How to Plan a Trip to Italy Without (totally) Losing Your Mind
- Camille Gonzalez, MPH
- Dec 17, 2024
- 13 min read
Planning a trip to Italy can be overwhelming, but it doesn’t have to be. Here are some resources and tips we found useful when planning our trip that we wanted to share with you. We did use other resources and whatnot, but what’s listed here are the resources that helped the most. As for the tips, these come from a combination of research and firsthand experience in Italy. In this blog, we’ll first go over the resources and later on we’ll provide some tips for planning and making your trip go smoothly.
Resources:
Reddit - r/ItalyTravel and subreddits for specific cities in Italy (r/Rome, r/Florence, etc)
Youtube
Rick Steves’ Italy
If we could only choose one resource to use while planning a trip to Italy, it would be this one. Rick Steves is the go-to guy for all things Europe and there is a good reason for this as he has traveled throughout Europe more than most Americans. Each chapter of Rick Steves’ Italy goes in-depth into everything you need to know about that particular area of Italy, from food to culture to notable sites and more. He lists places to stay, where to find public transport, and even information like where to get your laundry done. He is blunt about things and will be truthful about what areas or attractions are not worth visiting. Many chapters provide step-by-step detailed directions on where to walk in particular areas to maximize what you get out of it (we followed his steps in Sorrento, for example, which allowed us to learn a little bit more of the historical aspects of this tourist town. His “Heart of Tuscany” drive was another one we followed and really enjoyed as it allowed us to experience some of the scenic parts in the Tuscany area that we might have otherwise missed).
While there is a lot of useful information in Rick Steves’ Italy, there is no reason to read the entire book from front to end. Instead, what we did was go through the chapters of places we wanted to visit, took notes on the parts that were relevant to us and on places/activities we were interested in potentially doing, and then later on sat down and went through the list crossing out things we knew we couldn’t fit into the trip. We did this in conjunction with the information gathered from our other sources, though Rick Steves was truly our main guide. We brought all our notes with us on our trip so as to not lug around a book in our bags.
By the way, this book contains more than just basic information. Rick Steves also gives great recommendations for tour guides, places to stay, places to eat, and more that are truly top-notch. If it weren’t for his guidebook we would not have found the wonderful agriturismo to stay at in Tuscany or the amazing tour guide in Rome, for example. Rick Steves’ Italy truly is the go-to guide book for planning a trip to Italy.
Don’t feel the need to purchase the latest version of this book either - we rented ours from our local library for free. Any copy that's been published within 2-3 years from the date of your travels should suffice. I would avoid using any Italy guidebooks (Rick Steves’ or otherwise) that was published prior to 2022 as a lot has changed in Italy since the pandemic.
Our agriturismo in Montalcino, which we found in Rick Steves' Italy
Reddit can be a wealth of knowledge for a variety of subjects, and travel to Italy is no exception. When planning our trip to Italy, r/ItalyTravel was incredibly useful. For one, you can directly interact with others in order to get information or have questions answered about your trip to Italy, which is something you obviously cannot do with a guidebook. r/ItalyTravel allows you to post your potential itinerary and get feedback, which in our opinion was one of the most useful aspects of this subreddit. Our trip to Italy went flawlessly and we would say this was in large part due to the feedback we received on our itinerary. When posting your potential itinerary, make sure to include relevant details such as: the approximate ages of everyone on the trip, your budget, things you do and do not like to do, whether you’ve visited before, places/experiences of particular importance to you, etc. This allows redditors to get a feel for who you are and thus provide better feedback.
r/ItalyTravel and other Italian-specific subreddits are also wonderful resources for finding lesser known tidbits of information and in particular, restaurants. If you’re a foodie like us then you will become overwhelmed by the quantity of amazing restaurants in Italy. Further, it is absolutely vital that most of your dinners are reserved in advance. So knowing where you want to eat (particularly for dinner) is important when planning a trip to Italy. This is again where making posts about who you are and what you want to eat becomes useful. You can also simply read through old threads as there are a plethora of threads going over all types of food-related questions (and threads on a variety of other topics like shopping, whether places are accessible to disabled folk, how to take the trains, etc). Clearly we love food, so we’ll continue to use that as an example in this blog. Some of the best restaurants we ate at came from reddit. For example, a post made by an angry Roman who was dissatisfied by the restaurant choices American tourists were making helped us find Poldo e Gianna, the restaurant where we had the best carbonara of our lives. r/Florence helped us find the small but spectacular Enoteca Pitti e Golla, a truly local gem that blew us away with great wines and seasonal plates of food. Do some digging and you’re guaranteed to find treasure.
Tips for Having a Successful Trip to Italy
As you can probably tell by now, planning a trip to Italy can be a lot. So here are some tips that helped us have a pretty much flawless trip to Italy.
Plan your trip outside of tourist season - I know this can be tough for many but if you can, plan your trip outside of tourist season (which is May - September). If you can't, at least try to plan the trip at the outer edges of tourist season (April and October). Trust us when we say, Italy is packed with tourists even outside of tourist season. You will be miserable as you fight through crowds, especially in the summer heat. Also important to note that August is generally a month to avoid traveling to Italy as many Italians go on vacation during that time and thus many shops and restaurants are closed.
