Last Updated on 06/06/2021
Italy has long been a bucket list destination, but lately it’s been more popular than ever. A vacation to Italy can be whatever you want it to be. Want to relax by the beach and not do a thing other than eat gelato and get a tan? Done. Want to see stunning architecture and have days filled with tours and activities? Also doable. Italy is incredibly unique by region. The ancient city of Rome will offer an entirely different experience than the sun-drenched beaches of Puglia.
After years of living and traveling in Italy, I’m sharing my top tips for how to plan a successful trip (no matter what the agenda)! From researching transportation to booking tours, these steps will help you plan your vacation to Italy.
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Using Instagram and Pinterest
You’ve probably found inspiration all over Instagram and Pinterest already. But why not take Instagram a little further by finding people to follow that live in the area and dive into their geotags. Locals typically have all the insider tips on where to stay, the best places to eat and unique things to do. I really take advantage of the “Save” feature on Instagram. When I come across a place I’d like to stay or a cute coffee shop, I save it in my Italy folder. Same for Pinterest.
Pinterest isn’t just a place for recipes and dreamy interiors. It’s full of travel tips, packing guides and hotel recommendations that will help you plan your trip. Don’t forget to refer back to your saved images and pins when thinking about exact places you want to visit and things to do in Italy.
I’d highly recommend doing significant research to see exactly what’s feasible for your timeframe and budget. For me, research is the most time consuming part of planning a trip. Sure there are people that like to wing it. They just show up, rent a car, drive without a destination and hope to find a place to stay along the way. I am not one of those people. (With the exception of that time we left a window for two or three nights in the Dolomites when we were on our Northern Italian trip.)
Researching transportation ahead of time is crucial if you’re planning a multi-city trip by public transportation. It’s important to check the schedule of trains, buses and ferries ahead of time. The times and days they runs might affect how many days you stay somewhere. I book trains in advance directly on Trenitalia or Italo because it’s usually much cheaper than buying a ticket from the terminal. However, I always buy ferry tickets at the dock (personal preference). Rome to Rio is also a useful tool to see different routes and costs for various modes of transportation.
Planning a road trip? That’s a whole different beast. Tackle that one by reading my tips for driving in Italy.
Italy has so many festivals, Saint’s Days and public holidays. You’ll definitely want to research if any of those will be corresponding with where you’ll be and when you’ll be there. How disappointed would you be if you visited Tuscany and realized you JUST missed the famed Brunello wine festival? Or on the other hand, how annoyed would you be if you didn’t realize the day after Easter (Pasquetta) is a huge holiday and families traditionally go to the beach for a picnic. My friends were in bumper to bumper traffic for almost 4 hours from Naples to Positano on what they thought was an average Monday.
You might need to take into consideration who you’re going with. Is this a multi-generational trip where there’s something for everyone to do? Does everyone have the same physical capabilities? If not, is accessibility going to be an issue? Planning a packed day in Rome with walking tours, a trip to the Vatican and then straight to dinner might be physically feasible for some in your group, but not others.
Create your Itinerary
I use the notes app in my phone to keep track of what I want to do on which days. I start with the things I know I want to do that might only be offered on a particular day or are otherwise time sensitive.
Even if you’re only visiting one city, it’s best to have a vague idea of what you want to do on certain days. For example, the Vatican is open on Friday nights during the summer and it’s wonderful. You’ll want to pencil that in. Most museums in Italy are free the first Sunday of the month. If you’re on a shoestring, the long lines might be worth it. Rather spend money and not time in line? Plan your itinerary accordingly.
You’ll also want to keep in mind travel times between destinations in Italy. Make sure you have a little bumper of time for unexpected delays. Italy isn’t known for it’s punctuality. For example, if you’re traveling from Rome to Ischia, opt to take a later ferry just in case the train is late or there’s traffic in Naples.
When making your itinerary, you might have to give up a few things due to time constraint and it’s ok that you don’t see everything. I lived in Italy for almost three years and I still have a long list of place I want to go. You will stress yourself out if you try to pack too much in (ie trying to see Rome, the Amalfi Coast and Puglia in just 7 days). Part of traveling is experiencing the adventure. So, leave room to wander the area and don’t plan every single second.
Book Flights and Hotels
After I’ve done the research and have a loose itinerary scheduled, I start booking. I use Skyscanner and Google to research the best flights. If you’re flying from the States, airlines usually include one checked bag. A few transatlantic budget airlines are popping up and checked bags are usually not included so be mindful of that when booking.
Depending on what time of year and how long your trip is, you might even get away with a carry on. I once did three weeks in Europe in August with just a carry on. Those master packing skills will be shared on another day in another post.
I usually book hotels with Booking.com or directly from their website. They offer a lot of smaller properties, family villas and farm stays that might not have their own website or booking system. I sometimes check TripAdvisor for the “Traveler’s Photos” to get a more realistic idea. Depending on the location and length of trip, I’ll also look at Airbnbs.
Keep in mind your budget and don’t be disheartened if you find out that dream hotel in Positano you wanted to stay in is totally out of your price range. Sure, I’d like to stay at the Le Sirenuse too, but it’s just not practical for the average person. There are many wonderful places to stay in Positano and you can have a similar experience without staying at the most Insta famous place.
If you want to go to the most popular attractions, book ahead to save yourself from waiting for hours in lines. While this isn’t as necessary if you’re visiting Venice in the winter (there was absolutely zero line at the Doge’s palace), you’d want to book ahead for the Colosseum in July. Places like the Galleria Borghese will sell out weeks in advance and require pre-booking. I learned that one the hard way on my most recent trip to Rome.
Remember that super popular restaurant in Rome you saved? Better make a reservation! Italy loves reservations. Don’t make a reservation for every single meal, but you should for the places you have your heart set on. If you can’t make a phone call, try to contact them via email or Facebook messenger.
Use Google Maps
I am an avid Google maps user. If someone I follow on Instagram shares a coffee shop in just about any place in the world I might visit one day, I star it. If I read the latest Travel and Leisure magazine and they mention an interesting restaurant, I star it.
This will also come I handy while building your itinerary. You can visually see where stars are bunched. You’ll see you can hit the Trevi fountain, the Pantheon and Piazza Navona with ease. Don’t forget about the rest of the things you can’t miss in Rome.
Once you get to Italy, it will be easier to navigate the maze of cobblestone alleyways. If you don’t want to get an international plan, you can always put your phone on airplane mode and still use GPS. I download the map ahead of time and let that little blue dot be my guide.
Try not to overpack. You do not want to be that person that’s wheeling around a massive trunk on the cobblestones. The cars and elevators are smaller in Italy too. Your luggage simply might not fit in your rental car. Don’t forget an adapter!
Italy also loves cash. Most restaurants will accept credit card, but you should pay cash for smaller purchases like coffee and gelato. Instead of brining euros, I use ATMs to get cash. Be sure to get a credit card with zero foreign transaction fees.
Going to plan a trip to Italy one day? Pin this for later!