Two Weeks in Italy (2019)

September 16-27, 2019

Aside from recording the traveling we do while we’re living in London, my other motivation for this platform is having a place to store (and easily share) detailed itineraries and recommendations for some of the bigger trips we’ve taken in the past. The trip I get asked about the most is the two weeks we spent with Andy’s mother in Italy to celebrate her retirement and the completion of his MBA. It was Andy’s mom’s first time in Europe and there is also just SO much to see and do in Italy, so I spent a lot more time planning this trip than I typically would…and it paid off!

During our 12 days in Italy, we spent a few days each in Milan, Vernazza (Cinque Terre), Florence, Montepulciano (Val d’Orcia region in Tuscany), and Rome. (Side note: we didn’t go to Venice on this trip, but we went for a weekend in October 2021.) We also bookended the trip with a few days in Paris because there are so many options for flying between the Delta hub in Atlanta and the Air France hub at CDG…and also because I will use pretty much any excuse to spend time in Paris. I’ve included a day-by-day itinerary with details about each city we visited in Italy and some travel advice, as well as separate sections at the end of the post for the specific restaurants/bars and activities we enjoyed and general tips for traveling in Italy.

If you’re planning a trip to Italy, click here to access and download my Google Maps list of saved locations.


  • Day 1 – Milan
    • We flew from Paris (CDG) to Milan Malpensa (MXP) and took the Malpensa Express train to the city center. Taking the train was a lot faster than taking a taxi all the way from the airport, and it was easy to get a taxi from the train station to our Airbnb. We stayed right in the city center, which was convenient for sightseeing. However, it definitely lacked some charm and there wasn’t a lot open at night.
    • Our Airbnb was just a few blocks from the Duomo di Milano, the second largest church in the world, and we spent an hour or so during our first afternoon in Milan exploring the cathedral. The views from the rooftop were breathtaking! We ate lunch and had aperitivo at cafes in the Galleria Vittorio Emanuele II, which is the oldest shopping gallery in Italy and connects the Piazza del Duomo to the Piazza della Scala, and also did some shopping (obviously).
    • One of our very favorite parts of the entire trip was seeing Rigoletto at the Teatro alla Scala. Everything about seeing an opera at La Scala was incredible, but it was particularly special to see a Verdi masterpiece performed on his “home” stage. The tickets weren’t very expensive, but they typically sell out really quickly — I think I bought ours three months in advance.
  • Day 2 – Milan
    • The one thing we scheduled in Milan was a guided tour of The Last Supper. Da Vinci’s masterpiece is actually a mural painted in a nondescript church (Santa Maria delle Grazie), so there are a lot of preservation measures in place to protect and preserve it. The only way to see the painting is to book a time slot through a licensed tour guide, which I had to reserve several months in advance, but we were very pleasantly surprised at how much we enjoyed the experience. The painting is huge and is somehow even more impressive in person despite being one of the most famous pieces of art in the world, and the restricted group size meant that we actually got to appreciate the details — definitely a nice change of pace from craning to see tiny paintings like the Mona Lisa, etc. in a crowded gallery.
    • We bought walk-up tickets at the Castello Sforzesco (Sforza Castle), a citadel built by a Duke of Milan in the 15th century that is now home to an impressive museum and artwork, including Michelangelo’s last sculpture (the Rondanini Pietà) and a lot of da Vinci sketches, letters, and even a fresco. The castle and museum were very interesting, and also were located close to a beautiful park (Parco Sempione) and the old city gate (Arco della Pace).
  • Day 3 – Cinque Terre
    • It took ~3 hours (and ~€18 per person) to get from Milan to Monterosso by train, which definitely seems like the easiest and most enjoyable way to get to the Cinque Terre. The five villages of Cinque Terre are connected by a local train with tunnels through the mountains, and so it only took a few more minutes for us to get to our Airbnb in Vernazza.
    • We spent our first day solely in Vernazza, taking in some of the breathtaking views, eating fresh anchovies (surprisingly delicious), and drinking lots of local white wine. All five villages are packed, but Vernazza seemed like the prettiest and it was certainly less touristy than some of the other villages. It also has a sandy beach right in town, as well as a few decent restaurants — despite the Ligurian region being known for its seafood, pesto, focaccia, and other amazing foods, the Cinque Terre is full of mediocre and overpriced restaurants.
