Ahh, the beautiful country of Italy. Tom and I recently traveled abroad to explore parts of this beautiful country and we had such an amazing trip that I knew I wanted to write up an entire blog post after we had made it home. Our travels took us to Rome, Florence, and the Positano Coast and every bit of it was different, yet so magical. We would do the entire trip over if we could, and I really recommend our itinerary to anyone who is looking to book such a trip. It would be perfect for a nice vacation, an adventurous honeymoon, or even as part of a longer trip (although I did feel like 10 days was plenty!)
I had so many requests on Instagram to share where we stayed, what we did, and just overall HOW we planned it, so I’m diving in. Now note, we planned this entire trip ourselves with the help of recommendations from friends and family, but we never used a travel agent or any outside help for planning purposes. We really love to plan our own vacations because although it may take a lot more time and effort to make sure everything makes sense and we are staying in the best places/doing the best things, we feel like you can really customize your trip to make it exactly how you want.
I may change my mind about travel planners after we use one for our honeymoon, but for now, I am so type A that I love to plan everything exactly how I want it.
There are a few key things I like to think about when planning out vacations in new cities:
- Ask everyone you know for recs. I asked family, friends, Instagram, etc for their best recommendations for each city. I compiled a big list and then went on and individually researched each recommendation.
- Research where to stay – try to find places that are NOT touristy, places where locals stay, near areas with good food, and are popular among people your age.
- Use AirBnB to save money. Hotels were nearly double the price and with AirBnB you can be EXTREMELY picky and find the best location, tons of space in an apartment, and read thousands of honest reviews. We save so much money by using AirBnB and always have stayed in places that are incredible.
- Plan major activities for each city. Do not plan to just ‘walk around + explore’. This is boring and never works, so I highly recommend booking at least 1 activity per day. These can include historical tours, walking tours, food tours, classes, etc. Plan for 1-2 a day.
- Plan at least 2-3 hours of rest every day. No one wants to be overtired and you need to recharge. Don’t plan back to back to back.
- Plan meals ahead of time. Food is one of the MAJOR reasons why we travel, and we are huge foodies so take this with a grain of salt. There are so many touristy restaurants in many of these major cities, trying to usher you in, usually around tourist attractions. Please stay away from them. Do your research!!! Study bloggers who live in the area of the city you are going, use websites like Bon Appetit and Conde Naste. Make reservations ahead of time.
- Once all of the above is done, plan logistics. I put Tom in charge of all logistics, so he had to plan all planes, trains, and automobiles and booked everything ahead of time with flexibility when we needed it.
And that’s basically how we plan every trip. Key takeaways: Research, AirBnB, book ahead.
Tom and I are both vaccinated so it made traveling fairly easy. The biggest thing is to check the U.S. embassy for whatever country you are headed to. Also, our airline (American) prepared us a lot for what we would need and not need for traveling to Italy. Bottom line, each country is different and you have to do your research.
For us, as two vaccinated people, we had to have a negative covid test with 72 hours of leaving for Italy. We went to CVS and got Rapid tests. For coming home, we had to have negative covid tests, so we bought BinaxNOW take home covid tests. We took them 2 days before coming back into the states. It was easy.
We arrived in Rome FCO Airport after an overnight flight and took the train directly to Rome city because the airport is actually about 45 minutes away. This was regional rail and is called the Leonardo Express.
Because our AirBnB wouldn’t be ready until 3pm, we needed somewhere to store our luggage so we used a system called Nannybag which is exactly what it sounds like: a place to drop off your luggage at a local hotel so you can go and explore for the day while your backs are kept safe. We kept ours at Hotel California in Rome and then got to exploring.
The first day, we never book too much because we know we will be tired, so we decided now was a good time to just walk around and get the lay of the land. We saw the Colosseum, Palantine Hill, the Trevi Fountain, Pantheon, and lots of other Roman Ruins. We were hungry after walking a couple of miles around town, so we grabbed a few quick pastries, coffee (er, espresso because that’s what it is in Italy).
