In June of 2019, my husband Jeff and I got to visit Italy for the first time. It was a combined Honeymoon/One Year Anniversary Trip, and we were excited to finally check Italy off the bucket list!

I want to start off by saying that Italy was AWESOME. The land was beautiful, the wine was amazing, the history, architecture, and sculptures were spellbinding. We packed a LOT into the 10 days we were there, visiting multiple major cities, driving through countrysides, tasting wine, eating pizza, and walking the streets. This post is about the first half of our trip since there is too much to write about (and too many photos to show) if I did it all in one go.

GEtting There

So one of the things I tend to not think much about, or even see much about when other people write about their travels, is the actual TRAVEL part. When we decided to go to Italy, I thought (of course) about BEING IN ITALY, and not so much about the actual getting there. Since we lived on the West Coast of the U.S., getting there was going to be a big part of the trip. Luckily, our travels went well.

For us, New York was the first stop on our trip. We took two (TWO!) red-eye flights to get from California to Italy. We started at SFO (San Francisco International Airport), took a red-eye to the East Coast, spent a day in New York, and took a SECOND red-eye that night to Milan. And honestly, we had a blast during our 12 hours in The Big Apple! But if I’m going to be honest, doing back-to-back red-eye flights is not for the faint of heart. By the time we got there, my eyes were indeed red, my ankles were swollen into full-fledged cankles, and my body had no idea what time zone it was in.

Milan

Stop 1: Milan. We arrived in Milan after our arduous journey, and I’m not going to lie, we were both feeling a bit jet-lagged. Two red-eye flights and a nine-hour time difference will do that to you. We didn’t have the beeeessssttt experience picking up our rental car in that there was a lengthy wait to be helped by the representative at the car rental counter, but eventually we were packed into our petite, manual transmission, fuel efficient bug of a car and on our way to the hotel to check in.

This leads me to Italy Travel Tip #1: Don’t rent a car. Not that it was a terrible experience as a whole, but as you’ll see throughout this article, driving from place to place is 1) Expensive (both for tolls on practically ALL the highways and parking in any city area) and 2) Stressful (do Italians have something against street signs? Or lanes?). Lastly, pretty much all the vehicles are 3) Manual Transmission. Not a problem for us, but would be a problem for some. More on cars later.

So, we made it to Hotel Moxie in Milan, an affiliate of Marriott. Side note: Jeff travels a lot for work and therefore has a ton of Marriott Rewards Points. So to keep cost as low as possible, rather than book Airbnb’s as suggested by an Italy-travel-loving family member, we stayed in hotels at each location. Which leads me to Italy Travel Tip #2: Stay in Airbnb’s or other Bed and Breakfasts. Hotels are nice, but these major hotels are typically located in major metropolitan areas with expensive parking, lots of congestion, and less of a local feel than a country home. If you’re a city person, you might not mind, but since we aren’t big city people, we would definitely book B&B’s for our next visit. But again, I digress.

After a quick power-nap (remember the jet-lag and red-eyes), we headed to the heart of Milan for some sight-seeing and our first real Italian Dinner. Oh. My. Goodness. It did not disappoint!

We parked near downtown and kicked off our first adventure by walking through the Galleria Vittorio Emanuele. Wow.

Galleria Vittorio Emanuele, Milan, Italy

The place was packed with people but I couldn’t help the desire to stop and photograph this incredible atrium from every angle. Jeff, however, was good about keeping me from dwelling too long in any one spot; we had so much to see!

Side Note: If I was into shopping (I’m not), I would have gone crazy here. So many designer shops (see above photo: Prada, Versace…) with beautiful Italian clothing and leather! But luckily for my pocketbook, that’s not a temptation I fall into easily.

