Planning a Trip to Italy: Our 2-Week Itinerary

Italy has been on our bucket list for as long as we can remember! I’m so thrilled Johnny and I was able to spend two weeks in Italy for our honeymoon! We went south to north and had an absolute blast every single day. I got a lot of questions about planning a trip to Italy and I’m excited to share an overview of where we went and how long we stayed in each spot. Here is our 2-week Italy itinerary!

We did work with a travel advisor who helped us with planning a trip to Italy. We gave her our total budget and she helped build our itinerary, handle logistics for us of getting from place to place, booked tours and worked with the hotel concierge to make restaurant reservations for us. Plus, it was nice to know if something happened, we had someone to call to help us. We did have a hiccup or two, but I believe that is mainly at the fault of one of the hotels’ concierges (more on this below) and not her. As a note, we did book our flights and one of the hotels ourselves because we used points.

One of my favorite podcasts, All the Hacks, recommended Savanti Travel, which is how I ended up finding our advisor!


When To Visit Italy

Italy is most popular during the summer months! I’ve heard it gets absolutely crazy and packed June through August. If you’re planning a trip to Italy, know the shoulder months including May, September and October can be a great time to go and also save some money since it’s not peak season. May and October would give you more of a toss-up when it comes to weather, but it’s much less crowded. We went early to mid-May and on the chilliest day, it felt like 50 and on the hottest in the upper 80s. I remember freaking out looking at the weather app, but it wasn’t too bad. In Positano, there were two days it didn’t feel super warm, but it was still very nice. It was warmest in Lake Como where it felt like the upper 80s and we got a lot of sun and some color in our skin.

Flying Business Class

We cashed in a lot of Chase points to fly business class to Italy. Johnny did some research and United gave us the best flights and maximization of points. I believe we ended up using 500,000 points. From DFW we flew to Newark where we had a layover for a couple of hours. Since we were flying United Polaris Business Class, we got to access the Polaris lounge, which was phenomenal! Food was wonderful, lots of places to sit, kick back, shower, rest, everything you can think of. I do recommend the restaurant instead of the buffet if time allows.

The actual flight was lovely. We had an “overnight” flight, which was perfect since we landed in Naples in the morning. We had lay flat seats, which helped us both get some actual sleep. When booking your seats, look at the layout carefully. If the two middle seats look like they are close together and you’re flying with another person, book that one. You’ll simply have a divider you can raise or lower. If they do not have that divider, you want seats either in front or behind one another to be as close as possible.


We kicked off our honeymoon in Positano because it was a place we both had dreamed of visiting. Plus, when planning a trip to Italy we knew we wanted to start with some relaxation and Positano provides just that. We flew into Naples and it was about a 1.5-hour drive or you can take the ferry. We used Positano Car Service and our drive Peppe is the best! While he’s not a tour guide, he was so knowledgable about the area, pointing out important historic spots, telling us about the Amalfi Coast, teaching us a few Italian words and taking some great photos and videos of us! It was a great reminder that when planning a trip to Italy, some of your best moments will actually be unplanned.

One reason we love staying in Positano on the Amalfi coast is it’s the biggest and had the most things we personally wanted to do. Plus, the other towns are a day trip away! Positano was our favorite town with its picturesque views and Amalfi comes in second. I’ll do a full blog post on our time in Positano soon!


There are so many beautiful places to stay in Positano from luxury hotels to Airbnbs! Since this was our honeymoon and we’ve been saving for quite a bit, we wanted to have the luxury hotel experience.

Le Sirenuse

Overall our favorite hotel on our entire 2-week Italy itinerary! There aren’t enough words to describe how incredible Le Sirenuse is. From the attentive and kind staff, the views that don’t seem real down to the delicious food we are still dreaming of. One thing I noticed right off the bat is how impeccably clean it is. I know all hotels should be clean, but that just isn’t the case. I always saw staff sweeping, mopping, cleaning every little nook and cranny. The floor was so clean I could eat off of it and I’m not exaggerating.

Our first introduction to Positano was the breakfast buffet, view of the colorful buildings and clear water from Le Sirenuse’s terrace. It was simply breathtaking. We stayed in the Junior Suite Sea View with Balcony for two nights. One thing I wish I had done more research on about Positano was really paying attention to where hotels are located in context to the beach and stairs. Le Sirenuse is accessible via car so if we wanted to leave or go anywhere it was actually really easy and didn’t feel tiring. Plus, the staff speaks English well and are extremely accommodating. If you’re planning a trip to Italy and able to splurge on Le Sirenuse, I would definitely recommend it.

