The following content may contain affiliate links. If you make a purchase through the links below, I may receive compensation.

I’ve had a lot of requests for details on our recent trip to Italy. We spent four nights in Tuscany and three nights on Lake Como, and I’m going to break the visit into separate posts for each region. Como post coming soon!

(I shared all the outfits I wore here!)

Why/How We Planned Our Itinerary.

To set the table, I wanted to mention two things —

1) I would not necessarily recommend doing Tuscany and Como in one trip. These two exquisite regions are separated by about a five hour drive (shorter train ride, will explain more on why we drove later), which is a substantial amount of travel for a trip of just over a week. However. Landon and I travel abroad so infrequently, and these are two areas I’ve been dying to visit, and I simply wanted, needed, to make it work. If you travel more regularly or are perhaps less laser-focused on these two itinerary stops, I think it would probably make more sense to do Rome or Florence and then Tuscany, or Milan and then Como, if you have about a week. (Rome and Tuscany are about two hours from one another, depending on where you are in Tuscany, of course; Florence is a part of Tuscany; Milan and Como are about an hour from one another.) These shorter travel times would enable you to maximize your visit and waste less time in transit. I also think changing hotels / packing and unpacking takes a bigger toll than you think on your mood and vacation vibe — take that for what you will. Plus, so much to see and do in both Rome and Milan!).

2) There are many ways to travel, and many styles of traveler. Landon and I have specific priorities when traveling, and they may not map to yours — first, we like our vacations to feel restful, relaxing, restorative; second, we like to explore new regions and specifically go deep into local cuisines; and third, we like to take in culture/landmarks in smaller sips. Which is to say, we prioritize luxurious accommodations and typically schedule only one major activity each day. I have friends who go in the exact opposite direction. For them, travel is about discovery, and new experiences, and they navigate full-bodied daily itineraries, and spend less on hotel accommodations with the explicit goal of spending as little time as possible in bed / in their rooms. And this, too, is totally right. Sharing that up front because our priorities dictated a lot of our decision-making in selecting hotels, selecting activities, and how we traveled.

On Using a Travel Agent.

On this trip, we worked with a travel agent — Allison Spiegel from Elli Travel. We had never worked with an agent before, and I had no idea how the arrangement worked, so sharing here in case you’re in a similar boat. Elli has many competent agents, but Allison specializes in Italy, so we went with her. We had to pay an up front “travel design” fee, but then afterward, Allison was compensated by the hotels/partners she booked for us, and we paid no additional costs. We found working with her incredibly valuable for three reasons: a) she helped us think through logistics in a significant way, and specifically advised us on how to make the trip as seamless and stress-free as possible; b) she advised us well on which hotels to consider without us having to spend days trolling Reddit for suggestions, which was a top priority when we planned this trip — we were very short on time when mapping out this trip and it was wonderful to outsource that information-gathering and comparison to someone with expertise; and c) she was able to book us custom excursions/trips that would have been difficult to source otherwise.

Our Stay at Lupaia in Tuscany.

We arrived in Rome early Friday morning and Allison had arranged a “private transfer” (private car and driver) to pick us up from the arrivals area and drive us directly to our hotel in Tuscany, Lupaia (a two hour drive). This was expensive but I’m so glad we splurged because the last thing Landon would have wanted to do after an overnight flight was drive two hours on foreign roads — and some of the roads we used to access the resort were single-lane, dirt roads through fields. Allison had presented us with a few hotel options in Tuscany and we completely lucked out with getting into Lupaia — apparently you usually have to book a year out, as this tiny jewel box of a hotel has only twelve suites. Parts of the hotel date back to 1622 (!), but everything has been modernized, and every detail is absolutely perfect. You can tell that someone agonized over each light fixture, drawer pull, and potted plant. Absolutely every corner looks like a post card.

