Planning a Trip: Spring in Italy
A relaxed itinerary through Florence, Cinque Terre, Lake Como, Milan, Venice, and Rome
All the photos in this post are my film photos from the last family trip we took to Italy. Italy is beautiful on film.
Planning a family trip to Italy can feel overwhelming because there are so many incredible places to see. My family has been doing family trips with our significant others since we became adults, and we really enjoy spending time as a family so a trip through Italy while my brother is working in Milan felt like a great choice. My mother has also never been, and for a family that is obsessed with the culture and Italian food, we wanted to go here and eat, relax and enjoy. When we started planning this trip, we focused on creating a route that allowed us to experience some of the highlights of Northern Italy without constantly packing and unpacking. We knew we wanted a mix of culture, scenery, and incredible food, but we also didn’t want to feel like we were racing from one place to the next. This trip, we are just going as a family of four, and my husband is staying back to hold down the fort and take care of the dog. That means that as adults, with two of them in their early 60’s, we wanted to adapt the trip slightly to make sure that we didn’t exhaust anyone. The last family trip we went on, we sped from museum to museum and I ended up being a snappy version of myself because I was burnt out.
I think a key factor to traveling as an adult family is to carve out alone time. My brother is just excited to see us all, but my mother and I both have introverted tendencies and I learned the last time I was on a family trip with my brother and my dad that I need a few days of alone time, or taking the morning to myself or afternoon to myself so I can get some introvert time and ground myself. We are a family of talkers, and it can be a lot.
Our itinerary ended up being:
3 days in Florence
3 days in Cinque Terre (Just my mom and I)
3 days in Lake Como
2 days in Milan (to see where my brother lives)
3 days in Venice
3 days in Rome
It gives you a mix of art, coastal villages, lakeside scenery, and historic cities without feeling rushed. It felt like the right balance of cities, coastline, and slower lakeside days for a family. If you’re planning a similar trip, here’s how we approached the route, how we’re getting around, what we’re packing, and the highlights we’re most excited to experience in each stop.
How We’re Getting Around Italy
One of the biggest decisions when planning a multi-city trip is transportation. While renting a car can make sense in some parts of Italy (like Tuscany), the reality is that the train system makes travel between major cities incredibly easy. Most of our travel days will be on high speed trains with reserved seats and just a couple of hours between destinations.
A few tips that came up again and again while planning:
Book trains early if you can. Prices tend to increase closer to travel dates.
Try to pack lighter than you think you need. Many train stations have stairs and cobblestones waiting on the other side.
Download tickets on your phone so you don’t have to worry about printing anything. I love using Omio.
For smaller areas like Cinque Terre, the local train line connects all five villages and makes exploring simple.
Italy’s trains are comfortable, efficient, and honestly part of the experience. If you download the Omio app, or just go through the Trenitalia website, it makes it really easy to navigate. I’m personally a big fan of Omio for travel in general (not sponsored, just love it), and I think having everything in one place for a family makes the most sense.
What We’re Packing for Italy
Every travel guide says the same thing: pack light. However for an older family, backpacking isn’t always the most realistic, and roller bags aren’t the most practical. We’re attempting a blend of both and I’ll report back. Italy is one of those trips where lighter really is better. Trust me, you’ll end up buying a few things while you are there.
The essentials we’re packing include:
Comfortable walking shoes. This is non negotiable, and I have both a comfy pair of runners and sandals (Sorel’s are the BEST).
A lightweight crossbody bag for busy city streets. My favourite is from Lululemon and has so many pockets.
A portable phone charger for long sightseeing days.
A refillable water bottle because public fountains are everywhere in Italy.
A lightweight scarf or shawl for visiting churches.
And one thing I always bring on trips like this is a foldable tote bag. It’s perfect for markets, bakeries, or the inevitable moment when you buy something that doesn’t fit in your suitcase anymore or it needs to double as a snack bag for the plane.
Florence: Renaissance Art and Slow Evenings
Florence is our first stop, and it feels like the perfect place to start the trip and take some time and recover from jetlag. The city is compact enough to walk almost everywhere, but every corner feels like it holds a piece of history.
The main things on our list include seeing the cathedral complex and climbing to the top of the dome for views across the red rooftops of the city. The Duomo dominates the skyline and feels like the heart of Florence. After 3 trips here, I thought it made sense to go here this time as a family. We also plan to visit the Accademia Gallery to see Michelangelo’s David in person. Some pieces of art are so famous you wonder if they’ll live up to expectations, but everyone says this one absolutely does. Don’t forget to buy tickets in advance to make sure you can get a spot, especially if you are going in the spring or summer.