  • Day 4 – Cinque Terre
    • The villages of the Cinque Terre are connected by trails and it’s really popular to hike from town to town. I hadn’t used Airbnb Experiences before (I have now used it several times since and have loved every experience), but I was intrigued by a “wine tour hike” that had a lot of good reviews and I booked an early-morning time slot for our one full day in the Cinque Terre. Andy’s mom decided to skip the hike (which ended up being an excellent choice since the hike was a lot harder than we initially anticipated), but Andy and I had an incredible morning with our small hiking group and a local sommelier who took us through Riomaggiore and Manarola to a small winemaker and a mountaintop vineyard. It was easily one of the highlights of our trip.
    • The best way to see all five villages is by boat, so we booked a sunset cruise for our last evening. We were able to just walk up to the harbor in Vernazza and get tickets, which made it super easy. The views were unbelievable — truly something that pictures can’t do justice.
  • Day 5 – Pisa + Florence
    • We originally had train tickets booked from Monterosso to Florence with a short connection in Pisa and hadn’t planned on actually spending time in Pisa, but then at the last minute, we decided to switch our tickets for the second train so we could see the Leaning Tower of Pisa. The Piazza dei Miracoli was an easy walk from the train station and we had about three hours to spend in Pisa, which was plenty of time to see the Tower and have a nice lunch. I’m really glad that we decided to stop, but definitely wouldn’t have gone out of my way just to go to Pisa — the city itself is lacking in charm and is super crowded with cruise-ship daytrippers.
    • We arrived in Florence late in the afternoon and checked in at our Airbnb, which was in the city center by the Piazza della Signoria and the Palazzo Vecchio. The location was perfect because we were able to easily come back to our rooms throughout our stay to drop off bags and take a break from the heat between sightseeing and shopping. We spent our first evening in Florence just walking around the city and drinking wine at different enotecas before happening upon Ristorante Trattoria Angiolino for an incredible late dinner.
  • Day 6 – Florence
    • Anyone who has traveled with me before knows that I typically loathe group tours and doing anything that screams “tourist”…but in Italy, it’s almost impossible to see the major sites and artwork without an official tour guide. Tour guides in Italy are licensed by the local tourism bureau and are required to pass a written and oral examination about their city’s history, art, architecture, etc., so they actually provide a lot of value, and many of the major museums require ticket reservations through a tour company. There is also just SO much to see in Italy that I think it would be really challenging to try to do it on your own. I used the same tour company, Walks of Italy, in both Florence and Rome and all three tours we took were excellent and had fewer than 20 people per tour. Having an expert show us all the main highlights and provide background information/context for what we were seeing (plus the skip-the-line access at all the museums) was worth looking like a tourist and being stuck with random groups of people for hours at a time.
    • In Florence, we did the Florence In A Day tour, which was broken up into two parts. The morning portion started in the Galleria dell’Accademia, which is best known for housing Michelangelo’s original David and several of his unfinished sculptures. David is huge and was so cool to see in real life…I could have probably gone without seeing the rest of the museum, though. Thankfully, we didn’t spend too much time there before walking through the Piazza del Duomo to see the cathedral complex, including the Cattedrale di Santa Maria del Fiore (AKA the Duomo di Firenze), the Baptistery, and Giotto’s Campanile. The exterior of the buildings was absolutely gorgeous and I wish we would have been able to go inside, but the lines were insane. We also walked around the Palazzo Vecchio and the outdoor sculptures at Piazza della Signoria, as well as the Ponte Vecchio (a bridge over the Arno River known for its shops), before breaking for lunch.
    • We spent the afternoon at the Galleria degli Uffizi (Uffizi Gallery), which is home to most of the Renaissance masterpieces in Florence, including Botticelli’s Birth of Venus and Primavera, Michelangelo’s only surviving panel painting, Caravaggio’s Medusa, and several important paintings from da Vinci, Titian, and Raphael. The building itself is also exceptionally beautiful and there was so much artwork to see that it was a little overwhelming, so I’m glad we had a tour guide to keep us focused on the highlights.
  • Day 7 – Val d’Orcia
    • Andy was very excited about driving in Italy, so we picked up a rental car on the outskirts of Florence for the Val d’Orcia part of our trip. Val d’Orcia is an area of southern Tuscany that is known for its medieval “hill towns” and it is probably what comes to mind when you think about cypress-lined roads cutting through the rolling hills of the Tuscan countryside. It is also, without a doubt, the most beautiful and incredible place Andy and I have ever been — no matter how many trips we take, I’m not sure that anything will top our time in Val d’Orcia.
