1 Week in Italy: Florence, Tuscany, and Rome, First week of May
Just back from a week in Florence & Tuscany — full breakdown (4th trip to Italy, first time in this region)
We're a married couple in our early 30s who travel abroad often. I spent an embarrassing amount of time planning this and maybe it saves someone else some time. Separate wine post covers all the winery visits in detail. I don't recommend moving as much as we did if you're a first timer, but we got a great flight deal in and out of Rome, and this wasn't our first time in Italy.
Route: Rome arrival > Florence (2 nights) > Chianti / The Clubhouse Hotel (2 nights) > Montalcino / Capanna Suites (3 nights) > Rome (1 night) > home
MONDAY: ROME TO FLORENCE
Landed in Rome around noon, train straight to Florence, didn't get in until around 3. We walked our suitcases from the train station to the hotel. It's doable but it's not fun. Checked into Palazzo Ridolfi, apartment-style, huge amount of space, which was exactly what we needed after a long flight. No frills place, but huge which is hard to find in a city. Only weird moment: a maid (I think?) knocked at 2pm one day, didn't speak English, I think wanted to use the restroom in our apartment? That was a little sketchy, otherwise enjoyable. Staying in Santo Spirito was nice, away from the hustle and bustle a bit.
Drinks at Alle Logge rooftop for the views, which were great. Touristy and expensive, obviously, but nice. Dinner at Antico Ristoro di Cambi: jet lag was brutal, the food was decent, lots of tourists, but not a trap. Got pasta and osso buco. Gelato at Sbrino on the way home, yes.
TUESDAY: FLORENCE IN A TORRENTIAL DOWNPOUR
It rained the entire time we were in Florence. Not drizzle. Torrential, relentless, soaking-through-your-shoes rain that stopped and started every few minutes, never long enough to feel safe leaving the umbrella behind. We lost our umbrellas at some point anyway, because of course we did. It was also genuinely chilly, not what I packed for at all. We blow dried our jeans at one point. And our shoes. This probably helped with crowds though!
Climbed the Duomo at 8:15am with the first ticket of the day. Worth doing the first time slot! Bought perfume at Santa Maria Novella, which is a genuinely wonderful experience even if you don't buy anything, the store itself is something. Got a leather jacket at Misuri, slightly pushy but I got a great deal, I was just firm on not needing a $1k purse. Sandwiches at Panetteria e Stuzzicheria De Neri when they opened, excellent. Walked Ponte Vecchio, ate at Gustapizza (also excellent, no notes). Wine tasting at Enoteca Pitti Gola e Cantina was a genuine highlight, low-key, not touristy, great pours, highly recommend if you want a real wine experience in the city.
Had a reservation at Osteria Giglio d'Oro for dinner but by 8pm we were completely soaked and it was a long walk in the rain and we just couldn't. Last minute table at Braceria All'11 instead and honestly it was the right call. Had the bistecca, great steak, great service, barely anyone in there on a rainy weeknight. Would absolutely go back.
WEDNESDAY: FLORENCE TO CHIANTI
Walked our suitcases from the hotel to the rental car station in the puddles to pick up the car. Stopped at Antinori nel Chianti Classico on the way out, about 40 minutes from Florence. Full review in the wine post. Short version: I was warned, I didn't listen, I regret it. Also stopped at McDonald's on the way because sometimes you just need to and we love seeing what's different in McDonalds around the world.
Checked into The Clubhouse Hotel at Le Fontanelle that afternoon. This was one of the best stays of the entire trip, up there with San Montano in Ischia for us. Only about 15 rooms, no kids, incredibly personable staff, the kind of place where people actually know your name. The room was spacious and private, the views over the vineyards were genuinely unreal, and breakfast every morning overlooking the property was something I looked forward to every day. Do not miss this view. Dinner at The Clubhouse restaurant, good with some standout dishes.
THURSDAY: CHIANTI DAY
Started with a spa day at The Clubhouse. The spa was excellent and surprisingly reasonable, around 130 euros for a 50 minute massage, booked the day before. It was a bit chilly at first but warmed up enough for an afternoon by the pool. We preferred The Clubhouse property over La Fontanelle, for reference. Vallepicciola wine tasting in the late afternoon. The hotel drove us over, it's 5 minutes away. Full review in the wine post but the short version is this was one of the best value tastings of the entire trip and came completely out of nowhere. We bought a case. Dinner at La Fontanelle restaurant. Neither hotel restaurant was mind blowing but both had standout dishes.
FRIDAY: DRIVE TO MONTALCINO + FIRST NIGHT
Drive from Chianti to Montalcino is easy and beautiful. Stopped at Capanna winery before checking in. Lunch in town at Alle Logge di Piazza. The eggplant parm is one of the best things I ate on the entire trip and I am still thinking about it. The pici was also excellent, as was the wine, of course.
