Italy Unpacked: Our Planning Process, Top Tips, and 17-Day Itinerary
In a recent blog post, I shared more about our trip to Italy and talked about a few ways that I’m bringing Italy into my life in Billings. I have honestly not stopped thinking about our trip since we got home and love how it challenged me to think differently about certain things.
But with all the Italy talk (if you follow me on Instagram, you know I haven’t shut up about it 😂), I’ve had a ton of people asking how we planned for the trip, what we’d do again or do differently, and probably the most requested, our exact itinerary.
Originally I planned on talking about all of these things through a series of Instagram posts, but I just have way too much to say and I want all of this to be easily accessible for you in the future, so it felt right to wrap it all up in one blog post for you!
But don't worry, I’m not turning into an Italy travel agent and your typical real estate content isn’t going anywhere. We’ve got PLENTY where that came from, so you can just consider this blog post a little intermission from our regularly scheduled programming.
So, let’s get into it, shall we?!
How We Planned and Budgeted For Our Trip to Italy
When my now husband and I decided we wanted to travel to Italy, we quickly realized that the key to a smooth, stress-free trip wasn’t just about picking beautiful cities and sights – it was about preparation.
(A trip to Italy and real estate have that in common 😉)
When initially planning for this trip, we were working with a travel agent, but during that planning process, things just felt off so we decided to pause the planning and postpone the trip.
When we finally picked a new month to travel, I decided that I was going to take the planning into my own hands. It really excited me to do the research and plan accordingly, but that doesn’t mean it wasn’t overwhelming.
There are soooo many things to consider – there’s all your basics like flights, trains, taxis, hotels, meals, sightseeing, and then all the little extras like shopping and laundry. (Spoiler: I did NOT think about the laundry situation 😅)
But I’m happy to report that everything else went over pretty smoothly and I have my handy dandy spreadsheet to thank for that!
Plan and Budget with a Spreadsheet
If you’re thinking about planning your own trip, I highly recommend using a spreadsheet to help you do it! I OBSESSED over this thing to help me plan every step of the trip. Even though it might sound overly organized, trust me, it’s a game-changer.
On the spreadsheet, I included the most important categories:
Flights ✈️
Transportation (trains, taxis, Ubers, scooters) 🚊
Hotels 🏨
Food 🍽️
Major Sightseeing / Experiences 🍷
These were the high-level things that I knew we couldn’t leave up to chance. I knew that other things like shopping or just your average sightseeing would come up on its own, but anything that needed a reservation got added to the spreadsheet!
To make it easy, I broke the spreadsheet down by day, so I knew exactly what city we would be in and could book transportation, hotels, and experiences accordingly, along with making any dining reservations that we wanted!
When I started planning, I had our general budget in mind so I was able to keep track of what we were spending and where.
PRO TIP: when booking flights, leverage your points and miles if you can. I really love following Amanda Keane for this!
An oopsie I made though (that YOU can avoid!) is forgetting to convert dollars to euros. Because of this, it threw my calculations off a bit. 💸
Not all hotel booking sites display prices in dollars, so knowing the exact conversion prevents surprises. After the fact though, I realized that we didn’t need to budget as heavily for daily food as we thought. We found that most hotels include breakfast, which helped a lot!
However, we didn’t initially budget for laundry or extra taxis… and trust me, you’re going to want a laundry budget!
Lastly, we opted not to set a shopping budget, but just so you know, there are TONS of shopping opportunities and you’re more than likely going to want to take advantage of them.
For me, I didn’t want to set a number that I was forced to stick to, so instead I simply saved in a high-yield savings account for a few months prior to the trip. This allowed me to splurge a little without feeling guilty! Surprisingly though, I didn't go too crazy and only brought home a few new things that felt special.
Accommodations
Speaking of hotels, finding the right place to stay can truly make or break your trip – for us specifically, we stayed in a lot of amazing places, but we also experienced a few stays that landed on the “never again” list.
I think some of that is inevitable, but leaning on a mix of online resources and personal recommendations is key! Sites like Booking.com are excellent for research, but we learned it’s usually better to book directly through the hotel’s website because you can often get a better rate or added perks by booking directly.
My BIGGEST tip for this part of the planning process though is watching YouTube videos, reading Reddit threads, and even connecting with local Italian instructors or travel groups.
