SO I am writing this blog post as I am on the plane home from Italy. We are flying Rome to Toronto and then driving back to Detroit. It was actually half the price to fly from Toronto and they had direct flights. For us, this was a great option! This trip was absolutely incredible. A trip of a lifetime for us. We had never left our baby this long or gone away together in a while. It was hard to leave Miles, but we knew it was in good hands. Our perspective is that it was healthy for us and for him. Plus, his grandparents get a week with him at such a fun age!
Before I get into the details of our trip, I wanted to discuss a few topics that came up a ton in my DMs and in my Italy Q+A. For all outfit links from my Instagram click here.
WHY MAY:
We decided go in May for a few reasons. Primarily, this was Jacob’s last week off in residency. We also wanted to go before it got too hot (typically super hot in the summer) and before it was insanely busy. It was definitely busy at this time (especially in big cities like Rome and Florence), but everyone kept saying it doubles. So wild! On the Amalfi coast especially! It wasn’t as crazy as it gets. I think anytime you go, it will be amazing. Italy is just magical.
WEATHER:
We had heard that mid-late may was a gorgeous time. 70s, sunny and not too humid, but of course there is no guarantee. The days leading up to the trip I was stressing about the weather. It was showing rain almost everyday in both areas we were traveling. Rain and cooler temps in the 60s. I knew it was out of my control, so I just packed a few options. A second jacket and a rain coat / umbrella. In the end, we actually got super lucky. We definitely had rain, but it wasn’t as bad as I thought it would be. We ended up having a gorgeous day in Florence, rain during our wine tasting (indoors anyways) and two beautiful days on the Amalfi coast. SO grateful for that because the boat day was the best day! We were told that it rained for a week straight in the Amalfi before we arrived and it was raining the day we left. Everyone said it was not typical and that it is always sunny. So fingers crossed for anyone going there soon.
TRAVEL AGENT:
For some parts of this trip we used a travel agent (Emily from @lutz_travel) and she was great! She helped book all our car transfers and formal excursions (boat tour, wine touring etc). I really loved working with someone since I had absolutely no idea where to start. That said, of course you can plan trips totally on your own. A lot of excursions can be booked through hotel concierge and companies like viatours. We also worked with our hotel concierge for a few things too. They were so helpful!
GETTING AROUND:
Getting drivers / cabs around was something we decided to spend on because our trip was short and we wanted to pack a lot in! It is definitely the most efficient in some ways. We also took trains between big cities / areas (ex Florence to Naples) and really liked that experience. Within the bigger cities (Rome) you can get cabs on demand. On the Amalfi coast, the case is very different. There are buses that go between all the towns (ex: positano to Amalfi), but we heard they take a long time and the lines are super long. That said, for our totally open day in the Amalfi we decided to rent a little “twizy”. This is an electric mini car that we took to explore more towns on the coast. It was amazing! Our hotel helped us organize it the day before.
ON RENTING CARS:
We decided not to rent a car because we heard the driving in italy could be crazy. Having been, I can see why! Driving around in Tuscany is less of a problem, but as soon as you get to a village or even a city like Florence, the streets get super narrow and hard to navigate. There are tons of places you cannot park and historical landmark rules with cars. There were so many times when our drivers would wind around and I truly did not understand how they did it. On the Amalfi coast, there is ONE road, basically no parking on the street (only limited at hotels), and people drive like mad. Plus, we also wanted to drink wine at every meal 😉
ACCOMMODATIONS:
Our hotel in tuscany (Grotta Giusti) was beautiful and well known for the “grotto” / thermal pools. It looked like an old castle and had that old Tuscan charm. It was in a cute town (Monsummano Terme) that was not very touristy either. I booked it because it was in Tuscany and available on Marriott points. BUT, looking back we wish we stayed in Florence and did day trips to Tuscany since it is so close. We could have saved a bunch on drivers and got more time in Florence. So many hotels in Florence have tours you can easily arrange. Or even on Viatours. We did not realize that the hotel we booked in Tuscany was SO far. I actually wouldn’t recommend it unless you are going solely for the pools. It was in a gorgeous little Tuscan town and we really enjoyed our time there no question, but looking back staying in Florence would have been the better move for us. As I said, you don’t know what you don’t know!
