Guide to Italy
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Your Official Guide to Italy
I was that girl in college with a map of the world posted up in my freshmen dorm room, with pins in every country I had plans to explore. Being a Division I college athlete however, left little time (or money) to travel. Commitments to the team meant zero chance to study abroad, and off-season training took precedent over any summer traveling dreams. I graduated at 21 years old having never stepped out of North America. After college, my young eagerness to see the world lingered, so I look on two jobs and finally saved enough to book a ticket for my first trip ever abroad two years later. ITALY.
First time abroad circa 2015
Walking the streets of Milan and turning the corner to see the Duomo di Milano was a moment that changed my life forever. I am not trying to be dramatic- I even have an outline of that cathedral tattooed on my arm, along with a few other unforgettable places I have seen traveling the world. The travel bug bit me hard. From then on I constantly scanned the web for the next affordable flight, planning my next adventure (to read more about my traveling story click here).
Since that trip to Italy five years ago, I have traveled to over twenty countries. Yet, no where is quite like Italy. Being an Italian-American from Chicago’s Taylor Street (little Italy neighborhood) may give me an unfair bias, but I feel like many agree. The ancient history, romantic language, world-class art, passionate people, the fresh cheese, and did I mention...the wine? Italy is truly magical. I arrived to Italy the second time a much more seasoned traveler, yet the country possessed the same charm as if I were seeing it for the first time.
This Guide to Italy is great for first timers but helpful for all. I provided plenty of tips, but my biggest piece of advice: wherever you decide to explore, stay for at least a few days. Italy is incredibly diverse and unique, each region with a sense of identity, individualism, culture, and cuisine. Do not bombard yourself with every museum, activity, and tour. Embrace the best parts of Italian culture- sip on espresso or a spritz, drive through the Tuscan countryside, or relax on Positano’s beaches. I promise after your first trip, it won’t be long before you plan the next one back.
Ciao Bellas, Bon Voyage!
Italy Travel Tips
+If possible, plan your trip around a festival or event. Italians are very proud of their culture so seeing the locals in action will be unforgettable. We planned our trip around The Palio, Siena’s historic, medieval-style horse race.
Palio di Siena
+Trains are a great way to get around. Usually you can get one the day of but I would reserve at least a day (or more if possible) ahead of time to guarantee a seat. This is a great resource to answer all of your train questions.
+Pack minimally. You will be hauling your luggage over cobblestone streets and onto trains. Lots of older hotels and airbnb’s may not have an elevator either. I would recommend keeping it to a carry on. If you need help in this department, learn How to Pack Like a Minimalist.
+While you are packing minimally, just be sure to include only comfortable shoes- you will be walking miles.
+The Aperitivo or “apéritif” is probably the best Italian tradition you have never heard of, so listen up. Usually between 7PM-9PM, many restaurants/bars offer a light pre-dinner snack with purchase of a drink. Drinks are usually also light- prosecco, aperol spritz or campari. Think of it as the Italian happy hour. The food is not supposed to replace dinner, but for a budget traveler it absolutely can.
aperitivo in Siena
+Now you are thinking, if happy hour goes till 9PM then when do you eat dinner?! That’s right, Italians eat dinner very late. Make reservations between 8PM-9:30PM.
+To make sure you don’t fall asleep at the dinner table, embrace my other favorite Italian tradition the riposo or “Siesta”, aka afternoon rest. That’s right, most shops close in the early afternoon for a break. So do as the Romans do- go with the flow, relax, give yourself some “me” time, or get your nap on.
+The food is great wherever you go, but eating locally will blow your mind. Know what specialties are known in each region i.e. pizza in Naples, balsamic in Modena, Fiorentina steak in Tuscany, pesto in Cinque Terre, bufala mozzarella and seafood on the Amalfi coast, and much more.
+”Piazzas” or squares, are the heart and soul of the cities. These gathering spaces are great to settle for a coffee or aperitivo and people watch. Places here may add a small additional fee just to sit- which is usually worth it, just be aware. Also follow the general rule of avoiding a full meal on piazzas- they have great atmospheres but typically not great food. Save your meal for a block or two off the main square.
+Many restaurants offer their house wine by the liter or half liter for very, very cheap. Literally, Italy is the place where wine is cheaper than water.
