When traveling to Italy this summer, I realized I wanted a travel guide that would tell me exactly where to eat and how to experience Italy like a local. TripAdvisor and other blogs were either overwhelming or hard to trust. So I set out to create my own.
After crowdsourcing tips from many friends (some who either studied abroad or went there on their honeymoon) and doing my own online research, my boyfriend and I found some real gems during our trip. I hope this guide helps as you plan your own Italian getaway.
Day 1: Travel day + packing tips
I’ve always been somewhat of an overpacker, but after too many stuffed suitcases, I’ve learned how to pack just the essentials. The key is to bring basic bottoms that can mix and match with casual and fancier shirts. Oh, and you can’t go wrong with flowy dresses in the summer. Here are two dresses I bought for the trip from Free People (Dottie Mini Dress + Getaway Midi Dress in Tangerine).
*See packing list at the very end
Day 2: Getting settled in our Agriturismo
If you’re going to Tuscany (which I highly recommend!), renting a car is the way to go. We rented a small sedan for the entire trip, even though we only really needed it in Tuscany. The highway tolls, hotel parking, and gas added up quickly.
We arrived in Rome and went straight to our Agriturismo San Giorgio which was just about 20 minutes outside of Siena. This little farmhouse came with a pool, a charming breakfast, kitties, and seriously, the most amazing view. I would highly recommend this spot if you're looking for something reasonable and central.
Day 3: Exploring Pienza
After enjoying the homemade breakfast prepared by our AirBnb hosts, we changed into our swimsuits and spent the morning swimming and reading by the pool. We could have spent all day there but when in Tuscany, there’s wine drinking to be had.
Our hosts recommended Fanti Winery. They gave us a private tour of the winery and we were able to try four different wines and two olive oils. Because I ended up buying their Brunelo Reserve and olive oil, they waived our tasting fee (which would have been $25 euro with the wine tour included).
After wine tasting, we made our way to Pienza which is quaint little town in the province of Siena. We ended the night eating some delicious pizza at Pumamaro. Originally we wanted to go to Trattoria Latte di Luna to sample their pici pasta but sadly, they were completely booked. So go early and make a reservation.
Wines of the region: Brunelo di Montalcino
Day 4: Day trip to Siena
Our AirBnb was conveniently located just 20 minutes from Siena. After a short ride into town, we stopped for a small bite at Trombicche. This small restaurant and wine bar, run by two brothers, has a very local vibe. Everyone in there was speaking Italian and drinking wine. Then we meandered around the city square, ate gelato, and watched the World Cup in the main plaza drinking some Aperol Sprtiz.
Day 5: Wine tasting our way to Firenze
After making the most of our AirBnb, we got in one final swim and started making moves to Florence. On the way, we stopped at two very different but equally enjoyable wineries. The first was Antinori Nel Chianti Classico. This winery feels like you’re on a movie set and is architecturally impressive. We had lunch outside, tried two different flights of wine, and I ordered the one and only salad of the trip that was more than lettuce and olive oil. Then we made our way to Viticcio winery, a family-owned winery that sits in the hills of Chianti. The wine was so good that I ordered six bottles and had them shipped to SF.
Finally, we set out for Florence and got some late night pizza at Gusta Pizza. You can get an entire pizza for $5 euro and wine for $2 euro. (Admittedly, it was hard to go the $2 route after having such fine wine the past few days.)
Wines of the region: Chianti, Montepulciano, Vermentino
Day 6: Full day in Firenze
Florence was all about food, wine, and gelato. During our stay, we referred to the 36 hours guide from the NY Times pretty extensively.
First, we had lunch at a famous sandwich spot All'Antico Vinaio. While this spot is a tourist destination, it was also delicious, cheap, and worth the wait. Then we walked to Forte di Belvedere – mainly for the views. It’s a trek though so bring lots of water and wear comfortable shoes. We ended up walking almost twenty thousand steps that day — which is why we deserved our multiple gelato stops. First up was Gelatareia dei Neri, a recommendation from a friend who studied abroad in Florence. Really good and worth the walk outside the main city square.