Covo dei Saraceni

We transferred to a more budget-friendly hotel right down on the beach next to where the ferry and boats all leave. The view is the exact opposite from Le Sirenuse so it was great to see another picturesque landscape. If you are looking to save money, this is another option while still giving you that hotel view.

Located right on the beach next to shops and restaurants, which makes that part fun and accessible. However, it is not accessible by car. We had to budget in an extra 10 minute for walking up the stairs and hill to get to the “parking garage” which is where all car services/taxis/buses are.

The room itself had a beautiful view and even though we were in one of the nicer rooms of this hotel, there was no way to compare it to Le Sirenuse unfortunately. Our King bed was not a true king bed, but two twins pushed together and I fell in the “crack” when sleeping quite a bit, which led to me tossing and turning. Covo de Saraceni would hit a baseline of being clean, but I think for the price itself, it should have been better.

Stay tuned for my full Positano blog post with what to eat and do!


I feel like you really cannot visit Italy without at least seeing Rome once. We love history, art and learning when we visit a place. We opted for Rome to give us that city feel and having more activities to do after lounging in Positano for the first part of our trip. There is so much to do in Rome and I believe we’d love to go back and explore more! I know to some it can be pretty touristy, but we truly enjoyed it. We took a private car service to Rome and for us, it was worth it to be extremely comfortable, not worry about delays and to just relax. If you’re planning a trip to Italy, Rome is a must visit!

From Positano, we used a private car service, which took about three hours and cost about $300. The car had water, phone charger and it was nice not to worry about the chaos of a train station. I will say every time we used a car service, they are extremely prompt. They show up a few minutes before the actual arrival time, help with bags and get you to your destination on time.


Hotel Splendide

We were still “recovering” from Le Sirenuse so we wanted a more budget-friendly option while still getting nice hotel services. Hotel Splendide was perfect for that, although we wish it was more centrally located to shopping and dining. We booked the Superior Double Room, but I believe they upgraded us upon arrival since our room was massive! They do not have irons at this hotel, so you’re on your own. If clothes or wrinkled or you can pay for pressing services. They also have a sister location with a spa and pool, so that may be another option, too. When had a good breakfast every morning before leaving to explore, which was nice!

If we wanted to go the luxury option, J.K. Place Roma is one of the hotels we looked into!


Vatican Museum Tour: We loved this smaller group tour for up to six people. Our guide was so knowledgeable and we couldn’t imagine doing the tour without her.

Colosseum Tour: For this tour, we opted for a larger group since it’s outdoors. One note I will make is I recommend doing a reverse tour where you see the Colosseum at the end of the tour. It’s still a little unbelievable to think these stunning places were built so long ago without modern technology.

Spanish Steps: A beautiful scenic spot in Rome. When we went they were shooting Fast 10 so it was blocked off in the morning but it was stunning to see! We got to walk up and down the steps later in the evening and see the view!

Shopping: Next to the Spanish steps are a lot of high-end designer stores including Chanel, Hermes, Prada, Gucci and more. Don’t forget shopping in Europe tends to be favorable because you won’t pay taxes and Italian brands tend to be cheaper in Italy.


Pretty much every single restaurant we went to in Italy asked if we had a reservation. Make sure you either have your hotel’s concierge make them for you (and ask for a table with a view!) or call them yourself. If you have the Amex Platinum card you can use their concierge service.

Osteria Delle Coppelle: Hidden down a side street and tucked away, it feels like a locals’ only spot. The food is incredible and the gnocchetti is something Johnny keeps thinking of. The tables are small and the space overall is tight, so keep that in mind.

Cacio e Pepe: Incredible cacio e pepe like the name would suggest and the rigatoni is a must-try! We sat outside and tried a couple of different kinds of pasta.

Pizza Zizza: Our favorite pizza we had in Italy! We went here after our Vatican tour.

Life: One of our favorite meals. They do courses here so the crispy organic poached egg with burrata and truffle is divine. Everything was delicious and the decor is beautiful.


We didn’t expect to fall in love with Florence as much as we did! I wish we had more time to explore here, especially Tuscany. Everything is so walkable and despite being a heavy tourist destination, it’s so clean. I love seeing the Ponte Vecchio, especially during golden hour. The shopping is great and, of course, the food is unreal! We got so many recommendations on what to do in Florence I wish we could have gotten to everything and soaked it in. It’s a must visit if you’re planning a trip to Italy.

To get to Florence from Rome, we took the bullet train. Our travel advisor booked these tickets for us in advance and we got business class for space. We departed from Roma Terimini and arrived at Firenze S. M. Novella. One stressful part of travel is the platform number doesn’t go live until about five minutes before the train actually leaves. I say actually leaves because they can be delayed. So just be ready near the board and when your platform number pops up go right away!


