I think bucket lists are overrated. I’m very much an, “If I want to do it, I do it” type of person. No list necessary. BUT if I had a bucket list, visiting Italy would be at the top of that list. Growing up in the Northeast, I grew up around a lot of Italians. My impressions of what Italy is has been based on stereotypes I observed through people I knew, way too many mafia movies and shows (Mob Wives is one of the greatest reality TV shows ever. Also, #TeamDrita forever don’t @ me), and Olive Garden.
So, when the opportunity to take a two-week jaunt to Italy finally presented itself, I knew how I was spending my summer. Below you’ll find a comprehensive rundown of everything you’d need to know to plan your trip to Italy covering just over a dozen cities, and nearly 900 miles of movement. I took a little over 271,000 steps traversing around Italy, so strap your walking shoes on and get ready to retrace my steps as you work your way from Venice all the way to Sicily.
Don’t feel like reading the whole thing? Scroll down to the bottom to get my top travel notes on Italy.
Venice — Venezia
Must See
- St. Mark’s Square and Basilica. In the square, you’ll find the center of historical Venetian life.
- Acqua Alta, a bookstore on the water. The backdrop also makes for some great insta shots
- Bridges on Bridges on Bridges. Check out the Bridge of Sighs, an old bridge prisoners used to cross as they headed to jail. The most well-known bridge, the Rialto bridge crosses the length of the Grand Canal. The most recent bridge to grace the canals of Venice is the Constitution Bridge. More modern in design, this is one of the first bridges you’ll encounter as you make your way to mainland Venice and away from the canals.
Must Do
Gondola Ride.Water Taxi Ride. So a few things. Gondola Rides cost eighty euros. There’s no negotiation, that is the price. Your Gondolier probably won’t sing. My Gondolier started texting mid boat ride. After I finished the gondola ride, I hopped on a water taxi instead and had a far more enjoyable experience. Unlike Gondolas, you can actually ride up the Grand Canal and get some great shots of the Rialto Bridge from a waterfront vantage point. The water taxi can also cover much more ground and give you many more scenic views than you’ll probably get from a twenty-minute gondola ride. I’m not saying you shouldn’t take a gondola ride, all I’m saying is you should definitely take a water taxi ride.- Get lost. With nearly 400 bridges to cross and winding streets abound, take a walk and get lost in the ancient history of Venice. Sure, the tourist spots are nice but give yourself two hours and you’ll stumble upon some incredible hidden gems in no time. Getting back to the Square or Rialto area is easy too as there are signs posted on almost every corner.
Must Try
- Mozzarella in Carrozza. A bread fried mozzarella cheese patty sometimes stuffed with prosciutto.
- Spaghetti al Nero di Seppia or Squid Ink Pasta. Sure to turn your mouth black from the sauce but allegedly quite delicious and worth it.
- Bellini! Venice is home to the Bellini a mix of peach juice and Prosecco. You can grab one from the original place Harry’s Bar, or you can just grab a bottle from any store in Italy for less than 10 Euros.
Verona
Must See
- Where two star-crossed lovers first met. Yes, you can see the balcony where the fictional characters Romeo and Juliet met in Verona.
- Arena di Verona. The Colosseum in Rome may be the most famous but it’s not the only one in Italy. Still standing today, this smaller version is still used for public events in Verona.
Must Do
- Tour Castelvecchio, a small but hearty castle completed during the Middle Ages.
Must Try
- Technically you can get this anywhere, but Verona is a perfect place to make a quick pit stop and try some Gelato. Pistachio seems to be the national flavor of Italy, but most gelaterias have dozens of flavors to choose from daily.
Milan — Milano
Must See
- Duomo di Milano. Although not the largest, this is one of the largest cathedrals in Italy and Europe. This is also where I learned that Duomo isn’t singular to the Milan church but rather, it means “church” so almost all cities in Italy will have a Duomo.
Must Do
- Looking to spend on a bag on a bag? Look no further than Via Montenapoleone known as the Most Expensive Street in Europe. Get your Gucci, Louis, Fendi, and Prada. I sure did…
Must Try
- Risotto. A national dish that varies by region, Milan is known for its Risotto Milanese, which is made with saffron.
- Want a cheap eat and great drinks? Check out Manhattan Bar in the Ticinese district. Known for their 11 Euro Aperitivo special featuring one drink and a bottomless buffet of Italian dishes.
Lake Como — Lago di Como
Must See
- Lake views of the Swiss Alps. Take a boat ride to one of the many villages along Lake Como and get some incredible views of the Swiss Alps.
- Famous Celebrity Homes. George Clooney may be the most famous one, but Richard Branson is also a famous Lake Como homeowner.
