Italy: A Dream Itinerary
Italy has been on my mind more than ever these days. Each country is experiencing their own pain, but there’s something about Italy that makes theirs hit deeper. Maybe it’s the fact they were the first after China to be crushed by death and isolation. Or maybe it’s the image of Italy (and the wonderful people who make our Italy travel memories so vivid they’re almost tangible) experiencing such heartbreak and chaos that makes it feels personal. We were meant to travel to Venice and the Dolomites in April which, of course, we had to cancel. Then, Umbria, Italy the end of June to celebrate the wedding of dear expat friends, which has also been postponed, just as so many weddings around the world.
These cancellations have me pouring over our unforgettable trip to Italy last May. And until we are able to return, I will be here, endlessly scrolling our Italy photos, drinking wine and eating wheels of Parmesan.
Before this trip, Luke had only been to the Amalfi Coast. To him, Italy was glamour and expensive gelato. It was definitely time for him to see more. More history, more pasta, more locals smoking cigarettes and drinking espresso at the same counter they visit every morning. It was time for the unglamorous gelato.
Pin for later!
Day 1: “The City of Light”
We started the holiday in….Paris actually. Curveball!
It was Luke’s first time, but the reason for the detour was to see Mumford and Sons. It was during the Women’s World Cup and the energy was high and joyful. We spent the afternoon walking around the Louvre and pregaming with cheese and bread, as one does before embarking on a gluttonous, Italian food tour. It’s how we roll baby!
Once the travel restrictions lift, you better believe we will be visiting Paris properly. By eating baguettes and cheese without a time restriction.
Milano: 1 Day
We flew from Paris to Milan, Italy for a 24 hour whirlwind. The food in Milan is amazing and Risotto alla Milanese was high on our agenda. Osteria Conchetta is the place to satisfy the craving and, luckily, we were able to gorge ourselves without a reservation. I wouldn’t recommend risking it – it’s just too good! The location of the restaurant is in a super fun area known as Navigli. Which brings me to your ALL THE APERITIVO destination (praise).
Aperitivo in Navigli
Once the clock strikes 5pm, visit one of the many canal-side bars on the Darsena, where you can sit out by the water with your aperol spritz and the complimentary small plates that follow. It’s so much free food that you likely won’t need dinner, but we wouldn’t judge. Aperitivo is quintessential Italy living and experiencing this in Milan is a must, especially in this EXACT place. Trust me. You may even wander into a silent disco in a small side street if you’re lucky.
Duomo di Milano
One of the largest cathedrals in the world, the Duomo di Milano watches over the city with its unmistakable spires and gothic architecture. Pigeons flood the entrance, where scammers are ready pick pocket tourists, so be extra careful as you spin around in circles during your insta photoshoot.
We were too focused on food to take the time to tour the Duomo, but you can book a guided tour to avoid the massive line. The stained glass windows and paintings are remarkable and something we don’t plan on missing next time.
Shopping
I’m not going to lie to you, I’m a terrible shopper. We made it as far as the Nike store…Again, we travel for food. Lucky for you, Timeout put together a list of some of the best boutiques in Milan, Italy, ranging from high-end to budget friendly. Ok, that’s all I got. Bye.
Starbucks Reserve Roastary
Yes, Starbucks. But before you judge and think “Why would I go to Starbucks in Italy?? Why??”…Just calm down, ok? It’s impressive, I promise. Situated in the old post office, everything about the design is grandeur and fabulous. Sit at the marbled Arriviamo Bar and enjoy an inspired cocktail, or get extra caffeinated and take one of the fascinating espresso classes.
More Food
We had dinner at Obica Mozzarella Bar and man that Mozzarella di Bufala Campana DOP was incredible. Order all the cheese with a side of pizza and a glass or 3 of wine. Thank me later. This restaurant is, surprisingly, reasonably priced considering it’s proximity to the Duomo.