Get a good tour guide with connections to the places you are visiting - Let us explain. There are so many options for tour guides in Italy, each with varying degrees of quality. If you can afford it, pay extra for a really good tour guide as you are not only paying for a quality tour but also other perks like expedited entrances into places. For example, our tour guide for Rome (which we found in Rick Steves’ Italy) had previously worked in the Colosseum and through her connections (i.e. people still working there) she was able to skip the line and get us into the Colosseum faster. We had similar experiences with our guides at the Vatican and Pompeii.
Go to sites on days and times that will be less busy, and make sure you know what days sites are open/closed - This one might seem obvious but many people do not take this into account when planning their trips. Sometimes visiting a site on a weekend may be unavoidable but if you can, plan to visit the busiest sites on weekday mornings. We went to the Vatican on a Monday for this reason (it was still incredibly busy by the way, which it always will be. Our guide said Tuesdays and Wednesdays were the least busy days). But this is not only about what day of the week it is - many sites have “free days” which are the absolute busiest days for these sites. We would suggest avoiding free days all together unless you are on an extremely limited budget. Also important is knowing what days sites will be closed as it can sometimes be quite random. The time of day makes a difference as well. While in Florence for example, we visited the Academia (where the David statue resides) at 8:30am. While there were still people inside, we were able to get a good look at David and all the other fantastic pieces of art without fighting crowds.
Buy tickets in advance - This is another one that may seem obvious but can get confusing once you start diving in. Many of the popular sites (like the Pantheon, for example) will not release tickets until a certain time frame beforehand (for example, a place may not open ticket sales until one month prior to the date). To make things extra fun and confusing, these ticket sales dates will change out of the blue (this happened to us with the Vatican, which we almost missed out on). Figure out in advance the schedule of when places release their tickets online and create a calendar reminder for yourself for when to buy them. This is definitely something to stay on top of as certain tickets will sell out fast. Oh, and did we mention the websites for these ticket sales are clucky and difficult to navigate? Yeah. This is where having a good tour guide who can walk you through the process becomes useful (our tour guide for Rome gave us instructions on how to purchase tickets in an email). Reddit is also useful here if you are super lost and need guidance.
Have a plan, but also don’t - A perfect trip to Italy will strike a balance between planned moments and unplanned moments. We know it’s difficult to resist squeezing in as much as you can into every day of your trip, but believe us when we say it ain’t worth it! Italy is quite stimulating and you will find yourself feeling tired more quickly than usual. If you are exhausted, you will not enjoy whatever activity you decided to squeeze in instead of resting. On the flipside, if you plan every moment of every day, you will not have a chance to explore (which is a big part of the fun in Italy!). Believe us- do not plan every minute of every day. Instead space it out. Our days were varied but essentially, some days we had multiple activities planned, some days we had none. On the days with multiple activities, we had breaks in-between (so no plans back-to-back). We also planned our overall trip to be a mix of “busier” locations (Rome, Naples, Florence) and “calmer” locations (Sorrento, Tuscany). Our trip went from Rome -> Naples (where we also went to Pompeii) -> Sorrento ->Florence -> Tuscany. As you can see, our stops in Sorrento and Tuscany gave us breaks from the bigger, more hectic cities.
Do not engage with scammers at all - And by this we mean do not even say "no thank you" when they offer you something. I know it sounds incredibly harsh but many will start to haggle you the moment you give them any sort of entry. Even a "not interested" is enough for them to say "but...". Many scammers are not the stereotype you are picturing in your head but instead are often women and children. Some go as far as working in coordinated teams - think street performers everybody is distracted by while a pickpocket comes around. This is not to say you should walk in constant fear and paranoia (the internet makes scamming out to be a way bigger deal than it is) but just don't be stupid - Leave nothing in your pockets and hold your bag (zippers closed) in front of your body (FYI you will see many Italians hold their belongings this way as well. We also noticed many Italians with their phones on neck ties which was unexpected). How you dress plays a role here as well (more on that below in the clothing tip section). Be particularly cautious in crowded areas, popular attractions like the Trevi Fountain, and train stations.
Luggages should be small - Backpacks are the ideal luggage for Italy. Many places still don’t have elevators and believe us, you won’t want to be lugging heavy, large bags over flights of narrow stairs. We met a family from Arkansas who flew with multiple large, check-in size luggages only to realize their airbnb in Florence was up nine flights of tight stairs - Yikes. Not only that but most sidewalks are uneven and may be made of cobblestone, so rolling luggages are difficult to use. Also take into account the fact that for many European airlines, backpacks are the carry-on size. American carry-on sized rolling luggages are considered check-in for most European airlines. When wearing your backpack around town, be sure to lock the zippers to prevent pickpocketing (or do as we did, which was clip the zippers together in a way which was difficult to quickly unclip). More tips on how and what to pack can be found below in the Clothing and Packing tips section.
