Traveling to Italy has been on my bucket list for years and it exceeded all of my expectations! Today I’m sharing a full breakdown of my trip with every detail from the itinerary, outfits I wore, and tips & tricks I learned along the way. Lots of you requested specific information so I’ve made sure to cover all your questions in this guide and the FAQs below!
What I wore:
Dinner in Positano Vespa Tour and Dinner in Rome Exploring Pienza Travel day to Positano 
Boat day in Capri Exploring in Rome 
Pool day in Positano Dinner in Positano Dinner in Positano 
Pasta Making Class 
Pool Day in Tuscany Exploring and Dinner in Positano Dinner in Tuscany Wine Tasting in Tuscany Dinner in Tuscany
Shop more of my Italy outfits here
Where I went:
Rome
Where to Stay:
The Edition Hotel – I only spent one night in Rome so my priority for hotel choice was proximity to the city center and a good night’s sleep after the red eye flight. The Edition is part of Marriott so I was able to get some perks with my membership, but it meant that the hotel itself had less character than a lot of the other hotels in Rome. We got upgraded to the Courtyard Suite and it was very spacious, clean, and well-appointed. The room rate included breakfast so we took advantage of that after the red-eye. The food was okay – nothing life changing, but good enough especially since it was free. The hotel itself is gorgeous, and has a rooftop pool and terrace overlooking the city. Overall I would recommend this hotel, just know that you will not be experiencing the most authentic, historic version of Rome here.
Where to eat:
This was one of the most disappointing things about the trip. So I suppose this is more of a where I ate than where to eat. I was expecting to have the BEST food in Rome and sadly that was just not the case.
Campo de Fiori – we ordered a few different types of pizza and had a spritz at the nearby outdoor patio. The weather was amazing and it was a great place to people watch and just see the city in action. The food itself was ok. The pizza was not bad. I liked the flavors but it served room temperature which made it hard for me to be wowed.
La Tavernaccia – this place was on the outskirts of the city center near Trastevere and was recommended on a ton of niche food blogs and even major publications so I thought this would be a winner and not a tourist trap. We had a 7pm reservation which is equivalent to a 5pm reservation in the US. It was completely empty and the only people that were dining there were Americans. We tried everything from the carbonara to the amatriciana and a few meat dishes and didn’t enjoy any of them. I’m not sure if it was an off night or if the food was just not our style.
What to Do:
Vespa Tour – this was the absolute HIGHLIGHT of our quick stint in Rome. The tour was 3 hours long and took us through the city to see a few major sights and some hidden gems of the city. About halfway we stopped at a local cafe for an aperitif. It was a private tour and both Tre and I had our own drivers. This was crucial because the driving in Rome is insane and there’s no way either of us would have felt comfortable driving a Vespa around. I actually cried while we rode around it was so idyllic. The experience of being on a Vespa, taking in all the beautiful architecture and scenery of Rome was just surreal and something I’ll never forget. Our travel agent recommended and booked it, so I don’t know the name of the specific company but I’m sure there are many to choose from if you search for private Vespa tours in Rome.
Shopping – we went to Via dei Condotti to shop the designer stores and got to see the Spanish Steps while we were there. It was very busy and crowded even at 10am so be prepared to wait in lines. If you do make any purchases make sure to ask for a Global Blue receipt for tax refunds. You can get these validated at customs in the airport on your way home and save up to 22%.
Logistics:
Our travel agent arranged all of our transfers from city to city and to and from airports/train stations. We had a driver pick us up from the Rome airport and take us to the hotel which was SO helpful since the airport was extremely chaotic after baggage claim. The signage is all in Italian and English so it’s not too difficult to make your way around and the customs process was extremely efficient.
For traveling around the city we walked a lot since most things were pretty easy to get to by foot and we wanted to see as much as we could in the short amount of time we were there. We used Uber for longer distances and it was just as easy as it is in the US.