Other Restaurants that were recommended: Bar Luce (designed by Wes Anderson) and Drogheria Milanese
Dessert is important. ESPECIALLY in Italy. We never visited the places recommended to us because we’re impatient animals and stopped at the first gelato cart we saw, but maybe you’re more restrained: Marchesi 1824 and OGGI Gelato
Cinque Terre: 3 Days
We caught the 3 hour train to Cinque Terre in the morning and sat there mesmerized by each Ligurian coastal town passing by the window. Our list of cities to visit along the Italian Riviera grew exponentially. I suddenly wished I had a very large sun hat.
Our delightful host met us at La Conchiglia where she treated us to aperitivo and basically planned our entire 3 day stay for us as we sipped on Spritz’.
Where to Stay
Riomaggiore is the perfect home base for exploring Cinque Terre. We stayed in a cozy Airbnb that was recommended demanded by a good friend, and WOW was this the right choice. The view from our kitchen window alone was a dream, but our host was also the loveliest.
What to do
The local train is easy and quick to reach the other cities. On our first day, we explored the shops in Riomaggiore then took the train next door to Manarola. Manarola is where you’ll find the most instagrammed view point in Cinque Terre: Nessun Dorma.
Nessun Dorma
Get there for aperitivo, order an Aperol Spritz and one of the most beautiful charcuterie boards you’ve ever seen. Sit back, and enjoy the view of the multicolored houses and the waves of the Ligurian Sea.
Porto Venere, Italy
I’m sure you’ve heard you can hike to each of the Cinque Terre cities: Riomaggiore – Manarola – Corniglia – Vernazza – Monterosso. Well, if you’re a little more adventurous, you should head the other way to Porto Venere.
After breakfast with a view at a small cafe, we continued up the path, past a church and a cemetery (ominous?) until the tourists were behind us and we were surrounded by trees.
We continued hiking up, up, up for I don’t know how long. We were starting to worry it would be this way for all 8.3 miles (13.4 km), until an old man passed us, fully dressed in his sweater and slacks, swinging a walking stick and smiling. He said something encouraging in Italian and, immediately after, the trees opened up and we were at the top. The view was incredible! There is an old, abandoned church at the viewpoint, and this is where most people turn around and head back to Riomaggiore.
Not us! We followed the path to continue, and after about 20 minutes realized we were headed the wrong direction. So, we went back UP to the church, found the other trail and got back on track. Don’t ask Luke whose fault that was.
The Hike
The hike literally took all day. This was partly due to my navigation mishaps, we also took our time exploring and taking photos. We stopped at a little pasta restaurant midway for wine and carbs to refuel, as everyone should.
Once we arrived to Porto Venere, there is the most beautiful lighthouse in the distance guiding you in.
We ate mussels and drank wine at a small restaurant in the midieval old town, followed by gelato and a walk around the port. Porto Venere was just as charming and beautiful as any Cinque Terre city, and much less crowded. We can’t recommend it in enough.
Getting back to Riomaggiore
The most ideal way to do this, is to hike to Porto Venere, then take a boat ride back to Riomaggiore, or vice versa. Unfortunately, the waters were rough while we were there, so we had to take the bus to La Spezia, then a short train ride. This was also very simple, but obviously less romantic and took a little longer because of the schedule, which is tough when you’ve been hiking all day. Pro tip: If you don’t wave at the bus, they do not stop for you. This isn’t fun to learn the hard way.
Another Perfect Day
We wanted to spend our last day in Cinque Terre exploring the other cities, so that’s exactly what we did. We started the day with Luke’s idea of breakfast in bed and it was….full of variety….
Vernazza
Our first stop was Vernazza, where we walked around the cute little shops and bought a few canvases to remember our time here then grabbed a late lunch at my absolute favorite pizza place from my first visit. This brings me to my next pro tip. And if you take away nothing from this blog post other than this, then I will consider it all worth it: Eat pesto. EAT. PESTO. Pasta, pizza, from the jar. Whatever. It is so mind blowing here and you will never be the same.
Favorite pizza spot: Ristorante Gianni Franzi
Hiking Cinque Terre
After I cleaned the pesto off my face, we started our hike from Vernazza to Monterosso. All of the trails are stunning in Cinque Terre, but this might be my favorite. The view of the coast, the vineyards and trees, the sea breeze – it’s all such a dream.