    • We took our time getting from Florence to Val d’Orcia by stopping at a few vineyards along the way. The first place we went was Cantina Antinori nel Chianti Classico, which was by far the largest winery we visited. The Antinori family is one of the oldest winemaking families in Europe and they have several huge estates across Italy, but the winery itself is relatively new and is super modern. We took a very informative tour and had a lovely tasting before buying several bottles to ship back to Atlanta — one huge benefit of visiting a larger house is that they make it very easy to ship wine back. We enjoyed the smaller estates we visited a bit more than a large-scale operation like Antinori, but it was still really cool to visit, especially since the building and its views were so incredible.
    • The restaurant at Antinori looked really great, but we already had reservations for lunch at Osteria Volpaia, a restaurant affiliated with the Castello di Volpaia winery and further along on our route to Val d’Orcia. The medieval village of Volpaia was so charming, and our lunch at Osteria Volpaia was simply incredible — well worth the stop.
    • We finally made it to L’Orto Di Panza, our bed and breakfast located just outside of Montepulciano, in the late afternoon. I cannot say enough about how much we enjoyed our stay at this intimate B&B with spectacular views of the rolling hills. The rooms were somewhat rustic, but very spacious, comfortable, and quiet. It was conveniently located for going into Montepulciano and getting on the main roads to go to other villages– Montepulciano is on the eastern part of the valley, while Montalcino is on the western side, which makes them approximately 45 minutes away from each other (with Pienza, the other main town, roughly in the middle). The proprietress made a phenomenal breakfast every morning and was so friendly. She also had two little pugs, Alfredo and Agathe, that followed her everywhere.
  • Day 8 – Val d’Orcia
    • Our absolute favorite part of the entire trip (and one of my very favorite travel experiences to date) was a private cooking class at Fattoria Resta, a 400-year-old convent and winery in Buonconvento owned and operated by a woman named Anna Lisa and her daughter, Livia. They gave us a tour of the beautiful property alongside their terrier (Cru) and kitten (Chablis) and then helped us cook a traditional Tuscan meal of homemade pasta with a wild boar ragu, garden vegetables, and a heavenly tiramisu. The wine and the meal were divine, but Anna Lisa and Livia’s hospitality was truly what made the experience so special.
    • After we left Fattoria Resta, we went on another winery tour and tasting at Altesino, which was lovely and very personalized. We then capped off our picture-perfect day with a visit to the Chapel of the Madonna di Vitaleta, a tiny Renaissance-era chapel nestled in the hills of the Val d’Orcia between San Quirico d’Orcia and Pienza. All I can say is WOW…it was truly one of the most serenely beautiful places I’ve ever been.
  • Day 9 – Val d’Orcia + Rome
    • We ended up saving the best winery tour and tasting for last: Avignonesi. Aside from the fact that their Vino Nobile di Montepulciano is one of our favorite wines (and is fairly easy to find in Atlanta), our tour guide was delightful and the property was beautiful. They also had a really great store with a lot of unique and high-quality homewares.
    • From Avignonesi, we drove to Rome and immediately dropped off our rental car — despite how much Andy enjoyed driving in Tuscany, driving in Rome would have been a nightmare. Our Airbnb was next to the Piazza Navona, which ended up being an excellent location for both restaurants and sightseeing. We spent our first afternoon in Rome at the Pantheon, which was free to enter without tickets and very impressive (to say the least), and walked by some of the other famous sites, including the Fontana di Trevi.
  • Day 10 – Pompeii + Amalfi
    • We spent our first full day in Rome…leaving Rome to visit Pompeii and the Amalfi Coast as part of a private tour package I booked through MondoGuide. We took a bullet train from Rome to Naples and met our extremely friendly tour guide, Eddy, at Napoli Centrale. He drove down along the Amalfi Coast with several well-timed stops at some of the most scenic points, including longer stops in Ravello and Positano. It was a really good option for seeing some of the breathtaking views and experiencing some of the local charm without having to fight through the traffic or spend too much time in the jam-packed resort towns. I’d love to go back someday and spend more time at one of the nicer private resorts or historic hotels in Amalfi, but despite how beautiful the area is, I don’t think I would choose to spend time there over other places in Italy unless I could guarantee that we’d have some privacy and space away from the cruise-ship hordes. It was even more packed than the Cinque Terre, which is really saying something.
