Four Wonderful Day Trips from Florence, Italy

I couldn’t wipe the smile off my face if I tried to that day.

My jacket and shirt were soaked through, and my hair had probably never looked worse, but I sat in a restaurant full of chattering Italians listening to a new friend order food and wine for the table as if we’d known each other for years.

We discussed meat and cheese pairings in the same breath that we discussed true crime podcasts and the failings of US society, giddy from just one perfect glass of house red, filling up our glasses for another round.

The whole restaurant burst into song in time with the radio, and we listened as the men behind us explained the song’s significance in their mother tongue between choruses. It wasn’t until we left that we realized we’d been chatting with the owner, who sat an arm’s length away and treated us like old friends.

Siena’s locals in particular had a way of making you feel at home within the span of a single conversation. It’s a feeling that’s hard to find, but incomparable when you do.

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Florence, Italy is one of the most beautiful cities in the world, filled with incredible history, food, sightseeing and culture. Whether you’re planning a long trip there and want to venture out of the city on weekends, or are just using Florence as a transportation stepping stone to see other Italian cities, there are a countless number of beautiful spots that are a day trip’s distance from this iconic city.

DAY TRIP #1 - Siena

Siena is a no-brainer for a beautiful city to visit from Florence - it’s only one hour away by train or bus, and it’s full of beautiful scenery, amazing food and interesting history and tradition. Nestled in the heart of Tuscany, Siena is a quaint little city with endless streets to wander down and explore, making for a perfect day-trip from the more bustling streets of Florence.

THINGS TO DO AND SEE ON YOUR DAY TRIP TO SIENA:

Duomo di Siena (Siena Cathedral)

Siena’s cathedral is arguably my favorite out of all the cities I visited in Italy - the interior is so unique, with big, dark stripes contrasting the white marble of the church and gold stars peppering the dark blue ceilings. It’s gorgeous to see, and though it’s one of the only cathedrals I’ve seen that isn’t free to enter, the 8€ tickets are worth buying for sure!

Piazza del Campo

The medieval square in Siena’s historic center and one of the most highly regarded Piazzas in all of Italy. It’s home to the Palio di Siena, a horse race that takes place two days a year in the summer - if you find yourself in Siena during or around the time of the Palio, it’s a wonderful atmosphere to be a part of! The race isn’t geared towards tourists and is very special to the people of Siena, so even just visiting the city in the week following either race is exciting - the parades and late night parties will still be happening daily, and there’s a certain vibe in the air that’s really cool to experience.

Basilica Cateriniana San Domenico

This is one of the most important churches in the city - it contains relics of St. Caterina of Siena (including her head), along with lots of historical artworks in the nave of the church.

Key Largo Bar (or any bar in the Piazza del Campo)

We stopped at Key Largo for midday drinks, climbing their narrow stairwell to reach a tiny balcony overlooking the entire Piazza. The views and people watching are unbeatable, so grab a drink here if you can!

Wander down city streets

My favorite thing to do in a new city is just wander, and Siena is small enough that you can do so without ending up too far from your starting point. You’ll undoubtedly stumble across beautiful lookout points, unique streets and shops, and delicious restaurants no matter where you turn.

DAY TRIP #2 - Pisa

I think it’s actually illegal to go to Florence and not take a side trip to Pisa - it’s an hour away by train and one of the most iconic places to see in Italy, so how could you not visit? I will say: if you only have even half of a day to stop by, that’s enough time for Pisa. I will also say: I refuse to believe the tower only leans at a 5° angle. There’s no way.

THINGS TO DO AND SEE ON YOUR DAY TRIP TO PISA:

Climb the Leaning Tower of Pisa

This is a given - if you’re in Pisa, it’s because you’re gonna climb the bell tower. It’s best to book tickets ahead of time and put your bag in a locker before you get in line, if you have one. Try to book as early a time slot as you can, especially if you’re visiting in the summer. It’ll get hot waiting around and while you’re climbing!

Visit the Pisa Cathedral

When you’re done climbing the tower, head into the cathedral for a quick look around. It’s free to enter and pretty cool inside. There are a few other buildings you can check out too, like the Opera del Duomo Museum and the Baptistery, but I didn’t visit any of them so I don’t have any personal perspective on those.

Walk along the Arno River

I love looking at and taking photos of cool buildings, and the shops, homes and other buildings along the river in Pisa were a pretty great view honestly. That blue building in the first photo below might be my favorite building I’ve seen yet.

See Tuttomondo: Keith Haring’s last mural

If you’re a fan of Keith Haring (or just art in general), seeing his last mural, Tuttomondo, is a must-do when visiting Pisa. It’s only about 5 minutes from Pisa Centrale, and it’s right in front of a great lunch spot called ArtBurger. The restaurant is inspired by Haring and his art, and it’s got great food with a great view to take in before you head back to Florence!