Must Do
- Tour the gardens of Villa Carlotta. A botanic garden with art masterpieces covering over 70,000 square meters of land.
- Stop in the village of Bellagio and get a quick leg day workout in. Many of the stair laced alleys are full of shops and restaurants where you can grab a tasty lakeside lunch.
Must Try
- Although Lake Como isn’t known for any one specialty, it never hurts to grab another cup of gelato while you watch the boats sail by on the shoreline.
Cinque Terre
Must See
- What’s not to see? The five villages of Cinque Terre are known for their picturesque views and Instagram worthy photo op’s. Vernazza gives you one of the best vantage points from land but a boat cruise can make all five villages even more beautiful.
Must Do
- Hike to Monterosso. You can hike in between many of the villages but the hike to Monterosso is by far the most scenic and well worth it. When you’ve finally made your way into Monterosso you can…
- …relax on a beach. You can rent an umbrella and two beach chairs for about 25 euros and some reserved beach spaces have bars right on the waterfront.
Must Try
- Focaccia bread. Liguria (the region in which the Cinque Terre villages are located) is its true birthplace. Eat it plain, stuffed with cheese, or with toppings, but really no matter where you go, you can always find it piping hot.
Pisa
Disclaimer
I didn’t visit Pisa, per the recommendation of several people. It is quite far to get to and can chew up several hours of travel time just to take a photo posted up on a tower. However, if you are traveling from Cinque Terre to the Florence/Tuscany region and want to visit Pisa, this would be the ideal time to do so.
Florence — Firenze
Must See
- This is my favorite city in Italy. The entire city is literally a museum, every corner you turn, there’s some incredible work of art, a piece of history, or marvel in architecture.
- If you’re an art lover, visit the Uffizi (24 Euros for a reservation) to see the Birth of Venus and other works of art by Michelangelo, Rafael, and Da Vinci. You can also visit the Accademia Gallery (12 Euros) to see the original Statue of David (although there are several imitation statues around the city).
- I was pretty churched out at this point in the trip but the Duomo in Florence is truly worth exploring. Beyond the ornate designs and sheer size, this is just a beautiful work of art. The baptismal building has funky geometric designs that stand out in a city that is otherwise pretty stark in color.
Must Do
- Learn about the history of Gucci, at the Gucci Gardens. A museum located right off the Palazzo Vecchio.
- For good luck rub il Porcellino in the Piazza del Mercato Nuovo, a bronze boar said to bring good luck and fortune to those who drop a coin from its mouth.
- Tour the House of Medici and learn about the royal family that ruled for nearly three centuries. You can still see their family crest all over the city.
- Cross the Ponte Vecchio an insta worthy bridge known for its medieval history.
Must Try
- Pappardelle al Ragu di Chinghiale or Wild Boar Ragu is a Florence fave. I was a little nervous about eating “wild” meat as I’ve never been a fan of deer or other “wild” meats in America but it certainly was tasty.
Tuscany — Toscana and the Village of San Gimignano
Must See
- Rolling hills and picturesque views. If you pay a small fee and climb to one of the two towers in San Gimignano you can get an incredible view but if you walk around the town for long enough you’ll find picturesque views no matter where you are.
Must Do
- Eat more gelato! Gelateria Dondoli has been named “The World’s Best Gelato” several times now and after almost a week of trying various places, I can see why they’ve won. Their gelato tasted almost like ice cream as it had such a smooth and rich texture.
Must Try
- Chianti Wine and just wine in general. Tuscany is wine country. With rolling hills and vineyards abound, this is where you can get some of the finest wines in the country
- Vino Santo is the Italian equivalent of Sherry wine. It is nearly impossible to find sherry wines in America so when the vineyard I visited crafted their own, I jumped at the opportunity to buy a bottle.
- Bruschetta. Tuscan bread is made very bland without salt, so to jazz it up, try some bruschetta. Bruschetta –pronounced brew-skett-uh (we butcher it in America) — is bread topped with salt, pepper, tomatoes, basil, and olive oil.
Rome — Roma
Must See
- Everything! This is the center of the ancient Roman empire. Don’t surprised if you turn a corner and BOOM you’re suddenly face to face with the Pantheon or Trevi Fountain or some other two-thousand-year-old historical site.
- The Roman Colosseum is certainly impressive but right next to it is the Roman Forum. I was completely unaware and unprepared for what I was going to experience but I was in awe of the literal layers of ancient and medieval history unearthed right in front of you.
Must Do
- Run the Spanish steps. Built by the French, you can run the 135 steps that serve as a gateway to the Trinita dei Monti (also a French church). Although I didn’t opt to, I did see many tourists and Italians throw their fists up like Rocky when they made it to the top.