    • After a few hours of meandering along the Amalfi Coast, Eddy looped back up to Pompeii and dropped us off at the ruins and archaeological site for a private tour with an extremely knowledgeable and friendly licensed guide, Tiziana. She spent ~2 hours showing us all the key highlights and sharing history about the site, as well as recent/current excavation efforts. Pompeii was absolutely worth the visit — it’s definitely one of those surreal places that you’ve heard so much about and yet it is even more impressive in person.
  • Day 11 – Rome
    • We woke up bright and early the next day for the Pristine Sistine Early Entrance tour of the Vatican Museums, Sistine Chapel, and St. Peter’s Basilica — another small-group guided tour with Walks of Italy, which is the only company permitted to start its tours an hour before the general public is allowed in. I’m very thankful that I had read about this tour somewhere, and I HIGHLY recommend booking it if you want to visit the Vatican. Somehow even more so than any of the other places we visited in Italy, the crowds in the Vatican were insane, which is particularly unfortunate because it can really take away from its absolutely beautiful artwork, architecture, and history.
    • Being able to privately take in Michelangelo’s frescoes on the Sistine Chapel ceiling was truly a once-in-a-lifetime experience, but we also thoroughly enjoyed our extremely informative and interesting guided tour of the Vatican Museums (especially the ornate Stanze di Raffaello (Raphael Rooms) and the Gallery of the Maps) and skip-the-line access to the Papal Basilica of Saint Peter. In addition to being the largest and arguably the most important church in the world, St. Peter’s Basilica is simply beautiful. From the Michelangelo-designed Dome to Michelangelo’s Pietà (honestly the most breathtaking sculpture I’ve ever seen) to St. Peter’s Baldachin (designed by Bernini and where the Pope celebrates mass) to the Chair of St. Peter (also designed by Bernini)…it was all just incredible.
    • We spent the afternoon at the Colosseum, Roman Forum, and Palatine Hill as part of another Walks of Italy small group tour (Gladiator’s Gate). Maybe we were just getting tired at this point and a little jaded from all the other incredible sights we’d seen already, but I could have done without the Colosseum tour. The most interesting and impressive part was the exterior, so I would have probably preferred just to walk by it and not spend the time/money walking through the “interior”, which really doesn’t have much to see. The skip-the-line ticket for the Roman Forum and Palatine Hill was useful and it was interesting to tour one of the most important historical sites in the world, but it was also extremely hot and the area is really just one big archeological site with large ruins that could have been seen without actually going through the gates…so it really couldn’t begin to compare to some of the other places we had toured by that point.
  • Day 12 – Rome
    • After a wonderful coffee and cornetto at Sant’ Eustachio II Caffè, a super cool, old-school coffeehouse on the Piazza Sant Eustachio, we finally said “arrivederci” to Italy and headed back to Paris before flying out to Atlanta the next day.

Food & Drink

  • Milan
    • Trattoria Milanese – Dal 1933: We went to this traditional Milanese trattoria for dinner and it was one of Andy’s favorite meals in Italy. It has a great old-world ambiance, complete with in-house musicians, and the food was fantastic.
    • Arriviamo Bar at Starbucks Reserve Roastery: Never did I ever think that I would willingly go to a Starbucks outside of the USA (especially in the land of espresso), but Milan is the only city in Europe with a Starbucks Reserve Roastery and so I figured it might be worth checking out. Short answer = very cool; did not feel or look like a normal Starbucks whatsoever. It also has a really amazing bar, where we enjoyed more than a few espresso martinis and other coffee-inspired cocktails.
    • Bar Magenta: It wouldn’t be a trip to Milan without aperitivo, and Bar Magenta was an excellent choice for enjoying a few cocktails and (more than a few) snacks. It’s a large restaurant and seemed to be fairly locals-oriented, so it was easy to get a walk-in table.
  • Cinque Terre
    • Gelateria Il Porticciolo: Amazing gelato shop right by Vernazza beach…I’m pretty sure I went 5+ times during our three days in Vernazza.
    • Il Pirata delle 5 Terre: This little restaurant (that was conveniently located a stone’s throw away from our Airbnb) actually had a very decent breakfast menu (by Italian standards) and we went both mornings we were in town.
    • Belforte: Cute, family-run restaurant right outside the Doria Tower ruins with excellent views from its balcony and a solid menu offering traditional Ligurian seafood specialties.
    • Il Gambero Rosso Vernazza: Decent bistro-style restaurant along the main drag in Vernazza that has excellent table wine, fresh seafood, and homemade pasta.
