We spent the most amazing 16 days in Italy in May 2022--it is where my husband and I got engaged! This post will showcase the larger itinerary as a whole, while I will do more detailed posts on each of the locations.
We were flying to Italy from the Washington, D.C. area, with most flights from this location being overnight. I am not counting the day we left as a travel day since our flight was in the evening. This itinerary also involves renting a car, which we found the most efficient way to explore both the Tuscany and Dolomite regions, though we did drop off the car in the Dolomites and take a train back to Rome for our departing flight--it was much faster.
Compared to my European travels as a college student studying abroad, I have found myself wanting to dwell in locations a bit longer. I enjoy the slower pace and getting to discover more nuances in the areas that we travel. That is why this itinerary is on the longer side: we spent 4 days each in Rome and the Dolomites, with an additional 5 days split between the greater Tuscan region and Florence (and 2 travel days). We had a great time, but understand that not everyone can take this amount of time off--you can very easily cut off the last portion in the Dolomites and save it for another trip. The Dolomites was our favorite part, but you definitely want to dedicate a decent amount of time to the region, and I think 3 days would be the minimum.
We traveled to Italy towards the end of May (taking advantage of the Memorial Day holiday). This was also in 2022, which was the big post-Covid travel boom. Rome and Florence were definitely busy at this time, but not unbearable. Tuscany was not nearly as crowded and the areas of the Dolomites were were in was almost free of tourists (some of the hikes or roads may be closed at this time from snow).
Day 1: Arrive to Rome
We arrived to the Rome Airport (FCO) early in the morning. We tried to get as much sleep as we could and upon arrival we freshened up in the airport bathrooms. The most cost effective way to get into the city is to take the Leonardo Express train to Termini Station, but we were planning on staying in the Centro Storico neighborhood which was not super accessible by public transportation. We opted for a taxi, which was approximately $60 for the two of us. We dropped off our bags at our hotel and we wandered around the Centro Storico neighborhood down towards the Colosseum (~36 minute walk), stopping for a delicious cappuccino and some lunch along the way. We had a pre-purchased ticket and designated time for entering the Colosseum. Afterwards, we were quite exhausted after a night of little sleep! So we headed back towards the hotel for the end of the first day.
Days 2-4: Rome
We liked to start our mornings slow and enjoy a cappuccino near our hotel. For Day 2, we spent time at the Pantheon and Trevi Fountain before heading to the Roman Forum--most Colosseum tickets include the Roman Forum and are good for two days after initial entry.
Day 3 was Vatican day, which included climbing the dome of St. Peter's Basilica and pre-purchased tickets for entrance to the Vatican and Sistine Chapel. We finished the day with dinner in the Trastevere neighborhood.
Day 4 was centered around our pre-purchased guided tour of the Borghese Gallery, one of our favorite museums this whole trip. We also ended the day with another highlight of our entire trip: Dark Rome's "Dark Heart of Rome" Tour. Our guide was fantastic and the stories were all based on real events and gossip, adding quite a different perspective to the sites we had already walked past throughout our stay in Rome.
For a more comprehensive guide to our Rome itinerary, check out the blog post here.
Day 5: Drive to Tuscany
After picking up our rental car in the morning in the neighborhood near Borghese Park, we headed towards our Tuscan base of Pienza. We made one stop along the way which made our drive a very reasonable 3 hours.
Our road trip stop was at Civita di Bagnoregio, which was where my husband and I ended up getting engaged! We visited on a Monday and were greeted with barely any tourists. You have to park the car a bit away to walk to this beautiful hilltop village, but it was well worth the stop.
Pienza is a historic village that is also a UNESCO World Heritage site! It's architecture is striking, it's hilltop views stunning, and the local residents so warm and inviting. The village is small, but has several restaurants to choose from, cute shops, and a decent size grocery store. We loved our stay in a local agriturismo.
Days 6-7: Tuscany
Despite coming down with a cold, we did a lot of exploring while in Tuscany. Our favorite town in the area ended up being Montepulciano--it is bigger than Pienza and the views are just as impressive, but the hills are very steep. We enjoyed driving around seeing iconic cyprus trees and the old villages while enjoying delicious wine.
Our favorite night was our delicious dinner at a local agriturismo where everything was farm to table, with multiple delicious courses. We made reservations in advance, which is recommended. This is a must do while in Tuscany!
For a more comprehensive guide to our Tuscany itinerary, check out the blog post here.
Days 8-9: Florence
We drove about an hour and a half from Pienza to a car park outside of Florence to leave our car and take the train into the city. We opted for a lovely Airbnb in the center of town near the Duomo and used it as our base for exploring. We enjoyed Piazza Michelangelo for golden hour, shopping at the leather marking, and eating an embarrassing amount of paninis and gelato.
Other sites we visited included a guided tour of the Uffizi Museum and a stop at the Leonardo Da Vinci Museum. The Uffizi was spectacular and I have learned to appreciate having a guide in art museums. It helps me appreciate what I am seeing, and there sure was a lot of famous pieces to see! We ended up skipping the David statue at the Accademia Gallery this trip as I had seen it before and was not as impressed with the rest of the museum; while the David is spectacular, I was blown away by the Uffizi!
For a more comprehensive guide to our Florence itinerary, check out the blog post here.
Day 10: Driving Day
After checking out of the Airbnb, we headed up to the Dolomites region. We were originally supposed to head up towards Cortina d'Ampezzo to spend two nights to hike the famous Tre Cime di Lavaredo, but the road to the hike was still closed when we left the US and we did not want to risk it; we ended up canceling that hotel and booking a gorgeous mountain lodge in Tires, outside of Bolzano.
My husband had started to get sick, so though we had an ambitious list of road trip stops we only did one on our approximately 5 hour drive: Santuario Madonna della Corona. This striking church was built into the side of a mountain, with gorgeous views all around.
Days 11-12: Dolomites, Bolzano area
While recovering from being sick, we opted for a relaxing few days lounging around our gorgeous hotel. Most of the lodges in the area are typically ski lodges and therefore nearby gorgeous mountain trails.
After checking out of our hotel to head towards our Airbnb in Ortisei, we stopped by the beautiful St. John's church on the way.
For a more comprehensive guide to our Dolomites itinerary, check out the blog post here.
Days 13-14: Dolomites, Ortisei area
While still recovering from being sick, we spent a lot of time exploring the lovely mountain village of Ortisei. It is primarily a ski village, and was just opening up again for summer travelers when we were there the last few days of May and first few days of June. Plenty of restaurants and shops were open and while there were some tourists, it was not overwhelming at all.
The town has access to ski lifts/funiculars which, while a bit expensive, are definitely worth it. We took two: one up to the Seceda Ridgeline and the other up to the famous Alpe di Siusi. It is hard to put into words how scenic both of those areas are. My husband and I were pretty much in awe our entire time at both spots! There was lovely hiking around each spot and plenty of refreshment options.
Days 15-16: Head Back to Rome, Depart
Flights were significantly cheaper in and out of the Rome airport for us, so we spent this day traveling back. We drove about an hour and a half down to the bigger town of Trento to drop off our car and pick up our train. We had a few hours between, so we used Radical Storage to pay for a spot to keep our bags while we explored the town and Castello del Buonconsiglio.
Our train ride to Rome Termini station was about 5 hours and had lovely views. We then hopped on the Leonardo Express train to the Rome airport and spent the night at the Hilton Rome Airport prior to our morning flights.
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