My Italy by train itinerary took me from Rome to Venice and Florence, with an unforgettable day exploring the Tuscan countryside along the way. I visited in January, and traveling between cities by train turned out to be one of the easiest ways to experience several incredible parts of Italy in one trip.
This trip had a little bit of everything I love about traveling—beautiful hotels, incredible food, history, shopping, gorgeous scenery and experiences that felt uniquely Italian.
If you’re planning your first trip to Italy and want to see several of the country’s most iconic destinations without renting a car, this itinerary is a great place to start.
Quick Trip Snapshot
Route: Rome → Venice → Florence → Tuscany → Rome
Time of year: January
Transportation: Train between cities
Best for: First-time visitors, couples, girlfriends’ trips or solo travelers
Trip highlights: Rome cooking class, Venice gondola ride, Florence leather shopping and a Tuscany countryside day trip
Would I do it again? Absolutely.
First Stop: Rome 🇮🇹
I flew into Rome and made it my first stop in Italy.
Rome is one of those cities where you can turn a corner and suddenly find yourself standing in front of something you’ve seen in pictures your entire life. I spent my time seeing the major tourist attractions, walking through the city and, of course, eating plenty of Italian food.
Where I Stayed in Rome
The Inn at the Spanish Steps
I stayed at The Inn at the Spanish Steps, which gave me a fantastic location for exploring Rome.
Being near the Spanish Steps made it easy to walk around the city, shop, grab coffee and experience Rome without constantly worrying about transportation.
When I travel to European cities, I’m willing to pay a little more for a central location because being able to walk out of my hotel and immediately start exploring is worth it to me.
Planning your own trip to Rome?
Check hotels and current rates in Rome through Expedia
Affiliate disclosure: I may earn a commission if you book through one of my links, at no additional cost to you. Thank you for supporting Travel Well with Tracy!
One of My Favorite Rome Experiences: An Italian Cooking Class 🍝
One experience I definitely recommend is taking an Italian cooking class.
I booked mine with Eat and Walk Italy, and it was such a fun way to experience Italian culture beyond simply eating at restaurants.
There’s something about learning how Italian food is actually prepared while you’re in Rome that makes the experience even more memorable.
If you’re building your Rome itinerary, I’d leave room for at least one experience like this rather than filling every hour with sightseeing.
What to See in Rome
For my first visit, I wanted to experience the iconic Rome sights I’d always heard about, including the Colosseum, Trevi Fountain, Spanish Steps, Pantheon, Vatican City and Piazza Navona.
And don’t underestimate how much fun it is to simply walk around Rome. Some of my favorite moments in Europe happen when I’m not rushing to the next attraction.
Next Stop: Venice 🚤
From Rome, I took the train to Venice.
Traveling through Italy by train was much easier than I expected, and I loved not having to worry about renting a car, parking or navigating unfamiliar roads.
Venice was completely different from Rome.
There are no cars, so you get around by walking or traveling by boat—and that’s part of what makes Venice so special.
Where I Stayed in Venice
I stayed at Sina Palazzo Sant’Angelo, and this hotel was beautiful.
The location was fantastic, and one of the coolest parts was arriving by boat directly at the hotel.
It was one of those moments that immediately made me think, Okay, I’m definitely in Venice.
If you’re choosing a hotel in Venice, I highly recommend paying attention to location and water access. You’ll be walking a lot, so staying somewhere convenient can make a huge difference.
Looking for somewhere to stay in Venice?
Compare Venice hotels and current rates through Expedia
Gondolas, Shopping & Getting Lost in Venice
Of course, I couldn’t visit Venice without doing a gondola ride.
Yes, it’s touristy.
And yes, I would still recommend doing it.
Sometimes the famous tourist experiences are famous for a reason, and floating through the canals of Venice in a gondola is one of those things I’m glad I experienced.
I also spent plenty of time shopping. Venice has beautiful boutiques as well as high-end designer stores, so if you enjoy luxury shopping, leave some room in your itinerary—and your suitcase!
But one of the best things to do in Venice costs absolutely nothing:
Walk.
Get lost in the narrow streets. Cross the little bridges. Stop for coffee. Wander into shops. Look down the canals.
Venice is one of those places where exploring without a strict itinerary is part of the experience.
Next Stop: Florence 🤎
After Venice, I took the train to Florence.
Florence has such a different feeling from both Rome and Venice. It’s beautiful, historic and extremely walkable, and it became the perfect base for one of my favorite experiences of the entire trip—Tuscany.
Where I Stayed in Florence
I stayed at the Golden Tower Hotel & Spa, which put me in a convenient location for exploring Florence.
My stay was approximately $520, and once again, having a central location made sightseeing and shopping much easier.
Planning a stay in Florence?
Compare Florence hotels and current rates through Expedia
Exploring Florence
I spent time seeing Florence’s famous attractions and simply enjoying the city.
Florence is packed with Renaissance history, architecture and art, but I’ll admit that another thing I was excited about was the shopping.
Leather Shopping in Florence 👜
If you love leather goods, Florence is dangerous—in the best possible way.
The city is known for its leather, and you’ll find everything from handbags and jackets to belts and smaller accessories.