*Quick note on coffee culture in Italy. They don’t have drip coffee like they do in America. If you want something more than just espresso (un caffe) you will need to order a cappuccino. This is what Tom had every morning and I would get a macchiato (almost same size as espresso but with a little steamed milk). Also, no one really sits down to enjoy their coffee, and if you do, you will be charge with a table cover fee. It is very popular to just stand at the counter and drink your drink and then leave. Italians are known for doing this multiple times during the day, so it’s common to pop into a couple during the day. The coffees (espressos/espresso drinks) are very cheap.
Anyway, we had something to hold us over, then got word our AirBnB was ready for early check in. We walked back to our bags, grabbed them, then headed to our AirBnB. We quickly grabbed a slice of pizza after arriving near our location.
We stayed in the Trastevere area of Rome and I HIGHLY recommend staying here. The scene is AWESOME. It is very lively, there are tons of young people, tons of really incredible restaurants, lots of people out and about, and those cute quintessential European streets. It’s very safe and filled with the best energy. Plus, you can walk to everything from where you are.
Our AirBnB was perfect and I’m linking it here.
We were pretty tired at this point (I don’t sleep on planes). So we knew we needed to nap and we had actually built this into our schedule. We each slept for like 3 hours before it was time to head out to our first ‘aperitivo’ AKA happy hour. We went to Terrazza Borromini for the most epic and beautiful views of the entire city of Rome. I highly recommend going here for some drinks. We got Aperol Spritz of course, and then a bunch of little snacks.
Aperitivo is a hugeeeee deal in Italy. It happens every day between 6-8pm and is meant to be something you do before you go to dinner. Most restaurants offer it and we went to one every single night that we were in Italy! The most popular drink is an Aperol spritz and we drank so many throughout our trip, however you can get whatever drink you want! They also give you tons of snacks to eat for free while you’re drinking. It’s the best. It could bruschetta, crackers, chips, olives, little salads, little mini crostini…
For dinner, we walked back to Trastevere and went to Tonnarello for dinner. An overhyped Instagram famous place for pasta. It was good, but not our favorite meal we had on the trip. I just wanted to go because it is ridiculously popular on IG. Mind you, Tom and I are the first to tell you we are kind of food snobs, haha.
After dinner we got delicious gelato at Otaleg and headed home for the night.
We got an awesome night of sleep and headed out early the next day for a 9:00am Colosseum tour that we booked based off reviews on Viator. It was from 9-12 and was exactly what we were hoping for! It was informative, interesting, our guide was awesome and extremely knowledgeable and we learned so much. The tour also included Palantine Hill which was actually my favorite because I didn’t know anything about it.
We were starving after the tour and mainly just ate bananas and coffee for breakfast since we knew we would be having huge lunches and dinners. We went over to our favorite sandwich shop of the whole trip, Mizio’s Sandwiches, and got the most delicious sandwiches on fresh focaccia bread. SO INCREDIBLE and a must go to for lunch one day!
Fun fact: Rome has fresh water everywhere, so you can bring an empty water bottle and fill it up in any of the running spigots. It’s totally fresh and safe to drink! You’ll see them all over the city.
After lunch we walked back to our AirBnB for our afternoon break before we headed to a food tour later.
Our food tour was great. It took place in the Prati neighborhood, which is one that you probably won’t visit when you’re in Rome because it isn’t very touristy. They have lots of delicious food. We started at a local restaurant where we had appetizers, cheeses, meats, spreads, and wine of course! There were three more stops, including a butcher, a pizza shop, and a restaurant. We were STUFFED! There was so much good food and the history was also really cool to learn about. They took us a to a couple of foodie places and a couple of average restaurants.
Tom and I decided to stay out in Trastevere that night until 2am, and we grabbed drinks at a few places soaking up the nightlife.
This was our Vatican tour day! Once again, we got up decently early and headed on foot to our Vatican tour (booked through Viator again!). The tour was only two hours long but it felt plenty long for the day. We went through the Vatican, which is really like a huge art museum actually, and then through the Sistine Chapel. It was truly beautiful and such a sight to see. We had perfect weather too, so we got a great view of the whole Vatican City that day. Our guide, Guiseppe, was such a source of knowledge and was extremely friendly. We loved him!
