It starts with a wish list.
Planning your first trip to Italy? Your wish list probably keeps getting longer. Rome, Florence, Venice, a few days in Tuscany, and maybe the Amalfi Coast while you’re there. I get it. When you’ve waited a long time for a trip, it’s tempting to fit in as much as possible.
But every new stop means packing up, checking out, and getting settled somewhere else. I’m a big believer in leaving yourself time to actually enjoy the places you’ve come to see. Sometimes, that means saving a few for your next trip.
Rooftop view of the Colosseum in Rome, Italy
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Changing destinations and hotels takes more time than you think.
A two-hour train ride sounds easy enough to work into your itinerary. But that’s only one part of moving from one place to the next.
You’ll need to pack, check out, get to the station with time to find your platform, and then make your way to your next hotel. Your room might not be ready when you arrive, either. Before you know it, that quick train ride has taken up a good portion of your day.
On your first trip to Italy, it’s easy to overlook those extra steps. This is something I pay close attention to when planning an itinerary. I look at the whole journey between hotels and how much time you’ll actually have to enjoy each stop once you get there.
Leave room for the Italy you came to enjoy.
You’ll probably have a few things you don’t want to miss, and you should absolutely make time for those. But leave yourself some time to wander, too.
Maybe you find a little shop you want to browse, order another glass of wine over lunch, or spend an hour sitting in a piazza watching the world go by. Those moments deserve a place in your vacation, even if they don’t have a reservation attached.
One of my favorite things to do in Rome is enjoy the view from a rooftop terrace. I want time to sit there and take it all in without checking the clock.
Your first trip to Italy deserves that breathing room. Staying a little longer gives you more chances to enjoy where you are.
First spritz when arriving in Rome
Start of an amazing food tour in Florence
How many stops should you actually plan?
The right number of stops for your first trip to Italy depends on how much time you have and how you like to travel. Some people enjoy moving every few days. Others would happily spend a week getting to know one city.
I start with the number of nights you’ll actually have in Italy and your priorities. Geography matters, too. A stop that looks nearby on a map may involve multiple connections or an awkward travel day.
For my clients, I usually recommend at least three nights in each main destination, preferably four. Three nights gives you roughly two full days between arrival and departure. That fourth night gives you more room for sightseeing, exploring, and enjoying yourself without watching the clock.
Shorter stays can make sense, too. If a town on your day-trip list is somewhere you really want to experience, consider spending one or two nights. Part of the magic of Italian towns is being there after the day-trippers leave, when you can linger over dinner and enjoy a quieter evening.
When I plan an itinerary, I weigh that experience against the extra move. Sometimes another stop works beautifully. Sometimes an extra night where you already are makes more sense.
Enjoying a beautiful evening in Cortona (Tuscany). We settled in for a 5-night stay.
Start with what matters most to you.
Before you add another stop to your first trip to Italy, take a step back and ask yourself:
What would you be devastated to miss? Seeing famous works of art, exploring small towns, enjoying the food, or spending a few days by the water. What are you most excited about?
How often do you want to pack up and move? Be honest about how much you enjoy changing hotels.
How do you want your days to feel? Full of sightseeing, mostly leisurely, or a little of both?
Your answers can help you decide what belongs on this itinerary and what can wait. You don’t have to fit every destination into one trip to make it a memorable one.
Need a hand planning your first trip to Italy?
I’ll help you choose the stops, find hotels that fit your style, and work through the logistics so you can look forward to your trip without getting overwhelmed by the details.
Explore my custom Europe planning services to see how we can get started.
