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I spent 3 months in Italy studying so I’ll lend a hand at helping you out. I lived in Rome and traveled each weekend around Italy trying to get in as much as I possibly could. So I’ll let you know what I loved and what I wish I would have been able to do.
While you’re in Naples, the first bit of advice is watch yourself. Not for the mafia or anything like that, but because of the driving. They are the hands down worst drivers in the world, so just stay in the cross walks. If you can plan it right, I would do Sorrento the following way. Get there in the afternoon and enjoy your night there. Great restaurants and awesome night life is what makes Sorrento what it is. The next day hop on the ferry to get to Capri. Once there, it’s up to you whether or not you wanna take a little tour of the Grotta Azzuro (Blue Grotto) I say do it, it’s a quick tour but it’s a very interesting experience and if it’s a nice day, it’s pretty fun to jump in once you’re there. Otherwise, I would take the incline up the slope and begin a hike to the highest point. Maybe pack a lunch and eat up there. I kid you not, along with maybe Cinque Terre, Capri is the most unbelievably beautiful place on earth.
As you head North, I would definitely suggest seeing Pompeii, but not spending too too much time there. Hiking Mt. Vesuvius was awesome. The town itself is really cool too.
Now, my favorite part. Rome.
I know this may be tough but if you can, try and not see any of the city for the first time until the night. Once the sun goes down, get to St. Peter’s, have your breath taken away, and thank me later. The next few days for you will blow by so try and get up early and stay out late. I would commit at least one full day to the Vatican and St. Peter’s Basilica. Climbing to the top of the dome is a monster workout but it’s worth the one picture you’ll be able to take.
The Colosseum and the Forum can also be done in one day if you are efficient, and you can probably fit the Capitoline Museums as well. One ticket will get you access to everything so try and do it all. There are great vendors that line the street from the Vittorio Emmanuelle Capital to the Colosseum.
For the most part the general rule of thumb is to stay away from touristy piazzas and squares to get real authentic food. Not true about the area surrounding the Pantheon. You’ll get some of the best plates at an affordable price of anywhere, and you get to sit outside an incredible monument and people watch while you do it. If nothing else, go grab a glass of prusecco before dinner there. If you’re looking for something a little bit nicer as maybe a dress up night, Da Fortunato, also near the pantheon is fantastic. But if you’re really looking for a great Italian meal, Spirito di Vino is what’s up. It’s a restaurant owned by a father and son and not only is the food unbelievable, in the middle of the dinner the owner will come over to your table and start telling you a story about just how old his restaurant is. He’ll say “when you walk down to my wine cellar, each step you take you’re going back 117 years, all the way until you’re on the bottom, and then you are older than the Colosseum itself.” And then he’ll actually let you go down and see his cellar, and it is spectacular.
Bars are everywhere but the highest concentration are in Campo de Fiori and Piazza Navona. Campo has a more American base while Piazza Navona caters to locals. La Botticella is a personal favorite. It’s just off a side street near Piazza Navona, and it’s actually a Pittsburgh Steeler bar in Rome. For clubs, Akab, Gilda, and Alien are probably you’re best bets.
So getting off my fetish of Rome and back to the rest of your trip, Assissi is amazing. There’s not much else to say other than to really try and understand the history and what St. Francis committed his life to, and it kind of brings the city alive. If you have a chance to check out Perugia, the city under the hilltop Assissi, they have amazing food, wine, and nightlife because it is Italy’s version of a college town. The kids I was with wanted bud, so they just walked up to the fountain and steps at one end of town and about 5 people immediately approached them.
Florence is very cool but not really worth all that much time because it is sooo American that it almost doesn’t feel like it’s that different. The Uffizi galleries are amazing and the Accademia is worth going into to see Michelangelo’s David. The leather shops are also very cool if you’re looking to get gifts for anyone back home.
Venice is the coolest city in the world and to see it all takes about 12 hours. It is very small and easier to get around quickly so grab your camera and start shootin.
That wraps up my way too long tour guiding. Have a GREAT time and if you are teetering on the edge about whether or not you wanna do something, do it. there’s no way to regret experiencing more