Tip: don’t forget to wear something that covers your shoulders and knees or you won’t be allowed in the Sistine Chapel. Tom wore pants and I wore a jacket that covered my shoulders.
After the Vatican tour, we were starving so we were on a mission to get this really delicious pizza that we were tipped off to. Roscioli is a famous restaurant / bakery in Rome and we actually had dinner plans there at night, but their bakery is a totally separate building a few streets away and they have some of the best pizza and sandwiches in Rome.
We grabbed three different kinds of pizza. Regular, White cream sausage, and the best one: PESTO on thick focaccia-like bread. Please if you go to Rome, you MUST go here! I mean just look at these. These deserve all the love and praise for a reason.
We walked back about a mile to our AirBnB, put our feet up, and rested. This is often when I would recap our day on Instagram.
After about three hours, we headed out for drinks and then dinner. We grabbed aperol spritzes (DUH!) at 7Grammi and then walked to our favorite dinner in Rome yet, Roscioli Salumeria.
This was one of the restaurants we went to that we needed a reservation for, you can’t just walk in. We made ours about three weeks prior to our trip and it is well worth it to go ahead and make the reservation.
We started with a bottle of wine that we asked them to pick for us, along with the creamiest, freshest burrata we had had yet with the most delicious sun-dried tomatoes on the side. It was salty, creamy, and so delicious served on their basket of bread that they brought out. The basked had 4 different types of bread (two pieces of each kind) in it and I think we ate it all.
We decided to get the Holy Trinity of pastas and go BIG. We knew this could potentially be our best night for homemade pasta, so we got the Cacio e Pepe, the Carbonara, and the Amatriciana. If you are in Rome, they are famous for the Cacio e Pepe and the Carbonara, but we added in the last one just for good measure. They were absolutely DIVINE. We were ‘ooing’ and ‘aaing’ with each bite and just couldn’t believe how good it really was. They ended our night with these mini cookies and warmed melted chocolate and it was just so incredible!!! Roscioli is a MUST!!
And even though we were certifiably stuffed, we found room for dessert. SHOCKER! When in Italy, you must eat all the gelato necessary. We went to Frigidarium and OMG! Easily the BEST gelato we had had yet!!! So creamy and so delicious. They dip the entire thing in chocolate if you want, and of course, I want.
Day four began our travel day from Rome to Florence. We took at 9am TrainItalia train from the main train station in Rome (Roma Termini) directly to Florence. This was very easy. We took a FreeNow (taxi like Uber) directly to the train station. It took us two hours to get to Florence and it was a very quick trip. Once we got to the train station in Florence, we walked to our AirBnB with our luggage. It was a 15 minute walk but we wanted to get the exercise. We arrived to our AirBnB 2 hours early and I had been communicating with our host, and sure enough, it was ready early! If not, we would have put our bags in Nannybags for another few hours before we could check in.
We immediately checked in and then got to exploring Florence. A quick note on our AirBnB. IT WAS BEAUTIFUL AND AMAZING!!! I highly recommend this place if you’re looking for somewhere to stay in Florence. Not only was the host super easy to talk to and get ahold of, but the actual flat was incredible. The best part? The MASSIVE patio which overlooked the city. Honestly, Tom and I were shocked at how affordable it was for such a great place!
Anyway, we walked around and did our own thing for a little before stopping into Pino’s Salumeria for lunch. We were craving big sandwiches like we had had a few days earlier and I had seen this place on IG. They were delicious!! They warmed the bread which we really loved.
We continued our day by walking around and hanging out, the weather was absolutely perfect so we did a walking tour of the Duomo that we had downloaded on our Apple Podcasts. It was Rick Steves for those who are interested. We explored almost the entire city on foot, since its very walkable.
After a little afternoon siesta in our apartment, we headed out, grabbed a bottle of wine, and headed over to Piazza Michaelangelo to watch the sunset. This is a very common thing to do for locals and people traveling. You climb basically to the top of this hill and you can see the whole city of Florence, it is absolutely stunning. There is music playing, everyone sharing bottles of wine, people enjoying the views, and it is truly priceless. We stayed for about 2 hours and just soaked up the atmosphere.