On the coast, we were deciding if we wanted to stay in the actual town of Positano, Sorrento or elsewhere. At first, we decided Sorrento and then we actually switched to Praiano after our friends recommended it. I wanted to be closer to Positano on the other side of the coast (Sorrento is farther / closer to Naples and a larger city). We wanted something quieter. Our hotel in Praiano was 15 mins from Positano and had a shuttle. It was also in a cute little town that had a ton of great spots / restaurants and less touristy. Positano is insanely gorg, but in the actual city its super super crammed and busy. We loved being able to see it from the boat and experience it by foot vs staying there. I do know there are a lot of amazing hotels, I would just recommend one a little further from the beach if you want a quieter feel. Everything is stacked one on top of another and you get everywhere via stairs. Literally like hiking between buildings and alleys. SO if you are closer to the beach, you have to hike with your suitcase. Again, only ONE road. Everything else is alleys/ stairs. Our hotel was called Casa Angelina and it was the most special hotel we had ever stayed in. I have never had an experience like this and I doubt I will ever again! I’ll never forget it. All our accommodations were booked on points, so we figured we go all out for this one. Emily helped us book and we got an upgrade, breakfast and a hotel credit. It was awesome. That said, there were really beautiful hotel options in Praiano! The other town we would have loved to stay in if we had more time would have been Ravello. It was incredible and we loved our day there.
In Rome, we stayed at the The Westin Excelsior. It was great for the night! Good location and big rooms. Also booked on Marriott points.
WHAT TO PACK:
I have a whole separate blog post on what I packed here. I have to say I did great with outfit planning and not bringing too many clothes I didn’t wear. Packing light is KEY. I did bring a bunch of other stuff I didn’t touch. For example, cute “dinner” sandals (every night was a hike to dinner so no effing way I was wearing those. birks and cute white sneakers all the way). My hair tools. DO NOT BRING. All hotels have hair dryers. I busted my iron with a “special converter” that didn’t work. Plus, it’s so freaking humid.. just go natural. I also brought WAY too much makeup and skincare. I ended up keeping it super simple. I could have reduced both by half. Next time!
RESTAURANTS / FOOD:
I have always dreamed of going to Italy to experience my favorite cuisine and WOW it did not disappoint. The ingredients are just different. The tomatoes, the cheese, the meat, the olive oil and more! Amazing. I loved experiencing it all. We literally had pizza and pasta daily and I loved every second of it. I did a ton of research before and got lots of recos from IG (all included below). Some things we winged and some reservations were booked ahead. I would definitely recommend booking Florence and Rome spots a few weeks before if you can. Most restaurants only open for dinner at 7pm so that is the earliest.
Of course, I have had incredible Italian food at home, but experiencing it in italy is different. It is the simplicity of it all that I love! Definitely watch out for touristy spots (signs in front, people standing outside greeting you, overpriced menus, English looking signs). I was actually surprised at how affordable the dining was. Even the nicer spots we went to were a lot less than they would have been at home. We had some incredible 60 euro dinners with wine and dessert!
Ok now that all that “housekeeping” is done, below is our itinerary. Again, we were only there for 7 days, so there was a ton we didn’t get to. I will include those other recos at the bottom in case you are going and have more time.
OVERVIEW: One week in Italy
Day 1: Travel from Toronto (we drove from Detroit) to Rome, Stop in Orvieto, Arrival in Tuscany
Day 2: Florence
Day 3: Winery day in the Chianti Wine Region, Tuscany
Day 4: Train Florence to Naples, Naples to Praiano, Afternoon in Praiano
Day 5: Boat day on the Amalfi Coast
Day 6: Explore the coast. Visit Ravello, the town Amalfi and Positano
Day 7: Travel to Rome. Explore Rome.
