(without losing your mind)

Rome Colosseum, Italy, plan a trip to Italy, Italy travel planning, Italy itinerary, Italian itineraries — *The Colosseum in Rome on an absolutely gorgeous April afternoon. Look at that blue sky!*

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So you’re going to Italy!

(but now what??)

Italy is one of the most beautiful, most breathtaking places in the world. The country offers so much history, culture, architecture…and of course, the food! It’s no wonder so many have it at the absolute top of their Bucket List.

But with so much beauty, SO much to experience, and such limited vacation time, trip planning to Italy trip can also be overwhelming. Everyone has thoughts on what you “must do”, and there is almost too much info out there that it’s sometimes hard to figure out where to start.

If you want to plan an Italy trip, but have no idea where to begin, this post is for you!

Civita di Bagnoregio, Italy, how to plan a trip to Italy, Italy travel planning, Italy travel — Civita di Bagnoregio in Umbria

Let’s journey together!

In this blog post, I’m going to take you step by step through the planning process. I will be discussing initial planning decisions and also provide some helpful tips along the way. I’ll be covering:

First Things First - The When, Where, and How Long
Book Your Flight
Book Your Hotels
Book Your Transportation
Book Your Daily Activities - tours & dining

So, if you’ve dreamed about taking the Italian trip of a lifetime, but are overwhelmed and not sure where to start, keep reading! Planning a trip halfway across the world doesn’t have to be stressful and I’m here to guide you along the way!

First Things First -
Where are we going; when and for how long??

One of the biggest misconceptions people have (myself included!) when planning a trip to Italy is that you’ll be able to see the entire country in 1 or 2 weeks. Italy is a big country! Train travel definitely makes getting around super convenient and efficient. But traveling from north to south still takes a long time. Think about it…you wouldn’t plan a “tour of Florida” and visit Jacksonville, Orlando, Tampa and Miami all in 1 week, right? And Italy is 2.2 times as large as the state of Florida.

Every time you travel between cities or towns and switch hotel rooms, plan on it taking about half a day (you’ll be checking out of 1 hotel, taxi to train station, time at train station, train ride, transit to 2nd hotel, possibly dropping bags and coming back later to settle into your new hotel room, etc). So while train travel is super convenient throughout the country, it does take time to transition from 1 spot to another. Don’t underestimate your travel time or you’ll be hectically running from one place to the next! Make sure you give yourself plenty of time to enjoy and relax.

I recommend choosing 2-3 Top Spots to establish as your “home base”. Then you can sprinkle in some day trips or stops between locations on your travel days. If you have 7 days (not including your overnight travel day if coming from the US), I would pick no more than 2 cities/towns to stay overnight. With 10 days, add in a 3rd location. 10 days is a great sweet spot if you can manage it. If you have more than 10 days, even better! Add in another location or just plan to stick with 3 and truly immerse into the culture! Anywhere you decide to go, there is ALWAYS more to see!

How to pick your Top Spots -

To narrow down your list of “must visit” spots, check out some of my top destinations! Another good place to start is by grabbing the latest copy of Rick Steves Italy. Lots of great travel tips and details on several locations and how to find the best hidden gems! When picking your 2-3 Top Spots, you may want to stick to either northern or southern Italy, or a specific region. This reduces travel time in between locations.

Here’s a few 10 day Italy itinerary suggestions - great for first-timers

Classic Italy: Venice + Florence + Rome

Coast. City. Countryside in Southern Italy: Positano + Rome + Orvieto

Lakes of Northern Italy: Milan + Como + Verona + Venice

Under the Tuscan Sun: Florence + Siena + Montepulciano

Any of these give a great taste of Italy and would be plenty of time to enjoy in 10 days.
Plus, there are several small towns & spots for day-trips nearby to see even more without feeling rushed.

Book Your Flight

The first major item you want to book is your flight. Try to book as far in advance as possible. Most airlines open up air fares 11-12 months in advance. I recommend booking between 6-9 months out, if possible. Air fare continues to be on the rise. So if you’re waiting for a drastic drop in prices, it’s probably not happening anytime soon.

Start checking out prices on google flights, kayak.com or skyscanner.com. If your dates are flexible, play around with the actual day you fly out to find which is the cheapest option. If you’re flying from the US, more than likely, it will be an overnight flight to Italy. Consider premium economy. It doesn’t quite have all the benefits of Business Class but will allow more room and comfort than basic economy with a more tolerable price tag.

US Airlines or European Airlines

Price out different airlines - both your standard US airlines (Delta, United, American) as well as European airlines. Sometimes the European airlines may be cheaper. But note - you will usually have a layover (or 2) in a European city so make sure you have plenty of time for a layover. You will need to go through customs and immigration at the first EU city you fly into. European airlines also have smaller max carry-on dimensions and weight limits; and they tend to be more stringent as well.