Once we reached Monterosso, we stopped to enjoy a glass of wine then beach-front gelato.
Corniglia was our final city, and our time was running out before we had our dinner reservation. We only had 15 minutes, but were determined to check them all off our list. The square was adorable, and we were a little sad to not have more time to enjoy it.
Dinner
Our last meal was back near our Airbnb in Riomaggiore at Dau Cila. We had one last seafood dinner before leaving the coast for Lucca.
Pro tip: You will need to pay to hike the popular trails. Because of overtourism, they need a way to keep the trails maintained. There is a booth at the entrance where you can pay in cash, our you can buy a card online. For 7.50, you have a day pass to access all of the trails, or, if you also are taking the train, you can buy a day pass for 16 euros which covers everything.
Trails: For a list and descriptions of the footpaths available, as well as a helpful map, click here.
When to go
There’s a reason you’ve heard of Cinque Terre – Beautiful doesn’t even begin to describe it. The seafood, the hiking, the wine – it is truly incredible. But now EVERYONE is in on the used-to-be hidden gem. Going in shoulder season can be a bit risky with the rain since you are on the coast, but going during peak season honestly wouldn’t even be enjoyable at this point. It is that busy. We went in May and we hiked in shorts and tank tops and had beautiful weather. It rained on and off one day but that was worth avoiding the cruise ship crowds.
Lucca: 2 Days
Lucca, Italy is a city settled in Tuscany, encircled by 16th Century Renaissance walls. After the crowds in Cinque Terre, the quiet buzz of the locals on a sunny Sunday was a welcomed change. It’s hard to not instantly fall in love with the charm and ease of Lucca.
Where to stay
Definitely within the walls of the city – we stayed at this Airbnb and had an excellent experience here.
What to do
I’m going to be honest with you. Drinking a liter of wine and getting lost in this place is a blast. Especially if you stop at multiple gelato shops (maybe a repeat or two). Not that I’m speaking from experience….Annnnnyway, speaking of gelato, the locals’ favorite combination is lemon and dark chocolate. WOW. I couldn’t get enough. But that could also be the liter of wine talking.
Rent bikes to ride around the medieval walls, then head out of the city among the poppies. Our host encouraged us to ride out to a vineyard, but Luke got a flat and we only made it about halfway. Maybe you can experience it for us!
Check out Visit A City or Airbnb experiences for some fun cooking classes! This is something we wish would have made time for.
Where to eat
Luke had his absolute favorite pasta in Lucca. There are so many delicious restaurants. One thing to note: the bread is truly just a utility for the olive oil. The olive oil is wonderful…the bread, not so much.
Surprisingly, there is a budding cocktail scene in Lucca – Our dear friend at A SophistiCaited Liferecommended a Franklin 33, an inspiring and inventive cocktail bar. The bartenders are knowledgeable, and the menu is a clever, cocktail treasure map full of Italian flavors.
Greve in Chianti: 3 days
Getting There
Train to Florence, Italy
We blazed through Florence as a means to get to Greve in Chianti. We took the opportunity to check a very important spot off our list – Osteria All’antico Vinaio. I repeat: VERY IMPORTANT.
From Florence, we hopped on an old, Italian bus filled with high school students…because why not.
1 hour later and we arrived. Magic. This is the word that comes to mind when I think of Chianti. Pure, dreamland magic.
Where to Stay
We stayed at Borgo Del Cabreo through booking.com and can’t imagine staying anywhere else.
You have to hike up a hill to get there (and wearing heavy backpacks as we tend to do, this was a workout for sure), but it is so worth the climb! The scenery was a literal fairy tale and the owner was wonderful. Since it was not yet high season, they upgraded us for free and we had a delicious breakfast included every morning.
The view from the pool was also breathtaking.
Getting Around
Pro Tip: If you don’t have a car, it is really difficult to get to the other towns, visit Castello di Verrazzano, or taste at any winery outside of Greve. Everything is spread out and extremely hilly (go figure).