Day 8: Travel back to Toronto. Drive back to Detroit
Detailed Itinerary:
Day 1: ARRIVAL IN ITALY, ORVIETO
⁃ We arrived to Rome airport from Toronto in the morning. It was overnight flight. The Rome airport baggage took about an hour! Apparently this happens all the time. I am happy I had my AirTags in there so I knew it was there. We got our bags and met our driver in the customs area. His name was also Jacob and he was a Florence local and super super nice. He ended up being our driver everyday in this area which we loved.
⁃ The drive was about 3 hours so we wanted to stop somewhere in between. Our agent recommended Orvieto which is in the Umbria region (between Rome and Florence). It was pouring rain and then as soon as we arrived to this town, the sky opened up. We drove up and up to get to the little medieval village. As you are driving you can just see tons of little villages perched upon hills and it’s super beautiful. We got out of the car and the view was beyond! We were running late from our bags so we hurried off to lunch. Lunch was at a small local restaurant called Le Grotte Del Funaro and it was underground. You had to walk down stairs and it was basically in a celler. It felt exactly like that I thought a restaurant in this village would feel like. There was a beautiful window too overlooking the hills. We got wine, pasta, raviolis and charcuterie. The first of our meals like this for a week! It was so simple and so fresh! You could immediately taste like you are in italy.
⁃ After lunch, we explored the town for about an hour. Super small and cute. Lots of little streets. We grabbed Gelato at Cafe Montanucci Orvieto and made our way to see the Duomo. All the historic towns and villages are centered around the Duomos (church). This was really beautiful and intricate. It was funny because when we first got to the town there was a small beautiful church that we thought was the “Main duomo” and we ended up waiting there for 20 minutes for the driver thinking we made it to the meeting spot. Then when we realized it was 1/10th the size of the one we had to go to!
⁃ Once we go to our hotel in Tuscany we explored the grounds and spent time in the thermal pools which was really relaxing. We then got ready and walked to the village nearby called Monsummano Terme (very local / not touristy) and had dinner at a tiny little spot. No one spoke English and it was $17 euros for an incredible pizza and a bottle of wine! it was called La Rustichella. That was the first taste of Italian burrata and OMG. We then grabbed another gelato (forget the name) and walked home.
You can see a vlog of our first day here.
DAY 2: FLORENCE
⁃ We woke up early and had breakfast at the hotel. We then got a ride to Florence. We got dropped off at the Piazzale Michelangelo. We had 12 hours. It was a beautiful sunny 70 degree day. I LOVED it so much here. I wish wish we had more time here. I have a whole reel and on our day here, but below are the highlights.
⁃ Started at the top of Piazzale Michelangelo. THE VIEW! Amazing spot to take pics and see a panorama of the city.
⁃ Stated walking down the steps, through the gardens, across the river and then grabbed a cappuccino on the river at Rivarno cafe. Cute spot!
⁃ Explored the leather markets and Ponte Vecchio (bridge with a ton of jewelry venders). Jacob got a leather jacket and I got a fun pink purse. It was honestly the only thing we bought the whole trip!
⁃ Walked to Palazzo Pitti and through the Boboli Gardens. Really beautiful. It would be a great spot to sit and relax for a bit too if you wanted.
⁃ Made our way to get the famous sandwiches at Al’Antico Vinaio! Worth it. We got the “summer” and “paradiso” (the pistachio one. OMG). The line looked very long, but it went fast. We also got recommendations to go to Pino’s for a similar meal so if you do not want to wait in a line go there.
⁃ Walked to the famous Duomo (Cathedral of Saint Marie). We unfortunately did not have time to go in for a full tour, but it was magnificent to see.
⁃ Walked the shops Piazza della Signoria and got gelato at Perche No (recommend the rose, pistachio and chocolate). Tons of beautiful statues and landmarks to see.
⁃ We decided at this point we wanted a break for a spritz! Our first spritz of the trip. if you are not familiar, a spritz is an aperol cocktail with soda water, Prosecco and oranges. It’s amazing! It’s customary to enjoy in the the late afternoon with some snacks before dinner (“appertivo”). We ended up finding a rooftop overlooking the whole city at the Westin Excelsior. It was called Se-sto. Drinks were more $, but it was worth it for the view.