This is how I learned which areas to stay in and what to prioritize. A little research upfront ensures you’re in safe areas, close to attractions, and ideally positioned for your travel plans!
📍 My Top Hotel Recs:
Rome – Hotel Locarno
Amalfi – Hotel Miramalfi
Florence – Hyatt Tournabuoni
Chianchiano – Agriturismo Humile (Farmstay)
Transportation
Beyond your accommodations, the biggest thing you need to consider when planning your Italy trip is your transportation, because honestly Italy’s transportation can feel intimidating, but a little prep goes a long way.
First, pick where you’re going to fly into. We flew into Rome and from there navigated to Amalfi, Florence, and Tuscany. (Full itinerary below!)
Trains are perfect for traveling between all of the cities – they’re fast, reliable, and allow you to see the countryside as you go. For our trip, we chose Italo for all of our train travels, based on recommendation, but TrenItalia is another great option!
For shorter distances or getting from the train station to your hotel, taxis are the easiest option. And bonus, most hotels are happy to call a taxi for you, so you don’t need to stress about navigating local apps or language barriers!
In Rome, scooters can be a fast and cost-effective way to get around, especially when you want flexibility.
But ultimately, be prepared to walk a LOT! Italy’s cities are incredibly walkable, and exploring on foot often leads to the most memorable moments.
With that though, make sure you invest in some good walking shoes – here’s my pick. (And YES, they are Dr. Scholl’s and YES they are worth the hype!)
Beyond the Logistics
When it comes to planning for a trip to Italy, of course you’re mainly going to focus on your accommodations, transportation, and sightseeing, but there’s a few other things beyond the logistics that you want to consider as well!
Although these aren’t necessarily “required”, they felt like good extra steps that made life in Italy feel a little more comfortable.
Language Prep – do you have to learn the entire Italian language? Of course not! But I really wanted to know some basics, so we used Preply before traveling to learn the basics of Italian, which made interactions with locals smoother and more enjoyable. Knowing even a few phrases goes a long way in making connections and navigating cities.
Local Insights – the last thing I wanted is for our trip to feel like an ultimate tourist trap, so I really leaned into getting recommendations from friends and researching a tonnnn. I can’t emphasize enough how much watching YouTube videos and reading travel forums and even Reddit threads helped!
Attractions and Experiences – when planning, I really encourage you to go beyond the typical sights and seek out unique experiences that are meaningful to you.
When you start your research, you’re of course going to immediately find the iconic spots, like the Trevi Fountain, the Colosseum in Rome, and the Leaning Tower of Pisa (all of which ARE amazing, btw). But try not to fill your itinerary with only those things.
Seek out unique experiences that are meaningful to you. For us, that was a truffle hunt in the countryside and a hands-on cooking class, but other options could include:
A private wine tasting in Tuscany with a local sommelier
A Vespa tour through the streets of Rome or Florence
A visit to a local artisan workshop, like a leather or ceramics studio
A sunrise hot air balloon ride over the Tuscan hills
A behind-the-scenes tour of a historic vineyard or olive oil farm
There are SO many fun and unique things to do when in Italy, so don’t forget to go beyond the typical photos in front of a landmark, but also find a way to connect with the culture in a personal, hands-on way.
PRO TIP: Use the app Withlocals to connect with local hosts for unique, private, and personalized experiences, like food tours, city tours, and home dinners! This helps you have a non-mass tourism experience and allows locals to share their passion for the city with visitors.
We used Withlocals to connect with a local guide for our Colosseum tour and she was INCREDIBLE!
Our Exact 17-Day Italy Itinerary
Now that we’ve covered the planning and logistics of it all, let’s get into our exact itinerary in case you want to steal it (or use parts of it to help plan your own trip!).
Note: we were gone for 17 days – while it was amazing, we definitely could’ve shortened it to 14!
Day 1 – Monday (Travel Day)
Took an early morning flight from Billings to Chicago. We departed the Chicago airport at 4pm and arrived in Rome the next day!
Day 2 – Tuesday
Arrived in Rome at 12:30pm, checked into Hotel Locarno and fought our jet lag to enjoy a food tour in Trastevere! 10/10 recommend – even though we were exhausted, we LOVED this!