Overall thoughts:
Rome is absolutely beautiful. I couldn’t believe how stunning the architecture was and it just felt like a movie scene! As we walked around and explored I was VERY alert monitoring for pickpockets and overall safety but it ended up not being a problem. I just had one day and one night in the city, but it felt like the perfect amount of time for us. I didn’t have a strong desire to do any museums or churches, but I imagine if I did it would have been nice to have another day and night in Rome.
Tuscany
Where to Stay:
Castiglion del Bosco – we spent a lot of time researching the best place to stay in Tuscany and this was the clear choice for our preferences. It’s located in Montalcino, a small town in the tuscan countryside. Castiglion del Bosco is truly one of the most spectacular places I’ve ever been. We received a room upgrade upon arrival (major perk of using a travel agent) to the Terrace Suite and it was absolutely stunning. We had a massive bedroom, two bathrooms, a sitting area, and a breathtaking terrace overlooking the valley. The room was spotless and incredibly well appointed – a Dyson hairdryer, garment steamer, robes, slippers, you name it, they had it.
One of the things I loved most about this property is how many on-site activities they had available. There’s truffle hunting, cooking classes, hiking, bike riding, art classes, wine tasting and more. Anything you could think of that would be enjoyable to do in the Tuscan countryside is available at this hotel. We did a pasta making class and it was amazing! It was educational and hands-on, but didn’t feel like work at all. We made pasta, tiramisu, and ravioli from scratch and then the kitchen cooked and served everything to us in the restaurant overlooking the countryside. Pure magic. We also did The Brunello vertical experience at the on-site winery and it was unbelievable. They served local prosciutto and pecorino cheese from neighboring Pienza and that cheese changed my life! I’m still trying to figure out how I can get some at home. We loved the wine here so much that we bought bottles to ship home.
I cannot recommend this property enough. The service was excellent, our room was amazing, and the amenities and activities were top of the line. My only complaint is that a lot of the activities cost extra which was a bit frustrating at first, but after experiencing them it didn’t bother me as much. CdB is a splurge, but worth every single penny.
Where to Eat:
We ate almost every meal at Castiglion del Bosco. Tuscany is massive and very spread out so finding restaurants near your hotel can be a challenge. Luckily the food at the hotel was amazing. Our room rate included breakfast so we had that most mornings. Lunch was typically spent by the pool so we ate there. For dinner we ate at the casual restaurant Osteria La Canonica most nights and at the Michelin star fine dining restaurant Campo del Drago one night. Every meal we had was wonderful and the service was incredible.
What to Do:
Podere Le Ripi – this was my favorite winery of the two we visited off property. Lunch was included with our tasting and tour which was made with ingredients from their farm and garden. The wine was out of this world! Brunello di Montalcino is my new favorite. We ordered lots of bottles to ship home we enjoyed it so much.
Explore Pienza – after Podere le Ripi we stopped in Pienza. This is a storybook town. Every street looks like a movie scene. In fact while we were there Adam Sandler and George Clooney were there filming on set! We stopped for gelato at one of the shops and took in the views of the countryside. We only had an hour or so before our next winery but it was the perfect amount of time for us. If you were to do lunch there I think a half day would be perfect to explore, shop, and eat as it’s a very small village.
Salcheto – our last winery stop was at an organic biodynamic winery in Montepulciano home to the DOCG Vino di Nobile di Montepulciano. We did a tour and tasting but would skip the tour next time since we had just done a tour at our last winery. The wine was great, and the views were incredible. If I had to choose one winery to go back to I’d choose Podere Le Ripi but I think it’s because I enjoyed the Brunello so much.
Logistics:
It took about 3.5 hours by car to get to Castiglion del Bosco. It was a long but extremely beautiful drive. For reference, it is 2 hours from Florence so taking the train from Rome (1.5 hours) and then driving would have been just as long but much more cumbersome. I loved that our travel agent simply knew the best way to get around so I never had to worry if we were taking the most practical route!
As I mentioned before Tuscany is very spread out. If you want to venture off property (I think you should at least once!) definitely choose a day or two and either rent a car or hire a driver so you can make the most of your time and money. If I were to do it again I would have booked a dinner reservation for the same day as the wineries so that we could try a taste of the city outside of the hotel at least once.