⁃ We then stumbled upon an olive oil and balsamic vinegar tasting that was SO GOOD! It was just us and another sweet couple from Seattle. It was called Prunnetti. We ordered some to ship home!
⁃ Then we finally worked up an appetite for dinner at La Giostra. Unreal! We got the burrata and three pastas (pear ravioli, parpardelle boar Ragu and the penne sorrentina). The Florentine steak looked insanely good too. Next time. This meal was AMAZING. This was a spot I booked a few weeks in advance.
⁃ We then ended our day at the Piazzale Michelangelo where everyone was watching sunset and drinking wine. So fun!
DAY 3: WINE DAY IN CHIANTI HILLS
⁃ This was our WINE DAY! It was chilly and rainy this day so we were so happy to be inside touring and drinking. We started at Tenuta Torciano Winery in San Gimignano. San Gimignano is a super popular area in Tuscany to explore. Apparently the village is well worth a visit.
⁃ We started with a cooking class here (booked in advance). It was just me, Jacob and the chef. We made pasta and a sirloin steak. It was SO GOOD. It was amazing to learn how to make pasta from scratch and everything that goes into it. I am so happy we did this because it was definitely a highlight for me. You can see all the details on this class here on my IG reel.
⁃ We then made our way to another winery called Mazzei in the small village of Fonterutoli. It has been around since 1435! The had been making wine here for centuries all in the same family. The tour was really cool and the tasting was delish. We met some fun people too since it was a group tour.
⁃ If the weather was nice, we would have done more outside on this day and had lunch in the vineyard. I would definitely look into that if you are going to Torciano because I saw they had that option.
⁃ We then got back to the hotel and decided to venture into our local village of Monsummano Terme again for dinner. It was actually cold, rainy and super windy! We still made the walk to a local spot that had great reviews and we had an incredible meal. It was called Ristorante Pizzeria La Cantina Da Caino. Our fave was the pistachio tartufo! The pasta, pizza and wine was great too. Loved that it was all locals!
DAY 4: TRAVEL TO AMALFI COAST
⁃ We got up bright and early and got a ride to the Florence train station to make our way to Naples and then the Amalfi coast. I was a little anxious about train travel because I heard it happens super quick in Europe. I was worried we wouldn’t be in the right place at the right time. It ended up being SUPER seamless. Print your ticket before or get it printer there at a kiosk. You only need to be there 15 mins before. It was very straight forward all in one big row. 10 minutes before departure, your train number will get assigned a platform. You simply walk to the platform (to your carriage) and get on. They come around when you are at your seat to check your tickets. There is room above your seat for luggage. Big suitcases too!
⁃ The train was about 3.5 hours. It was so fast! It rained the whole train ride so the views weren’t amazing, but it was still relaxing.
⁃ Our driver met us in Naples and we asked him if we could stop somewhere in Naples to get a pizza (we had to!) before going to the Amalfi coast. He took us to a great place called Trianon and it was there since 1923. We got a classic Margherita and it was amazing. The dough, the tomatoes and the cheese – beyond. So simple and delish. We ate it in the car. The drive was about 1.5 hours to Praiano, but one you hit the coast and start driving the views are so beautiful it went by so fast.
⁃ Once we got situated at the hotel, Casa Angelina, the sun came out! We went down to the pool and had a spritz. Then we got ready and walked to dinner in Praiano. The walk to dinner was up stairs and through alleys. Very typical Amalfi. It is so fun! Wear comfy shoes. I wore my Birkenstocks. We had dinner at sunset overlooking the water and it was so beautiful. We kept looking at each other saying how is this real. We basically said that the entire time we were on the coast.
⁃ Dinner at Kasai Praiano was amazing! We go the crispy scallops, the zucchini blossoms, the squid pasta (wasn’t my personal fave, but very good) and the local fish, which we both loved. Our fave part was the TIRAMISU! Don’t skip that.
DAY 5: BOAT DAY ON THE AMALFI COAST *BEST DAY EVER*
⁃ We were so happy when we woke up to sunny skies because it was boat day. We heard from so many people that booking a private boat tour was a trip highlight and that we had to do it! Emily organized it for us and it was through a company called BluRide. We first went to the wrong beach entry point and had to walk all the way back up to the road. We ended up loosing almost an hour, but we totally forgot by the time we got to the boat. We by chance got upgraded to a huge boat. Just our luck! Our captain’s name was Alex, he was great! He was super knowledgeable and made it such a good time.
