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Tuscany and Bologna Summer 2022: Honeymoon Trip Report

I owe a lot to advice/trip reports from this forum and elsewhere on the internet, so here is my way of giving back! Beware, it will be LONG--but I have tried to break it into sections for easier navigation.

- Travel Preferences/Context
- Motivation for Trip
- Itinerary

- Tours
- Experiences
- Museums
- Views
- Drink
- Food
Things we wouldn’t do again

SUMMARY (Travel Preferences/Motivation/Itinerary)

Travel Preferences
My partner and I are in our early 30s and both prefer to take vacation travel slow, trying to stay at least two nights in any given location and building in flexible time for surprises. We take a “we’ll return” approach to travel, so don’t pack in activities: I usually schedule one major planned/prebooked activity per day and many optional activities in the neighborhood to add on as we like. We’re naturally frugal people, but based on our preferences and careers, days off are more precious than dollars spent while traveling, so we’ll pay for convenience and memorable stays/experiences if the value feels right to us.

My partner is a homebody and probably wouldn’t do a lot of international travel without me, however he LOVES food. Therefore, I plan our vacations around unique/memorable food experiences, and he’ll happily go along on any history/art/nature activities (my interests) make sense between eating. However, he has joint conditions that make extended walking difficult, so I plan in downtime to avoid being on our feet an entire day and try to balance heavy walking days with something like a travel day where we are more stationary.

This trip was originally to take place in June 2020, but was moved due to Covid. As a delayed honeymoon, we wanted to take it even more slow than usual, planning for lingering dinners and afternoons just wandering through pretty towns or neighborhoods. Goal achieved! This turned out to be one of our favorite trips ever.

This trip was 16 nights, flying out of Chicago O’Hare the evening of Tuesday, August 23 and returning Friday, September 9. When our schedule allows, I always look at how flight costs change when we +/- a few days on either end of our planned trip–it can make a huge difference. This particular schedule saved us something like $600 vs shifting the dates forward a day or two, and had the added benefit of a weekend to readjust after the trip, which meant we were in great shape for work the following Monday.

Our itinerary was:
Arrive 2:30pm in Florence. Stay 3 nights.
Pick up rental car at 11am; drive to Agriturismo near Pienza. Stay 7 nights.
Drive back to Florence, drop off rental car; take train to Modena. Stay 1 night.
Train to Bologna. Stay 3 nights.
Train to Florence. Stay 2 nights.
Late morning flight from Florence.

This itinerary worked very well for us in practice. If push came to shove, I would have taken a night off of the Tuscany countryside and given it to Bologna, but our agriturismo had a 7 night minimum during this peak travel time.

Italy in August was not my original plan, but with the COVID delays and other work considerations, it’s the time we were able to take, and we’re glad we did!

Let’s not mince words: it was HOT (peak of 85F most days, up to 95F). We worked around this by making sure all accommodations had air conditioning and by planning any site visits without aircon for first thing in the morning (looking at you, Florence Duomo). We also built in time to return to our hotel/airbnb during the hottest part of the day (2-5pm), stayed hydrated, and used the excuse to justify extra gelato. ;)

On the positive side, it was very dry, with only 2 or 3 days of rain during our entire trip. We found the Tuscany countryside to be bafflingly pretty, regardless of sun or cloud cover. It really did look like a painting the entire time.

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We do carry-on only, and leave room for souvenirs. We each pack a large backpack in addition to our roller bags.

Given the heat, I packed exclusively cotton and linen in colors that would go together, and since I’d planned out travel to give us access to clothes washing every ~4 days, we didn’t need to bring too much (I packed undergarments/socks to last at least a week and outfits to last 5-6 days, and that was just right). I opted for comfortable Keds as my standard shoe, and also brought a pair of cute but comfortable sandals that could work both for nicer restaurants and the pool.

For the first leg, we stayed an Airbnb in Oltrarno right next to the Ponte Vecchio. To mix it up, on the return, we stayed at an Airbnb near the Duomo. Both were good options, but I’d stay in Oltrarno exclusively next time, as we preferred that neighborhood and its food options.

Tuscan Countryside
We stayed at La Moscadella for a full week (7 nights). It’s a wonderful location right near Pienza, which was our favorite hilltown of the whole trip. La Moscadella was stunning, and we liked having so many activities on site. Normally, that wouldn’t be something we’d go for, but it helped cut down on some driving, especially at night (my night vision is not the best, so I prefer not to drive unfamiliar roads when possible). The staff were so thoughtful and kind the entire time; they gave very good suggestions for places to go, and arranged many of our bookings during this leg of the trip. Also, that view from the restaurant and terrace!! We’d go back in a heartbeat.

We stayed at Casa Maria Luigia which was a major splurge, but worth it because we wanted to try Osteria Francescana. The grounds and amenities are incredible, and staying for one night feels like a cheat code–we arrived as early as possible and left as late as possible!