For an apertivo, we made our way to Enoteca Pitti Gola e Cantina, an elegant little wine bar with a handful of marble-topped tables and tall bookshelves lined with bottles of the high-end, small-production variety. The staff were so knowledgeable and the gazpacho was light and refreshing.
Our last stop was dinner at Il Santo Bevitore. This place reminds me of a restaurant you might find in SF – a little more modern than your typical trattoria and didn’t feel touristy at all. Pro tip: Make a reservation ahead of time and get a drink at their bar right next door. Charming hole-in-the-wall spot with an excellent wine selection.
After dinner, we got our sweet fix at Gelatareia La Carrai, another recommendation from my friend who studied abroad here. When you go, get the Biscottino “cookies” flavor. Best gelato I had all trip.
Day 7: Naples to Amalfi
If you want to experience the best pizza of your life, make sure you make your way to Naples. We didn’t have too much time so just passed through on our way to Amalfi. We split a Margarita pizza at Pizzeria da Michele — the perfectly cooked dough was super light and almost elastic so you didn’t feel overly full afterwards.
Then we drove to Amalfi and landed at our cute AirBnb in Minori. We chose Minori out of all the towns in Amalfi because it's a) less touristy b) cheaper. While Positano and Amalfi are gorgeous, there’s more hype so everything is more expensive and overcrowded.
Day 8: Paradise in Positano
No trip to Amalfi is complete without a day trip to Positano. We took a ferry from Minori to the beautiful beach town. We decided to splurge on lounge chairs ($30 euros) but totally worth it. We spent our day swimming, drinking, reading, and napping — it was perfect. After we had enough sun, we walked up to Le Sirenuse, an insanely beautiful hotel my friend recommended. Since they were overbooked, we ended up getting a bite at Bruno instead. You can sit outside overlooking the gorgeous cliffs and colors of Positano. Plus, the mussels were incredible.
Day 9: Roaming romantic Ravello
We heard amazing things about the small town of Ravello which is up on a hillside. The only drawback is that it’s a trek to get there. You can take the bus up but we decided to hike the one thousand plus steps instead.
Once we made it up there (sweaty and calves burning), we explored the beautiful grounds of Hotel Cimbrone. We enjoyed a post-hike glass of wine and gelato overlooking all of the Amalfi coast. We had dinner in town which was just okay, but mainly went to catch the final semi-final game of Croatia vs. England.
Day 10: Last day in Amalfi
Because we loved our time in Amalfi so much, we ended up staying an extra night to check out Maori, Minori’s neighboring town. We splurged on our hotel at Club Due Torri (which we booked on Hotel Tonight). We basically spent all day there enjoying drinks by the pool. We got dinner in Maori at Pineta 1903. A great spot with an expansive patio shaded by hundreds of lemon trees.
Day 11: Rome
Since we extended our stay in Amalfi, we only had one day in Rome. We were both going for more of a relaxing vacation vs. the city feel. However, once we made it to Rome, we both wished we had had more time there. It’s the one place during the trip I could have seen myself living abroad.
Some highlights for us were walking around the neighborhood of Trastevere and getting a drink at Bar Del Fico in the City Center. It was super lively and filled with locals drinking Negroni cocktails and smoking cigarettes. We ended our night at the Trevi Fountain which is very touristy, but for good reason.
Day 12: Heading home
We left early for San Francisco for the long day of travel. Overall, the trip was better than I could have even imagined. We found the perfect balance of relaxation and exploration. If I had to choose a favorite place, it would have to be Tuscany. Lucky for me, Napa is just an hour away from San Francisco so I don’t have to travel too far to get my fix of rolling hills and local wine.
For more photos, check out my FB album.
Wine. All the Time. by Marissa A. Ross —This book takes a humorous and laidback approach to wine drinking. I found it super informative when wine tasting in the different regions of Italy.
Hotel Tonight — If you're like me and don't plan too far in advance, Hotel Tonight will be your best friend while traveling. You can find awesome deals on luxury hotels and book day-of.
36 Hours - NY Times — Leave it to NY Times to put together a curated list of things you'd want to do (while beating the crowds). We used these guides in most of the cities and they never let us down.