⁃ For the entire day we boated around the coast, seeing all the towns and views. We visiting the surrounding islands, grottos, caves, the town of Capri, the town of Nerano, by Positano and back. It was so relaxing and fun. We had drinks, snacks and great music. One of the best days of my life. I will never forget how relaxed and present I felt surrounded by that much beauty. Just two of us <3
⁃ We got off at Capri and walked around the main shopping area. It was really beautiful, but kinda felt a bit commercialized tbh. Like every store was an expensive designer. If you are into that shopping, you would love it. For us, we spent like 40 mins walking around and felt we had enough. We did get gelato at Buanocore and it was SO GOOD (we got almond lemon and pistachio). Jacob also got a lemon slushee type thing and it was delish. Everything is lemons in this area! If I went back to Capri, I would want to go to the other parts of the Island and stay at one of the amazing hotels. We loved boating around it! There was so much beauty.
⁃ We then made our way over to the little town of Nerano which is around the bend from Sorrento on the coast. We stopped our boat close to the dock and then a skipper came and boated us over to the land. We ate at a very famous restaurant called Lo Scoglio. Been there for decades and truly incredible. We got the famous zucchini pasta, gnocchi sorrentina and the fresh sea bass. The fish came in lemon sauce and was served with potatoes and olives. SO GOOD. Cannot recommend this spot enough. It was my fave of the trip! I will never forget it.
⁃ After our boat day we relaxed at the hotel by the pool and went to dinner in Praiano at a spot called La Cucina Del Tramonto d’Oro. It is a boutique hotel that also looked beautiful. The views were unreal at sunset. The linguine Limone was my favorite!
DAY 6: EXPLORING THE COAST
⁃ We rented a cute little electric car called a “Twizy” and decided to go explore Ravello. It was a last minute rental and it was such a good call. The roads are SO tiny and windy and the Vespa situation seemed a little dangerous. This car was hilarious. It is big enough for 2 people and was the perfect way to zip around.
⁃ Ravello was breathtakingly. It is perched up higher than the rest of the towns on the coast. It has gorgeous hotels, restaurants, galleries, shops and hiking around it. We first walked around the square and then checked out two of the villas and their gardens. Absolutely beautiful. The first was Villa Rufolo and the second was Villa Cimbrone. Definitely do both, the second one was about a 10 minute walk so don’t miss it. The views are unforgettable at the top there! We actually went the wrong way at first and ended up doing a 45 minute hike around the mountain by mistake. That was also beautiful so no regrets!
⁃ We grabbed lunch at Mimi Pizzeria. Ask to sit in the back terrace. It was AMAZING. My favorite pizza of the trip! We also got spritz’s of course!
⁃ We drove back to the hotel and hung out by the pool and then got ready for dinner. We went into Positano to explore and get dinner. It is so stunning. This buildings are all on top of each other connected by stairs and pathways. The colors and so cool. It’s unlike anything! We loved exploring the streets and just walking endlessly. We even walked over past the boat area to the other beach. The town was definitely crowded and the beach was super busy. If I were to stay in Positano, i would want to stay a little higher up from the beach since it was so busy. There are some amazing hotels and the views are just endlessly beautiful.
⁃ We had dinner at Chez Black which is a famous spot since it was one of the first in the village. It was a cool vibe and right on the beach, but we felt the food was a bit overpriced and overrated. We enjoyed it for sure, but for next time we would skip it. I would go to Tre Sonte Wine bar or Ristorante Max.
⁃ We walked into Franco’s bar (connected to the famous le sirenuse hotel) to get a drink and watch over the Positano lights, but when we sat down we realized we were to tired and didn’t want to spend $25 Euros on a cocktail. We ended up just sitting at the top of Positano on a bench watching it all until the shuttle came. Core memory!