Give yourself time to browse rather than buying the first thing you see. There are plenty of options, and shopping for Italian leather became part of the Florence experience for me.
My Favorite Experience: A Day in Tuscany 🍷
If I had to choose one experience from this trip that really stood out, my Tuscany day trip would be near the very top of the list.
Our day included:
Siena → San Gimignano → Pisa → lunch and wine in the Tuscan countryside
After spending so much time exploring busy cities, getting out into the countryside was a completely different experience.
The rolling hills, vineyards, historic towns and beautiful scenery looked exactly like the Tuscany I’d imagined.
Siena
Siena is a beautiful medieval city filled with winding streets and historic architecture. It felt completely different from Florence and was a wonderful addition to the trip.
San Gimignano
San Gimignano was another favorite stop.
This small Tuscan hill town is known for its medieval towers and beautiful views over the surrounding countryside. It’s the type of place where you want to slow down, wander around and take pictures of everything.
Pisa
And yes—I went to Pisa.
Seeing the Leaning Tower of Pisa in person is one of those classic Italy moments I wanted to experience at least once.
Lunch at a Working Tuscan Farm & Winery 🐄🍷
This was easily one of my favorite parts of the day.
The winery we visited wasn’t simply a place set up for tourists—it was also a working cow farm, which made the experience even more memorable.
I was able to see the animals while we were there, enjoy the countryside and then sit down for lunch and wine surrounded by the beautiful Tuscan landscape.
After several days of sightseeing in busy Italian cities, spending time on a working farm in the countryside felt completely different. It gave me a chance to slow down and experience another side of Italy.
Good food, Italian wine, animals, vineyards and those incredible Tuscan views?
This was my kind of day.
If you’re staying in Florence, I would absolutely make room for a full-day Tuscany excursion.
My Italy by Train Itinerary: Getting Around 🚆
One thing I loved about this itinerary was how easy it was to travel between cities by train.
My route was:
Rome → Venice → Florence → Rome
I didn’t need a rental car for the main portion of the trip, and taking the train allowed me to relax and enjoy the journey rather than worrying about driving, parking or navigating unfamiliar cities.
For a first trip to Italy—especially if you’re visiting the major cities—I’d absolutely travel by train again.
Visiting Italy in January: Would I Recommend It?
Absolutely.
January isn’t necessarily the first month people think about when planning an Italian vacation, but there were some definite advantages.
It felt less hectic than traveling during peak summer season, and I was still able to experience the cities, shop, eat incredible food and explore the countryside.
You’ll want to pack layers and be prepared for cooler weather, but don’t automatically rule out Italy during the winter.
For travelers who care more about exploring than lying on a beach, January can be a wonderful time to experience Italy.
What I’d Do Again
If I were planning this Italy itinerary again, there are several things I wouldn’t change.
Travel between cities by train. It made moving around Italy surprisingly easy.
Stay centrally located. I loved being able to walk out of my hotel and start exploring.
Take the cooking class in Rome. Experiences like this made the trip feel more personal.
Ride the gondola in Venice. Tourist attraction or not, I’m glad I did it.
Shop for leather in Florence. Just remember to leave room in your suitcase.
And most importantly…
Take the Tuscany day trip.
If you only have time for one excursion outside the major cities, Tuscany would be high on my list.
Ready to Plan Your Own Italy Trip? ✈️
One of my biggest tips for planning a multi-city Italy vacation is to choose your hotels carefully. Being able to walk to restaurants, shopping and major attractions made a huge difference for me in Rome, Venice and Florence.
Start planning your trip:
🏨 Search hotels and travel through Expedia
🗺️ Explore accommodations through Stay22
A Travel Card Worth Considering 💳
If you’re planning an international trip, travel rewards can also help offset some of the costs of flights and hotels.
I use Chase Sapphire, and if you’ve been considering one of the Sapphire cards, you can use my referral link to see the current offers for the Chase Sapphire Reserve® or Chase Sapphire Preferred®.
👉 See the current Chase Sapphire offers here
Disclosure: This is my personal Chase referral link. I may receive a referral bonus if you apply through my link and are approved. Credit card offers, terms and eligibility can change, so review the current offer directly with Chase before applying.
Final Thoughts
Italy is one of those destinations where you could return over and over and still feel like you’ve barely scratched the surface.
Rome gave me history, incredible food and that unmistakable big-city Italian energy.
Venice gave me canals, gondolas, beautiful shopping and a city unlike anywhere else I’d visited.
Florence gave me Renaissance history, Italian leather and easy access to the countryside.
And Tuscany gave me one of my favorite days of the entire trip.
If you’re planning your first trip to Italy, don’t feel like you have to see everything. Pick a few cities, travel between them by train, leave room for experiences beyond the major tourist attractions—and definitely give yourself at least one day to escape into the Italian countryside.
Planning a longer European trip? You may also love my Switzerland itinerary, which includes Zurich, Lucerne, Grindelwald, Zermatt and some of the most beautiful train journeys I’ve ever experienced.
Some links in this post are affiliate or referral links. If you make a booking, purchase or apply through one of these links, I may receive a commission or referral bonus at no additional cost to you. I only share hotels, destinations, experiences and travel products I genuinely recommend.
Travel well,
Tracy ✈️