DAY TRIP #3 - Milan

Contrary to what some people might say, I think you can definitely be satisfied with seeing Milan in one full day. We only had about 6 hours there (we stayed there for one night before our weekend trip to Lake Como), and we felt pretty good just seeing the Duomo, the Galleria Vittorio Emanuele II, and walking the 30 minutes to and from our Airbnb. There are definitely some other landmarks and popular neighborhoods you can check out if you have a full day to spend in the city, and since it’s only 2 hours from Florence by bullet train, it’s super easy to plan a whole day of activities there!

THINGS TO DO AND SEE ON YOUR DAY TRIP TO MILAN:

Visit the Duomo di Milano

Having probably the most iconic and impressive exterior of all the churches in Italy, the Milan Cathedral is an obvious choice for sightseeing in Milan. Be sure to book your tickets early, and get one that includes the rooftops as well as the archaeological areas and museum! Seeing the city from the roof of the cathedral was such a cool experience, and the archaeological area was really interesting to explore, too. We didn’t have enough time to see the museum before it closed, but the whole collection of areas to explore takes up a good few hours of time.

Shop at the Galleria Vittorio Emanuele II

You can’t visit the fashion capital of Europe without walking through the world’s oldest shopping mall. If you’re not looking to spend an arm and a leg on designer clothes or high-end brands, even taking a stroll through the mall’s four floors and spinning on the bull for good luck (three full turns on your heel) is enough to get your fill of this beautiful building. There are some lovely restaurants here as well, if you’re looking for a posh dinner spot (La Locanda del Gatto Rosso has an amazing carbonara).

Visit the Teatro alla Scala (La Scala)

One of the world’s most famous opera houses is located at the opposite end of the Galleria from the Duomo. We didn’t get a chance to visit La Scala on our trip to Milan, but it’s a must for theatre buffs and architecture lovers alike!

Explore Navigli Milano (Canals)

If we’d had a full day in Milan, we would have loved to go down to the historic Navigli area to walk along the canals. It looks like a beautiful area filled with vintage shops, great food, and pretty streets - if you want a cool spot to explore away from the big business-y buildings that fill the city, this looks like the spot to do it!

Visit Castello Sforzesco

Another spot we didn’t get to see (but that looks gorgeous) was Castello Sforzesco, a 15th century castle that’s been rebuilt over different centuries. It’s a popular spot to walk around and includes a number of museums, fountains, courtyards, and more.

DAY TRIP #4 - Lake Como

Now, Lake Como can (and should) be explored in more than one day - but if you only have the one day to visit, it’s definitely still worth it just to go explore the lake for a handful of hours. To get there from Florence, you’ll most likely take a train to Milan (about 2 hrs), then take another direct train to Como (another 45 minutes). Once you get there, you can take the main ferry from Como to pretty much anywhere on the lake. It’s one of the most beautifully impressive places I’ve ever traveled, and I can’t recommend it enough, even if it’s only for a quick day trip to get yourself near some water.

THINGS TO DO AND SEE ON YOUR DAY TRIP TO LAKE COMO:

Visit Villa Balbianello

One of the most recognizable and popular Italian destinations is Villa Balbianello, used for scenes in movies like Star Wars Episode II: Attack of the Clones, Casino Royale, and more. Not only is it a chance to visit this famous film location, it’s also just an incredibly beautiful villa with gorgeous grounds to explore. If this is the main attraction for your day trip, get tickets with access to both the inside of the villa and the gardens. Also, be sure to take the taxi-boat from Lido di Lenno to experience the water entrance!

Rent a boat from Varenna or Bellagio

If you want to go swimming in Lake Como (uh, obviously?), one of the funnest options is to rent your own motorboat for an hour or two. They’re super easy to drive, and you get free reign of the lake–giving way to ferries, of course–for your allotted time slot. You can just cruise around the lake and take in the sights, or pull off and go for a swim in front of some beautiful celebrity villas (George Clooney, I’m looking at you).

Eat pasta by the water

The typical goal of a trip to Lake Como is to have a relaxing day(s) on the water, eating and drinking and exploring in style. My favorite part of any trip I take is the food, so obviously I have to recommend having a lovely lunch or dinner by the lakeside, taking in the scenery and (hopefully) beautiful weather while you enjoy a plate of fresh Italian pasta. I can vouch for Caffe Varenna having an amazing pasta menu, a beautiful view of the lake, and a great glass of Pinot Grigio! Another popular town to grab a bite and relax for a bit is the tourist hotspot Bellagio, which has no shortage of delicious food and beautiful views.

Take a private boat tour

If you’ve got money to spend and want a truly one-of-a-kind experience, I’d suggest splurging on a private boat tour across the lake. There are lots to choose from that leave from different towns on the lake, and you can see multiple villas, have time to swim, and often get snacks and wine included! This is a great option if you’re with a group of people, on a couples trip, or even if you’re solo and want to treat yourself.