Overall thoughts:
Tuscany is an absolute must if you’re looking to relax, drink great wine, eat delicious food, and experience scenery out of a fairytale. It was a welcomed change of pace from the hustle and bustle of Rome. I can honestly say I’ve never been so awestruck by nature as I was in Tuscany. It’s a bit of a hike to get there but so incredibly worth it.
Positano
Where to Stay:
Hotel Le Sirenuse – This hotel has been on my bucket list ever since I wanted to go to Italy. It is one of the Worlds 50 Best hotels and a landmark in Positano. That said, it is extremely expensive. When I say I’ve wanted to stay here for years I also mean I’ve been saving for years. It was SO worth it! It’s located in the heart of Positano, walking distance to the main beach, all of the shopping, and tons of restaurants. We stayed in the Executive Sea View Room which had a view of the water, historic church, and iconic hillside town. The room was massive, exceptionally well kept, clean, and exactly what you envision when you think of luxury in Positano
Similar to Castiglion del Bosco, Le Sirenuse offers a wide variety of activities and excursions at the property but 90% of them are no additional charge! Everything from boat trips, to cocktail making classes, to olive oil tastings, guided hikes, and more. We did the cocktail making class which was a really fun way to start our trip. We met some great people and got to learn how to make some classic Italian cocktails. Afterward we took the Le Sirenuse sunset cruise (also included with our stay). It was absolutely breathtaking to see Positano by boat lit up at night. They served light bites and endless Prosecco while we cruised around the Amalfi coast.
Everywhere you turn in this hotel you will be blown away by the stunning details and unparalleled views. The pool itself is a work of art! The service was wonderful and they were able to accommodate every need we had. One really nice perk of staying here is that you get to skip the line at the extremely popular Franco’s bar next door.
This hotel is very well known and frequented by many, including people who are not staying at the hotel so it can be quite lively especially in the evening when people are coming in to go to the bar or restaurant. We like a bit of a scene so this was the perfect speed for us but if you prefer to be completely off the grid and secluded, Hotel Il San Pietro is a great spot.
Where to Eat:
Our travel agent booked all of these reservations for us in advance. A lot of places are by reservation only so the earlier you can reserve the better!
Next2 – Beautiful modern restaurant with great food and gorgeous outdoor seating. This was our first dinner in Positano and we really enjoyed the food and atmosphere but once we ate at other places the meal became less memorable.
Casa Mele – we were originally going to eat at La Sponda (the restaurant at Le Sirenuse) but ended up canceling after hearing one of the guests rave about Casa Mele. I’m SO glad we listened. It’s walking distance from Le Sirenuse, the food is delicious and presented beautifully. This place feels like a fine dining establishment with a more approachable vibe and menu.
Da Vincenzo – another highly recommended restaurant! It’s situated on the hill and if you take 10 steps from the entrance you get some of the most incredible views of the town. You could tell that a lot of tourists come here but everything we ordered was very good.
La Taverna del Leone – this was by far my absolute favorite meal! We had quite a few locals tell us they love this restaurant. You must order the diavola pizza with buffalo mozzarella. It was the best pizza I’ve ever had. We also did the chicken which ended up being another favorite dish of the trip.
Da Adolfo – !!WARNING!! Only go to this restaurant if you can go by complimentary boat shuttle. The day we went for lunch they shut it down due to rough seas so we had to walk down 400 steps to access it. We probably should have just cancelled but we heard so many good things and didn’t want to miss it. It would have been fine but I was in sandals and once we got to the bottom there were no more stairs, just wet rocks and I slipped and fell. It kinda ruined this day since I was a bit flustered and in a lot of pain. I can totally see why people love it so much though. It has a super familial, laidback atmosphere and the food is no frills but really good. We did the pesto pasta, mozzarella in lemon leaves, and aglio e olio and all were delicious. Usually you’d be able to rent beach chairs and enjoy a day there before or after lunch but due to sea conditions that wasn’t possible when we went. I will definitely go back but only by boat 🙂
La Conca del Sogno – technically this is in Nerano which is a 30 min boat ride or a ~1.5 hour drive from Positano. It’s a beach club and restaurant and best accessed by boat. It has a super chic and elevated vibe and the view and food is fantastic. Everything we had was delicious but I will never forget the spaghetti alla nerano – I think this was my favorite pasta I had in Italy!
