• Want to blend in?  Don’t drink cappuccino after 10:00 AM.  
• Don’t eat at any restaurant named after a monument, city or famous artist.  These are usually geared toward tourists.
• For the best food, head for the source: Parma for prosciutto, Capri for ravioli caprese, Umbria for truffles, Tuscany for steaks, Liguria for pesto genovese.  Beyond that, every town has its own specialty.
• Emilia-Romagna is Italy’s best food region, and Bologna, its capital, is Italy’s best food city.
• Drink the house wine — always.  It’s delicious and almost laughably cheap for the quality that you get.

• Visit the Jewish Ghetto (Ghetto di Roma) for some Roman Jewish food the likes of which you won’t find elsewhere in Italy.
• Don’t visit the Vatican on a Monday — you get the overflow tourists from Sunday, when the sights are closed.
• Don’t expect to grab lunch around the Trevi Fountain — there is a surprising dearth of decent restaurants in this area.
• Bring an umbrella to the Forum if you’re sensitive to the sun — there’s very little shade.
• Go to Trastevere at night to experience typical Roman life, away from the tourist crowds.
• The best sunset view is from Castel Sant’Angelo, overlooking Saint Peter’s Basilica.  Unreal.

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Florence

• For a great view that nobody knows about, go to the department store across the street from Piazza della Reppublica and climb to the very top, including the unofficial-looking staircase on the top floor.  There is a cafe up there with an amazing panoramic view of the city next to the Duomo.
• Get great shots of the Ponte Vecchio and the river from the Ponte delle Grazie, the bridge east of the Ponte Vecchio.
• Everyone goes to see the sunset at Piazzale Michelangelo, but go a bit further to San Miniato al Monte for an even better view at one of the city’s oldest churches.
• Go to Il Latini for the best Tuscan meal of your life.
• Some of the best restaurants are in the winding streets between Piazza della Reppublica and Piazza Santa Maria Novella.
• The best tiramisu is at Le Collinine, around the corner from Santa Croce.
• Florence is where you should buy quality souvenirs — buy gold (the city only permits 18k gold and up!) on the Ponte Vecchio and leather in the boutiques near Santa Croce.
• There is surprisingly good shopping in the basement of the train station!
• Don’t admire the statue of Neptune in Piazza della Signorina — Florentines consider it the worst art in the city, and it’s often debased.

Tuscany

• Visit Pisa, but don’t make a day of it — you don’t need to spend more than an afternoon.
• Pisa and Lucca, with the bulk of the time spent in Lucca, make an easy Tuscany day trip from Florence.
• Tuscany is still a great place to rent a villa for a week.  The best Tuscany villas are the ones in towns that aren’t mentioned in your guidebook.
• The Chianti region is part of Tuscany, and October is harvest time.
• Fiesole is the easiest Tuscan day trip from Florence — just a 20-minute ride on the public bus!
• To see the most of Tuscany, rent a car — that way, you can hit up five towns or so in one day.

Venice

• Consider visiting Venice in winter.  It’s far less crowded and the city gets an ethereal feel.
• If you’re going to ride in a gondola, just show up and wait.  The gondoliers will do the bargaining for you.
• It may be less romantic, but cram as many people as you can into the gondola (up to six people) — the price is supposed to be the same, no matter the number of people.
• Get lost.  Venice is a great city in which to wander the streets and end up in somewhere totally random.
• Don’t waste your money on a Bellini at Harry’s Bar — unless rich old people and package tourists are your kind of crowd.
• Take the boat to the island of Murano for a glassblowing demonstration — it’s definitely worth it.

Other Destinations

• In Capri, the best things to do are in Anacapri — hike the island and take the chairlift up to Monte Solaro on top of the island.
• In Assisi, climb Rocca Maggiore, the tallest mountain in town, for an unspeakably scintillating view across miles and miles of the Umbrian countryside.
• In Orvieto, check out the instruments of medieval torture displayed in the middle of the town.
• In Santa Margherita, skip the beach and head to the art-selling markets instead.

You can find the best prices on hotels in Italy here. As with any destination, I recommend purchasing travel insurance before heading to Italy. I never travel without it and always use World Nomads.