If you have a credit card with airline points or are already a frequent traveler, for sure, go with that airline and find the best cost/flight times within your search.

Plan a trip to Italy, Italy travel planning, Italian itinerary, where to visit in Italy — What airport to fly into?

There are 2 international airports with direct flights from the US:
-> Rome - Leonardo da Vinci–Fiumicino (FCO)
-> Milan - Milan Malpensa Airport (MXP)

Depending on your travel itinerary, it might be more convenient to fly into one city and out of another. There’s plenty of other international airports all over Italy as well. It might make more sense to fly into the airport closest to your first destination. For example, if you’re starting in the Amalfi Coast, Naples airport is the closest. But you’re probably still connecting through Rome on your layover (or another European city). Price out options and flight times to fly into both Rome or Naples; which is cheapest and which gets you to your hotel room the quickest.

If you find yourself stressing out on where to fly into, just keep it simple. If you plan to stay south or central, fly in and out of Rome. If you’re going to be in the north (Venice, the Lakes, Cinque Terre), Milan is your best option. You can easily grab a private transfer to anywhere (although not exactly a cheap option). Or you can just jump on a train to get you heading where you want to go.

A few tips on picking flights:

-> When checking a bag, try to schedule as few layovers as possible. I also highly recommend Apple Airtags to keep close tabs on your luggage.

-> You’ll go through Customs & Immigration (C&I) in the first country you land in. So, if you have a layover somewhere in Europe, that’s where you’ll go through C&I. Make sure you have plenty of time on your layover; preferably minimum of 1.5 hours. Try to avoid Paris’s Charles de Gaulle Airport (CDG) for a layover if possible. It’s massive and crazy busy! You don’t need that stress if you can avoid it. Note - Once you’ve gone through C&I at any EU city, you won’t have to go through again at your final destination. (Example - if you fly from NYC to Brussels to Rome, you’ll go through C&I in Brussels, but not again in Rome. You will pick up your checked luggage in Brussels and recheck it for the flight to Rome).

-> Once you find a good flight with a decent price and minimal layovers, track the prices for a week or 2. But if they haven’t budged, go ahead and grab those flights before it’s too late! More than likely, the price will increase once more tickets are sold.

-> And by all means, if you find a fantastic deal on a great flight, GRAB IT IMMEDIATELY! Do not hesitate!

Book Your Hotels

Once your flights are booked, start looking to reserve your accommodations. When booking hotels, decide on the neighborhood or location in the city that you want to stay in first. In the cities, do you want to stay in the city center near the main sites? How walkable is the area? Are taxis and public transportation conveniently located nearby? In the country, do you have means to get around? If you don’t have a car, are taxis readily available into town?

A lot of hotels throughout Italy will include breakfast. This is a nice perk to start the morning off with some fuel for a full day of walking/exploring! Hotels in Italy don’t always have elevators and/or air conditioning. If either of these are a deal breaker for you, make sure you check the amenities before booking. 3-star hotels in Italy are usually very nice. Look for smaller, boutique style hotels for friendly staff and a personable experience!

Once you’ve narrowed down your dates, town and neighborhood, search for hotels here.

Book Your Transportation

Personally, I do not recommend renting a car unless you’re traveling in the countryside, say Tuscany/Umbria or up north near the Lakes. Driving in or near the main cities in Italy is chaotic. I’m sure there are plenty of Pros, but there’s also a TON of Cons, including hefty fines for driving where you’re not allowed. If you’re looking for car rental tips, there’s plenty of other info out there. I mainly stick with trains, taxis or private transfers so that’s how I’ll guide you.

Once you’ve chosen 2 or 3 “home bases” for your trip and booked your hotels, you will need to decide how to get to and from each location. Rome to Rio is a great tool to see the different possible options of transportation between cities/towns. You can view their website online or download the app.

Travel by Train:

Train travel is very convenient throughout Italy and can be done pretty cheap as well. You’ll want to download the Trenitalia app to purchase and store your train tickets. Once you have your flights and hotels booked, start looking at booking your train tickets. If traveling from one large city to another (Rome, Florence, Naples, Venice, Milan), you will want to book the fast trains. They are a little more expensive than the regional trains. But far less stops and the fast trains are just…well… faster (like really REALLY fast!). Book your fast trains in advance; about 1 to 2 months beforehand. Regional trains can be booked a couple days in advance. You can always purchase train tickets at the train station windows as well. But, it’s just super convenient to purchase them in the Trenitalia app and have them saved all in one place on your phone.

