“To have an ‘A’ trip, be an ‘A’ student.“ - Rick Steves

All of our travels have been prefaced with hours of research and prep. Every single time we have had a great trip, it has been from our utilization of Rick Steves’ books. Do yourself a favor and get his book on Italy and comb through the cities that you are interested in, you won’t regret it.


Alright, let’s begin. Italy is incredible, and you're in for a treat. Since you'll be in Umbria for the wedding, here are some of our favorite nearby experiences that are perfect for first-timers:

Must-See Cities:

  • Florence - Absolutely unmissable. Spend at least 2-3 days exploring the Duomo, Uffizi Gallery, and wandering the streets. Don't miss a spritz or the steak.

  • Siena - A charming medieval hilltop town with stunning architecture and the famous Piazza del Campo (extra special to us—we got engaged here!).

  • Assisi - A beautiful hilltop town rich with history. Learn about St. Francis and the Franciscan monks, visit the stunning Basilica, and grab lunch at La Bottega Dei Sapori we had amazing sandwiches there from the nicest man.

  • Rome - If you have time, the Colosseum, Vatican Museums, and Sistine Chapel are bucket-list worthy.

Food Experiences You Can't Miss:

  • Bistecca alla Fiorentina - Massive, perfectly-cooked Florentine steak (try it at The Antico Ristoro di Cambi in Florence)

  • Fresh handmade pasta - Look for small family-run trattorias, especially in Umbria and Tuscany

  • Piazza del Campo, Siena - Enjoy the spacious piazza where we got engaged and learn a little about the yearly horse race here. Arrive around sunset for a drink and you’ll get a light snack too.

  • Hilltop wine towns - Visit Montalcino, or Montepulciano for wine tasting with incredible views

  • Aperitivo culture - Evening drinks with complimentary snacks—a must-do Italian tradition

Art, History & Architecture:

  • The cathedrals are stunning throughout Italy. Each region has its own style. Don't miss the Duomo in Florence, Siena's striped cathedral, and the Basilica of St. Francis in Assisi.

  • Smaller museums often have shorter lines and incredible collections. Consider the Bargello Museum in Florence or Galleria dell'Accademia (home of Michelangelo's David). But don’t miss the Birth of Venus in the Uffizi!

Food Culture:

If you're used to Italian-American food, authentic Italian cuisine will feel refreshingly different:

  • Smaller portions, multiple courses - Meals are structured into courses (antipasto, primo, secondo, contorno, dolce) with modest portions focused on quality over quantity. Don't expect a giant plate piled high with pasta!​

  • Simpler, lighter sauces - Italian sauces are lighter and let the pasta and fresh ingredients shine, rather than drowning everything in heavy cream or tomato sauce.

  • No chicken on pasta - Italians rarely mix meat like chicken with pasta. Dishes like chicken alfredo or chicken parm don't exist in traditional Italian cuisine. Pasta is served with vegetables, seafood, or simple sauces, while meat comes separately.​

  • Cheese is an accent, not a blanket - Cheese is used sparingly to complement dishes, not cover them.​

  • Pizza is personal-sized and thin - Expect thin-crust pizzas with minimal toppings, fresh mozzarella, and light sauce, meant to be eaten with a knife and fork.​

  • No garlic bread - What Americans know as garlic bread doesn't exist here. You might get bruschetta (grilled bread with olive oil and fresh toppings) instead.​

Coffee Culture:

  • Espresso is the default - When you order "un caffè," you'll get a shot of espresso, not a large cup

  • Want something closer to American coffee? - Ask for "un caffè americano" (espresso with hot water added). It's the closest you'll get to drip coffee, though still more concentrated than what you're used to back home.

  • Cappuccino is for breakfast only - Italians don't drink milky coffee after 11am (it's considered too heavy for digestion after meals)

  • Coffee is a quick affair - Italians drink their espresso standing at the bar in about 2 minutes, not sitting for an hour. Sitting down often costs more!

  • No to-go cups - Coffee isn't meant to be portable; it's a moment to pause and reset

Getting Around Italy

  • Trains - Italy's train system is excellent for traveling between major cities. Trenitalia and Italo are the main operators, offering frequent high-speed connections between Rome, Florence, and other cities. Book tickets in advance for the best prices, and remember that train stations are typically in city centers, making them more convenient than airports. For trips to smaller towns like those in Umbria, you'll likely need to transfer to regional trains.

  • Renting a Car - For exploring the Umbrian countryside and smaller hilltop towns, renting a car gives you the most freedom. We've had excellent experiences with Europcar throughout Italy—they're reliable and have locations at major airports and train stations. Remember that U.S. drivers need an International Driving Permit (IDP) in addition to your regular license, which you can get from AAA before your trip. Automatic transmission vehicles are available, and Italians drive on the right side of the road, just like in the U.S.

  • Taxis & Rideshares - Taxis are readily available in cities, but always use official taxi stands or have your hotel call one for you. Uber is limited in Italy, so don't rely on it like you would back home.

Speaking Italian:

  • You don't need to be fluent, but learning a few basic phrases goes a long way. Italians genuinely appreciate when you make the effort to speak their language, even if it's just "buongiorno" (good morning) or "grazie" (thank you).

  • A simple attempt at Italian will earn you warmer service and more authentic interactions than defaulting to English immediately.

  • Check out this helpful guide to essential Italian phrases to get started. Focus on greetings, basic courtesies, and ordering food—these will be your most-used phrases.

Pro Tips:

  • Book museum tickets in advance to skip the lines

  • Wear comfortable shoes. You'll be walking on cobblestones

  • Learn a few basic Italian phrases, the locals really appreciate the effort!

  • Trust the regional specialties. Each area does certain dishes best

  • Try to avoid modifications or substitutions; the chef knows what works

Explore our interactive map to discover locations that hold special meaning for Melanie and me. Click on each pin to learn about the cities we've visited and our favorite hidden gems throughout Umbria and Tuscany.