  • Florence
    • ‘ino: Quite possibly the best sandwich shop I’ve ever visited, and the perfect place to grab a bite before or after touring the Uffizi Gallery.
    • Ristorante Trattoria Angiolino: This delightful Tuscan restaurant is located in Oltrano, which is on the south side of the River Arno by the Pitti Palace and Boboli Gardens. We went here for dinner on our first night and Andy and I both had the most incredible bistecca alla fiorentina, which we are still dreaming about two years later.
    • Caffè Cibrèo: Located near the mercato di Sant’Ambrogio, Caffè Cibrèo is the more casual (and less expensive) offshoot of the popular Ristorante Cibreo. We went here for a lovely dinner, and it felt very local and home-y.
    • Gelato: I ate a lot of gelato in Florence and it was all excellent, but my favorite gelaterias were Perché no!…, Gelato Vivoli, and Gelateria dei Neri.
  • Val d’Orcia
    • Osteria Volpaia: Lovely homestyle Tuscan restaurant in Volpaia that is affiliated with the popular Castello di Volpaia winery. Their set lunch menu is incredible and very affordable, especially if you have their (excellent) house wine.
    • Podere il Casale: We had an amazing dinner at this charming garden restaurant on an organic, family-run farm in Pienza and I wish we would have been able to spend more time on the farm. They produce and sell all kinds of foods, from cheese (mainly Pecorino), to fruits and vegetables, to olive oil, wine, bread and pasta, salami, honey, balsamic vinegar, and even grains, flour, etc. I would have loved to have taken a cheesemaking class or farm tour, but the dinner alone was still wonderful.
  • Rome
    • Salumeria Con Cucina Roscioli: Very cool (and delicious) restaurant in the Campo di Fiori neighborhood with a modern Roman menu and a phenomenal wine list. We went to the restaurant itself for dinner, but there’s also a bakery, deli counter, and wine shop.
    • Casa Bleve: Traditional Roman restaurant and wine bar housed in the courtyard of a beautiful 16th-century palazzo near the Pantheon. The food, wine, and service were spectacular.
    • Sant’ Eustachio II Caffè: Excellent coffee shop and bakery by the Pantheon that opened in the 1930s. In addition to the high-quality coffee, they also have some really cool coffee-related merchandise in the shop (we bought espresso cups).
    • Forno Campo de’ Fiori: Traditional local bakery outside the famous market at Campo de’ Fiori that is known for selling some of the best pizza al taglio (takeaway pizza slices) in Rome. It didn’t disappoint, and its central location makes it a perfect place to stop for a quick lunch.
    • L’Angolo Divino Enoteco Vineria: Just around the corner from Campo de Fiori is a wonderfully intimate wine bar that’s been open for 70+ years. The wine list is amazing and surprisingly affordable, and the food menu has great options for small plates.

Activities & Attractions

  • Milan
    • Guided Tour for The Last Supper: 100% worth visiting, but the only way to see the painting is to book a time slot with a licensed tour guide and you typically need to reserve tickets a few months in advance. I used Get Your Guide (~€40 per person) and we were very happy with the experience, which only takes up about an hour.
    • Duomo di Milano: The second largest church in the world and one of the most ornate and beautiful (that I’ve seen, at least). We bought our tickets the day of for ~€28 per person and spent an hour or so exploring the cathedral — mainly the rooftop, which is by far the coolest part.
    • Galleria Vittorio Emanuele II: Italy’s oldest shopping gallery is just across the Piazza del Duomo and the building itself is so beautiful that it almost overshadows the amazing shops and boutiques, including the original Prada store that Mario Prada opened in 1913.
    • Teatro alla Scala: Anyone who is even remotely interested in opera/theatre should prioritize trying to see a show at La Scala, one of the most famous opera houses in the world. Tickets sell out quickly, but I booked ours around three months in advance (the same day I booked our tickets for The Last Supper) and paid €48 per ticket for decent-ish tickets in the upper gallery. The experience of seeing an Italian opera in an Italian opera landmark was “bucket list”-worthy.
    • Castello Sforzesco (Sforza Castle): A 15th-century fortress with a very impressive museum and important artwork, including Michelangelo’s last sculpture (the Rondanini Pietà) and a room with ceiling frescoes painted by da Vinci. We bought walk-up tickets and I don’t think we even had to wait in line anywhere, but it would have been worth seeing the highlights (especially the da Vinci frescoes) even if it hadn’t been so easy.
