Because I lived in Italy, people are always asking for my advice on where to go and what to see in their Italy trip planning. I pulled several emails I’ve sent over the years and culled all of my advice into this post.
The first thing with Italy trip planning is to figure out the region you want to visit. Much of your trip planning will also depend on how much time you have. My one big piece of advice is to plan out your trip before you book your flights. You may decide to fly out of a different airport since the country’s best sights are rather spread out, and you can save a day in traveling between cities. You might fly into Rome and out of Venice.
If you have one week, I suggest 3 days in Rome and 2 days in Florence with one day trip either to Tivoli (from Rome) or Tuscany (from Florence).
If you have two weeks, I suggest 4 days in Rome, 3 days in Florence and the surrounding cities, 1 day in Tuscany, 2 days in Venice. You’ll lose a couple of days in travel times.
If it’s your first time in Italy, most people start with Rome. When we first moved to Italy, I spent 3 weeks in Rome and never got tired of it. There are the main tourist attractions – Pantheon, Vatican, Coliseum, Forum – you have to check off your list. Most of these can be seen in about 2 days. Naturally, if you enjoy museums, you’ll want to stay longer and allocate at least a half day to each museum (the Vatican and its museums can take a full day). Schedule in an afternoon to unwind and spend a day in the Borghese Gardens. A great day trip and one I highly recommend is Tivoli, about 2 hours south of Rome where you can see Hadrian’s Villa and Villa d’Este. We hired a private driver and it was the perfect way to experience these sights.
Once you’ve done Rome, take the train to Florence (it’s about 3 hours). Train travel is great in Italy and the easiest way to get around. Seeing Florence is at least a full day or day and a half (that’s a minimum. There’s certainly plenty to do for an entire week). Block off several hours to see the Duomo and plan at least four hours to see Michelangelo’s David at the Galleria dell’Accademia (I’d suggest making an advance reservation). Be sure to wander the streets of Florence and enjoy the street markets and walk across the Ponte Vecchio.
For the not faint of heart, I would suggest renting a car to see areas outside the city – the trains won’t take you into the country. You can do it all from Florence if you don’t mind a lot of driving. My favorite towns are Siena, San Gimignano and Lucca. My best advice? Skip Pisa. If you’ve seen a picture of the tower, you’ve seen Pisa.
If you’re driving adventure went well, I would suggest spending a day driving the Chianti trail – again, it starts about an hour outside of Florence and it’s a beautiful drive through Tuscany and you can stop at vineyards along the way and taste wines.
Venice is certainly a must-see and it’s about 2 hours by train from Florence (then you can train directly back to Rome if that’s where your flight is). Venice is great for just meandering through the canals, people-watching and eating some great food. I would suggest a trip over to Murano, where the famous colored glass is blown.
The Italian countryside
On your second trip to Italy, I recommend spending a bit more time in the country since you’ve seen the major tourist areas. I absolutely love the countryside of Italy and I when I travel there, I skip the major cities and head straight for the less populated regions of Tuscany and Umbria.
In Umbria, I highly recommend the Lungarotti winery and the Goretti winery. Nonna Marcella (the grandmother) also offers cooking lessons. Last summer, we rented a 4-bedroom villa near Perugia and hired a private to chef to come in and give us cooking lessons and prepare meals. We also stayed at L’Antico Forziere on another trip and it was modest accommodations (not luxurious) but the owners and the food were amazing! It’s in the middle of nowhere so you’d need to plan day trips (the owners of these small inns are very helpful in arranging things for you).
In Tuscany, we stayed at a fabulous agriturismo (apartments on a working farm), Belagaggio. You can eat some meals with the family and really experience day-to-day life on a farm. The owner let me stand in the kitchen and watch her cook and my kids would go with her to round up chickens and rabbits for dinner. For wine in Tuscany, I recommend the Baracchi winery. It’s in Cortona, an absolutely beautiful hillside town, where “Under the Tuscan Sun” was filmed. It’s a very small winery but they have a fabulous luxury hotel and restaurant (the hotel is rather pricey but if you can manage lunch there, I’d suggest it). There is also a great cooking school/chef in Siena, Ecco la Cucina. I met Gina when she was here in the states and I’ve had several friends attend her cooking school.