After our sunset happy hour, we headed over to have dinner at Osteria del Cinghiale Bianco, which is where Stanley Tucci dined in Searching for Italy. We got the famous Florentine Steak, because of course, when you are in Florence you have to eat the Florentine steak! It was absolutely delicious.. like I have no words it was that type of good. They sear it and serve it rare with huge flaked salt on top…it is truly delicious! We got a truffle burrata, and a pasta dish on the side and both were also delicious. And of course – we split a bottle of wine that we asked them to pick for us!
After dinner, we headed out to Gelateria Dei Neri which was highly recommended to me by many of you. They had this one flavor, I can’t remember the name, but it wasn’t actually gelato, it was just like thick hot fudge and it was absolutely divine. Tom and I couldn’t even believe what we were eating it was soooo good!!! We knew we would be back. Our night ended there as we prepared for a big day in wine country the next day!
We woke up so excited because we were about to head out on a Tuscan Wine Tour. This has LOONGGG been a dream of mine, wine tasting in Tuscany all day long?! Count me in! We booked this trip through Viator, it was called the Chianti Tuscan Wine Day Tour and I will recommend this tour to anyone and everyone I know who will be going to Florence.
They picked us up in the most epic 4×4 vehicle. The thing was an absolute monster and just made the experience so much better because we were able to go off-roading into the coolest hills, mountains and wineries. We were with 7 other couples and we all became very good friends throughout the day (wine will do that to you, eh?).
The tour met in Florence which was perfect, and then we headed out about an hour to the first vineyard. Our tour guide, Lavi, was so incredibly knowledgeable and was actually training to be a Sommelier, so her level of knowledge about wine was out of this world. Not only was she super smart about the wine and the process, but she was funny and relatable.
The whole day was 9 hours and it was so worth it! We went to three different vineyards, had an INCREDIBLE pasta lunch at one of the three wineries out in the vineyards, drank so much delicious wine (mostly made from Chianti grapes), and had the best experience. Each winery had a food pairing with the wine, so besides the pasta lunch, we also had meats, cheeses, nuts, crackers, etc at each stop. It was truly amazing!
Honestly one of my favorite parts was driving home at sunset, a little wine drunk in the 4×4 as it drove around the hills of Tuscany, and the sun was setting on all different parts of the hills. Magical.
We got home around 6:30 and since lunch was at around 1, we were hungry again. We headed out to grab a quick bite at Gusta Pizza, which is a pretty famous pizza place in Florence, and sat on the Ponte Vecchio bridge and enjoyed our slices. We headed home shortly after because we were exhausted…
That’s when we laid out on our patio for an hour and decided we wanted gelato…we are sick! LOL! But really, you’re only in Italy once, right? So we headed out in our pajamas to the local gelato place Perche No across the street and it hit the spot.
Our last day in Florence was meant for exploring, shopping, and delicious food (but is there anything new here?) We started our day with our first and only exercise of the trip, a run from our AirBnB to the Piazza Michaelangelo. To be fair, we haven’t really needed to exercise because we have been averaging 24k steps a day. It was about 4 miles round trip and was the perfect way to get our day started.
After showering up, we headed out to do some shopping. Florence is known for their gold and their leather so I knew I wanted to get a nice gold bracelet before I left, and I had my eye on some of the ones I saw on the Ponte Vecchio. But first, we walked over to the Mercato Centrale and to be totally honest, it wasn’t that impressive. A lot of vendors were closed due to covid, and we have Reading Terminal Market in Philly…this was about 1/8 of the size. I would skip.
Anyway, we headed to the bridge, I got my gold bracelet and Tom went into a specialty shoe store to get real Italian leather loafers. I absolutely loved them and we both were so happy with our purchases!
After shopping, we worked up an appetite so we headed to the FAMOUS All’Antico Vinaio for sandwiches. We both got ‘The Boss’ which had prosciutto, truffle cream, and pecorino. It was very very good, and definitely lived up to the hype, however, we both still loved our sandwiches from Rome more. We ate these while over looking the river, and truly just soaked in every moment.