Our room looked out over the iconic patchwork fields of Tuscany, straight towards Montepulciano, which glows like gold at sunset. It was the most picturesque, relaxing vista to take in, and it was hard to talk about anything else but how spectacular the views were. I loved this hotel because it was quiet and intimate and cozy — had the vague feel of being in someone’s beautifully appointed home — but boasted every luxury amenity you could want, including a WhatsApp number you could text if you wanted a cocktail anywhere on the property, cleaning service that seemed to know exactly when you had left your room and would be in and out before you’d return, modern (rain shower head) showers (not a given in Italy), high speed Internet, etc. The staff was both warm/friendly and discreet, offering lots of privacy but also available whenever needed. If you go, I can’t wait for you to meet Silvio, the charming bartender and wine afficianado. I could have listened to him talk (passionately!) about the local wines forever. I could go on and on — but this hotel will always have a place in my heart. To give you a sense for ambiance, I would say most of the patrons were couples, a strong subset were honeymooners, and there were a couple of families with grown children. This felt like a romantic destination to me. Though it has a pool and plenty of open space to explore, I don’t think it would be optimal for very young children, as the walks are all gravel — would be impossible to push a stroller / difficult for tiddkers to walk.

If you do stay there, know that the roads to get there are challenging to navigate with a large car — twists, turns, and one lane. If a car is coming towards you from the other direction, sometimes one or the other has to back up until you can find a place to pull over. We had rented a Mercedes GLE300 and let’s just say I did a lot of the “making gasping noises and grabbing the handle of my door while he is driving” on this trip. (Marriage is…)

Visiting Montepulciano and Pienza: Charm, Copper + Pecorino.

The day we arrived, we relaxed at the hotel and enjoyed dinner there, too. They offer a prix fixe, multi-course meal each day, and will bring out the menu in the morning for you to review. The food was lovely, and the dining room adjoins the kitchen; fun to watch the cooks at work. I would guess that most hotel visitors eat there most nights because Lupaia is somewhat remote and it’s not…fun to drive those roads at night. We did overhear that some hotel patrons had the concierge call cabs for them, so I do think that’s possible, but in my opinion, you really need a car in Tuscany.

Allison had arranged to have our rental car delivered to us at Lupaia the day after we arrived (to the tune of a meaningful surcharge). When it arrived, we took off for Montepulciano, which is about 20-30 minutes from Lupaia. We used the Rick Steves guide book for this visit, as he has a suggested path for exploring old Montepulciano by foot. It was helpful in orienting us and providing us a few points of interest and brief histories. The guide even features suggested parking lots to use, of which we availed ourselves. We walked the entire route Steves laid out, stopping to shop at the copper boutique I mentioned yesterday, and wandering through the wine caves of Palazzo Contucci, before we stopped for lunch. We had a few possible dining spots flagged through Landon’s research — Le Logge del Vignola and Ristorante ai 4 Vente — and went with the latter, which ended up being one of our favorite meals of the trip. It was foggy and chilly outside, and we tucked into hearty bowls of hand-rolled pasta with meat ragout sauces, and the most delicious glasses of Brunello wine I’ve ever tasted. Someone in Como described the food in Tuscany as having “honest prices,” and it was true — the portions were enormous (! – don’t fill up on the bread) and the prices unbelievable. I want to say our pastas were maybe 12 euros and we could have easily split one. The glasses of Brunello would have easily retailed for $50/glass in the US and were 14 euros apiece — which seemed expensive in the context of the menu, as most other glasses of wine were around 7 euros. We ate well, and were happy.

We wandered a bit more and then stopped for cappuccinos at Lalma Cafe and Tearoom (photo below), which was off the beaten path from the main Montepulciano drag and seemed populated primarily by Italians. While we were there, the owners were enjoying a traditional Tuscan stew of beef tongue and other “off cuts” of meat that their kitchen had prepared for them. I was so charmed by their casual midday braise at one of the tables! (Clearly, the stew was not on menu for customers — it was just for the owners.) The coffee shop was modern and bright with high-speed Internet — not exactly on theme with the rest of ancient Montepulciano, but a nice pit-stop for resting and reading for an hour or so.