    • Parco Sempione: A few blocks away from the castle is a beautiful park, Parco Sempione, and the impressive Porta Sempione city gate marked by a triumphal arch called “Arco della Pace”.
  • Cinque Terre
    • Sunset Cruise: By far the easiest and most beautiful way to see all five villages. I can’t remember how much it cost, but there were lots of options in the harbor and we didn’t have to book anything in advance.
    • Wine Tour + Hike: We booked the Stairway to Wine Heaven experience through Airbnb for ~€60 per person and it was definitely a highlight of our trip. It’s run by an Italian woman (who was our guide) and her American husband, and the whole experience was so well done. The hike itself was from Manarola to a little village called Valostra and it was a bit harder than we anticipated (it was basically straight uphill the entire way), but it was beautiful and only took about an hour. In Volastra, we visited a local winemaker and then enjoyed (several) glasses of wine in his private vineyard overlooking the sea.
    • Ruins of Doria Tower: The ruins of a thousand-year-old castle in Vernazza include a circular tower with incredible views. The only way to get there is up a (very) steep and narrow staircase, but the views are worth the short climb. There’s also a nice, family-run restaurant near the base that makes a good reward for the exercise.
  • Florence
    • Scuola del Cuoio (Florence Leather School): Founded after World War II by a group of monks and Florentine leather artisans to give war orphans a practical way to earn a living, the Scuola del Cuoio is without a doubt the best place to buy leather goods in Florence today. The storefront is massive and we bought quite a few gifts…and quite a few things for ourselves, including belts for Andy (for <€35 each?!) that one of the leatherworkers hand-cut for him while we were there.
    • AquaFlor Firenze: This legendary perfumery is an incredibly ornate palazzo-style space near the Basilica di Santa Croce. Everything is displayed on antique tables and mahogany-and-glass cabinets, and is just so beautiful…and obviously smells amazing. Andy and I both bought scents that we still wear today, and we also got some great gifts for family and friends.
    • Florence Factory: Another very cool store in the Santa Croce area, and it’s dedicated to Florentine design and craftsmanship. This is a great place for handmade jewelry and unique gifts or souvenirs.
    • Cattedrale di Santa Maria del Fiore (Duomo, Baptistery of St. John, & Giotto’s Bell Tower): As mentioned in the itinerary above, we didn’t go inside the Duomo or any of the other buildings in the cathedral complex because the lines were absolutely insane — entry is free and you can’t reserve tickets, which makes it particularly popular. However, it is worth fighting through the crowds in the Piazza del Duomo to at least get a closer look at the pink, white, and green marble exterior of the Duomo di Firenze, the Baptistery (with copies of the original bronze doors famously designed by Lorenzo Ghiberti), and Giotto’s Campanile.
    • Galleria degli Uffizi (Uffizi Gallery): One of the most important (and beautiful) art museums in the world, and extremely overwhelming because there is just SO much to see. This is where you’ll see most of the Renaissance masterpieces in Florence, including important paintings from Botticelli, Michelangelo, Caravaggio, da Vinci, Titian, and Raphael. I definitely recommend booking a tour guide who can help focus on the highlights and provide context for all the famous artwork and the history of the building.
    • Galleria dell’Accademia: Most famous for housing the original statue of Michelangelo’s David, as well as several other Michelangelo sculptures. David was both artistically and physically (it is like 17 feet tall) impressive, but the rest of the museum is underwhelming compared to other well-known art museums. From what I remember, the best way to visit is to book a guided tour (which is what we did with the Walks of Italy Florence In A Day tour) so that you get skip-the-line entry.
    • Palazzo Vecchio: The Florentine town hall overlooks the Piazza della Signoria, which is full of famous sculptures (including a copy of Michelangelo’s David). The building’s courtyard is particularly beautiful, especially with a tour guide who can explain its Medici history.
  • Val d’Orcia
    • Fattoria Resta: As mentioned in the itinerary, the private cooking class we took at Fattoria Resta in Buonconvento (~15 minutes from Montalcino and ~1.5 hours from Florence) was the highlight of our entire trip. I can’t say enough about how much we enjoyed every minute with Anna Lisa and Livia, and the meal we made together was incredible. They don’t advertise at all and prefer to work with referrals from previous visitors or friends, but I believe you can fill out a contact form on their website.
