Italy
I planned a 3.5 week trip to Italy and Croatia, it was the time of our lives! We spent a little over 2 weeks in Italy and went to the Amalfi Coast, Rome, Tuscany, and Florence. We had the best food and wine ever. We saw and experienced so many amazing things along the way. We were able to relax in Tuscany and learn about all the history and art in Rome and Florence. I’ll go more in depth about what we did and liked best in this blog. If you are planning a trip to Italy, check out my itinerary that has almost every single day planned out and includes links to what we did and how we got around, restaurants, our stays, costs, and more!
Positano
We flew into Naples and started our trip in Positano. We got in around 8am and it was a 2.5 hour drive to our B&B. We stayed at Hotel Pupetto. We settled in and had lunch here, then went to explore the town and of course, went shopping. I made us dinner reservations at Da Vincenzo in advance, it’s a really great restaurant in a cave. We were the first people on their list so we got the best seats in the house! One thing I love the most about Italy is the food and wine. Before heading back in for the night we stopped to get gelato. We could eat so much gelato and feel great, unlike here in the U.S.
Day 2 Explore we slept in and had breakfast at our hotel. Our breakfast was included which was a plus! For today I had planned to do the Path of Gods hike, but unfortunately the first few days we were in Positano it was POURING and pretty chilly, which was rare because we went mid-May. Anyways we ran into some locals while shopping and they recommended we do not do the hike, because it would be too slippery. Instead we did some more shopping, I got Italian leather handmade sandals, had lunch and my first aperol spritz! We found ourselves hiking anyway, just not on the Path of Gods. We decided to hike along the winding roads in Positano (probably not the safest thing), but we ended up at probably the tallest point of Positano, we were definitely not in the tourist area anymore. We walked for at least an hour or more and went up and down a ton of steps. It was an adventure! Even though it was rainy and chilly for half our time here we still made the best of it.
We ended the night at Il Tridente, it’s one of the iconic spots to go to in Positano, very esthetically appealing and amazing views. The reservations open 2 weeks in advance at a cretain time so you REALLY have to be on top of it, it is trully wild. I was only able to get us cocktail reservations, I even tried twice and both times I was only able to get us in for cocktails. For today we went around 6pm, it was beautiful and very romantic. We had a bottle of red wine and they served snacks which were free. The snacks included chips, nuts, and a few pieces of this really yummy gnocci.
Even if you can only get cocktail reservations I highly recommend it! After Il Tridente, we got a slice of pizza and gelato, went down to the beach for a few and ended the night.
Day 3 My Birthday! Today we went to Capri. Let me tell you, not the easiest thing to do! Our ferry did get cancelled but thankfully we were able to catch another one about an hour later. We arrived in Capri around 11:30, bought tickets for the funicular to Capri Town and sat down in the square to enjoy a nice cold rosé and pizza while people watching. We then walked around all the fancy shops and then tried to check out the Gardens of Augustus but didn’t have enough time because we were scheduled for a private boat tour at 2pm.
Our boat tour was amazing! The best thing we did in the Amalfi Coast. We boated around Capri for about 2 hours, took a dip in the sea, and just relaxed. This is one of the best things to do, I HIGHLY recommend! Ours was private, I wanted to splurge a little for my birthday, but I’m sure a group one would be super fun as well. I always love meeting new people across the world on group tours.
After the boat tour we had to get in line to catch the ferry back to Positano. I was planning to have more time on Capri but due to the hiccup with the first cancellation we had to change some things around. Overall I liked Capri but it deserves more time. From the research I did everyone said to stay there for a few days but I still decided to make a day trip out of it. If you’re spending 4 or more days in the Amalfi Coast, I still think it’s probably worth it to take a day trip to Capri because it is so beautiful but definitely try to be gone the whole day and don’t schedule too much for the day.
To end the night we had dinner at our hotel then went back to Il Tridente for cocktails, but this time at 9:30pm so it was dark. It was truly magical seeing Positano at night. The waiter knew it was my birthday so they brought out a little dessert and sang happy birthday to me, it was beautiful! If you only have enough time to go to Il Tridente once, I would suggest going at night, it’s lovely.