Other random tips in no particular order - Use the bathroom wherever you can as public restrooms are rare and usually cost money. Always carry a euro with you for when you must use a public restroom (Camille put a one-euro coin in her pocket everyday before heading out for this purpose). Carry baby wipes on your person especially if you gotta go poop in the public restroom (FYI most hotel and home bathrooms have a bidet. It is a separate seat from the toilet). Keep a foldable fan in your purse/bag as it comes in handy both for cooling off and for blocking out the sun. We found having a collapsible water bottle extremely handy, especially in Rome where public water fountains are abundant (the water is completely safe to drink by the way). If you’re like Camille and love snacking and hate wasting food, keep a ziplock bag in your purse for storing small snacks (you will be given free snacks if you stop somewhere to get a drink or small bite; it accumulates!).
Ultimately, go with the flow and take things in stride. Don't try to resist the chaos and embrace those things which are foreign to you. - This one is self-explanatory, but also necessary to state, especially if you’re someone who isn’t used to cultures other than your own. Do not expect Italy to be the United States - it isn’t. Cultures, customs, etc. are different. Just be open to it all and embrace it. (Don't be like that same family from Arkansas who, upon finding out that a lampredptto sandwich was made with finely chopped tripe, proceeded to make faces in disgust and throw the entire sandwich away without giving it a taste. Rude, narrow-minded, and, quite frankly, embarrassing.)
Clothing and Packing Tips
Before we end this, we did want to chat a little about clothes and what to wear in Italy as this is usually an area people stress about. We get it, you’re in Italy and want to look good. But here’s the other part travelers don’t take into account: What you wear influences how others perceive you, particularly scammers. So while you may or may not be a fashionista, having a basic sense of what to wear is important.
Italians are known for their casual yet put together look - they aren't trying too hard to look "cool". When packing clothes for your trip to Italy, however, keep this in mind: You are a tourist; you will not blend in as an Italian. However, NOT totally standing out as a tourist offers protections from people like pickpockets and scammers. We will admit we were worried about pickpockets as we read so much online about them. Within hours of arriving in Italy, though, we could immediately tell who these pickpockets and scammers were targeting - Men in basketball shorts and raggedy t-shirts, crocs and flip flops; Women trying too hard to look fashionable. Lululemon leggings. Baseball caps. Tourists in T-shirts with things like Disney characters on them. You don't need to dress over the top to look acceptable in Italy but you also don't want to dress down too much and become a target. Just go with casual, simple outfits (and by casual we do not mean what you wear at home on a lazy Sunday). Anyway, onto more specifics.
LAYERS! You hear this all the time and there is a reason for it. Unpredictable weather necessitates layers. This includes a shawl (which Camille will admit she’s never been a shawl person but it genuinely came in handy pretty much every day of the two week trip). Comfortable sneakers are a must. Besides comfort, shoes with heels are a genuine tripping hazard as most of the sidewalks and streets are not evenly paved. The great thing is that right now, as we write this in December 2024, walking sneakers are trendy. Many Italians (of all ages, we must add) are wearing walking sneakers with loose baggy trousers/pants, skirts/dresses, etc. Take advantage of this! It means you can look trendy and be comfortable! Just make sure to break in your shoes before your trip. Speaking of sneakers, SOCKS. Bring more than you think you'll need. It was not the change of shoes that relieved our feet but the socks. After walking all day long, being able to put on a fresh pair of socks for night was much needed. We would also suggest everyone, men and women, have a bag with them they can wear on day-to-day adventures. Camille thrifted a medium sized floppy, lightweight, neutral colored bag and it was perfect for storing everything she wanted to bring with her throughout the day (a small water bottle and shawl both fit in the bag). Nate wore a crossbody, slim brown bag that went well with all of his outfits. We would stay away from any backpacks as you want to wear your bag towards the front of your body to avoid pickpockets (the exception here is your actual luggage, which backpacks are ideal for, as described above).
For fashion inspiration, @romansinrome is a cool instagram page if you are curious to see what actual Italians are wearing. You can also look at pictures posted on instagram via geolocation. For Camille, a helpful resource was the youtube channel “Stay Fabulous”. She has videos posted on what to wear and how to pack for each season. She’s also got many other Italy-related videos that are very useful for planning your trip (for example, videos on customs you should know as a tourist).
When packing, the youtube page “Away Together with Nik and Allie” was incredibly useful. If you are like Camille and struggle with overpacking, Nik and Allie are great guides. Another useful packing method is the “5,4,3,2,1” method of packing. Essentially, you pack 5 tops, 4 bottoms, 3 shoes, two dresses, and one accessory “kit” (which includes jewelry and sunglasses). This will be modified based on your trip (for example you can replace the dresses with jackets/sweaters if it’s a cold trip, and if it’s a summer trip you will want to add a bathing suit) though the overall idea is the same. To make things even easier, stick to a color scheme so that your items can easily be mixed and matched.
So there you have it - How to plan a trip to Italy without losing your mind. We hope you find this useful when planning your next trip to Italy!
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