Italy is one of my favorite countries. The people, the food, the sites, the history, the culture, everything. One of the few I've been to more than once and definitely want to visit again. There is so much to see. Italy was my first trip to Europe back in 2010 through Trafalgar. Then I returned again in 2013 on my own with a friend. For first time travelers to a new country where you're unfamiliar with the culture and language, booking a tour is great. You get to see how it's done, it can be cheaper due to group discounts, and you'll likely get insider information. Plus you have a translator. Once you become more experienced, it's way more fun to plan a trip on your own. My trip back was a road trip through Italy's beautiful countryside and revisiting Rome and Florence. Certainly touristy and certain places can be expensive, with modern day travel tools, Italy can be very affordable and certainly worth the visit.
Last Visit: 2013
Cost: $-/day
Stayed: 14 days
Suggest Staying: 1-4 weeks
English: 3.5/5
Safety: 4/5
Currency: Euro
Transport: Taxi, metro, bus, train

My Favorites

1. Rome


Highlights: Historic Sites, Art, Nightlife, Food, Beaches
Suggest Staying: 5-10 days
Stay Around: Piazza Navona or Trastevere
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Rome is quite possibly my favorite city in the world. I’ve visited twice and have every inclination of returning. There is such rich history that you are never bored and are in constant amazement. There is romance, attractions, art, churches, and tales of adventure. The food is like nowhere else in the world. Even your average hole-in-the-wall sandwich shop will blow you away. In the U.S. our idea of “Italian” food is not even on the same playing field, and Rome is the epicenter in my opinion. Of course each region throughout the country has its own variations. The best thing to do in Rome is to just walk the city and use the metro system. See what you see and you’ll likely stumble across some amazing family owned restaurant, local butcher, or piazza that is surely a hidden gem.

Here’s a fun story at the expense of my sister that illustrates the wonderful charm of Rome…My sister was just getting over food poisoning and still feeling ill as we raced to catch our flight directly from the hospital. Upon our arrival, my sister felt no improvement. We had arrived several days early before our tour throughout Italy began. Our tour operator, who loved the phrase “Mama Mia,” was so wonderful. She and the hotel arranged to have a doctor come to our room to check on my sister. A tiny old man with tiny hand bag full of doctor gear arrived in our room, only speaking Italian. The hotel helped translate as he did a checkup, gave her some medicine, told her to rest, and wrote us a bill on a piece of paper. I felt like we were in an old movie. Luckily my sister recovered in a couple days and we had a fantastic trip around the country.

See & Do

  • Colosseum. Where the ancient gladiators fought. Tours can really enhance the experience. Do make sure you see it all.
  • Roman Forum. Ancient ruins.
  • Circus Maximus. Site for games, chariot races, and other entertainment.
  • Pantheon. Great historical landmark.
  • Trevi Fountain. Beautiful fountain, possibly my favorite attraction in Rome behind the Colosseum.
  • Spanish Steps. The always popular steps and fountain.
  • Via del Corso. Main street and shopping area.
  • Piazza Navona. Wonderful piazza that’s great during the day and at night for totally different experiences.
  • Pizza del Popolo. Interesting sculptures.
  • Villa de Borghese. A beautiful park once lived in by the famous Medici family. You will find beautiful gardens, views, fountains, and street performers. Villa Medici, Viale della Fontana Rotunda, Viale Tarragona. We happened to come upon a random roller blading spectacle where people where jumping up ramps like it was an olympic high jump.
  • Santa Maria Maggiore. Landmark basilica.
  • Castel Sant’Angelo. Castle fortress.
  • Venezia & Monumento a Vittorio Emanuele II. This didn’t come up in any of my guidebooks, but it’s right at the city center. I used it to help orient me from wherever I was in the city. Go inside and have a look, it’s free.
  • Trastevere. Fantastic hidden gem of a neighborhood my cousin took us. Great food, unique shops, less touristy, more humble, and just across the river.
  • Castello Orcini. About an hour drive outside the city where they filmed the princesses from Bill & Ted’s Excellent Adventure.

Food & Drink

  • Bar del Fico. Appetizers and drinks with a full restaurant.
  • Grom. Gelato.
  • Gelatteria del Teatro. Awesome gelato.
  • Open Baladin. Craft brewery with 40+ beers and sandwiches.
  • Bar del Fico. Nice bar.
  • Fluid. Cool lounge type bar.