    • Cantina Antinori nel Chianti Classico: Beautiful, award-winning vineyard and estate in Bargino (~35 minutes outside of Florence). We booked a winery tour and tasting (€35 per person), and the tour was great. We also bought quite a bit of wine that they shipped back to Atlanta for us.
    • Altesino: We took a lovely private tour of the winery and had a five-wine tasting with snacks, which was ~€40 per person. Altesino is located just outside of Montalcino, which makes it very easy to get to from just about anywhere in Val d’Orcia.
    • Avignonesi: The guided tour and tasting we booked at Avignonesi (located ~20 minutes outside of Montepulciano) for ~€25 per person was by far our favorite. The vineyard was absolutely beautiful, and the tour guide was so knowledgeable. They also are one of the leaders in biodynamic winemaking and have a serious commitment to sustainability. Last but not least, we really enjoyed their gift shop, which had a lot of options for unique gifts and food-/wine-related items.
    • Chapel of the Madonna di Vitaleta: This tiny, Renaissance-era stone chapel is tucked away in the hills is just off the road between San Quirico d’Orcia and Pienza. It’s one of the most photographed places in Tuscany, and for good reason — it is simply stunning. The pictures we took there were incredible, but don’t even begin to do it justice.
    • Podere il Casale: We only had dinner at this organic, family-run farm in Pienza, but they also offer a lot of really cool classes and farm tours that I wish we would have been able to do. They’re primarily known for running a large-scale cheese production and focusing on Pecorino (which is what Pienza is known for), but they also produce and sell all kinds of foods — the honey and balsamic we bought were both delectable.
    • Montepulciano: We stayed just outside of Montepulciano, one of the larger medieval hill towns in the region, but we went up to the town a few times to walk around and eat. The town truly looks like something out of a movie, and we were told that several movies (including the Twilight sequel, New Moon) were filmed in the Piazza Grande and surrounding area. Montepulciano is also home to Vino Nobile di Montepulciano, a DOCG red wine that is exclusively produced in the surrounding vineyards and is Andy’s and my very favorite of all the Tuscan red varietals.
    • Montalcino: We also explored Montalcino, which is one of the other major hill towns, and it was equally as beautiful as Montepulciano. It’s dominated by the medieval Fortezza di Montalcino, but is probably most famous for being home to Brunello di Montalcino, another DOCG red wine that is much heavier than Vino Nobile and is usually very expensive if you happen to find it in the USA.
  • Rome
    • Pantheon: The Pantheon is one of those surreal places whose importance and incredulity are impossible to understand until you see it in person. Originally a Roman temple commissioned during the reign of Augustus (27 BC – 14 AD) and rebuilt by the emperor Hadrian around 126 AD, it’s been a Catholic church, Basilica di Santa Maria ad Martyres (Basilica of St. Mary and the Martyrs), for more than 1,400 years. It is one of the best-preserved ancient buildings in Rome, and its rotunda (containing the world’s largest unreinforced concrete dome) has an oculus that provides beautiful natural light throughout the building’s interior, which includes the burial places for the famous Renaissance painter Raphael and two of the most famous Italian kings, Vittorio Emanuele II and Umberto I. Perhaps best of all, it’s free to enter and doesn’t require tickets.
    • Fontana di Trevi (Trevi Fountain): One of the most famous fountains in the world, in large part due to appearances in so many famous movies, including Roman Holiday and The Lizzie McGuire Movie (my fav). It was sooooo crowded when we went and it’s in an extremely touristy and overcrowded area, but it’s still worth walking by if you’re in the area.
    • Campo de’ Fiori: One of the main squares in Rome, and home to a huge market for flowers, fruits and vegetables, and artisan gifts. It’s right in the historic center of the city so it’s worthwhile to walk through and grab a quick lunch.
    • Colosseum: We toured the Colosseum as part of the Walks of Italy Gladiator’s Gate tour, but honestly, I would probably recommend not wasting time/money on an actual tour and just walking around the exterior part instead, which is by far the most impressive and interesting part of the building.
    • Roman Forum & Palatine Hill: Palatine Hill was the centremost of the legendary seven hills of Rome, and the Roman Forum was the main plaza of Ancient Rome surrounded by the most important government buildings, and although they are technically separate sites, they’re in the same archeological area and share a ticketed entry. The Gladiator’s Gate tour we took for the Colosseum also included a brief tour of the Roman Forum and Palatine Hill (and skip-the-line entry), which was enjoyable enough, but the most interesting parts were the larger ruins… that definitely could have been viewed without actually going through the gates.