As we passed through the atrium, our awe only grew as the Duomo di Milano (Milan Cathedral) came into view. I had never seen a cathedral like this in my life, and I was momentarily silenced by its beauty and craftsmanship. The amount of detail in this monumental cathedral was simply astounding. It’s size alone would be impressive enough: it is the largest church in Italy, the third largest church in Europe, and the fifth largest church in the world. From far away and up close, every element of the Duomo di Milano was pleasing to the eye, and well it should be given that it took nearly six centuries to complete (started construction in 1386, completed in 1965) and renovations and maintenance continue to this day.

Lake Como and Bellagio

The next day we made the drive up to the town of Como where we had booked a ferry ride to Bellagio. It was a beautiful, sunny, comfortably warm day; perfect for a trip out on the water. There was a slight breeze as we stationed ourselves on the top deck of the boat, but the sun kept us from getting cold.

This visit to Lake Como was one of the things I had been most excited about when planning our trip to Italy. It is famous for several reasons. It is the third largest lake in Italy and is in the distinctive shape of an upside-down “Y”, with Bellagio at the center point of the three sections and the town of Como in the Southwest corner. It is known as a destination point for celebrities and aristocrats alike, George Clooney being one of the most famous recent homeowners, and has been a destination for the wealthy for centuries. But the real reason behind my excitement had more to do with the landscape of the area. The natural beauty is astounding, with tree-covered hills rising up out of the water, views of the Alps in the distance and the border of Switzerland just to the West and North of the lake. The Villas that line the shore look like they are straight out of a fairy-tale or a movie, with beautifully manicured gardens and lawns bordering the houses and the water, and expensive yachts and speedboats docked right along the water’s edge.

The lake was a bustle of activity, with speedboats and ferries on the water, planes in the air, and people all along the shores. And all this activity that I speak of was merely what we saw from on board the ferry.

When we arrived at our destination of Bellagio, the bustle only increased. Since the ferry made several stops to pick up people along the route, we had quite a full boat upon our arrival, and people piled off in droves and dispersed into shops, restaurants, and along cobblestone streets.

Our goal upon arrival was naturally to find a spot for pizza and wine (duh). So we hiked up some stone steps and found a cute restaurant called “Ristoro Forma & Gusto” on a narrow side street only minutes away from where the ferry had dropped us off.

Bellagio was beautiful, and I enjoyed wandering down its narrow streets, past its cute shops, and watching all the different people who came here to visit. But, if I am going to offer any advice, it would be this:

Pack well. (Let’s make that Italy travel tip #3)

Jeff and I realized upon our arrival that the warm Italian sun was quickly turning our skin into an unsightly red color, and since we had packed none, decided to go purchase some sunscreen. Not only was it incredibly expensive (as to be expected in a small, VERY touristy area), but the one we ended up with turned out to be excessively oily, leaving us wondering if it would have been better to just be burnt. I would also recommend bringing some water and light snacks to save on money. As with any small, high-end tourist destination, prices were markedly higher than at a local supermarket, so either come prepared to spend some extra moolah or pack the basics that you wouldn’t want to buy for at least 1.5x the normal cost.

Alrighty. Moving on. Next stop:

Florence

Spoiler Alert here: Florence (Firenze) was our FAVORITE location of the whole trip. Lake Como was a close second, but there is just something magical about both the city of Florence and the surrounding countryside. The history and architecture alone were enough to put me in a perpetual state of awe, and then add in the beauty of the river flowing through the city with the bridges arching over it and the sight of vineyards stretching over rolling hills, and you just can’t beat it.

We did several fun activities in Florence in addition to our usual walking around and having pizza and red wine. One of these activities was the amazing Chianti Wine and Food Safari Tour. Yes, you heard that right: SAFARI. We got to ride from downtown Florence to three different wineries in the Chianti region in a HUGE 4x4 vehicle, and YES, we did actually go on some rugged dirt roads! At each location we got a tour of the winery with interesting historical information, as well as wine and food pairings. I would highly recommend this tour, especially if you get Martina, the best tour guide ever :)

Florence: The Surrounding Countryside

We booked this tour through Viator but the company itself that runs the tours is called Walkabout Florence. You can book through either site. It is an all-day activity, and the cost of approximately $170/person covers the transportation in the 4x4, food and wine pairings at three wineries, and a lovely tour experience.