  • Getting Around. Use the metro system. It’s cheap, easy to use and stops along all the major tourist attractions. There are only two lines (at least last I was there). Beggars may come up to you and “help you” figure out how to get a ticket and then ask you for money for their help. Just ask them to leave you alone, it’s not complicated. Otherwise you can also use taxis which may be helpful for nightlife. Otherwise the city is large, but the neighborhoods are very walkable.
  • Safety. Generally I found Rome to be quite safe, though as in pretty much every major city in Europe, watch out for pickpockets, especially in large crowds. Don’t wander aimlessly with your money, phone, or camera out.
  • Food & Drink. While I obsessively use Yelp when traveling, I’ve never done any research for restaurants in Rome and have never been disappointed. Pretty much everything is great. I would suggest veering out of the main piazzas and streets which are often overcrowded and overpriced, and instead wander around to seek out smaller restaurants that will likely have better food, ambiance, and prices. Also try the wine. I’m not a wine drinker at all, except in Italy.
  • Tickets. For any attractions that require tickets, I strongly suggest looking them up online to learn about logistics. Due to popularity or other things, tickets may quickly sell out, require advanced booking, or require visiting only on certain days. My first trip to Rome was through Trafalgar so lucky for us everything was handled. For the Colosseum, beat the long line and get tickets at the Palatine box office on via di S. Gegorio 30.

2. Florence

Florence Duomo

Highlights: Art, basilicas, food, wine
Suggest Staying: 2-5 days
Stay Around: City Center
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Florence is a wonderful, thriving art city with an incredible history of Renaissance artists. It’s more low key than Rome, but still plenty to see, do, and eat. I absolutely loved this city. Even walking around town, you will see amazing artwork from street artists which you can purchase for relatively little money. Just need to figure out how to get it home. You can also explore the beautiful areas of Tuscany and Chianti known for wine and food.

See & Do

  • Uffizi Gallery. One of the most well known art galleries in the world and one of my personal favorites.
  • Duomo. The main duomo in Florence. It’s massive, beautiful, and visible throughout the city.
  • Galleria dell’Accademia. Home to many works of art including the world famous Michelangelo’s David. It really is quite impressive in person.
  • Santa Croce. Historical basilica home to the tombs of figures such as Michelangelo and Galileo.

3. Cinque Terre

Cinque Terre

Highlights: Small town charm, beaches, food, wine
Suggest Staying: 1-3 days
Stay Around: Monterosso al Mare (Albergo Al Carugio)
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The beautiful “five towns” along the coast of Italy is a site not to be missed. While extremely popular, first time visitors often skip this destination because it’s not included in typical tours or they opt for the major cities of Rome, Florence, and Venice then call it a day. There’s a bit of work required to get here, but the easiest is to just rent a car, but you can also take a train. You could probably do everything in a day if you rushed, but I’d budget at least 2-3 to relax and enjoy yourself. Check out the beaches for sure.

See & Do

  • Monterosso al Mare. Most resort-like, largest beach.
  • Vernazza. Pretty, visitor-friendly, lingering in a cafe and watching waves.
  • Corniglia. Along the cliff.
  • Manarola. Most photogenic.
  • Riomaggiore. Cliff clinging.


  • Getting There. Do yourself a favor and drive if you can. You’ll need to know how to drive a manual stick shift transmission. The roads once you get there are pretty windy and mountainous, but nothing very steep. Parking is a bit of a pain, but manageable.
  • Getting Around. Take the train between the five towns, it’s silly to drive since they’re only like 2 miles apart and there’s no parking. You can also hike from what I hear.

4. Venice

Doges Palace

Highlights: Waterways, gondolas, parties, food, wine
Suggest Staying: 1-3 days
Stay Around: Piazza San Marcos
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You’ve no doubt heard about Venice, as it is such a highly visited and popular city around the world. There are many attractions, gondola rides through its waterways, and celebrations to be had. In the evening, you’ll find people overflowing into the piazzas drinking wine, listening to music, and having a good time. There are also several nearby small islands worth visiting. Personally, I liked Venice but have not felt a need to return. It’s definitely worth seeing, but Rome and Florence are way better in my opinion and certainly easier to get around amongst all the tourists.

