Ah, Italy! Just saying the name conjures images of ancient ruins, Renaissance masterpieces, rolling Tuscan hills, and, of course, food that makes your soul sing. My wife, Krystal, and I embarked on a 12-day whirlwind tour through Venice, Florence, Tuscany (including Siena and San Gimignano, plus a classic stop in Pisa!), Rome, and the stunning Amalfi Coast with a visit to Pompeii. This wasn’t just a vacation; it was an immersion into a culture so rich and captivating that, we confess, we seriously considered not coming home! It was picturesque, memorable, and utterly extraordinary. Krystal still says it was one of her “top trips” and such a positive memory. If Italy isn’t on your travel bucket list, it absolutely should be. Let us share some highlights and insights from what we can only describe as one of the best adventures ever.
Our Itinerary
Planning a multi-city tour of Italy can feel like assembling a beautiful, complex mosaic. Our initial thoughts, jotted down with boundless enthusiasm, were a lively brainstorm (as you might have seen in a previous version of this post with my handwritten notes!). We eventually translated that excitement into a more structured plan to make the most of our 12 days. Even with a detailed itinerary, Italy has a delightful way of surprising you, and embracing those spontaneous moments is truly part of its magic. Feel free to reach out for a copy!

A trip of this scale benefits immensely from advance planning, especially for accommodations and the efficient Italia Rail train system that connects major cities. Booking these in advance, particularly high-speed Frecciarossa or Italo trains, often means better prices and securing your preferred travel times. We also learned that traveling in December was perfect – fewer crowds than in summer, and the weather was quite comfortable with just a jacket and maybe a scarf.
Travel Smart & Earn Rewards:
đź’ł Pro Tip for Booking: Using a travel rewards credit card for flights, hotels, and train tickets can be a game-changer. We relied heavily on our Chase Sapphire® card throughout this trip. If you’re planning your own Italian escape, you can earn 60,000 bonus points with either Chase Sapphire® card after meeting the initial spending requirements. Those points can significantly offset costs for future adventures!
Navigating “La Bella Italia”: Maps & Staying Connected
Our primary navigation strategy involved using downloaded offline maps via Google Maps. This was a lifesaver in the charmingly confusing alleys of Venice and the bustling streets of Rome, especially when trying to conserve phone data. Before departure, I meticulously pinned key points of interest – creating a digital breadcrumb trail.
While offline maps are fantastic, having some data connectivity for on-the-fly research, checking train schedules, or finding a hidden gem of a restaurant is also very useful. Consider picking up a European Travel SIM Card or a Portable WiFi Hotspot. Don’t forget a Universal Travel Adapter for your electronics!
Venice: A Floating Dream (Nov 30 – Dec 2)
Our Italian adventure truly began after a long flight into Rome (FCO), followed by a remarkably comfortable fast train journey all the way up to Venice. Krystal particularly loved that the train had horizontal sleeper beds! Even though it was about a six-hour ride, we could lay down with blankets and sleep, making it feel much shorter and not inconvenient at all.
We arrived in Venice at night. Stepping out of the Venezia Santa Lucia train station, we were initially a bit worried. It was dark, quiet, and Krystal noted how the incredibly narrow alleyways leading to our Hotel Fontana felt a little unnerving at first. However, the next morning revealed the city’s true magic. Venice is not only very safe for tourists but astonishingly beautiful. Krystal was captivated by the buildings standing shoulder-to-shoulder along canals brimming with water, the charming bridges connecting everything, and the constant stream of boats passing beneath. It was a city of endless photo opportunities – we have so many of us just wandering and soaking it all in!



Being there in December had its own unique charm. As Krystal mentioned, it wasn’t nearly as crowded as it would be in the summer, and it wasn’t uncomfortably cold – a good jacket and scarf were all we needed. Plus, Italy goes all out for Christmas! The city was adorned with lights, and giant Christmas trees graced the main squares, creating a truly magical atmosphere. One particularly Venetian winter experience Krystal found fascinating was the “acqua alta” (high water). In some central locations, they set up raised wooden ramps so tourists could still navigate the flooded squares without getting their feet wet!


We spent a whole day on free walking tours, which were fantastic for understanding Venice’s rich history, learning about its university area, the age of the buildings, and their past uses. We saw some intriguing modern sculptures too, like the striking “Support” installation by Lorenzo Quinn (the giant hands appearing to hold up a building from the canal – Krystal loved this!).

Our explorations included:
- Piazza San Marco (St. Mark’s Square): The grand “drawing room of Europe,” where we saw the Campanile (the “big tower looking thing”) and the magnificent St. Mark’s Basilica (the “big chapel looking thing”). Krystal even got a picture next to a cool statue of a lion, a powerful symbol of Venice.
- Doge’s Palace: A stunning Gothic palace (entry ~20 euros, voucher recommended).
- Bridge of Sighs & Rialto Bridge: Iconic Venetian landmarks.
- Gondola Rides: We saw many gliding by, a classic Venetian scene.
- Libreria Acqua Alta: This unique bookstore, with its books stored in bathtubs and gondolas, was a highlight.
- Cafes & Hot Chocolate: Krystal was incredibly impressed by the Italian hot chocolate – rich and thick, “like a liquid chocolate bar,” so different from what we were used to! Venice also had charming cafes offering this delightful treat.