Hotel Lungarno

The reviews for this hotel are unbelievable. Practically everyone gave it five stars and I can see why. Located right on the bridge with beautiful views it’s in a beautiful location. The staff and concierge are so attentive and they even use WhatsApp to make communicating with you super easy! Want to make a reservation? Send them a WhatsApp message. Want in-room dining? Same thing.

Similar to Rome, we opted to save money here and went with the Double Room with a street view. The hotel is actually owned by Salvatorre Ferragamo so everything was impeccable from the decor to linens to art. Plus, you get a discount if you shop at Ferragamo, too!


Introduction to Florence Tour: A lovely walking tour with an expert in Florence’s history, culture art and Michelangelo’s David. Turns out a lot of things I thought were French are actually Italian haha! Make sure to wear comfortable walking shoes.

Cathedral of Santa Maria del Fiore: The scale is unbelievable. We didn’t get a chance to go up to the top, but be sure to ask if you can! This was absolutely stunning to see in person.

Michelangelo’s David: If you don’t do a tour, I would absolutely recommend getting tickets to see David. He is actually quite massive and I never realized his scale until seeing him in person. To see the veins, muscles and attention to detail carved into marble was aweinspiring.

Day Trip to Cinque Terre: I plan on doing a breakout blog post on this, but we were able to visit three of the five towns! They are absolutely beautiful and definitely worth the day trip! We had a driver who took us out to the first town. Then we took a boat to the second and the driver met up with us and drove us to the third town before bringing us back to our hotel.

Vespa Tour: A true highlight of our trip, we took a vespa tour through Tuscany and it was so beautiful! Johnny drove the vespa and I hugged him from behind so I could take videos and pictures. This tour does include two winery stops, which also provide picturesque landscapes. We also bought olive oil from one of the wineries!

Via de’ Tornabuoni: All of the high-end shopping you can dream of! From Hermes, Chanel, Gucci, Versace… they are all here or near this street. I was able to pick up something for myself at the Chanel boutique, too!

TAF: A beautiful local shop with hand-embroidered linens and the most adorable baby and children’s clothes! I couldn’t help myself and bought a few baby items.


Golden View: You must eat here for dinner if you’re in Florence. It is a fine-dining experience and you get the most beautiful view of the Ponte Vecchio. The night we were there a few celebrities were dining, too!

Loggio Rooftop Bar: A beautiful spot to take in Florence, the cathedral and have drinks before dinner, aka aaperitivo! Ask for a table by the edge so you can get a good view of the city.

Osteria del Pavone: We walked by this restaurant and Johnny fell in love with bistecca Fiorentina. We attempted to get takeout only to be told that wasn’t allowed, so they let us sit at the bar, which literally filled up in minutes and we had a delicious meal. The brown butter sage ravioli was incredible.

Vivoli Gelato: the best gelato in Florence! Our tour guide recommended it as the place most locals go and I can see why. Everything was so creamy and the flavors simply divine. My favorite flavors are pistachio, rice and cafe!


The most magical place we went in Italy. A must if you’re planning a trip to Italy. For us, we would absolutely go back to Lake Como again and again. For us, it was the perfect way to end our trip and truly do nothing or as the Italians say, dolce far neite. We love how private, secluded and quiet Lake Como is compared to the more bustling beach town of Positano.

To get to Lake Como, we took two trains from Florence. We departed Firenze S. M. Novella and arrived in Milano Centrale after 2 hours and 40 minutes. This train was delayed about 15-20 minutes and unfortunately we missed our connecting train to Trenord. The way the train system is set up is it won’t let you book a connecting train unless it’s possible for you to actually make it. If your first train is delayed you can hop on the next connecting train free of charge. We departed Milano Centrale and arrived in Como San Giovanni after 40 minutes. We did business/first both times.


Il Sereno

We cashed in all of my Amex points to stay at Il Sereno for three days. It was worth every single penny and we felt like we didn’t want to leave. It was heaven on earth for us. The service is five stars, the rooms are unbelievably clean and the view is divine. We stayed in the Grand Lago Suite, but we actually wanted the Alcove Suite, which is less expensive. However, it was already booked. The reason Il Sereno stood out to us is because it is the only modern hotel on Lake Como. Everything else is steeped in tradition, old-world charm and sometimes can be a little too ornate. Plus, since I used my Amex points, we got breakfast for two, guaranteed late checkout at 4 pm and they will upgrade your room if available.

From the infinity pool overlooking the lake complete with comfortable cabanas, the best rain shower we’ve ever had to boats being able to come right up to the hotel, everything was sublime.

I will do a more in-depth post on Lake Como coming shortly since it was one of our favorite stops you need to go to if you’re planning a trip to Italy!

Read about our wedding here!

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