the Vatican, then dropped off our rental car—an ordeal that took nearly an hour and a half due to the chaotic Friday evening traffic. Note to self: avoid driving in Rome during rush hour! After dropping off the car, our Roman adventure began with visits to the Trevi Fountain and the Pantheon, marveling at the architectural wonders. We enjoyed dinner at a local eatery and took in all the wonders of Rome. Near our AirBnB, we found a little live music bar called Mr. Songs. We enjoyed a few beverages there before heading in for the night.

Day 7: Rome’s Iconic Sites

We joined a City Wonders tour, starting with the Colosseum. Walking through this ancient amphitheater was awe-inspiring. Next, we toured the Vatican Museums, a treasure of art and history. The Spanish Steps were our next stop, followed by a visit to a charming bar in Trastevere, where we soaked in the local ambiance.

Day 8: From Rome to Naples

After checking out of our Airbnb, we picked up another rental car and drove to Naples. Our adventure took an unexpected turn when we got hit by a car—thankfully, no one was hurt. We calmed our nerves with some of Naples’ famous pizza before heading to Pompeii. Exploring this ancient city was a highlight of our trip. We then continued to Mount Vesuvius, the infamous volcano that looms over the region. Finally, we drove to Amalfi, where we settled into our accommodation.

Day 9: The Beauty of Capri

The next day, we took a boat tour from Amalfi to the island of Capri, known for its stunning natural beauty. After a day of exploring, we returned to our condo for a relaxing dinner, reminiscing about the day’s adventures. In my opinion, the boat ride was more exciting than Capri. As beautiful as Capri was, it was very busy with tourism. The boat ride itself offered a full view of beautiful Amalfi, and it felt like we were living on a movie set.

Day 10: Emerald Grotto and Ravello

The day began with a visit to the mesmerizing Emerald Grotto, a sea cave with stunning green waters. We spent the afternoon at the beach in Minori, enjoying the sun and sea. Dinner in Ravello, with its breathtaking views, was the perfect end to a wonderful day.

Day 11: Back to Rome

Again, all roads lead to Rome! We made our way back to Pompeii for a final visit before driving to Rome. We checked into our Airbnb, again by the Vatican, and then headed out for the evening. We visited the Trevi Fountain again but there were far less people. We enjoyed a nice dinner and met some friendly folks from Iceland. We had a few drinks with them and shared travel stories and tips.

Day 12: Homeward Bound

With heavy hearts, we packed our bags and headed to the airport for our flight home. This Italian adventure was one for the books, filled with unforgettable sights, delicious food, and countless memories. We can’t wait for our next journey!