DAY 7: ROME
⁃ We got to Rome around 1pm and it was pouring. We checked into the hotel (Westin Excelsior that we also booked on points). Since we only had half a day basically we wanted to just walk around and see as many of the sites as possible. We basically walked for 5 hours. We hit up Antico Forno Roscioli for their famous pizza. The line was 20 mins and WORTH IT. We got a few slices to try and the cacio e pepe arancini balls. Do not miss this spot! They have 2 other restaurants (Roscioli Salumeria / Roscioli Rimessa) that are super well known, but very hard to get into. I tried! We then made our way to Fridgidarium for gelato. It was the best of the whole trip!! Wow ill be thinking about that for a while. Don’t forget to get it dipped.
⁃ On our walk we checked out famous historic sites like the Trevi Fountain, Pantheon, Spanish Steps, and the Colosseum. If we had more than half a day, I would have loved to do proper tours or even gone to the Vatican.
⁃ On our way to dinner walked through the Travastere neighborhood. It is a bustling, neighborhoody, trending feeling area. That is where all the great restaurants are that people recommended. It was fun to walk through and see!
⁃ For dinner, we went to Felice a Tesstacio which is very famous for their cacio e Pepe. It was rated one of the top spots in Rome for this famous dish! It did not disappoint. We also got the bucatini all’amatricana – another famous Roman dish. The server talked us into trying their house special the lamb and potatoes and omg! Incredible meal!
⁃ After dinner i went back to the hotel to pack and of course Jacob went out to see some jazz! He went to Gregory’s Jazz Bar and had a blast!
⁃ Overall, I wish we had another night in Rome so we could do more exploring and eating of course. It has a big city feel, but like ancient. Very cool.
DAY 8: HOME
⁃ We headed to the airport first thing to start our long journey home. 9 hour flight to Toronto and then a 4 hour drive back to Detroit. It was a super long day and we were so tired, but we had to get back!
Hope this helped and gave you some ideas for your trip. I also have two highlights and a q+a going live on my IG soon.
Below are more recos I got for the places we went that we didn’t get a chance to go to.
ROME RECOS:
⁃ Terrazza borromini (more for views / appertivos)
⁃ Tonnarello
⁃ Taverna Trilussi
⁃ Da Francesco
⁃ Rome Sparita
⁃ Piccolo Buco
⁃ Otaleg gelato
⁃ Duecento gradi sandwiches
⁃ Pincers Rome
⁃ Mizio’s sandwiches
⁃ Roscioli – holy trinity of pastas
⁃ 7Grammi (drinks)
⁃ Frigidarium Gelato
⁃ Mimi & Coco
⁃ Da Enzo
⁃ Dar Poeta for pizza
⁃ Ciampini for Gelato
⁃ Altar of the Fatherland drinks
⁃ Nerone
⁃ Osteria La Fortunata
⁃ Cul De Sac
⁃ Ad Hoc
⁃ Armando al Parthenon
⁃ Da Cesare
⁃ Bonci Pizza
⁃ Cantina Dei Papi
⁃ Felice a Testaccio
⁃ Al Morro
⁃ Giolotti Gelato
⁃ Taverna dei fori Imperiali
⁃ Bona Pizza
⁃ La tavernaccia
⁃ Piccolo Bucco
FLORENCE RECOS:
⁃ Tratoria 13 Dobbi
⁃ Osteria Santo Spirito
⁃ Osteria Del Cinghiale Bianco (Stanley Tucci went here)
⁃ La Giostra
⁃ Antico Macelleria Cecchini
⁃ Gusta Pizza
⁃ Yellow Bar
⁃ Osteria Pastella
⁃ Buca Mario
⁃ Berbere
⁃ GROM Gelato
⁃ Gelateria Dei Neri
⁃ Il Profeta
⁃ Acqua al due
⁃ Trattoria Za Za
⁃ Panini Toscani
⁃ Osteria Delle Tre Panche
⁃ Tratoria 13 Dobbi
⁃ Perche No Gelato
⁃ Il Profeta
⁃ La Buschetta
⁃ Trattoria sostanza
⁃ Pino’s Salumeria Sandwiches
⁃ The Arts Inn (drinks)