+Make plans for aperitif or dinner in a different neighborhood. With general safety practices, Italy is pretty safe for travelers so do not be afraid to venture! You can find some of the best food and local life in neighborhoods right outside the major sites.
+However, there are lots of tiny streets and alleys. To avoid getting lost, download MapsMe to use offline maps and star yout lodging, restaurants, and attractions ahead of time.
+Gelato- stay away from the stuff that is stacked high in a fluffy display. While eye-catching, this gelato is usually full of chemicals and air that take away from the craft and flavor.
daytime gelato is the best gelato
+Italians are lovers. They are extremely passionate about culture, art, music, fashion, and… beauty. PDA is the norm, and do not be surprised if you get stared at, cat-called by a complete stranger. It’s generally harmless so just go with it. Let’s face it, there are worse things in life than being flirted with by a beautiful tan guy named Lorenzo.
+I’ll say it again- a year wouldn’t be enough time to see all of Italy. Do your research about where you want to spend your time and stay for a few days. Italians take their time and so should you while you are visiting!
ROME
Roma. Roma. Roma. I have been to countless cities all over the world, but I must say Rome is still my favorite. Ancient structures like the Colosseum and Roman Forum sit within this lively, sophisticated city. There is plenty to do here, so if only staying 2-3 days, choose your tours wisely. I suggest staying in the Pantheon area which is very central to most sites and piazzas, but still walkable to other neighborhoods.
*Pro-tip- pack a reusable water bottle and fill up at the many public water fountains (nasone, aka fontanella). Yes, you can drink this water!
TO DO
Colosseum
A visit to this ancient site should be at the top of your list. You can visit for free or get standard adult tickets for 12 euros for entrance to the Colosseum. To get the full experience and learn the history, I would suggest looking at the many tours offered that include seeing Palatine Hill and the Roman Forum.
to get THIS exact photo overlooking the Colosseum, head across the street to the Colosseo metro stop. Turn left and climb the steps that will be on your left.
Vatican City
Although tours are long, this is also a major site to see in Rome. Try to see the Vatican in addition to St. Peter’s Basilica and the Sistine Chapel.
Spanish Steps
The famous steps that connect the Piazza di Spagna at the bottom with Piazza Trinita dei, have been in Rome since 1725. Go early or late to avoid the crowds and take your time walking up! Although pricey, head to Hotel de la Ville after walking up the steps for a coffee or cold drink on the rooftop.
Trevi Fountain
Walking distance from the Spanish Steps, you cannot miss one of the oldest water sources in Rome. It’s made of travertine stone, the same material as the Colosseum. You are not allowed to sit on the fountain edge, but make sure to toss in a coin for good luck!
Pantheon
Known as the 8th wonder of the ancient world, this architectural masterpiece is unforgettable. One of the most historic and most captivating structures in Rome, stop by for an espresso or drink outside to enjoy the view. Make sure you also head inside to view the unique interior spaces.
Piazza Navona
A picturesque square with fountains, cafes and restaurants, grab a drink and people watch. When visiting make sure to walk a few blocks further to Via dei Coronari - one of the most beautiful streets in the city full of cafes, shops, and art galleries.
Store front on Via dei Coronari
Campo di Fiori
During the day you can find Rome’s most famous market while at night, the area turns into a lively spot to enjoy an aperitivo.
market during the day in the square
COFFEE
Sant Eustachio il Caffe dating back to 1938, this famous cafe makes their own blends, roasts their own coffee, and even uses water from the ancient aqueduct system. Sit outside for an espresso before heading over to the Pantheon.
Antico Caffè Greco one of the most famous cafes in Rome, stop in to sip on coffee in the same spot as 19th century Romantic poets such as Keats and Byron. Head in before or after visiting the Spanish Steps.
Giolitti although a little touristy, this coffee shop always delivers a crowd of locals and visitors. Grab a coffee or late night gelato here.
EAT/DRINK
Terrazza Borromini after checking out the Piazza Navona, turn the corner to one of the most sophisticated rooftop terraces in Rome for sunset. Even just for drinks I would make a reservation in advance.
Terrazza Borromini rooftop terrace
SALOTTO 42 check out this lounge for cool vibes, cocktails with homemade ingredients, eats and brunch!
Dar Poeta cross the river for the night to the Trastevere neighborhood. Walk around, grab an aperitivo and do not miss making a reservation here for the best pizza in Rome and wine by the liter.