Thankfully, we met an Austrian couple on their honeymoon at THE BEST pizza place in town, La Cantina. We toasted them with glasses of Champagne, shared a few laughs, and hiked back to our Villa to be super classy and eat it on the floor.
Thinking we would never see them again, we were so excited when they walked right into our little breakfast nook! We had coffee together and they graciously invited us to hijack their honeymoon and join them at Dario Cecchini’s restaurant in Panzano: Solociccia.
The Mad Butcher
As soon as you walk into the restaurant, you feel at home. “The Mad Butcher” himself is behind the counter with various cuts of meat, the host immediately fills your glass with red wine, and you’re directed to a large aperitivo spread as you wait for your table. Once everyone arrives, you are directed across the street into another room that houses just one long wooden table.
We made life long friends at this table. Topping off each other’s wine glasses and sharing stories over beautiful dishes with people from all over the world. It is one of those travel memories that sticks with us. An example of how travel deeply impacts us and opens our hearts to people we would have never met otherwise, let alone share a meal with.
The Wine
Wine: The reason we’re here! Chianti Classico is our favorite go-to Italian red. The region stretches between Florence and Siena, including the entire territory of Greve. Basically, we were in Chianti Classico mecca and we dedicated a day to tasting, visiting 2 wineries.
Montefioralle Winery
We walked to through rolling hills of vineyards to the medieval town of Montefioralle. This was a lovely, family owned winery. We really enjoyed the intimacy of the atmosphere, only joined by a delightful couple from Australia. We shared stories of travel over delicious wine and local cheeses.
Viticcio Vineyards
Viticcio is a larger, well-known winery, so the tour was less personal, but our group made the experience for us. It was me and Luke, a few friends from Romania, and a large, boistrous group of American women celebrating a 50th birthday. We absolutely loved them.
The vineyard itself was exactly what you picture when you think Chianti, Italy.
After all the wine, we took the long way back to our villa.
Wine bar
On our way out of Greve, we made one last wine stop at Enoteca di Greve. This is where we actually learned the most about Chianti Classico and the defining pink label with the Black Rooster seal. This particular label is the symbol of the Chianti Classico Wine Consortium, founded in 1924 to protect, promote this wine and prevent wine fraud. Time for a wine nap on the bus back to Florence.
Rome: 2 days, 3 nights
We caught the fast train from Florence to Rome that evening and set off to our last city of the trip: Roma.
It was a first time for both of us and wow were we blown away. Luke is a major history buff, but I was honestly expecting it to just feel cramped and claustrophobic, maybe a little underwhelming, especially after having the most magical time in Chianti. I was so wrong! Literally everywhere you turned there was something spectacular and wildly historic. Walk down the street and, BAM!, Colosseum. Turn right and, BAM!, Trevi Fountain. Sit down on a bench and, BAM!, there’s the best gelato you’ve ever tasted straight ahead. You get it. Gelato is a love language I’m pretty sure. Anyway, we also had the best food we had the entire trip. Everything about Rome was so next level, yet at the same time, so seemingly effortless.
Rome is one of those places where about 1 in 3 people you know have recommendations. We like these places. There wasn’t a meal we had that wasn’t suggested, and boy did we eat. Let’s start at the beginning.
Where to Stay:
We were told to stay central, near Piazza Navona, which was absolutely perfect. The neighborhood vibe is local, but from here you can easily walk to all of the major tourist attractions and still get to Trastevere for dinner and drinks.
Night 1:
We dropped our bags at the Airbnb and walked to Old Bear, tucked away next to the Museo Nazionale Romano. Luke STILL talks about this meal. The ambiance, the service, the quality – it’s all quite memorable. We were lucky enough to sneak in without a reservation with the ol’ “we’ll only stay an hour” trick. This rarely fails us, but maybe just go ahead and make that reservation.
Keeping our streak alive, we waddled our pasta bods toward gelato and ended the night at Giolitti. Then watched Gladiator to get pumped up for our whirlwind Roma finale!