After that night near Modena, we trained to Bologna and stayed at an Airbnb halfway between the train station and main piazza. Any accommodation would have felt deflated after Casa Maria Lugia, but it was a good example of scrimping in one place to splurge in another and worked out well.

Within Florence and Bologna, we walked exclusively and never regretted it.

For the Tuscan countryside leg, we rented a sweet little Fiat from Europcar via Auto Europe, picking up from their downtown office near SM Maria Novella train station. They have a map with directions into/out of Florence that avoid ZTLs, and I took a photo of that to compare to Google directions: worked like a charm. Pick up and drop off were both super quick, and we didn’t get any surprise charges.

I’m experienced with driving in both major cities and on narrow country roads, and had very little problem with driving in Italy; I actually found drivers to be quite polite for the most part. However, our rainiest day happened to be during our travel day from Florence to our Agriturismo near Pienza–nice for the schedule since we were protected by the car, but I was white knuckling it on those Tuscan hills with the sheeting rain, especially when the hail started. Luckily, the hail was small and we didn’t get any damage! There were a few spots I could have pulled over if needed, but decided to just keep going.

We dropped the car back in Florence at the end of our Tuscan countryside trip and went straight to the train station for a prebooked train to Modena. We trained between Modena and Bologna, and also back to Florence. No regrets, as this gave me a break from driving and was an affordable and efficient way to get around.

We easily hailed a taxi from the Florence airport to our Airbnb in Oltrarno, and it was not expensive (it’s a fixed rate). We had a little more trouble getting a morning taxi back to the airport; the stands by Piazza della Repubblica didn't have any cabs by 9am. We ended up calling two cab companies, and one was able to send someone for us.

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Winner: In Modena, we did a food tour with Caterina Schenetti and I would strongly recommend it. She is such a delight, and so knowledgeable and enthusiastic about Modenese food. Know that she doesn’t run these tours on Sundays because the main market is closed.

Runner up: we did a Free Tours by Foot Medici tour the evening we arrived in Florence. I didn’t prebook since I wasn’t sure we’d make it if there were a flight delay/if we’d want to go based on our level of jetlag, but they made room for us upon arrival. It was a good overview of the city, especially for my partner, who didn’t do any pre-research before arriving. However, it was a bit long (it ran over, and ended up being close to 3 hours!). I’d still recommend this or something similar to get a feel for the city in person. I’d read a lot before arriving, but getting the anecdotes and moments of history in context was still really cool.

Winner: Pecorino/cheese making lessons and lunch at Podere Il Casale. These were some of our favorite encounters with fellow tourists on the trip, too! What can I say, cheese people are good people.

Winner: The Opera del Duomo Museum was our favorite–beautifully laid out and so interesting. The gates of paradise alone are worth entry. This comes with the Duomo climb ticket; don’t let it go to waste!

Runner up: The Uffizi was very crowded of course, but worth it if you love art. The sheer amount and quality of art is pretty astounding. I admit I laughed internally at the people who ran up to snap a photo of Botticelli’s Venus and then immediately turned around and went off to another room. To each their own. My favorite art moment of the entire trip was my time in the Terrance of the Map Room. We probably stayed for 15 minutes and I easily could have doubled it and been happy.

Winner: We had an 8:30am entry to the Florence Duomo our first full day in Italy, and what a way to kick off a vacation in Italy and a stay in Florence! I would definitely recommend doing this first. I’d tentatively planned in the Campanile for a couple of days later since our ticket included it, but we opted for a quiet morning that day instead. This worked out for us, but I’ll want to do Campanile or the Palazzo Vecchio viewpoint whenever we return. All this to say, I can’t compare the Duomo view to the Campanile, but we loved the view we got! Stairs up weren’t so bad–stairs down were much worse since I don’t light heights and you realize just how STEEP they are on the way back down. I still recommend it, though.

Runner up: Literally anywhere in the Tuscan countryside. :D Just find a rise somewhere and sit.

Wine tasting:
Winner: Volpaia. They were so accommodating when it rained out our vineyard tour, and our tasting guide was delightful and knowledgeable while also giving us time to just enjoy and discuss the wines without hovering. They also have some seriously delicious wines.

Winner: Manifattura in Florence. Delicious cocktails and steller service.

Gelato (we got a LOT of gelato, so this list is truly our best of the best):
Winner: Buon Gusto in Pienza. I will not embarrass myself by counting the number of times we went here during our week nearby. SO. GOOD. I will dream about this gelato until I can go back.

Runner up: Cremeria Santo Stefano in Bologna. Just go and buy a scoop of everything. You’ll thank me later.