- Right behind the Spanish Steps is the Villa Borghese garden. It’s like Rome’s Central Park. Grab some more gelato or just lay out a blanket and enjoy the tranquility of being in nature.
Must Try
- Gelateria Della Palma with over 150 flavors to choose from (I chose spring cream and cheesecake) you’ll never run out of options and combinations to try. Just steps away from the Pantheon on “Gelato Road” you can try flavors until your heart and belly are full.
- Pasta! You can get pasta everywhere, but Rome offers many places that serve fresh made-to-order pasta.
Vatican City — Citta del Vaticano
Must See
- The Vatican Museums. Room after room of Renaissance art.
- St. Peters Basilica. The largest church in the world. Do you love Jesus? The Italians of the Renaissance sure did and they built a church as big as a football stadium to prove it.
Must Do
- Take your time in the Sistine Chapel. It’s much bigger than you could ever imagine and no photos or talking is allowed which means you can truly take in everything that Michalanego created in the moment. It was breathtaking, awe-inspiring, and emotional just as everyone says it is. You won’t be rushed to leave so take it all in.
Must Try
- Visiting the Vatican is another great opportunity to grab some pasta.
Pompeii
Must See
- Ancient Ruins. I was not at all prepared for what Pompeii would be. It was overwhelming and incredible in every way. I don’t want to spoil it either but I will say this: If there’s one place you visit in Italy besides Rome, make the ancient ruins of Pompeii your next stop.
Must Do
- Take your time imagining what life was like nearly two thousand years ago. It’s quite humbling to think of how insignificant we are in the grand scheme of things. You’re on earth for maybe 100 good years and then it’s done. To see something preserved from so long ago was just wild to imagine.
Must Try
- You’re close enough to the Naples region that you can get an “authentic” pizza pie. A Napoleon pizza is arguably the truest form of Italian pizza.
Amalfi Coast — Costiera Amalfitana
Must See
- Sand in your toes. Take a break. Grab a beach chair and just relax. The cliffside views are absolutely stunning and the miles of coastal beaches and high point views are incredible.
Must Do
- Relax. The Marina Grande beach is at the base of the cliff side town of Positano and is the most recognized beach in the town.
Must Try
- Seafood. Sadly I’m allergic but if you’re fortunate not to be, now would be a great time to chow down on Spaghetti and Clams.
Capri
Must See
- The isle of Capri by boat. Take a boat tour and cover the many islands in just under two hours. You may even see a celebrity yatch or two…
- Gardens of Augustus. Towards the top of the main island, you’ll find a retreat into a natural paradise, complete with unforgettable panoramas.
Must Do
-
Take a boat ride through the magical Blue Grotto, a natural cavern that is filled with an eerie light reflecting on the very very blue water. There are dozens of caverns and inlets all around the island that show of the natural beauty of the island.
- Window shop until you drop. I stopped in a store to look at a butterfly ring. There was a 4 with many zeros following the price. I put it down gently and walked out. Moral of the story, look, don’t touch because this island is too expensive for the average traveler.
Must Try
- Buffalo Milk Mozzarella. Elusive to America, take advantage of trying of this brighter, creamier version of the cheese we’ve all grown to love.
Sicily — Sicilia
Must See
- The Godfather. Well sort of. Much of the movie that was shot in Italy was done in Sicily so you can see filming spots from the movie all over.
Must Do
- Hike Mt. Etna and try some wines native to Mt. Etna and the island of Sicily.
- Visit the Ancient Theatre of Taormina. A Greek built theater that provides gorgeous views of Mt. Etna in the background
Must Try
- Nero d’Avola. This hearty red is Sicily’s most popular. Often compared to Syrah, it is sometimes blended with other reds but usually allowed to stand on its own.
- Canoli’s. The true test to get the best Canoli is to get a place that has just the shells and will fill with the cream in front of you. If it’s prefilled you have no idea how long it’s been sitting.
Too Long Didn’t Read
Here are my observations on Italy…
- As is true for most of Europe, water isn’t really a common drink. I kid I kid. It’s just that wine is much more common. Be prepared to pay for water everywhere you dine and specify you want “aqua naturale” or else you’ll get sparkling water.
- Bring a scarf for churches. There are churches or duomo’s everywhere and they are strict about the dress code. You will have to keep your shoulders and knees covered. There will always be people trying to sell you scarves so just buy one in the first city for no more than 5 Euros and hang onto it for the rest of your trip.
- There is no such thing as spicey meatball in Italy. In fact, meat in your pasta isn’t really a thing. Also, the sauce is not slopped on top, it is stirred into the pasta. Lastly, fettucini alfredo is not poppin’ in Italy. You will get laughed at if you ask for it at a restaurant.