Wandered the town, which is tiny and wonderful. Two afternoons during our stay we ended up at Enoteca Il Leccio, a tiny local bar with great Italian house music and essentially zero tourists. We stumbled in and kept coming back.
Dinner at Il Passaggio by Capanna: I booked this without realizing it was a full tasting menu, but we were staying at Capanna Suites so we committed. Around 200 euros per person with wine pairing. Pacing was surprisingly fast for an Italian tasting menu, service was outstanding, shoutout to Yosefina who sent us home with a bottle of Moscadello. The meal was great, and interesting, and probably incredible for the right person. We've been to the French Laundry, but I'm decidedly not an Italy tasting menu person, I just want loads of pasta. It felt like they're trying for a star though, and if you like tasting menus in Italy, this is for you. The pigeon was surprising, and the vegetable courses blew our minds.
SATURDAY: WINE DAY + BOCCON DIVINO
Castiglion del Bosco in the morning, Poggio Rubino for lunch, Cantina di Montalcino on the way back (one minute from Capanna Suites, wall to wall locals, 10 euro tastings, great spontaneous find). Full breakdown in the wine post.
Dinner at Boccon Divino. We were hesitant since we'd done a tasting menu the night before and we are again not tasting menu people, but a friend recommended it, and there's a cancellation charge within 72 hours. First seating at 7:30. We left at 11:30. I cannot stress enough how long this dinner is, and I'm used to long Italian dinners. The truffle gnocchi and onion soup were standouts, nothing else blew us away, portions are small, we left a little hungry. Prices were fair, I think 65 euros pp for one of the tasting options. A bottle of Fuligni recommended by the sommelier was a highlight. Worth going once but know what you're signing up for.
SUNDAY: WINE + BEST DINNER OF THE TRIP
Podere Le Ripi in the morning (see wine post, this one is special), lunch at their affiliated restaurant, Patrizia Cencioni in the afternoon.
Dinner at Re di Macchia, a rec from our guide Irene at Podere Le Ripi. She worked with the owner in Napa. We showed up around 8 with no reservation, which I do not recommend, we were the only table without one and got lucky. The owner ran the entire restaurant himself the whole night. Bistecca fiorentina, truffle ravioli, and eggplant parm, all excellent, paired with a Rosso di Montalcino from Casanova di Neri. Tiramisu to finish. This was the best dinner of the trip, maybe one of the best meals I've had in Italy across four trips. Stop by in person the day before to make a reservation. Do not just show up and hope like we did.
MONDAY: DRIVE TO ROME
About 3 hours, easy and pretty until you hit the highway. Returning the rental car near Roma Termini was an ordeal. We drove around for 20 minutes before finally finding the Hertz parking garage. Find the pin in advance, go straight to the garage, save yourself the stress.
Checked into Hotel Palazzo Dama, beautiful hotel, big room, wish we had more than one night. My third time in Rome for me so mostly just soaked it in. Lunch at Osteria Gnocco, pleasantly good. Drinks at Les Etoiles rooftop in Prati, one of the only genuinely sunny days of the whole trip, we sat up there for a while and enjoyed it. Wandered to the Vatican for golden hour. Bought another watercolor from Salvatore Cosso (Art Atelier Coronari on Google Maps, u/art.atelier.coronari on Instagram), we bought from him last year too, beautiful and affordable original art, highly recommend if you want to bring something home that isn't a magnet. Suppli at Supplizio, then dinner at Il Sorpasso in Prati. Three different prosciuttos from different regions plus two pastas. Shoutout to Anton for being an exceptional server. This was the best meal of the Rome leg and one of the best meals I've ever had in Rome. Gelato at Gelateria Cremilla after, 10/10, no notes.
TUESDAY: LAST MORNING
Out at 7am for one last walk. Trevi Fountain and the Spanish Steps at that hour are a completely different experience, almost no one there. Espresso and a maritozzo, then the airport. Perfect way to end it.
A FEW NOTES
The rain was genuinely relentless through most of Florence and I was not prepared for it. I've done Rome and southern Italy and assumed May would be similar. It was not, but I've heard that wasn't normal weather for the region at that time. Montalcino is worth building multiple days around rather than doing as a day trip if you love wine and if you love Brunello. We heard others at the wine tastings say things like 'we don't really love bold wines' while IN MONTALCINO. Read the room! Also — learn Italian! Speak Italian. It gets you a long way, even just saying please and thank you. Try to embrace the culture you are enjoying, and be respectful.
Happy to answer any questions! Grazie Italy, I'll see you again soon!