Day 3-6 – Wednesday-Saturday
We spent days 3-6 exploring and enjoying Rome. At first, I was a little worried because I didn’t make many plans for Rome, but it ended up being SO great this way!
This gave us the opportunity to explore on our own timeline, find our own adventures, our local shops that we just stumbled into, and our own favorite restaurants.
Did we get lost a few times? You bet. 😂 At one point we even accidentally ended up at the top of the Spanish Steps, which was the best mistake!
When in Rome though, we of course found the Trevi, toured the Colosseum, visited Palestine Hill and the Roman Forum, shopped a TON, and even had ourselves a little nail day. 💅🏼
Day 7 – Sunday (Travel Day to Amalfi from Rome)
On day 7, we traveled to Amalfi! We took a train from Rome to Naples and then had a driver from Naples to Amalfi. I found this driver on Reddit and he picked us up right at the train station – he was mentioned multiple times and honestly the hype was so real! It was definitely the most comfortable way to get to the coast.
In Amalfi, we stayed at Hotel Miramalfi – I chose this one specifically because I expected Amalfi to be crowded and I didn’t want to deal with beach clubs or large crowds. This hotel had a private sea swimming area with a deck and pool, all with beach club service! It was amazing because we really didn’t have to leave if we didn't want to, but in case we DID, they offered a shuttle that took you to and from city center.
If you’re traveling to Amalfi, just know it really is SO insanely crowded. 🫣 Beautiful and worth the visit? Absolutely yes! But just prepare yourself.
Day 8 – Monday (my favorite day ever!)
This was our wedding day! We eloped and it was literally perfection from start to finish. To end our day, we booked a private boat tour with Lucibello and trust me when I say, it’s a MUST!
Day 9 – Tuesday
After a packed wedding day, we opted for a relaxing pool/sea day at our hotel and it was just what we needed.
Day 10 – Wednesday (Travel Day from Amalfi to Florence)
After 2 days in Amalfi, we traveled to Florence. We were originally supposed to take the ferry from Amalfi to Naples to catch our train, but after seeing the crowds I got too nervous and texted Alfonso (our previous driver) to see if he could save the day – no surprise that he could!
He is truly your one stop shop when you come to the coast. Driver, tours, boats – a true connector. Our two favorite Amali places were his recommendations! I found him via Reddit of all places, but here’s his info to save you a search. 🫶🏼
We checked into Hyatt Tournabuoni and it was honestly incredible.
Day 11 – Thursday
Explored Florence, which meant seeing the Duomo, touring Uffizi, shopping at Fendi (duh!), and eating the BEST sandwiches from All’Antico Vinaio – trust me on this one. So. Good.
We also ate dinner at La Giostra – I made reservations here weeks in advance and it was WELL worth it.
Day 12 – Friday (Travel Day from Florence to Tuscany)
We decided to rent a car from Europcar to drive from Florence to Tuscany so we could enjoy the countryside views! On our way we stopped at a Euro McDonalds… turns out, it’s just a McDonalds with macaroons. 😂
We opted for a farmstay in Tuscany and OMG, I still think about this place!
Day 13-16 – Saturday-Tuesday
We spent days 13-16 exploring and enjoying Tuscany, which consisted of visiting wineries, truffle hunting complete with a cooking class, and honestly just enjoying the views and slowness of the area. It was all so magical!
Day 17 – Wednesday (Travel Day from Tuscany to Rome)
After soaking up the magic of Tuscany for 3 days, we traveled back to Rome to prepare for our longggg travel day home. At this point, I was actually feeling ready to go back!
Don’t get me wrong – I LOVE Italy and the experience was amazing (and we will be back.) But I was missing my dogs and was excited to bring bits of Italy back into my daily life.
I learned that we easily could’ve done this trip in 14 days, so when we go back, we’ll opt for 2 weeks instead of longer!
Day 18 – Thursday (Travel Day from Rome to home!)
We left Rome on an early morning flight, traveled to Chicago, and then finally made our way back to Billings around midnight. It was a VERY long travel day and I was so thankful when I got to walk into the doors of our home.
So, there ya have it – all the ins and outs of our Italy trip, from the planning and budgeting, to the exact itinerary we used.
My hope is that this helps you plan your own European adventure – it’s something that I really think everyone should do at least once. 🫶🏼