Verso Sera near the Campo di Fiori, make a reservation outside for this traditional spot.
Hotel Minerva grab a drink at the beautiful rooftop garden overlooking the Pantheon.
FLORENCE
Home of Italy’s finest art, history, and architecture masterpieces- Firenze is the capital of Tuscany and the Renaissance era. Former residents include The Medici Family, Dante, Machiavelli, Michelangelo and Leonardo da Vinci. There are many sites and museums, however I believe Florence is best enjoyed sipping coffee or aperol overlooking the Duomo. Take a bicycle or walking tour when you first arrive to get your bearings, see the sites, and learn the impressive history of the city. You will not be able to do every museum here if only staying a few days, so pick and choose wisely to better enjoy your time.
TO DO
Duomo di Firenze
AKA the Cathedral of Santa Maria del Fiore, Brunelleschi’s Duomo is one of the most celebrated cathedrals in the world. Entrance is free, however you need to buy a single "Grande Museo del Duomo" ticket ahead of time to climb up the Dome, bell tower, and visit the Baptistery.
Ponte Vecchio
AKA “Old Bridge” the Ponte Vecchio was the only bridge across the Arno in Florence until 1218. Although the current bridge was rebuilt after a flood in 1345, it was the only bridge not destroyed during World War II. Take your time to cross (and shop) on your way across the river to the Santo Spirito neighborhood- a much more casual area in Florence to get a better feel for local life.
Piazza della Signoria
Known as the center of political life in Florence since the 14th century, this has been the main square in Florence for centuries. Make sure to look out for Palazzo Vecchio which overlooks the piazza.
Palazzo Vecchio
Ufizzi Gallery
Once offices for the Medici family, the Ufizzi is now considered one of the most important Italian museums. Grab a ticket or tour to see one of the most beautiful art collections in the world, including Botticelli’s “The Birth of Venus” and da Vinci’s “Annunciation”.
Accademia Galleria
Best known to be home of Michelangelo's sculpture David, you can get a quick guided tour.
EAT/DRNK
Il Fratellini this tiny shop has been handing out sandwiches since 1875. Grab a bite and glass of wine, sit back and enjoy the break between site seeing.
yes, you can drink in the streets
La Giostra grab a reservation early because this is a must! The twinkling lights, candles, and quiet location give this place the perfect atmosphere, while the warm hospitality and authentic Tuscan cuisine may make this your best dinner in Italy. Make sure to order the burrata appetizer and pear ravioli. Animated chef Ubaldo Tornarelli is often in house so keep your eyes peeled!
Trattoria Giovanni for traditional, but exceptional Tuscan dishes. Located in the Santo Spirito neighborhood, go early to experience a different and lively part of town with the locals.
La Davina Terrazza this sophisticated rooftop bar at Grand Hotel Cavour provides one of the most impressive Duomo views. Cocktails can be a bit pricey, but head up at sunset and I promise it will be worth it.
Westin Excelsior rooftop although pricey, the views of the city on one end and the stunning Tuscan hills on the other are breathtaking. Reservations require a downpayment, so to avoid the possible cancelation fee, head over as early as possible for an aperitivo to grab a seat.
TUSCANY
The beautiful landscapes, stunning hills, and world class wine. No trip to Italy is complete without seeing one or more of the ancient medieval towns of Tuscany. Consider transportation beforehand since trains do not operate to the countryside. Lots of people rent a car (you can hire a driver, however this can get pricey) but this can be nerve-wracking on the tiny, windy roads. Look up routes & parking ahead of time, and make sure to get a car with GPS. If renting a car is an absolute NO for you, consider seeing Tuscany as a day trip from Florence by bus or driver- it’s worth it.
*Pro-tip- if renting a car specifically request an automatic if that is what you know how to drive. You don’t want to get stuck with stick shift unless you are extremely experienced.