And of course, we want time to simply wander. Florence is the kind of city where some of the best moments happen when you’re walking across Ponte Vecchio at sunset or grabbing gelato and going for a wander along the water.
Here’s a quick guide:
Top 3 Things To Do
1. Visit the Duomo: The cathedral complex is incredible. Climb the dome if you want an amazing view of the city.
2. See Michelangelo’s David: The statue inside the Accademia Gallery is one of the most famous sculptures in the world.
3. Walk across Ponte Vecchio: The historic bridge filled with shops is one of the most recognizable landmarks in Florence.
Where to Eat
La Gratella – Tuscan cuisine with a largely gluten-free menu.
Quinoa – A fully gluten-free restaurant with traditional dishes and modern options.
Sgrano – Known for gluten-free pasta and sandwiches.
Cinque Terre: Colorful Villages on the Coast
After Florence, my mother and I are headed for Cinque Terre to have a couple days on the coast and to enjoy some time in the water. Cinque Terre is made up of five small villages built along dramatic cliffs on the Italian Riviera. It’s one of the most photographed places in Italy, and for good reason. The villages are connected by train, hiking trails, and small boats, so exploring them feels more like wandering than structured sightseeing. We’ll likely be only taking the train back and forth just due to the fact that my mother can’t hike around, especially in heat. Even if you’re not hiking the full routes, taking the train between villages is easy and gives you the chance to see them all.
Manarola is known for having one of the best sunset views in the area, so that’s definitely on the list. For food, there are some great options that aren’t focused on just fish (I’m allergic) and have good gluten free.
Il Pirata delle Cinque Terre is known for having gluten free options and amazing breakfast pastries. Nessun Dorma is famous for its views and fresh bruschetta, and Ristorante Miky is often recommended for traditional Italian pasta dishes.
A Quick guide:
Top 3 Things To Do
1. Hike between the villages
The trails offer incredible coastal views.
2. Take the local train between towns
It’s the easiest way to explore all five villages.
3. Watch sunset in Manarola
This is one of the most photographed views in Italy.
Where to Eat
Ristorante Miky – Known for great pasta dishes
Il Pirata delle Cinque Terre – Excellent breakfast and gluten-free options
Nessun Dorma – Famous for views and bruschett
Lake Como: Slowing Down by the Water
After the colorful energy of Cinque Terre, Lake Como feels like the place to slow the trip down. The lake is surrounded by small towns, historic villas, and mountains in the background. It’s the kind of scenery that makes you want to linger over coffee a little longer than usual.
One of the towns we’re planning to explore is Bellagio, often called the pearl of Lake Como.
Another stop is Villa del Balbianello, which has some of the most beautiful gardens in the region and has appeared in several films.
But the real highlight of Lake Como is simply taking the ferry between towns. Seeing the villas, mountains, and villages from the water is part of the experience. It’s a great cost-effective solution instead of taking a boat tour because you get to zip around for less expensive, and then you get to chose where and when you go.
For meals, restaurants like Ristorante Bilacus offer gluten free pasta options, while places like La Punta and Osteria del Beuc are known for classic Italian dishes and beautiful views.
Top 3 Things To Do
1. Explore Bellagio
Bellagio is often called the “pearl of Lake Como.”
2. Visit Villa del Balbianello
Villa del Balbianello is famous for its gardens and film appearances.
3. Take a ferry around the lake
The ferry system connects all the towns and offers incredible views.
Where to Eat
La Punta – Amazing views and pasta dishes
Ristorante Bilacus – Italian classics and gluten-free pasta
Osteria del Beuc – Cozy and traditional
Milan: A Quick City Stop
Milan is a shorter stop on the itinerary, but it’s still worth visiting. The city has a very different feel compared to Florence or Venice. It’s modern, stylish, and known as the fashion capital of Italy. I personally don’t love it here, but my brother lives here right now, so its’ a must-stop to see where he lives.
The first thing we’ll see is the Milan Cathedral, which is one of the most elaborate churches in the world. Walking on the rooftop terraces gives you a completely different perspective of the city. Make sure to book this ticket! Another must see is Leonardo da Vinci’s painting of The Last Supper, which requires booking tickets well in advance. They are released in chunks, its not a rolling 30 days, so unforauntely I missed the boat (for the second time) to get these tickets. If this is really important to you, you can join a Get Your Guide tour, but it is a bit more expensive. And then there’s the Galleria Vittorio Emanuele II, one of the most beautiful shopping arcades in Europe. It’s fun for a wander through, and if you are coming with plenty of pocket change then a great stop.
Top 3 Things To Do
1. Visit the Milan Cathedral
Milan Cathedral is one of the largest cathedrals in the world.