Day 4 Photoshoot & Beach Club Last full day in Positano and it was an early morning! I scheduled a vintage car ride photoshoot along the Amalfi Coast. It was 6:30-8:30am because after that the traffic gets a little crazy! We rode in a vintage yellow fiat 500 and the driver would stop and take literally the best pictures of us, WITH MY IPHONE. I highly recommend this experience! Check out Positano Vintage on instagram.
After the car ride we headed to the Arienzo Beach Club. I got us second row chairs, we were greeted with a bottle of rosè and we really just laid out and relaxed. We also had lunch here and the food was really good. When you buy tickets to Arienzo Beach Club they have a free boat shuttle that’ll pick you up at the main beach in Positano, it also includes lunch and whatever bottle comes in the row you get. Going to a beach club is a must do in the Amalfi Coast. I really liked the vibes of Arienzo Beach Club so definitely check it out!
We then went back to our hotel and worked for a few hours before heading to the shuttle pickup for our dinner reservations at La Tagliata, another very popular place. La Tagliata has no set menu, you pay a certain price and they serve you pretty much everything, it’s A LOT of food. They also offer free shuttle pickup because it’s far up in the mountains and difficult to get to. Our shuttle was almost an hour late! We thought we might miss the dinner but nope! So be patient if you choose to use the shuttle lol. After finally getting there we did get some of the best seats in the house. We also met some really great people and talked to them the whole night. I have to be honest, I didn’t love the food, there’s definitely better restaurants but the experience is awesome, you have amazing views of the sea. It was 60 euros per person which is really good for a 5 course meal and unlimited wine. They also gave us limoncello shots at the end. Honestly probably a restaurant I would only go to once, we still had a great time!
Rome
Day 5 Heading to Rome & Trastevere We headed to the train station in Naples early afternoon, it was my first time using the train station in Europe (fun!) it was pretty easy to navigate. We were off to Rome! It took an hour and 10 minutes and then we hopped in a taxi to our Airbnb. I know some people really love or hate Rome but I knew from the first moment I arrived I was going to LOVE it.
After settling into our Airbnb we explored the popular neighborhood Trastevere, a very cute and aesthetically appealing neighborhood. We went to a restaurant our Airbnb host recommended in Trastevere, Pasta e Vino Osteria. It was delicious! It looked like a little hole in the wall, we passed a lot of really pretty looking restaurants (but most are just tourist traps). Go to the restaurants where there aren’t people outside trying to attract you in.
After dinner we walked around more and stumbled upon some Roman Forums, what I love about Rome is the history. You walk down what seems to be a normal street and then look to your left and there’s Roman Forums. It’s amazing. We went into some shops and I got a bottle of red wine which I enjoyed a glass before ending the night.
Day 6 Trevi Fountain, Colosseum, & Roman Forums We got to the Trevi Fountain at 8:30am, it’s less busy in the morning, we got some great pics, and of course made a wish and tossed a coin in the fountain. Then we headed to the Roman Forums, we had a private guided tour (highly recommend!). Our tour guide was great and super knowledgeable. We were standing where Julius Caesar was buried, we saw how the Roman Forums would have looked back in the day, and more. This was our favorite experience in Rome. It’s surreal being there and seeing everything. I was never a big history person in school but when you’re actually there and you have a guide that is passionate and knowledgeable, it changes things. Now I’m way more interested in history than I ever thought I would be.
Next, we headed to the Colosseum for our tour. This was with a group. Not as great as the Roman Forum tour but still being in the Colosseum and learning about the history is surreal. We got tickets to see the underground area which just opened up a few years ago. I recommend booking the underground tickets!
After the Colosseum we had lunch nearby. We did a lot of walking and had a very light breakfast so we were starving! After lunch we started walking to the Vittoriano, it’s a national monument and museum inside (more modern), on the way there it started pouring out of nowhere! We got up to the Vittoriano and were soaked, but it didn’t stop me. The outside of this place is gorgeous, even more gorgeous at night. It was more modern looking, very big and grand inside. I prefer more of the ancient museums in Rome, I would recommend just driving by or walking by it because in my opinion, that’s the coolest part.
We came back, showered and got ready for the evening. We did some shopping by the Spanish steps and then headed to dinner at the popular Osteria de Fortunata. There was a line but it went by pretty quickly for us. Let me tell you, it’s worth it! Best carbonara we ate in Rome. Definitely a must go to place.