I wrote about this in more detail here, but you really feel the wild expanse of history in Montepulciano. It was spectacular. I will note that the main drag is fairly clogged with tourists. You’ll want to see it all, too, but a lot of the best vistas are off the beaten path! Take some chances and wander.

After Montepulciano, we visited Pienza, which felt like a quieter, slightly less touristic version of Montepulciano (although guided tours and clusters of tourists abound here, too). We had planned to stop into one of the many meat and cheese shops on the main strip, but we were so stuffed from lunch, we skipped it. I might propose you do Montepulciano and Pienza on different days for this reason. That way one of your lunches can be a meat and cheese platter in Pienza — they are specifically known for their pecorino, which is unlike anything we have in the US. The Pienza pecorinos are soft, young, and slightly creamy, while we tolerate the aged, crumbly stuff here. We were able to taste Pienza cheese later at our hotel, which sources from all the local farms and purveyors, and it was delicious. We went back to the hotel then, relaxed, and had dinner again in the main house.

A Day in Florence: Sorry, Guys, I’m in Love with Her.

On the third day, we drove to Florence. Allison had advised us against this, suggesting a private car and driver, but since we had the rental, and Florence is only about an hour from Lupaia, we went our own way. Her suggestion was understandable, though: you cannot drive into the center Florence. (As Rick Steves puts it in his book: Don’t even try.) There is a complex set of rules that even Florentines find confusing that involves “DTZ” zones; if you drive into one of these zones, your car is photographed, and you automatically get a pricey ticket. If you accidentally drive into and out of these zones, you rack up multiple. The point is, we narrowly avoided entering one by following Siri’s driving instructions — yikes! We ended up parking in a public lot on the outskirts of city center and then walking about twenty minutes to get to the Uffizzi Art Museum.

We had heard the Uffizzi was a must. It has the greatest collection of Italian art in the world. If you plan to visit, you absolutely must book tickets in advance, and they are timed, and rather strict about the timing, FYI. Otherwise, there is a line a few hours long to get into the museum that looks like hell. I will be honest: Uffizzi was the low point of our Italian adventure. It was unbelievably crowded (think The Louvre), and we spent thirty minutes waiting in line to see the Tribuna, an octagonal room now closed off to visitors that you can only see through a few doors. It holds an impressive set of artworks and sculptures, but the experience of viewership detracts from its magic. You wait in line, then you have basically thirty seconds to frantically take in as much as you can while people are breathing down your neck for their turn. Not my preferred method for viewing art. Honestly, I barely remember what was in that room — and we’d waited a long time to see it. Of course the museum also boasts masterpieces by Da Vinci, Michelangelo, etc, but the crowds…! Still, I’d advise you go; just be alert to its thronginess. We stood for five minutes staring at Botticelli’s “Birth of Venus,” which made the entire visit worthwhile in my opinion. That one painting is spectacular in scope, style, and story.

After the Uffizzi, our day zig-zagged across the Arno several times, which we didn’t mind — we both love exploring by foot — but was probably a sub-optimal way to get around the city if you’re not wanting to walk as much. (I think Landon’s watch said we clocked six miles this day.) You might do better by tagging some of the places on a map and then charting a more logical course! I will say crossing the Ponte Vecchio multiple times was harrowing — it, as well as neighboring piazzas, are as busy and chaotic as Times Square, and we really hated the crowds. (We’re such curmudgeons!) As the day went on, we wised up to this and tried to avoid the most clogged areas.

