Italy Vacation & Travel Specialist

Spanish Steps, Rome, Italy

Planning a trip to Italy usually isn't difficult because you're struggling to find somewhere you want to go. It's the opposite. Rome, Florence, Venice, Tuscany, the Amalfi Coast, Lake Como, Cinque Terre...pretty soon that ten-day Italy vacation has three weeks' worth of places on the list.

That's usually when I start talking about what we can leave out.

I know that sounds a little backwards, but one of the biggest differences between a good Italy itinerary and an exhausting one is giving yourself enough time to actually experience the places you've traveled so far to see. Italy isn't a destination I think you need to rush through just to check another city off the list.

For some travelers, a first trip to Italy really does mean Rome, Florence and Venice. For others, it might mean slowing things down with a few nights in Tuscany, spending time along the coast, or heading north to Lake Como and the Italian Lakes. There isn't one itinerary that everyone needs to follow.

How you move through Italy matters, too. Italy's train system makes rail travel a great option between many major cities, while a private driver can make it much easier to explore the Tuscan countryside or smaller towns without the stress of navigating unfamiliar roads. Sometimes the best choice is a combination of both. I look at the entire itinerary before deciding what makes sense rather than trying to use the same transportation for every part of the trip.

Where you stay can change the experience just as much. A centrally located hotel can make exploring Rome or Florence much easier, while an agriturismo in Tuscany gives you an entirely different side of Italy. In places like Cinque Terre, Lake Como or the Amalfi Coast, location can be especially important because a hotel that looks perfect online isn't always convenient once you consider trains, ferries, hills and luggage.

Then there is everything you want to experience along the way. Private tours, food and wine experiences, museums, historical sites and day trips can add a lot to an Italy vacation, but I don't believe every day needs to be scheduled from morning until night. Some of the best parts of traveling through Italy can happen when there's enough room in the itinerary to wander, sit down for a long lunch or decide that you aren't quite ready to leave yet.

I've planned custom Italy vacations for couples and families, including trips that combine several regions of Italy as well as longer European itineraries that connect Italy with destinations such as Switzerland, France, Germany and Austria. Bringing together hotels, Italian rail travel, private transfers, tours and the right amount of time in each destination is where thoughtful planning can make a complicated itinerary feel much simpler.

Italy will almost always give you another city, village or experience you could add to the itinerary. The harder, and often more important, decision is knowing when you already have enough. A well-planned Italy vacation shouldn't feel like a race to see how many places you can check off a list. It should give you enough time in each one to understand why you wanted to be there in the first place.