Day 7 Vatican Museum It was another early morning, we took an Uber to the Vatican and got there around 9am. We had skip the link tickets (I recommend) and were able to pretty much walk right in. It was beautiful and so many great works of art, it feels almost impossible to see it all. I was really excited to see the Sistine Chapel, by the way, you can’t take photos in the Sistine Chapel. It was beautiful, I felt like my head might fall off from staring at the ceiling so much. We spent a few hours at the Vatican then headed back to our Airbnb.
The afternoon we shopped, had lunch, went to the Pantheon (it’s free!) and then had the best gelato at Giolitti, definitely go here! We headed towards the Spanish steps for more shopping and it started pouring out of nowhere again. We thankfully were by the Babingtons Tea Room, which was somewhere I really wanted to go in Rome. It’s such a cute experience, the tea was great and the whole place is such a good vibe. Great way to relax and get a break from the busy crowds.
Then we headed to our Pasta Cooking class where we made homemade tiramisu and carbonara. This is super fun, you meet new people, drink wine and limoncello, and the food was great! You have to take a pasta cooking class in Rome. The class was about 2 hours then we walked back to the top of the Spanish steps and had wonderful views of Rome at night.
I really wanted to see the Trevi Fountain at night so we went back and it truly is magical. A lot more people though. We even saw a couple get engaged! It was so beautiful. Overall I really loved Rome. The food, the history, the art and architecture, the shopping, it’s all amazing. Rome just gives off a vibe I really like. However it is pretty big compared to Florence. In Florence we pretty much could walk anywhere in less than 30 minutes. Rome is also very busy, lots of people, and smells like gas fumes and cigarettes lol. In my opinion, the pros outweigh the cons and I would definitely go back.
Tuscany
Day 8 Headed to Tuscany We took an Uber to pickup our rental car in Rome, I chose a pickup spot that was almost out of the city so we weren’t in the crazy driving areas. It took 2.5 hours to get to our Airbnb in the Val d’Orcia area of Tuscany. The pickup and drive was easy. Tuscany is a lot more chill and less people, so I would highly suggest renting a car here.
We stayed at a farmhouse villa. There were only about a dozen rooms, a pool, a reception area where we had breakfast and dinner, and a nice outdoor patio overlooking the Tuscany hills and a view of a medieval village in the distance. The property was gorgeous! The rooms were very old and medieval looking, you won’t really find many modern stays in Tuscany (at least not at a decent price) but we didn’t mind at all because it contributes to the character of the area, plus you spend a lot of time outside the room anyway.
Our first day we just settled in and drink lots of wine at the villa. It was very relaxing and peaceful. We met other people that were staying there and chatted with them. To end the night we had a full course dinner at the villa and headed to bed.
Day 9 Wine Tastings and Photoshoot We had a wine tasting at Il Palazzone in Malcino at 11am. It was about a 45 minute drive from our villa but it was a very scenic drive. We were the only people there so it was pretty cool having a private tasting, they showed us the vineyard, the cellars and told us how they make the wine, and then we sat down for a tasting and of course left with a couple bottles. My fiancé and I love wine, so it was really interesting to us to learn about the process and learn how to do an accurate wine tasting.
We then headed to our second wine tasting at De’Ricci, it’s a cave in Montepulciano where they age wine. The family that owns the villa we stayed at recommended this winery. It was a very different experience from our previous wine tasting. They took us down into the cellar and showed us the ‘wine cathedral’ as they call it. There were huge 100 year old barrels (not used anymore) but it just shows the history of this place. A really cool story they told us was way back in the day when Montepulciano would get attacked, the citizens would hide in the caves where they’d make the wine, and they’d be down there for long periods of time so the people would actually drink the wine to stay alive because they couldn’t drink the water, the attackers would poison their water, so all they had was wine. Our tour guide said that’s why there’s the saying “wine saves lives“.
After the wine tasting, we had coffee in the Montepulciano square and people watched. The Montepulcino square is a popular place, you’re surrounded by old charming buildings, and you have views of the Tuscany hills in the distance, I recommend checking it out! Then we headed back to the villa so we could get ready for our engagement photos.