After Uffizzi, we went to lunch at a spot Landon had scouted — he had flagged a number of recommendations from following Missy Robbins and Tony Montuano — called Trattoria 13 Gobbi. It was blessedly off the beaten path, and we had a lovely meal of pasta there. We wished we’d ordered the Florentine steak, as it seemed to be what most other patrons were ordering, and is one of the region’s iconic dishes, but followed our stomachs instead. We then walked back to the Uffizzi area for timed entry to the Boboli Gardens. There were multiple beautiful vistas to take in (see below), and we had a spectacular day for it, but neither of us felt that it was a highlight of the trip. Take that for what you will…

We then walked over to Caffe Gilli in the Piazza della Repubblica, which has been around since 1733! It’s somewhat touristic but the aperitivi/coffees are delicious, and it’s a great perch for watching the world walk by. I saw so many chic Florentines as I sipped a cappuccino, and then an aperol spritz, here. It was also lovely to rest our legs for awhile. We were only a few feet away from the iconic Santa Maria Novella apothecary, so after my cocktail, we walked over and picked out some gifts to bring back. I treated myself to one of their classic “scented clays,” in the shape of a pomegranate, which slowly releases its perfume in the air. It now sits in my closet, perfuming all my clothes and reminding me of that magical trip. I think I’ll be giving these as housewarming gifts from now on. A few Magpies have written to say they do the same — and also keep them in all their linen closets!

We window shopped through the high-end shopping area (Bottega! Gucci! Etc!), and then I noticed we were walking right by Palazzo Strozzi, a museum I had read about earlier this year, as it was showing the largest collection of Helen Frankenthaler paintings ever assembled. I had flagged it as a possibility for visiting while in Florence but after our harried tour of the Uffizzi, wasn’t sure I was up for more art. Seeing as we were walking right by, and there was no line, we decided to wander in. I’m so glad we did. The exhibit was almost empty — at times, we were alone in the rooms! — and I am an enormous fan of hers. We were in and out in about 30 minutes, and both of us were speaking in exclamation points. A little surprise windfall that felt special and intimate.

From there, we walked to Il Santino (recommended by both Missy and Tony), a narrow wine bar patronized almost exclusively by Italians, which meant it was both intimidating and implicitly good. We had the most delicious spread of meats and cheeses, and the kitchen brought out some complimentary snacks as well — crostinis with truffles and honey and cheese. The wine was exceptional. But the real treat of the evening — and I shared this story on Instagram and have never received more comments! — was when our soigne and slightly edgy server was discussing the wine menu with us, and a handsome man appeared in the doorframe and started to speak to her in passionate, urgent Italian. Our server seemed cool, almost eye-rolling, in response to his entreaties, turning back to take our order with an air of impassivity. I wasn’t sure what was happening — was he a colleague? — and then the man turned to us and said, animatedly: “I’m sorry, guys, I’m just in love with her!” (!!!) The waitress smirked and took our order. (!!!!) It was one of the most romantic things I’ve ever witnessed. I need to know more about this story. (They were beautiful to watch, too! The waitress had a Daisy Edgar Jones look, and was wearing a black dress with moto-ish boots, and her boyfriend (?) had a Fabien Frankel thing happening.) Romance is alive and well.

Truffle Hunting in Tuscany: Daje! Daje! Daje!

On our last full day of Tuscany, Allison had arranged a private truffle hunting tour for us. If you are not working with an agent, I would recommend asking your concierge for a lead, as the area if known for its truffles. If that does not pan out, Podere Il Casale (a working farm, venue, and restaurant) might be able to point you in the correct direction. Our truffle hunter seemed to have an arrangement with them; the kitchen prepared the truffles she had found for us.