Franco’s Bar – technically no food here just drinks but we loved this place! It has panoramic views of Positano and such a cool vibe. The drinks are great and the side of popcorn and olives is a really cute touch. We loved coming here before dinner to see the sunset. Be warned that there is ALWAYS a line out the door before 5pm when they open. It’s a super popular spot so make sure to either be prepared to wait or come closer to 7:30 for a much more manageable line. As I mentioned before, Franco’s is part of Le Sirenuse so hotel guests get priority.
What to Do:
Arienzo Beach Club – if you want to avoid the chaos of the main beach in Positano, you have to check out Arienzo. I will warn you this place is not cheap. Chairs range in price depending on location but even the “worst” chair is expensive. Reservations are required and a bottle of champagne, 2 starters, and 2 entrees are included with your chair/towel/umbrella reservation. It’s highly coveted because of the prime location. The water is stunning and the views of Positano are unmatched. They also offer a complimentary boat shuttle from Positano which is definitely the way to go otherwise you’ll be climbing 300 steps. We had rough seas this day too so it wasn’t as lively as it usually is but we still had an amazing time and would go back in a heartbeat.
Boat Day – I’m partial because I just love being on the water but this was my favorite thing we did in Positano! Our travel agent recommended and booked an all day private boat tour with Premium Charter Italia. I’m not sure if our agent arranged this or if it’s included with the boat but we had a greeter come to our hotel lobby to escort us to the beach to board our boat which was such a nice touch especially since there are tons of boats and it would have been difficult to figure out which one was ours. The captain was wonderful and made sure we were comfortable and taken care of the entire day. We brought a bottle of wine but the boat came with wine, light snacks, and towels. We cruised the Amalfi coast and around the isle of Capri. We were initially scheduled to have lunch at La Fontelina in Capri but we moved our boat day due to weather so we missed our reservation. I still want to go there next time we’re in Positano! We ended up stopping in Nerano for lunch instead and it was fantastic. We got to see lots of cool caves and coves and drive under The Faraglioni Rocks. It was such a surreal day. I highly recommend this boat company! Which reminds me that this is another benefit of the travel agent we used – I felt like everything they recommended was extremely well vetted and top tier.
Shopping – you have to spend a few hours just walking around the city center and exploring. There are so many beautiful little pockets of this town that can only be accessed by foot. A lot of shops are super touristy and kinda kitschy but it’s still worth walking around you never know what might catch your eye. I did really like CB (quilted small goods), Ceramica Assunta (hand painted ceramics), Theodora (clothes), and Missoni (designer clothing boutique).
Logistics:
We took a private car service from Tuscany to Rome train station. Then took a train from Rome to Naples. Then had a private car service from Naples train station to Le Sirenuse in Positano. Because we had a driver drop us off at the hotel lobby we did not need a porter. If you arrive by ferry be aware that you will have to pay a porter to take your luggage to your hotel or you will have to carry it yourself. Positano is a town built vertically into a hill so you will be climbing steps everywhere you go. Heels are completely unnecessary and impractical here. Even if you’re going to a super nice restaurant or to the night club you don’t need them.
Once you get there taxis are readily available should you have reservations that are out of walking distance. We just asked the concierge to schedule a pickup 15 mins before dinner every night.
Overall thoughts:
Positano is a beautiful coastal town with incredible food, amazing scenery, and a laidback vibe. I imagined it being much more boujee than it actually is. The beauty of this place is indescribable. Positano is more of an experience and a magical feeling than can’t be captured in photos and videos. You really have to see it to believe it. I was worried that Positano wouldn’t live up to the hype but it exceeded it.