See & Do

  • Doge’s Palace. Lavish palace.
  • Rialto Bridge. Famous bridge you can walk across or see via gondola ride.
  • Piazza San Marcos (St. Mark’s Square). Main area of the center which is super helpful as a base for getting around the confusing maze of streets. Just follow the signs if you get lost.
  • Murano Island. Home of famous glass products. Check out a glass blowing demonstration.
  • Burano Island. Wonderful, quaint fishing village with fresh seafood. Dip into an alleyway or secret door among the colorful houses to reveal a secret area.
  • Gondola Ride. Despite being a super touristy thing to do, it’s still awesome. If you speak Italian, you might get some funny commentary from the gondoliers.


  • Getting Around. A vaporetto, or water taxi, is the way to get around the city of venice.

5. Vatican City


Highlights: The Vatican
Suggest Staying: 1 day
Stay Around: Rome
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Technically its own city-state, Vatican City is surrounded by Rome, and even walkable just over the bridge at Castel Sant’Angelo. Obviously the main attraction is The Vatican. Regardless of your religious beliefs, the Vatican holds some of the most amazing works of art in the world. The Sistine Chapel is the most famous and is absolutely incredible. A tour through the Vatican takes you past countless priceless works of art. The building and grounds are also amazing.


  • Tickets. It gets insanely crowded as you can imagine, so get your tickets early and in advance. Doing a tour will provide details of the Vatican’s rich history. There is also after hours 7-11pm. The Scavi (catacombs) are separate.

Other Considerations



Milan is know as the fashion capital of the world and I had heard you might see various celebrities in the fashion districts in town. The food is great of course, and you get a bit of a different flavor in this region. The Duomo and Castello Sforzesco are worth visiting. Also you can check out Santa Maria delle Grazie to view The Last Supper by Leonardo da Vinci. (book tickets early). Otherwise, I didn’t find Milan all that great personally. If you have the time and interest, you could spend a day or two, but otherwise there are places I would put ahead of Milan.


Lamborghini Museum

The main reason we stopped here was to visit the nearby town of Maranello, home of Ferrari, and the Lamborghini Museum. Modena is a very lovely town in its own right and the home of the best balsamic vinegar in the world. It’s where most of it comes from, plus of course there is amazing food. The city center is restricted to avoid too many cars, so watch out for signs about traffic or you could receive a huge fine. The Ferrari museum should be booked in advance, especially if you want a tour of their track.

San Gimigano

San Gimigano

This charming medieval town was an optional excursion on our tour that of all the excursions offered, our tour leader recommended above all others. Both my sister and I loved it. It was our first exposure to a medieval town, and it was wonderful. Well preserved. Nicknamed the “medieval Manhattan” of Tuscany.



Wonderful food, the birth of spaghetti bolognese. Pasta here is handmade and the best I’ve ever had. There is also a leaning tower like the one in Pisa, just not as big or touristy. Kind of makes you wonder about what the architects were drinking back then when they were building…



Assisi was a short stopover for us (like an hour) to see the Basilica Papale di San Francesco Assisi and take a bathroom break on our tour. The area is very beautiful and a nice break in your trip if you have the option to stop.

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Leaning Tower of Pisa

Home to the famous leaning tower of Pisa which is certainly an awesome spectacle to see in person. It’s easy to get to from Florence and you basically just spend an hour or two taking funny pictures and avoiding people trying to sell you stuff.

General Tips

  • Water. This was my first trip to Europe and if it's yours, you should note that there is both mineral and carbonated water available. Or as they like to call it "gas" (bubbles) or "no gas" (flat). If you hate sparkling water, there is nothing worse than walking through the streets of Rome on a hot day and chugging a bottle of sparkling water without knowing it. Also you'll notice lots of fountains around town given Rome's intricate aqueduct system that runs throughout the city. I'm still not sure if the water is drinkable, but I heard it's spring water. I'd exercise caution in filling up your water bottle with it though. You can also ask for cheaper "tap" water at restaurants as opposed to bottled which was perfectly fine to drink (at least when I was there). Check with the locals and do your research though.
  • Trains. It was my experience that trains in Italy are horrible and unreliable. We had a trip and purchased tickets to Naples (which apparently is not very safe) en route to the city of Pompei. Needless to say we paid extra for an express train to get there earlier that was delayed and I don't think ever came. So we were "forced" to spend another day in Rome. I know, tough life. Just be aware trains can be horribly unreliable and late, so don't make plans that require trains to get you to your destination on time.

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