The hunt was fascinating and exciting — we went with the hunter and her 2.5 year old Lagotto Romagnolo, which are the most popular dog breed for truffle hunting. In Italy, it is illegal to hunt for truffles with pigs, as they destroy everything in their wake, including tree roots and any remaining part of the truffle itself; it’s a conservation thing. We understood why after the visit. Enormous tranches of earth had been displaced by wild pigs; they left a mess anywhere they’d been. Our dog (named “Puppy”) found three black truffles and one rare white truffle in about an hour. The truffle hunter indicated this was a lukewarm performance, but the white truffle was a true victory. You can find black truffles most months of the year in Tuscany, but white truffle season is usually late October-November. You can truly smell the difference between the two: the white is definitely more complex, and powerful. Truffle hunters are highly competitive, so when we went out, our hunter was trying to train the dog not to bark (and therefore give up our location). The three major commands we heard: “Vieni qua” (come here), “Daje! Daje! Daje!” (let’s go, let’s go, let’s go — meant as an encouragement), and “bravo” (good job!”). Lan and I now say “Daje daje daje” to one another all the time.

If you go, this activity does require appropriate attire. I’m so glad I brought waterproof, heavy-soled boots — it was the only time I really needed them, and you honestly couldn’t get by with sneakers (or at least, not happily). For much of the hunt, you’re traipsing through mud, brush, thick grass, thickets, etc.

After, we returned to Podere Il Casale and, as mentioned, the kitchen prepared the truffles our dog had found in a few different ways — over eggs, on toast with cheese, and over pasta. Delicious, and the views were spectacular.

Farewells + Final Notes.

The final evening, we ate a small supper (not the prix fixe menu) at the hotel and went to bed on the early side. The hotel offers complimentary breakfast each morning and we fueled up before our five hour drive to Como. I loved the breakfasts at Lupaia. They have a fairly extensive menu and you are able to order absolutely anything you want off of it — a stack of pancakes alongside a plate of meat and cheese, or two eggs served however you please with a bowl of oatmeal, a fresh juice with pastries, etc, etc. I am thinking warmly of the cappuccinos and scrambled eggs I enjoyed in the crisp morning air; you could eat indoor or out and it was such a gracious way to start the day.

After checking out, we climbed into our car for a somewhat long trek to Como. You could drive to Florence and then take the train if you want to avoid the road trip, but we decided it would feel the most fluid (least schleppy) to just throw our bags in the car and drive to our Como hotel ourselves. Allison was able to arrange to have the car rental service pick our car up from the Como hotel for us. These rental car drop offs / pick ups meant everything felt seamless and we could just arrive at the hotel and enjoy ourselves versus going out to an airport to drop off the car, arranging a taxi to the hotel, etc. I think this amenity was worth the expense. We had also originally planned to stop in Bologna or Modena for lunch to break up the trip, but there had been terrible flooding in the Emilia-Romagna region while we were there, and we were advised not to stop, as some parts of these cities were still under water. This was devastating to hear for these cities and their citizens, and a bummer for us as visitors; we had tentatively planned to visit the Ferrari museum and have lunch in Modena, which would have made the drive feel more “useful” in some way. But, que sera sera. Instead, we listened to the entirety of the Good Kid, m.A.A.d City album (Kendrick Lamar) as the Italian countryside flew by us.

I felt like we maximized our time in Tuscany and were able to cultivate a good sense for the region. If I’d had more time there, I might have taken a day trip to Parma, Modena, and/or Bologna, which aren’t too far away, but have fantastic culinary and cultural attractions. I could have also spent a couple of extra days in Florence — I loved that city, and there were so many other museums and shopping destinations I would have loved to visit. (I would also have enjoyed going back to the wine bar to get an update on the “sorry guys, but I’m in love with her” situation.)

I slightly regret not taking a dip in the spectacular Lupaia pool or hot tub — I don’t know why we didn’t wander down there one afternoon/evening — but suffice to say there was more to avail ourselves of at the hotel that we never got around to. (They also have a collection of board games in the library, and offer wine tastings most evenings.) The weather in Tuscany in October was lovely temperature-wise — 60s-70s — and even though we had a few afternoons/mornings of rain, we managed to see everything we wanted to see and do everything we wanted to do without much trouble owing to drizzle. It was in fact kind of romantic to take in Montepulciano on a gray, grizzly day. That said, I definitely recommend packing flat walking shoes, a rain jacket, and an umbrella if you are going this time of year. And one final note on the time of year: October seemed perfect for visiting Italy. It was much less crowded, and hot, than in peak season. Plus, if you have young children like we do, it felt ideal to have our kids well-adjusted to the school year and its rhythms (I think would have been more challenging to leave them in September), and to have them engaged most of the day (for childcare reasons). I think that when we are able to travel again, just the two of us, we would opt for October for these reasons.