TO DO
Visit (or Stay in) a Medieval Town
My favorite towns are San Gimignano, Cortona (where Under the Tuscan Sun was filmed), Montepulciano, Moltalcino, and Siena for a bigger town and more lively stay. Each beautiful hill town has it’s own character, but in Tuscany you cannot go wrong!
sunset in Montelpuciano
Siena
Wine Tour
You cannot go to Tuscany and not schedule a wine tour. You just cannot. There are many itineraries and regions to choose from such as the Chianti Classico route or Brunello di Montalcino route. Just know wineries are not typically commercialized here like they are in America, so I highly recommend contacting wineries for tours ahead of time or scheduling a tour with a private company that can accomodate. We loved our experience with Tuscany Travel Experts, which coordinated three visits to organic, women-owned wineries including Col di Lamo and Poggio Rubino .
view at Poggio Rubino Winery
Cooking Class
You can find exceptional cooking classes throughout Italy, however use some of your quiet time in Tuscany for this now. Learn to make your own pasta from scratch or traditional Tuscan dishes you can recreate back home, impressing your family and guests for a lifetime.
Rent a Vespa or Bike
If renting a car seems a bit intimidating, once in Tuscany use these modes of transportation to experience the countryside. Tuscany Cycle offers vespa or bike tours from Florence, or look where you are staying for other options on rentals/tours.
Attend the Palio de Siena
If you can make it work, attending the The Palio is a once in a lifetime experience. Offered twice a year on July 2 and August 16, this medieval horse race has origins in Siena since the 6th century. The Sienese take this complex race VERY seriously. Although welcome, tourists should educate themselves on the practices and traditions of the race. Educate yourself here, and watch the documentary on Netflix, Palio. To really immerse yourself, look into getting tickets to a contrade dinner dinner the night before.
EAT
Caffe Poliziano (Montelpuciano) for incredible Tuscan views, head in for your morning espresso, breakfast, lunch, dinner, or even late night gelato. This place has is all!
Caffe Poliziano
E Lucevan le Stelle (Montelpuciano) perfect to watch the sunset. Grab a drink and small bite on the patio.
La Taverna San Giuseppe (Siena) if coming to Siena, make a reservation here for a traditional Tuscan dinner.
POSITANO
As John Steinbeck puts it, “Positano bites deep. It is a dream place that isn't quite real when you are there and becomes beckoningly real after you have gone”. I could not agree more. This cliffside beach town on the Amalfi coast is the perfect place to relax after hustling around the big cities.
*Pro-tip Positano can be reached by ferry, train, bus, and private driver. Since this is a steep hilltown, be conscious of your luggage, and where you stay in proximity to restaurants/beaches.
*Pro-tip #2: be aware that Italians often vacation to the Amalfi coast in August and there may be lots of foreign and local tourists.
TO DO
Rent a Boat
There is no better way to experience the Amalfi coast than by boat. I highly recommend Valentine’s Boat Rental which can take you up the coast and stop by a seaside restaurant only available by boat. We opted out of visiting Capri due to the crowds in August, but this comes highly recommended as well!
Spiaggia Grande
The main beach in Positano, head down early and prepare for a 20 euro fee for a chair and towel rental (more expensive for front row).
Spiaggia Fornillo
A little less pricey than the main beach, relax here with less crowds and still impressive view. I recommend one day at each beach! There is also a path connecting both beaches which is a fifteen minute walk.
EAT/DRINK
Casa e Bottega for breakfast or a refreshing fruit smoothie.
Collina Bakery for a quick espresso or the best nutella croissant of your life.
Da Vincenzo this was my favorite meal in all of Italy. Reserve early and ask for a table outside!
Hotel Montemare sit outside for beautiful ocean views for an aperitivo.
Chez Black great location right on the main beach for lunch or dinner. Reservations recommended.
La Sirenuse Hotel for the poshest drink and dinner, look no further than the Champagne Bar at Le Sirenuse and dinner at Michelin starred restaurant La Sponda. Make sure you dress to impress because although the views are incredible and the ambiance is perfect, the bar and restaurant are very pricey with a scent of snootiness if you are not a celebrity guest. If you want to see what the hype is all about, make a reservation in advance. If this does not sound like your jam, instead go to:
Don Giovanni terrace sea views just as great without the snootiness and sky high prices.
Don Giovanni
Il Tredente at Hotel Poseidon great location and beautiful views for an drink.
Bucca Di Bapo right off the main beach, cool off here with the best gelato in town.
From the northern Dolomites to southern Sicily, there is still so much you can include on your trip! I know I cannot wait to plan my next time back to Italy to see it all. I hope this helps with your Italy planning, or maybe inspires you to book your trip!
Have you been to Italy or are thinking about making the trip? I would love to hear from you! Leave a comment below or find me on social media.
XO,
Jac