With full bellies, we headed out for more walking and went to the Boboli Gardens and wandered throughout there for the next hour or so. It was very peaceful and very beautiful. I highly recommend going here in Florence! We headed back to our hotel to put our feet up on our beloved balcony.
When it was time for Apperitivo, we headed to The Arts Inn for cocktails and had a couple of spritzes, and then we headed to Regina Bistecca for dinner. Both amazing! But our dinner the first night was better than the one at Regina Bistecca.
We headed back to Gelateria Dei Neri (our absolute fave in Florence) and then called it a night! We had a big travel day the next day.
Day seven started out early, with a 5:30am wake up so we could head to Positano. We knew it was going to be a long day and we wanted to spend as much time as possible in Positano, so we planned to leave early.
In order to get to Positano from Florence we had to take TrainItalia (same train we took from Rome to Florence) all the way to Naples. This train stops in Rome. We took the express. Once we got to Naples, we had to take a local line to Sorrento. This was the only point during the trip where we truly felt like outsiders because we didn’t speak Italian. It was difficult to navigate the Naples Train station, and we needed to figure out how to get to the local train. We ended up leaving the station to find another station and it wasn’t what we needed to do.
After about 20 minutes of frustration, I googled it and we figured it out. We waited for our train to Sorrento along with about 100 other people all shoved in a tiny area waiting for the train. This train also goes to Pompei, so there were a lot of people who were traveling from Naples for a day trip to Pompei.
We eventually got on and it took us 90 minutes to get to Sorrento. Once we got to Sorrento, our plan was to take another Train or Bus to Positano, but at that point we were so tired of lugging our suitcases around that we took a taxi who was waiting outside the train station. This cost us around $80 and we both felt that it was WELL worth it to be dropped off door to door.
It was in that moment that we decided we would also take a car directly back from Positano to Naples to avoid any confusion in the future. No stopping in Sorrento.
Once we got to Positano, it was only noon! That is why we left so early, so we could get there with a full day. We immediately were in AWE!!!!! Positano is absolutely stunning, our jaws were on the floor the entire time. It was pure magic.
Our AirBnB wasn’t ready yet, but we were able to store our bags at their family store, which was awesome. We headed down the many flights of steps to the beach area and grabbed lunch at the famous Chez Black. We both got pizzas and aperol spritz, and we were so happy. We explored the area for a while and quickly understood that the only way to get around Positano is by climbing steps. Thousands of steps. I would just warn anyone who is going that you will need to get around by climbing, even if you take the road (the paved path) down. We honestly liked it because it felt like we were working out so we could eat more pizza!
We headed back up to our AirBnB and got our swim suits on and headed down to Fornillo beach. This was my favorite moment of the whole trip. We snagged two beach chairs at the Beach Club, grabbed two aperol spritz, and laid on the beach for a few hours. We swam in the ocean which was so warm and soooooo crystal clear, and honestly just felt like we were in heaven! Staring up at the beautiful cliffs above us. We had a few more spritzes, YOLO! We were on vacation.
We ventured (hiked) back up to our AirBnB to get ready for dinner. Our AirBnB was amazing. It had the most stunning balcony overlooking part of Positano and we were out there as much as possible. The whole place was also gorgeous, the owner was amazing to work with, she left us food, snacks, and was just a peach to work with. The location was also PRIME. We were essentially a 10-15 minute walk to everything. HIGHLY recommend.
Tom and I headed to Il Tridente for drinks and apperitivo. We really wanted to go to La Sirenuse (the nicest hotel in Positano) for drinks because it has the best view of Positano and the cliffs, but when we got there they said that they were fully booked. I was so upset because this was a dream to get drinks here!! They don’t typically take reservations but they had enough people at the hotel who wanted to get drinks there that they were fully booked.
However, Il Tridente was another absolute highlight of the trip….sitting on beautiful couch lounge chairs, live music playing in the background, the sun setting, the most beautiful part of Positano in front of us, and sipping on drinks and eating snacks. It was incredible. We split a bottle of rose and had quite a few snacks that they gave us.
We also ate dinner at Il Tridente and both didn’t really like it, to be totally honest. We understand we are food snobs, but it was below average. Skip!