Overall we highly enjoyed this tour. It was a great way to learn about the region, the history, and the way the people and the land interact through wine and olive oil production. It was also a great way to connect and converse with other travelers and to see places we otherwise couldn’t have seen, as none of these wineries are open to the general public. In that way, wine tasting in Italy was notably different than the wine tasting experiences I’d had in California, where many (dare I say most?) of the wineries are open to the public without appointment.

It was a fun day full of delicious food, incredible wine, beautiful views, and interesting history. In the following photos, you can get a small taste of this experience as you can see us not only touring the barrel and tasting rooms, but the exquisite gardens that were a part of these ancient and ornate estates.

One of the olive trees used for the highly renowned olive oil production at Villa le Corti

Our first stop on the tour was at the famous Villa le Corti of the Corsini family, whose history at this Estate date back to the 16th century. Villa le Corti encompasses 250 hectares of land, 49 of which are vineyards of Sangiovese for their Chianti Classico and IGT Principe Corsini wines, and 73 of which hold olive trees used to produce their Chianti Classico DOP Extra Virgin Olive Oil. Not only did we get to taste the fabulous wines, but we got to tour the historic winery and incredible garden.

Location of our second wine tasting, Villa Rignana which also included a side-by-side olive oil tasting experience

Our second stop, at the Fattoria and Villa Rignana, was somehow even more picturesque than the first, with stunning views of vineyards and hillsides stretching for miles. We tasted an amazing Rose under a wooden gazebo with a long wooden table, poised perfectly to take in the surrounding views, and followed the wine with a side-by-side blind olive oil tasting, where we not only learned what to look for in a high-quality olive oil, but also learned about the way in which olive oils are produced and graded. We then walked up a short flight of steps to an open-air dining room where we sampled more foods and wines local to the region.

Our third stop was at a beautiful winery called Lamole di Lamole. We parked a short distance away from the winery itself and got to take a mini scenic hike through grasses and next to vineyards; a nice way to stretch the legs after our drive from the previous winery. Once at the winery, an associate from Lamole di Lamole gave our Martina a short break from her tour narration, and told us a bit about the winery herself. Consistent with the previous two locations, Lamole di Lamole holds ancient roots, as the Romans identified the area hundreds of years ago as an excellent region for the cultivation of both grapes and olives for wine and olive oil production. We toured the winery, set in a building dating back to the mid-14th century, while pieces of history throughout the winery remind us of the age of the place.

Yet, while the presence of the history and feeling of antiquity are strong, Lamole di Lamole also provides a side of modernity. As seen in the photo below, a unique egg-shaped barrel, originally designed by the French company Taransaud, has been incorporated into this historic Italian winery’s tradition starting in 2014. This barrel, made completely of French Oak and costing around $29,000 (or more), is designed to create a constant, convective flow of wine through the barrel and give the wine a more complex, well-rounded flavor. And while the location of Lamole and the winery, cellars, and castle have a longer history, the “Historic Vineyard” (as opposed to the newer “Experimental Vineyard”) was planted in 1945, mere decades rather than centuries ago.

A short hike along the scenic hilltop path in Lamole

Pieces of wine-making history at Lamole di Lamole

After this third winery, we surprisingly had a small amount of time to spare before having to head back to downtown Florence. Our tour guide, Martina, suggested we stop at the main square of Greve in Chianti, Piazza Matteotti, known for its cute shops, tasty meats, and of course, wine. The meat shop had a stuffed boar in front, so naturally (after wine tasting all day), we had to take a quick photo with him. We then progressed to a wine shop that had wine on tap and sold it by the ounce, so we were able to select the wine of our choice and then walk around the town with our glass of wine in hand! I knew I liked Italy…

Some of the wines you could choose from for tasting at Greve in Chianti. Small, Medium, or Large pours available

Needless to say, we were tired and happy at the end of the day following our Wine Tasting Safari, but still excited to explore the city of Florence itself the next day.