    • Vatican City: 100% worth prioritizing a visit. We took the Walks of Italy Pristine Sistine Early Entrance tour of the Vatican Museums, Sistine Chapel, and St. Peter’s Basilica and I HIGHLY recommend doing the same since it enables access to the Sistine Chapel and some of the highlights in the Vatican Museums (including the Gallery of Maps and Raphael Rooms) an hour before they open to the general public. It is more than worth waking up early for the tour so that you can avoid some of the craziness — the crowds make it really hard to appreciate all of the beautiful artwork, architecture, and history of the buildings. Having a tour guide was also really useful since there is just so much to see.
    • Pompeii: Definitely worth visiting. We took a bullet train from Rome to Naples (~1 hour and ~€50 per round-trip ticket) and toured Pompeii as part of the private tour package I booked through MondoGuide. After driving a loop through the Amalfi Coast, our driver dropped us off at the ruins of Pompeii for a 2-hour private tour. We thoroughly enjoyed our time with Tiziana, who made it easy to see the key highlights in just a few hours and had so much information about the history of the site and ongoing excavation efforts.

Travel Tips

  • You need to be dressed appropriately to enter a church, which is inevitable for just about any day spent sightseeing in Italy. For both men and women, that means covering your shoulders and wearing something that goes past your knees. In general, Italians (and most Europeans) will only wear shorts at the beach so if you want to blend in, I would just avoid wearing shorts in the cities altogether.
  • Perhaps the only negative thing I have to say about Italian cuisine is that it can be really hard to find a place to eat a “real” breakfast — most Italians just have an espresso and a cornetto (Italian croissant) or other small pastry in the morning. Also, if you want to order a latte with breakfast, make sure you order a “caffè latte” — “latte” means milk in Italian, so ordering a “latte” will get you a cup of milk. Another important but random coffee fact: hot espresso drinks with milk are only drank at breakfast, Italians absolutely do not drink cappuccino (or caffè lattes) after ~11 AM and you will get some weird looks if you try to order one in the afternoon (especially with a meal).
  • Italian business hours can seem kind of random, so I recommend double-checking when businesses, museums, and churches will be open before visiting. Shops are generally open from ~9 AM – 1 PM, and then open back up at ~4 PM after a “riposino” (siesta)…but it can really vary from place to place. Also, a lot of museums, shops, and attractions (including most vineyards) are closed on Sundays and/or Mondays, and restaurants typically won’t open for dinner before 7 PM. Last but not least, August is when Italians take summer vacations so things often shut down for a few weeks in the cities and beach resorts will be more crowded.
  • Unfortunately, train strikes are somewhat common. The good news is that strikes are scheduled in advance and therefore you shouldn’t have to worry about being caught off guard while you’re traveling. ItaliaRail (the exclusive online provider of Italian train tickets outside of Italy) has a pretty good explanation of how to deal with train strikes if you want to learn more.
  • Speaking of trains, it would also be worth reviewing ItaliaRail’s FAQ page to understand other quirks about train travel in Italy. Trains are by far the best way to travel between cities, but there are some nuances that might not be immediately apparent. For example, you need to validate every ticket you purchase (including buses and trams) at an inconspicuous machine that would be easy to miss. The best way to address this is by using e-tickets with “ticketless” confirmations so that you can simply board a train without printing or validating your ticket. Another potentially helpful tip is that unless you are planning to take a LOT of trains, it’s much better to buy individual city-to-city tickets for each journey instead of a rail pass — a rail pass does not guarantee a seat on a train, which would be extremely frustrating. Even if your original travel plans change, it is usually very easy and inexpensive (or even free) to change your train tickets on the Trenitalia app.
  • Uber is only available in a few cities (I think just Milan and Rome), but taxis are typically easy to find. If you want to guarantee a ride (e.g., your flight arrives super late), I highly recommend a company called Welcome Pickups — we didn’t use it on this particular trip, but I’ve used it in several other European countries in the past year and have always had excellent service.
  • As I mentioned in the itinerary, it’s almost impossible to see the major sites and artwork without an official tour guide. Tour guides in Italy are licensed by the local tourism bureau and so they actually provide a lot of value. I used Walks of Italy in both Florence and Rome, and all three tours we took were excellent and had fewer than 20 people per tour. Having an expert show us all the main highlights and provide background information and context for what we were seeing (plus skip-the-line access at all the museums) was more than worth it.

One thought on “Two Weeks in Italy (2019)

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