Fun fact, I had this trip planned out for a long time and few months after I planned it Evan and I got engaged so I thought how perfect would it be to have our engagement photos done in Tuscany! The picture perfect place. I ended up finding our photographer on Instagram @photographertuscany
The experience was unforgettable and our photographer was incredible. We had him for about 2 hours and we followed him to 5 or 6 locations to capture all of the best landscapes of Tuscany. It did rain for about the first 30 minutes, our photographer was so concerned and just wanted to make sure I was alright, I really appreciated how much he cared and it shows to his level of passion and professionalism. Honestly I didn’t care, no one can control mother nature and I was just so grateful and blessed to have my engagement photos done in Tuscany, Italy. The photos turned out incredible, even with my hair a little wet. Just look how magical they are!
Day 10 Pienza & Thermal Spa Today we explored Pienza where we visited many local shops and had an amazing lunch overlooking the Val d’Orcia. Pienza is such a cute medieval town, a must visit! We spent a few hours here and then headed about 30 minutes away to go to a thermal spa called Bagno Vignoni. Then we headed back to drink wine at our villa the rest of the day, had dinner, and chatted with some of the other couples.
Tuscany is the best place for relaxing and slowing down, I’m so glad I threw this in between Rome and Florence, it gave us a good break and allowed us to see a different side of Italy. I highly recommend saving just a few days to stay in Tuscany. I could actually see myself retiring here! Honestly the best thing to do is just drink wine and take in the views of Tuscany and the towns. The nature and medieval villages are breathtaking. I love it here.
Day 11 Moterigionni and Florence Before getting into Florence we stopped by the medieval town Monterigionni, known for it’s walls and watchtowers. It was a defense town for Siena. We walked around the walls and had great views of the countryside and also the town. It’s a very small town with a few shops and restaurants. We had a nice lunch in the square and bought a few bottles of wine to take to Florence.
Florence
We stayed at La Terrazza Sul Duomo, the B&B has a rooftop with perfect views of the Duomo. The rooms are very royal like and we had a small window that opened up to the street with views of the Duomo. After unwinding we headed out to go shopping. Florence has amazing shopping and I loved the fashion there. We then headed to the Ponte Veccio bridge, got some photos, and did more shopping. We topped off the night with a wonderful dinner at Osteria del Porcellino, highly recommend this place, I had the best lasagna I’ve ever had.
Day 12 A Whole Lot! We headed to the Uffizzi Gallery at 8:30am where we had a timed entry ticket and spent a few hours wondering the gallery in awe of all of the art, it’s truly amazing. We saw many famous paintings including the birth of venus, I love that one. We bought a headset that we could listen to and guided us through each room. I highly recommend doing this so you can understand the rooms and what you’re looking at. We didn’t do this in the Vatican in Rome but I wish we did. At every big museum moving forward we’re going to use these headsets. They’re inexpensive and really adds value to the experience.
We then headed to see the David Michelangelo, I had been SO excited to see this for months. It truly is enormous and so iconic. For this gallery we bought skip the line tickets. Again, highly recommend. At all the big museums during this trip we bought timed entry or skip the line tickets. Some of the lines are so long and I didn’t want to waste any time standing in lines if it was only going to cost an extra $10-$30.
For lunch we went to Shake Cafe, if you’re wanting a break from Italian food, this is the place to go. It was nice to get some greens in! After lunch we headed to the Boboli gardens. We spent hours exploring the gardens, it’s huge and absolutely gorgeous. We then did more shopping, stopped to get coffee, and then headed to the wine window. They serve you wine out of this little cute window in one of the back streets. It’s definitely a cool experience!
We had dinner at Regina Bistecca, known for their Florentine steak which you have to try while in Florence! It was a very romantic dinner, good food, and good wine. The steak is massive! Totally worth it. Then we headed back to our B&B and sipped on wine on the rooftop. One of my friends who went to Florence years ago convinced me to ride the carrousel, it was so fun! I used to love carrousels growing up, you have to do this, especially at night while a little wine tipsy, I mean why not?! We topped off the night getting a drink in the square and watched a band play.