FAQ’s
• Did you use a travel agent/how did you book experiences/ tours? Yes, I used KK Travels Worldwide and they were fantastic. They helped with everything from planning the best route for the cities we wanted to visit to coming up with a preliminary itinerary, to booking all of the hotel’s, restaurants, andfinal activities and excursions. They also offered 24/7 communication so if I had a question or was having an issue with anything while on the trip they were there to help. I highly recommend them and we will absolutely use them again!
• Did you rent a car? No, our travel agent setup car service to transfer us from place to place. Uber was available in Rome, taxis were available in Positano, and in Tuscany we had a car service since neither of those were readily available.
• Did you book everything in advance/ reservations? Yes! I did most of the research on restaurants and asked my travel agent to book them for us. The travel agent also booked all of the excursions/activities we did as well!
• Did you have any problems with the language barrier? Not at all. Everyone speaks English so it’s very easy to communicate with people. I did try to learn common phrases in Italian before the trip and knowing Spanish helped me understand better when people were speaking Italian since the languages have a lot of similarities.
• Is it doable to travel with a check suitcase? Absolutely! I packed in this trunk because it has a side handle making it easier to carry and get in and out of cars, trains, etc. I almost brought a carry on suitcase too and I’m SO glad I didn’t. It would have just slowed things down and been an inconvenience.
• How did you manage the jet lag? I requested express meal service on the way to Rome and went to sleep immediately after. I didn’t wake up until they came over the speaker and said we were beginning our descent. Once we arrived I was a little tired but it was totally manageable. I think getting the most sleep possible on the plane is crucial. Around 1pm we got super tired and laid down for a 30 min nap. We went to bed around 11pm and the next morning felt fully adjusted. On the way back I slept a lot on the plane and even took a nap once we got home. I felt exhausted. The next day I was completely fine.
• Was safety ever a concern? No but I was extremely cautious in train stations, airports, and in Rome. Everywhere else I didn’t feel the need to be as on edge about it.
• Favorite hotel? Castiglion del Bosco – it was magical! I’ve never seen a more beautiful property in my life.
• What shoes do you recommend for walking around? Sneakers! I wore my black sambas a lot during the day but also wore flat sandals and that was fine too, just make sure they’re broken in! I only wore heels twice – both times we had dinner at our hotel so I didn’t have to walk far or on rugged terrain.
• Did you feel like your trip was enough time? We did 9 days and 9 nights and it was plenty of time for our itinerary. We did 1 night in Rome, 4 in Tuscany, and 4 in Positano. If I could change anything I would have done 1 more day/night in Positano.
• Something that was pricey but totally worth the money? We splurged on our hotels and that was definitely worth it to me. I don’t like feeling uncomfortable in a hotel room and I really appreciate how much exceptional service can transform a trip.
• What city do you wish you had more time in? Positano! There’s just so much to see and do and so many restaurants to try. I feel like you could never have enough time there!
• What did you pack that you didn’t use? Steamer – every hotel had one! And a few clothing items that I added last minute “just in case”. Y’all know I’m a very efficient outfit packer since I plan my outfits in advance. Luckily I didn’t have a ton of unused things.
• How to use your phone internationally? I have Verizon and I think it was $5/day to use international data and messaging. For communication with people in Italy like drivers and concierge I used WhatsApp which is super easy to use and free!
• What were the crowds like? Rome was pretty crowded but that was to be expected. It wasn’t any worse than NYC. Tuscany was a tranquil oasis so really not crowded at all. I think the hotel was at occupancy but we never felt like it was full because everything was so spread out. Positano was also crowded. The streets are super narrow so it felt even more crowded than it probably was. I definitely think we picked the perfect time because everyone we talked to said it gets absolutely insane in June/July.
• What was your favorite location and why? It’s a total toss up between Tuscany and Positano. Both were so beautiful but too different to even compare.
• Something you didn’t have time for but would have loved to do? Capri! We cruised around but didn’t stop in the town and I would have loved to shop there. I also wish we would have seen the Blue Grotto. Our captain said it is not worth it and the line was super long but if we had more time I would’ve waited just to have the experience.