Florence & Tuscany: Renaissance, Pasta, and Pisa! (Dec 2 – Dec 5)
An early train on December 2nd took us from the watery wonders of Venice to Florence, the heart of the Renaissance. We settled into our Airbnb in the vibrant Oltrarno district, near Santo Spirito, which Krystal loved for its local feel and excellent cafes. She particularly enjoyed our quiet mornings, sipping coffee and reflecting on our adventures so far.
Florence is an art and architecture lover’s dream:
- The Duomo (Cathedral of Santa Maria del Fiore): Krystal called it a “huge Duomo,” and she was right! The sheer scale is breathtaking, and knowing Brunelleschi’s Dome was built without modern technology is incredibly impressive.
- Galleries & Museums: We visited the Uffizi and Accademia (to see Michelangelo’s David), and the Galileo Museum, marveling at works by so many iconic Italian artists.
- Piazzale Michelangelo: Offers the most stunning panoramic views of Florence, especially at sunset.
- Palazzo Vecchio & Ponte Vecchio: Essential Florentine landmarks.





Our full-day Tuscany tour on December 4th was a definite highlight. Krystal still raves about it: “The pasta was the most delicious pasta I’ve ever had, and the wine was delicious! The scenery of Tuscany was breathtaking, and the tour guides were so nice and hospitable.” To our surprise, the tour included a stop in the incredibly picturesque medieval hill town of San Gimignano, a fortified ancient town, and a fun visit to the Leaning Tower of Pisa. Krystal loved “taking a picture acting like the building was leaning toward you and you’re holding it up!”







Food in Florence and Tuscany was, of course, incredible. Beyond the tour, we sought out local trattorias. For anyone visiting, grabbing a legendary sandwich from All’Antico Vinaio is a must, and the Mercato Centrale is a fantastic food market experience. A good Guide to Tuscan Food & Wine could help you plan your own culinary adventures.
Rome: Imperial Grandeur & Our Favorite Airbnb (Dec 5 – Dec 9)
A mid-morning train on December 5th brought us to Rome. Krystal declared our Airbnb here her favorite of the trip! It was located above a restaurant, and every morning, they provided a delightful buffet-style breakfast just for us – tea, crepes, various pastries. “It was so delicious, a full spread, and it made us feel so welcomed to the country,” she said.
Rome is a living museum:
- Ancient Wonders: The Colosseum and Roman Forum are simply awe-inspiring. We got our tickets in advance (~18.50 euros with a voucher) to avoid lines. The Pantheon, with its magnificent dome, was another favorite.
- Iconic Fountains & Squares: We, of course, tossed a coin in the Trevi Fountain.
- Vatican City (Dec 7): Our tour of the Vatican Museums, the Sistine Chapel, and St. Peter’s Basilica was an unforgettable experience. The scale and artistry are beyond words. Krystal made sure we stopped at Old Bridge Gelateria nearby afterward!
- Neighborhoods: We explored the charming Trastevere district and the unique Coppedè architectural area.







Initially, we had a cooking class scheduled, but as Krystal remembered, we opted to “EAT INSTEAD,” fully embracing Rome’s incredible dining scene. We tried many of the spots on our list, like Osteria da Fortunata for their famous handmade pasta.
Southern Sojourn: Pompeii & the Amalfi Coast (Day trip from Rome – Dec 6)
Our day trip south on December 6th was incredible. Krystal vividly recalled “seeing the beautiful Mediterranean Sea expanding” before us on the Amalfi Coast. We enjoyed some delightful Limoncello there, soaking in the views. Then, we stepped back in time at Pompeii, walking the ancient streets and learning how people lived before Mount Vesuvius’s devastating eruption. Seeing the preserved Greek and Roman city was truly impactful.







đź’ˇ Travel Tip for Pompeii & Amalfi Coast: These areas require a lot of walking, often on ancient, uneven cobblestones. Comfortable and durable footwear is absolutely crucial. I was so glad I had invested in a solid pair of men’s durable & comfortable travel shoes, and Krystal had her favorites too. It makes all the difference in your ability to explore and enjoy!
An Italian Culinary Rhapsody
Krystal summed up our culinary experience perfectly: “It was delicious food, pizza, everything was so good. We ate the best gelato, we had the best pasta, we had the best breakfast, we had the best Limoncello!” Italy truly is a food lover’s paradise. Every meal felt like a celebration. If you want to try recreating some of these flavors at home, consider getting an Authentic Italian Cookbook or even a Pasta Making Kit.
Reflections: “One of My Top Trips”
Echoing Krystal’s sentiments, Italy was undeniably one of our top trips. The sheer diversity of experiences, from the romantic canals of Venice to the artistic heart of Florence, the ancient grandeur of Rome, and the sun-kissed beauty of the Amalfi Coast, was astounding. The culture, the history, the “vibes” of each city, and, of course, the incredible people we met along the way made it an unforgettable journey. The trip “flowed” beautifully, even with a packed itinerary, and left us with a deep appreciation for this multifaceted country and a definite desire to return.
All that walking, exploring ancient ruins, and climbing Duomo steps was incredible! It certainly makes you appreciate your fitness. If you’re looking to build or maintain your fitness for future adventures like this, or just want to find great classes to stay active or recover, you might find something like ClassPass useful. My friends get an exclusive free trial plus 20 bonus credits!
👟 Try ClassPass! Enjoy an exclusive free trial plus 20 bonus credits—available only to friends of mine: Get Your ClassPass Trial
Final Thoughts on an Italian Masterpiece
Italy is more than just a country; it’s an experience that stays with you long after you’ve left. If you’re considering a trip, our advice is simple: go! You won’t regret it. We certainly took the “best pictures” and had an amazing time.
What are your favorite Italian memories or dream destinations in Italy? Share them in the comments below!
My Favorite Services & Deals For You
I genuinely use and love these services. If you sign up with my link, we often both get a bonus—a true win-win!