Second and third runner up: Gelateria Artigianale La Sorbettiera in Florence and Gelateria Della Passera, also in Florence

Sandwiches (we also got a lot of sandwiches, to balance out the cost of the pricier restaurants):
Winner: Ino, Florence

Runner up: Mò Mortadella Lab, Bologna

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Sit down meals:
Winner: Enoteca Pitti Gola e Cantina. My partner loves steak, so we got a lot of bistecca alla fiorentina on the trip, but this was our favorite (much to our surprise, as generally folks recommend the bistecca outside of Florence as a better value/quality).

“Famous” Restaurants:
We went to both Dario Cecchini’s Solociccia and Massimo Bottura’s Maria Luigia “best of” Osteria Francescana. We liked the ambience/clientele at Solociccia much better, and even befriended a nice Italian couple there. We found these dishes to be more hit and miss, but definitely worth it (this is the “whole animal” restaurant of Cecchini’s, so very interesting to see what they were able to come up with). I’d recommend this to anyone who would be in the area who likes meat and interesting preparations. It’s not a cheap meal, but it is a lot of food and a very fun experience!

Osteria Francescana’s dishes were creative and delicious, as one would expect. It is hard to recommend this restaurant given the extreme expense, but ultimately we did feel it was worth it. Personally, we felt the dishes that were not featured on Netflix were the best tasting/most interesting.

Things we wouldn’t do again (unpopular opinions ahead!)
We enjoyed the Boboli gardens, but felt they were a bit overrated–very dusty, and the gardens themselves were just okay compared to other parks and gardens we’ve seen in London, NYC, San Francisco or, for example, Park Güell in Barcelona. I’d consider going back in the spring when more flowers might be in bloom, but it wouldn’t be top of my list.

We did a long drive to Siena from our Agriturismo near Pienza in one day, and I regret it. We made it too late to go inside the Duomo, but I’m not sure that alone would have changed my mind (the outside was very beautiful, but I preferred the Duomo complex in Florence). Overall, it felt like the city was in an odd space between the size of Florence and the charm of smaller hilltowns.

Piazzale Michelangelo. It’s totally overrun by tourists. Not pleasant, and there’s really not a very good picnic spot. The view from Abbazia di San Miniato al Monte was much better.

We adored this trip and had so many great experiences! I hope these notes can be helpful to someone planning a trip to the same areas in the future.

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Thanks for taking the time to share your wonderful trip with us!

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Fantastic report and super helpful! What did you think of Modena - could you have spent more time there?

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Thank you both, Priscilla and CaliMom!

I liked Modena and it definitely deserved more time than we gave it! Modena could also be a nice spot as a hub, if you wanted to go to Parma and other food-obsessed cities in the area, or tack on time to visit the Ferrari museum. It's a pretty, quiet town, and could be a haven in the midst of busy travel. I do recall from planning that a lot of the factory tours or best restaurants would have benefitted from a car, which we knew we wouldn't have by that stage of the trip.

We saw the outside of the Cathedral but didn't go inside, and I would do that if we went back. There were also so many cute stores and coffee shops that we didn't get a chance to go into. We had planned to explore Modena more after our food tour, but we were tired that day, so after the food tour we trained back to Bologna and had a nap and quiet evening wandering.

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Hey fellow Chicago Ricknik.

Bookmarking as we’re returning to Florence for our 20th anniversary in 2025, and then taking off for some mix of Tuscany and Emilia-Romagna, possibly with more time in ER than Tuscany. As I have a trip planned between now and then, and two years to plan, might have questions for later.

How was the countryside around Modena?

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Hi Max! Always great to meet another Chicagoan!

Our mode of travel may have been unfair to EM: in Tuscany, we drove and were able to explore the beautiful hills and valleys. In EM, we trained. The views from the train were not that pretty: fairly industrial, and the nearby land was flat. It actually reminded me a lot of the US midwest, and not the prettiest parts.

The food in Bologna and Modena was incredible, and that coming after some really excellent food in Tuscany--so I'd balance time depending on some of those tradeoffs; doing both is a great idea, and transit between them very easy.

We had considered keeping the rental and driving up along the eastern coast, then hooking back to Bologna, but that would have meant additional driving we preferred not to do, and it was hard to find a rental company that would allow car pick up in Florence and drop off in Bologna. Depending on what time you have, though, that might be a good option, and the views around Modena and Bologna might be prettier than by rail.

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Thanks, Avens.

We've found, in a couple trips to Italy, that the countryside by train can be less attractive than the countryside as seen by car on the roads, as opposed to the autostrada. Our first trip, we trained Rome to Florence to Cinque Terre to Milan to Venice to Rome, and, aside from discovering that "renaissance trees" were real, the trains tend to go through the backside of anywhere. I mean, 5Terre is an absolutely beautiful place, but if you took the train through, not so great. Then, we drove around Piemonte and VdA for our second trip, and HOLY WOW for most places; we did laundry in Cinzano, and, you would be forgiven for confusing it with the area around Midway airport, only with Italian signage.

Any rate, thanks for the response.