After dinner, I really wanted to try La Sirenuse again, and even though Tom thought I was crazy, we headed back there. Lucky for us, they had the best seat in the house open…. it was truly breathtaking. We ordered dessert and a bottle of champagne and sat outside for a few hours, soaking in the absolutely breathtaking Positano view. Stunning. A moment to remember forever.
Day Eight started with a little bit of rain, which was a bummer since we only had limited time in Positano. The rain stopped around 10am but because of the conditions, we were unable to do our scheduled 9 hour boat day to Capri. Very sad but this is absolutely something you need to do if you make it to Positano!!! We didn’t let that stop us though.
We headed out to La Zagara for lunch and of course, we both got pizza! It was delish and the rain cleared up so we were able to sit on the patio and enjoy the beautiful view. After lunch, we walked around and did some shopping, we both wanted to get some stuff and Positano is known for ceramics. We picked up some gifts for family and friends!
After shopping around, the weather cleared up enough so we headed back to the beach to lay! It was nice because it was quiet and peaceful.
After hanging on the beach, we went back up to our room and sat on the balcony and drank a bottle of white wine we had gotten at one of the vineyards we went to in Tuscany. It was so perfect. We listened to music and reflected on our trip…so special that I got to do this trip with my soon-to-be husband.
After our little happy hour, we headed to Da Vincenzo, a Michelin star restaurant in Positano. Where to eve begin… we had done a little bit of research so knew exactly what we wanted to order.
We split a bottle of wine, shared the mussels (OMG), I got the spaghetti alla nerano, which is a Positano specialty. It’s spaghetti with fried zucchini and cheese and it is absolutely divine. You must try this dish. Tom got the linguine with lemon and shrimp and it was divine. We really loved our meals here and highly suggest!
Grabbed gelato at Collina Bakery to end the night (it was just okay, especially after all of the Gelato we had already had).
We woke up and waited for our scheduled driver to take us back to Naples. I cannot stress this enough, hiring a driver to take us back to Naples saved us hours of time, stress, lugging our luggage around, etc. It was so worth it.
Once we got to Naples 1.5 hours later, we weren’t going to just hang out in Naples without getting famous Napoleon pizza…I mean, Tom and I travel most specifically so we can eat good food. So we did what we do best and lugged our luggage over to L’Antica Pizzeria de Michele, named ‘The Best Pizza in the World’, waited 45 minutes for our pies, and then ate it on our suitcases right out side in the street. IT. WAS. FABULOUS. and just what we needed to get us through the next 90 minutes back to Rome.
We hoped on TrainItalia and headed back to Rome for our final night. Once we got to Rome, we checked into our AirBnB and laid down for a little before heading back to our favorite area, Trastevere for one last apperitivo and dinner.
Several people had recommended we have apperitivo at Mimi + Coco’s so that’s where we went and it did not disappoint. We each ordered an aperol spritz and it came with an entire charcuterie board full of mini crostini, bruschetta, salads, olives, nuts, and hand snacks. And remember, that is INCLUDED in the cost of the drinks. We had 2 aperol spritz each as we sat outside and people watched in our favorite area of town. Btw, the whole cost of the apperitivo was $27 for four aperol spritz and that whole plate of snacks.
After our little happy hour, we headed to dinner. One of the places we had heard about was Da Enzo so we decided to make our way over. We waited in a line for about 30 minutes before being seated but it was well worth it! The pasta was delicious and the wine was soooo cheap and good. TIP: order the house wine and it typically comes out in an entire carafe and is about $5-$6. We headed to our favorite gelato place in Rome (and of the trip) while we were there, Frigidarium, and got our gelato. Incredible and a must do while you are there, be sure to ask for the chocolate dip!
We headed home after this because we knew the next day was a travel day back home!
It was finally time to go home! We took an FreeNow to the train station where we took the Leonardo express back to the airport. Headed home from there, Rome to Madrid to JFK. We did need to follow the instructions for the Spain covid protocol, just so you know. We had to download their app and upload our documents. We didn’t know this until we got to the airport but luckily it was a breeze. After about 16 hours worth of travel from leaving our door in Rome, we made it home. Such an amazing trip of a lifetime!
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