Let me know if you have any questions. I tried to be as thorough as I could be!

A few post-scripts…

+Freda Salvador is offering 20% off all loafers with code LOAFERLOVE. This is the one pair of shoes I didn’t bring that I wish I had — it seemed that every well-appointed Italian woman was either wearing dressy sneakers (Loewe, etc), a black flat slightly heavy-soled boot, or loafers just like these. The shoes I did pack: VB Valentinas (wore these the most), Dolce Vita mesh ballets (super comfortable – I walked the entire Florence day in these), Chanel ballet flats (chic but not great for long walks – conserved these for evenings mainly), a pair of velvet pointed toe pumps that I wore to one nice dinner — probably would omit these next time, and my Isabel Marant Duertos (wore these a lot more than anticipated — they work with dressier outfits for evening just as well as jeans for day). I also tossed in the lug-sole boots (old Madewells, similar here) I wore for the truffle hunt and really did need them that day, but did not wear otherwise, which was kind of annoying — they took up a of space in my suitcase! I’d thought I’d need them more often because a lot of rain was forecasted, but I managed with my other shoes just fine — though I did wish I’d brought the loafers as an alternative to my Valentinas for certain outfits!

+I wore this cashmere sweatsuit for the travel day but I also think this Frank & Eileen set would be wonderful — I just wore it yesterday while back home and it’s chic, pulled together, and so comfortable. It’s $$$ for a sweatsuit, but I will say it’s my go-to set if I’m running out the door for drop off, or in need of a lounge outfit. And you could wear the sweatshirt separately, just with jeans or cords. You can get $50 off with the code APPLE, OR a Magpie reader wrote to say that this Amazon set is a really, really good look for less, and it’s under $50.

+Speaking of good Amazon buys, I routinely get questions from Magpies about this hair claw! Looks like Celine, costs $5. I bought all the colors and have given several away as little gifts to friends.

+My beloved luggage. So gorgeous and smartly designed. This is also the best travel duffel — has a compartment for laptop, has a sleeve that slips over a roll-a-board handle, and fits a lot.

+Chappywrap has offered us 15% off with code JEN15. Their blankets make a great holiday gift, and also their new shawls would be SO DREAMY for travel. This was another regret of mine – I forgot to pack a wrap! I would definitely have used this on the flight and also for a few of the evenings out and chilly mornings where I could have used a little extra warmth at the neck/around the shoulders. I love the ones from Alice Walk for a slightly dressier feel, and these White + Warren cashmere ones are classic (select colors temporarily on sale!)

+This reminds me that Shopbop’s sale ends today! So many great buys temporarily discounted — my top picks here.

+I would recommend this rain jacket (so chic/sleek) and Davek’s mini umbrella for travel (small but mighty).

+The day we left for Italy, I had Glamsquad come by my house to blow out my hair — it was THE best decision! I felt great rolling onto that flight and pulled together coming off of it / not in need of an instant shower to re-do my hair. They’ve given us $20 off for new users with code JenniferS and $15 off for repeat users with code JenniferS15. I’m obsessed with the luxury of having my hair blown out at home! Will be doing this before I travel moving forward!

+These are my favorite organizational pouches. I initially bought for babies/kids stuff, but they’re roomy, carry a ton, and great for organizing softer things like socks, underwear, etc.

+I’ve written about these a ton, but these eye patches saved me the day after travel. They erase tired eyes! They come in individually packaged sets so you can toss one or two in your travel vanity bag. The brand just emailed me to offer us 15% off with code JENSHOOP.