- Tiny cars are the norm. At one point during the trip, I asked what the average height of an Italian was because pretty much everyone drives little tink tink cars like Mini Coups, Fiats and other compact vehicles. Gas is also very pricey (like $100 to fill up a tank) so most people just walk.
- If you can speak Spanish, you can circumlocute your way to getting Italian words although most Italians aren’t just going to be speaking Spanish to you all willy nilly.
- Be prepared to be hawked. There are tourist traps in every city but it felt like no matter where I went in Italy there was always someone trying to sell something or someone begging for something. It became quite irritating to constantly try and enjoy a meal or sit on the beach and be approached by a half a dozen people selling bracelets, selfie sticks, trinkets, and other unnecessary stuff.
This is great! Italy is definitely on my bucket list so I will have to check out this guide again when I go,. 🙂
What a fantastic post, Shay! Very ingenious.
¶ It’s obvious you put a great deal of time and consideration into creating this handy on-the-go resource. You’ve managed to craftily distill a lot of helpful and insightful information into a concise reference anyone can quickly pull up on their smartphone.
¶ I’m amazed you covered so much territory in just 2 weeks. And to have walked your way through it all (“271,000 steps”), no less. I’m originally from NYC, and so no stranger to walking, but you must be an energy bunny! It took me 5 weeks to visit about two-thirds of what you accomplished (Milan, Venice, Florence, San Gimignano, Assisi, Rome, and Vatican City) and my feet were aching.
¶ Thanks for rekindling my Italy wanderlust for Pompeii, the Amalfi Coast, Capri, and Sicily.
Wow! You really did it all!!! Looks like your Italian adventure was bucket list worthy. Love that photo of you sitting atop of all those books. I loved Venice and luckily for us we went in the winter so we dind’t run into hoards of tourists. My Italian highlight has to be the Vatican museum and of course the Sistine Chapel. That was really something else. Oh and of course the food and wine…… yummo!
I need to go to Italy SO badly!!! This all looks amazing.
-Emily
Love this so much, it takes me back to when I went to Italy with my family. I was only 12 at the time so I couldn’t enjoy the “adult” things like drinking wine and looking around at the beautiful scenery. Thanks for sharing!
Italy without wine?! How awful lol but then again wine at 12 probably isn’t good lol
Wow! I love all the specific suggestions! Thanks for all the great info.
I would love to do this some day. Where can I sign up?
This is great!! I still have yet to travel outside the country, but this makes me want to book a flight to Italy ASAP!
Your images are gorgeous. I am now more eager to visit Italy. Thanks for all the tips of things to see .
Thanks so much!
There are so much to see in Italy. I hope to visit there and until then it is going to be in my non existing bucket list.
You really saw quite the places while touring Italy. This is a great run down of things to do in see. Italy’s on my list of countries to visit (one of them). I will be sure to reference this article when i do plan for it.
Girl, you were all over the place! This is a huge list and even if I only get to Italy once in my lifetime, I’m going to have to pull this one back up again!
Italy is one of my favorite places! I was there last September and I fell in love with it!
Wow! You hit all the major spots in Italy! Looks like an amazing trip. I particularly loved Florence, but I still need to hit up everything in southern Italy.
southern Italy is perfect for relaxing. Just sitting and tanning and drinking all day lol
WOW You’re really making me miss Italy! I’ve been to Venice and Rome but I’d love to go to all these other places! What a great travel list!
these photos give me so much envy – i’m dying to go to Italy!
I have always wanted to go to Italy. It looks absolutely amazing from the buildings to the food.
Absolutely gorgeous! I’ve always wanted to travel aboard definitely one of goals in life. Just stunning scenery.
This post makes me miss Italy so bad! I LOVE Italy and have been a handful of times, most recently a few years ago on a two week study abroad trip in Rome. Cinque Terre is incredibly beautiful, and the history nerd in me was obsessed with Pompeii! I never made it to Capri, Sicily, or Lake Como but they are on my list for next time!
How awesome. I would love to return back to Italy one day now that I’ve figured out what places were my faves.
Love the post! Went to Rome and Venice last month. Planning for positano and Almafi coast next
This is so comprehensive girl! I went to Italy (Rome, Florence and Venice) a couple years ago with my mom – it’s amazing there!
I think this is the best review I’ve seen! So beautiful. And I’m such a bucketlist person. Hope Kenya is on your places to visit!
Wow thanks so much and no shame in that lol. All of Africa is on my list so Keyna is a must!
One of my nicknames is Shay Shay too lol. Italy is definitely on my wishlist of travel destinations.