Florence: The City

However, our plans didn’t go quite as expected. We had reserved a time to tour the Duomo di Firenze and climb the 463 steps to the top, the only way to see the Duomo and the subsequent views of Florence, as there is no elevator. This isn’t a first-come, first-serve type of activity; due to the narrowness of the stairs (not originally built with the intention of having so many people traverse them), the city limits the number of people who can tour this monument at any one time, and we had booked our spot weeks in advance. However, unbeknownst to us until the day of, a person of high religious or political importance (don’t ask me who, I can’t remember his name for the life of me), had the audacity to die and a ceremony in his honor (at the Duomo) was scheduled for the day we had planned our visit. And for some wild reason, his ceremony took precedent over our visit (imagine that!). Therefore, we had to be satisfied with visiting the Duomo and admiring it from the outside, which in itself was an awe-inspiring treat.

We didn’t let this change of plans dampen our spirits in the least. We instead enjoyed some more walking about, eating of gelato, and treating ourselves to a rooftop drink at the exquisite restaurant at the top of our hotel which overlooked the city and the river.

The view from the top of our hotel was exquisite, and we felt quite fancy as we sipped Prosecco and gazed down the river, across to the Piazzale Michelangelo, and over the various historical churches, monuments, and squares. It was actually this view that inspired me to go on a jog along the river and up to the Piazzale Michelangelo the following morning; one of my favorite jogs of the trip!

This leads me to Italy Travel Tip #4: Exercise. It took me awhile to realize that one of the reasons I would tend to have less energy and feel more bloated on trips was not only from eating different (and typically richer) foods and drinking more alcohol, but I wasn’t getting my CARDIO in! Running is a big part of my life and it keeps me feeling good, so when its safe (key element here), I try to go for jogs when travelling. Not only do I work off some of the extra calories I’m consuming (and feel better for it), but it is an EXCELLENT way to explore and enjoy new places! I realize running might not be everyone’s favorite thing, but I do find that exercising while traveling is a win-win. So whether its an early morning power-walk or a bike ride along a river, keeping active will keep you feeling less guilty about those extra slices of pizza or glasses of Prosecco.

View of Florence from my morning jog to Piazzale Michelangelo

Along the same lines, Italy Travel Tip #5 would have to be: Make Use of Your Mornings! I realized on my morning jogs that every city was quietest in the mornings. I didn’t get up crazy early, maybe 7am, but it was incredibly peaceful to jog through these famous cities before the throngs of tourists emerged from their hotels and clogged the cobblestone streets. Getting out in the mornings gave me a different view of the places that Jeff and I had sometimes explored the evenings prior. Don’t get me wrong, being out in the evenings when the cities were alive and bustling with activity brought its own kind of joy. We loved the people watching, we loved the energy. But there is something about the stillness and quietness of the mornings, when you see locals biking to work rather than tourists plodding along taking photos every ten steps (like I did from time to time).

Also, for the photographers among you readers, the soft light of both the early mornings and late evenings makes for great photos, but the advantage of the mornings is that you will likely get less people standing at inopportune locations while you’re trying to photograph a beautiful landscape or historic building.

As it was, I found myself occasionally wishing I had woken up even earlier, to catch the moments before the sun rose rather than just the moments right after it started to light up the streets, and perhaps next time I will. I certainly hope that we will get to visit Florence again, and the next time we go, we will go with more knowledge. I think we would spend even more time out in the countryside, staying at B&B’s, going wine tasting, and maybe even doing a bike tour. There is just so much to do and so much to explore in this big, beautiful world; the possibilities are endless :)

Wrap-Up

This is the point where Italy Adventures Part I comes to a close, but don’t worry! Part II will be coming shortly, so keep your eyes peeled for continued adventures, stories, and photos from Bologna, Rome, and Genoa.