Train Ticket Validation - all train tickets need to be validated. This is another reason it is more convenient to purchase train tickets online and have them saved on the Trenitalia app. If purchasing paper tickets at the train station, you will need to go to a separate kiosk to validate your ticket. If you purchase through the app online, it’s all right there. Fast train tickets will automatically be “validated” on the app within 24 hours of departure. For regional train tickets, there’s 1 small additional step. Within 24 hours of departure, go into the app and locate your ticket; click the “validate” button. (Very similar to the same process when you “check-in” for a flight).

You will still pass through a metal detector and show your ticket to the gate agent at the train station. But it is not like airport security. You do not check your bags and pass anything through a security conveyor. Just walk through the gate with all of your belongings.

I was SUPER nervous and having major anxiety about using the trains in Italy. They turned out to be pretty easy to navigate and a very convenient way to travel. Just be sure to give yourself plenty of time before your train. That way, you can get a good understanding of the layout of each train station and know exactly where you’re going when your platform number comes up. The Man in Seat 61 is a great site for all the details and step-by-step guide for train travel.

Private Transfers:

Look, sometimes it’s just better to avoid the stress and spend the extra money for a private car transfer. For example, when we were looking at booking flights last summer, airlines were REALLY struggling with delays, missed connections and lost baggage. Even though I knew we were going to start our trip in Positano, we decided to fly into Rome instead of Naples and avoid a potential issue with our layover. So we would be traveling from the Rome airport directly to Positano after landing. We could have taken the Leonardo Express train from the airport to the Rome train terminal; then a train from Rome to Naples; then a car from Naples to Positano. But, thinking about trying to figure out the train system our first time in Italy immediately after an overnight 9-hour flight (where we probably would not have much sleep) was giving me major anxiety. To me, booking a private transfer to pick us up right at the airport and take us immediately to our hotel in Positano was well worth the extra cost. Sometimes it’s just better to spend a little more for convenience and peace of mind.

For our Rome to Positano private transfer, we used Joe Banana Limos. They were fantastic! Good communication, professional drivers, great vehicles, always on time, and great customer service. We ended up adding a stop in Naples for lunch; and booked them for our Positano to Naples transfer as well. They assisted us with booking times and were very communicative throughout. I would highly recommend them for any transfers in Italy!

Taxis - easily available in all the major cities. Most take both credit card or Euros. Just ask your hotel for the nearest pickup spot. There’s usually a taxi line near all the major attractions. Make sure to look for the white cars with the “Taxi” sign on the top for the official taxis. These taxis have set prices. Other “non-official” taxis will charge you much more! (We learned this the hard way!!) If you’re staying in smaller towns, your hotel should be able to call for a taxi for you. Just let them know earlier in the day to make sure there’s availability when you are needing it. Many smaller towns may only have 2 or 3 drivers total, and will be transporting visitors all afternoon/evening.

“When dealing with complex transportation issues, the best thing to do is pull up with a cold beer and let somebody else figure it out.”

— Anthony Bourdain

Booking Your Daily Activities

Now that you have your main travel details planned, start thinking about your day to day activities; including day trips, tours and restaurant reservations.

Tours - Start with booking your main “must see” sites. You will want to pre-book all tours or entrances at all major tourist sites and museums (Colosseum, Vatican, Uffizi Gallery, Academia, etc). Otherwise plan on spending lots of precious time waiting in long, hot lines. These book up quickly, so don’t wait too long to book. See my City Guides below for recommended private tours, small group, and group tours. Book your major tours first. Then plan the remainder of your days around those plans.

Day trips - If planning a day trip to somewhere near your home base, book your train tickets if traveling by train. Plan to head out earlier in the day to make the most of it and don’t cut your time too short. Plan plenty of time for travel to and from. Go ahead and book the tour as well so you have the time accounted for. Viator offers plenty of great tours all over Italy. Check out a small group tour for reasonable prices per person but still with a personalized touch. Start your search from your home base. Many times, transportation to and from your hotel is included.

Meal reservations - if there is a restaurant that you ABSOLUTELY have to experience, make a reservation if possible. Plan to book a few nice dinners ahead of time. But also allow yourself to wander into charming cafes and interesting osterias. For the best meals with local, fresh ingredients, ask your hotel for their recommendations. Beware of restaurants right by major sites that have signs with photos of the food and someone out front trying to usher you in. Many times, these are tourist traps where you’ll get mediocre meals for a higher price tag. TheFork is Italy’s version of Open Table for easily making dining reservations, and it works very similarly. View their website or download the app. They don’t have a TON of restaurants included and the “view menu” option can be lacking. But if you’re trying to find somewhere near your accommodations or a specific site, it’s a good tool to use to ensure you can get reservations.

Most important tip - don’t overly plan every minute of the day. Leave plenty of time to shop, wander…and of course eat! Italy is enriching, enticing and exhilarating. But it can also be exhausting! Embrace the Italian way of life and enjoy an afternoon siesta!