Day 1: Vatican City
We walked into another country to check off our list in the morning to join our Vatican, Sistine Chapel and St. Peter’s Basilica Tour group. I can’t even begin to describe the beauty here. I’ll just have to show you in pictures.
Lunch
To top off the experience, we went to Ristorante dei Musei for lunch and let me tell you…Maria. SHOWED. UP. Our friends strongly recommended this family-owned pasta joint, warning “don’t even bother ordering because they will bring you whatever”, and they were spot on. It’s kind of an unassuming atmosphere when you walk in, and you may sit at your table for a bit before being greeted, but once you are, the wheels come off. A number of questions were rapid fired: Red or white? Pasta or pizza? You like sausage? Ok I know what I’ll make you! And that was that. We drank a liter of wine (which became a standard for most meals by now), ate about 4 meals, took a shot of “homemade Ukranian Schnapps” (whatever that is), scarfed free tiramisu they had just made, and finished with limoncello. Once we were ready to break free and go back into the world again, she pulled out a piece of paper, scribbled some illegible notes, handed it to us and charged us maybe 40 euros.
You will need a long walk and a nap to recover from Maria.
Dinner:
We pretended to be hungry because all we do in Italy is overconsume, so we walked to the other side of the River Tiber to the Trastevere neighborhood, but we didn’t quite make it. Just on the edge of the neighborhood, there was a restaurant bustling with locals – families, friends, couples alike. We knew immediately this was the place to be. Miraggio Ristorante Pizzeria was where we ordered an array of small plates of all the Roma must eats…about 90% of this was fried.
Day 2: Ancient Rome
Today was another day of walking, so we popped into Ex Circus for breakfast sandwiches and espresso on our way to our final walking tour of the trip.
Our last day was a rainy one, but wow was did we have a blast. We did the Ancient Rome and Colosseum half day tour, which explored the Colosseum, Palatine Hill and The Roman Forum. The line at the Colosseum is especially crazy, so I wouldn’t even recommend going without a guide who can bring your group through the fast line. This special line will lead you to a metal detector accompanied by a security guard hard at work, watching YouTube videos on his phone. So don’t worry, super safe.
Lunch:
We wandered into the Quartiere Ebraico (Hebrew Quarter), which was once the Jewish Ghetto, in search of artichokes. And when it comes to food, we always find what we’re looking for. Lunchtime on a Saturday was hoppin’ at this place. There was a long wait since the restaurant is about the size of a shoe box, but we were able to stroll around and notice memorials scattered throughout with names of Jews arrested during WWII.
Nonna Betta was tiny. We were ushered a few steps back and squeezed in next to a couple of wonderful Italians catching up on life and telling us where to eat next time we visit. We ordered artichokes and wine and enjoyed conversation with our table mates. That artichoke must have been excellent because I literally took one picture of our entire experience in the Jewish Ghetto. Enjoy.
Trastevere:
Trastevere is this funky mix of bohemian and traditional. Buzzing bars and restaurants intertwined with religious shrines and crumbling brick buildings. Vibrant green plants cover the alleyways as a backdrop to the young professionals and college students sharing aperitivo and getting their evening started. We joined the crowd on the busy Piazza di Santa Maria and ordered negronis at Pimm’S Good, which were delivered with a bomb snack plate. The cocktails at this place were really fun and the vibe was great. Our final meal (tear shed) was just down the street.
Dinner
One of my clients visits Rome, Italy every year and told me about one of his favorites: Trattoria da Augusto. His insider tip? They don’t take reservations, so if you want to guarantee a seat, you have to shuffle into the line formed before the doors open. As you walk in, you wonder how everyone in line will even fit. We were placed at a 4 person table next to two wonderful cousins from Munich on their annual cousin trip. I ordered rabbit and Luke ordered a very basic, yet incredible pasta and our last liter of wine.
We ended the night with another much needed walk to the Trevi Fountain. We ate our gelato from Venchi Cioccolato, threw a coin into the fountain and silently reflected on all of the joy that is Italy travel.
Until next time, Italy. We hope it is very soon.
Pin for later!