Day 13 Pisa, Siena, & San Gimignano I booked us a day group trip to these three locations. We saw the falling tower at Pisa, had a wine tasting in the Chianti region, visited Siena, and our last stop was San Gimignano. It was a full 12 hour day. We took an uber to our meetup point outside of the city and took the train back. We had a double decker bus, let me tell you, it was NOT pleasant. There was no AC and no air circulation, we felt like we were dying the whole day. It may have just been the bus but I would not do this again lol.
It was great experiencing Pisa, I loved seeing the falling tower and getting the iconic photos, I also enjoyed the wine tasting and lunch, we tasted multiple wines, olive oils, and balsamic. Siena was also really cool, the Cathedral is absolutely stunning. I recommend checking out this church while in Siena. We really didn’t get to appreciate much of San Gimignano because we just felt so sick and tired, but it had very medieval vibes and was very unique. It was still a good experience but the bus was really really rough. I would have preferred to have rented our car an extra day and went to a few of those places ourselves. Just being honest with you guys. A smaller tour would have been better.
After a long day we enjoyed a whole pie of pizza each from Mister Pizza, it’s by the Duomo and very good! We waited a while but it’s worth it.
Day 14 Duomo & Piazzale Michelangelo Today we went to the Duomo in the early afternoon. It does look like a long line but we only waited 30 minutes. The Duomo is beautiful, I really don’t know how they could paint in detail on the ceiling like that, but it’s breathtaking. We then headed to lunch on a quaint little street, very authentic food. It’s actually crazy because we ran into my fiancès cousin he hasn’t seen in almost a decade, their mom had texted me that they were here but we weren’t able to reach them but then we saw them on the side of the street in Florence. Crazy! We made plans to meet up with them later.
Our next stop was touring one of the Medici Palace’s (I ended up going to the wrong one and didn’t find out until I got home, the actual palace is attached to the Boboli gardens.. I remember saying “who’s palace is that??” because it was huge!) I’m not sure exactly what the palace was that we went to but google said it was the Medici Palace, but it’s wrong. It was a small palace, still very beautiful, not too far from the Duomo. It had paintings of the Medici family, artifacts that were found in the palace, and other works of art.
We then met up with my fiancès cousin and her husband and spent the rest of the day drinking, walking around Florence, catching up, and had dinner together. After dinner we headed to the Piazzale Michelangelo for sunset, it was PACKED, the entire place was full, we were somehow able to squeeze in on the stairs. It’s the perfect view of Florence and they have a band play. People literally come here hours before sunset just to secure their spot. I recommend taking a bottle of wine and maybe some light snacks and come an hour or so before sunset, we came almost minutes before because our dinner ran a little late.
We met a really cool couple from Scotland that we chatted with and drank with for a while. We were chilling there for an hour or two. Then we all walked back home and went up to our rooftop, chatted and drank more wine with my fiancès cousin and her husband. It was an awesome day and perfect night. I loved the feeling of roaming Florence at night with friends. It’s so fun!
Summary
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Summary ~
We absolutely loved Italy. Positano was beautiful, amazing views, and the cliffside town is very cute and picturesque. We wished the weather was better but we still really enjoyed our time there and loved the town. It’s pretty expensive and honestly wouldn’t be a place we’d go back to every year. Though my mind could change if we went back and had a different weather experience!
Rome was magical. We both loved Rome. The history, art, architecture, food, and views makes it one of the best cities I’ve ever been to. We didn’t love the pollution and smells but all the positives out weighed that.
Tuscany felt like a fairytale. The old medieval houses amongst the rolling green Tuscany hills and vineyards is one of the most beautiful and peaceful landscapes. Learning about the wine making process really makes you appreciate the wine even more. The wine there is really one of a kind. We loved the medieval towns, it makes you feel like you’re back in time. It’s so much easier to live in the present here. Tuscany was also a nice break in between the busy cities.
Florence was beautiful, smaller than I expected (thankfully), not as much walking as Rome. Florence felt like a city I could actually live in because it did have a more modern feel to it. It’s easy to get around, they have amazing fashion, lots of cool people, great art, and awesome food. I would love to spend a few months in Florence and really learn the culture and language.
Italy is definitely a country we will be going back to and exploring more of. I would go back to all of these cities again. If you need some guidance on planning your trip to Italy, check out my itinerary! It has links to almost everything we did, how we got from place to place, restaurants, and more. I can even help organize and plan different days if you’re going for a shorter or longer period.