2. See The Last Supper
Leonardo da Vinci’s famous painting is located at Santa Maria delle Grazie.
3. Walk through the Galleria
Galleria Vittorio Emanuele II is a beautiful historic shopping gallery.
Where to Eat
Mama Eat Lab – Gluten-free Italian classics
Risoelatte – Traditional Milanese dishes
Nerino Dieci Trattoria – Excellent pasta
Venice: Getting Lost on Purpose
Venice is one of those places that almost feels unreal when you arrive. The canals, the bridges, the historic buildings rising out of the water. It’s unlike anywhere else in the world and it’s only here for a short time. The entire city is built upon logs and a marsh (learn more about that when you’re there), and it’s gradually sinking. Be prepared for there to be the occasional flooding, which is why you’ll see lots of places having a metal barrier across the door or risers that can be easily deployed to help people walk through a watery street. A summer trip avoids the flooding season (October to March approx.) but something to watch out for.
Of course, St. Mark’s Square is on our list. It’s the heart of Venice and home to St. Mark’s Basilica and the Doge’s Palace. We are staying at a place nearby to the square so its an easy place to get to in the morning for a quick cappuccino and pastry before going around for the day.
A gondola ride might be one of the most touristy things you can do, instead just get a transit pass while you’re there (worthwhile if you’re going to be doing any transiting around), and take the vaporetto across the canals to save time, but also get the feel for being on the water without shelling out $$$.
What we’re really looking forward to is wandering through the quieter neighbourhoods away from the main tourist routes and just enjoying the atmosphere. This trip is about relaxing and good food. Last time we were here as a family we accidentally planned it at the same time as the Venice Film Festival and we got to hop the vaporetto over to Lido and see Daniel Craig. An absolute life highlight for my Dad who is a massive James Bond fan and such a cool experience!
Top 3 Things To Do
1. Visit St. Mark’s Square
St. Mark's Square is the heart of Venice.
2. Take a gondola ride or take the vaporetto.
It’s touristy but unforgettable.
3. Explore the smaller canals
Walking the quieter neighborhoods is often the best way to experience Venice.
Where to Eat
La Zucca – Incredible vegetable-focused dishes
Ristorante da Rioba – Venetian cuisine and gluten-free options
La Tecia Vegana – Vegan and gluten-free friendly
Rome: Ending the Trip with History
Rome is where the trip wraps up, and it’s a city that almost feels like an open air museum. The Colosseum is one of the most iconic landmarks in the world and something to see in-person. That being said, its my fourth time there so we are prioritizing just seeing it from the outside with my mother (who has no interest in going inside anyways), and its so romantic to see it at night
We’re also planning a half day exploring Vatican City, including St. Peter’s Basilica and the Vatican Museums as that is such a unique and beautiful place. Spending some quality time at the museums in the Vatican are something that I have not done yet, so hopefully there is some time for that. And of course, no trip to Rome feels complete without visiting the Trevi Fountain and a visit to the spot I got engaged a year and a half ago.
One of the best parts about Rome is the food scene. Restaurants like Mama Eat Roma specialize in gluten free Italian dishes, while Rifugio Romano and Piccolo Buco are well known for gluten free pasta and pizza options.
Top 3 Things To Do
1. Visit the Colosseum
Colosseum is one of the most iconic landmarks in the world.
2. Tour Vatican City
Visit St. Peter's Basilica and the Vatican Museums.
3. Throw a coin into the Trevi Fountain
Trevi Fountain is one of the most famous fountains in Europe.
Where to Eat
Mama Eat Roma – Entire gluten-free Italian menu
Rifugio Romano – Great gluten-free pasta options
Pizza in Trevi – My favourite spot by the Trevi Fountain and they have gluten free pizzas. They take safety so seriously and it’s in such a great spot. Make sure to make a reso well in advance for weekend slots (I made mine 6 weeks ahead of time) because they book up! They also have a sister gelato spot right next door with wonderful gluten free options too.
When you’re planning a trip with this many stops, it’s easy to get caught up in the must-sees and try to fit everything in. But honestly, some of the best parts of traveling through Italy aren’t the big attractions. They’re the slower moments, like sitting down for dinner after a long day, catching a sunset by the water, or wandering into a street you didn’t plan on exploring. This route through Florence, Cinque Terre, Lake Como, Milan, Venice, and Rome gives you a really good mix of art, history, scenery, and food, but what makes it work is having just enough time in each place to not feel rushed and to actually take it in.
If you need any receommendations, or off the beaten path suggestions let me know! I love Italy so much and having travelled most of the West Coast including Sicily, I have some great options if you want to add more time onto your trip.
Love, M