We got SO MANY questions about our recent trip to Italy, so we wanted to address them all. From transportation to packing tips, to which cities we recommend most, we’re not holding back! Hopefully this helps when you go to plan your next trip.

Disclaimer: When answering these questions, we will be talking about just the cities we went to on THIS trip and not comparing them to other cities we didn’t go to this time.

Q: Which cities did you go to and in what order did you travel to all the towns you went to? How long was your trip and did you feel it was enough time?

A: We started in Rome (2 nights) and then went to Tuscany (3 nights), Cinque Terre (2 nights), Positano (3 nights), Ravello/Amalfi (2 nights), Capri (3 nights), Taormina (4 nights), and back to Rome (6 nights) – in that order. We were in Italy for a total of 26 days and although we were able to SO MUCH we also feel like there’s never enough time to see it all!

Q: Which cities would you go to that you didn’t go to on your trip?

A: There are SO many cities that we haven’t been to and would like to see! Some of the more popular cities include Portofino, Bologna, Lake Como, Sorrento, Ischia, Siena, and the Puglia region (Polignano a Mare + Alberobello). Some other lesser known cities that we’d love to go to are Ponza, Monte Argentario (Porto Ercole + Porto Santo Stefano), and Syracuse.

Although we’ve been to Florence and Venice in the past, we didn’t go during our recent trip and would LOVE to go back and explore! 

Q: Would you suggest staying at one place in the Amalfi Coast or change hotels? 

A: Although we chose to stay in both Positano and Ravello during our trip, we’d prefer to stay in just one. We loved Positano, especially our hotel (Il San Pietro), so we would choose to stay there and take day trips to Sorrento, Amalfi, and Ravello. Even though Capri (and Ischia, which we didn’t visit) is very close, we would prefer to stay there at least two nights. There are several other towns on the coast that would be great for day trips as well: Praiano, Nerano, Minori, Maiori, Cetara.

Q: Stay in Positano or Capri with a day trip to the other?

If possible, I’d definitely recommend staying at both for at least a couple nights each. If that’s not an option, then I’d say to stay in Positano and make Capri a day trip. That way, it’s less of a hassle because you don’t have to take all your luggage to an island and you’ll also have the option to hop over to Amalfi, Ravello, Sorrento, or any other town in the Amalfi Coast.

Q: Best hotels in Amalfi Coast? 

A: There are so many amazing hotels along the Amalfi Coast but one really stood out to us. Il San Pietro is easily our favorite hotel in the world. It’s such an incredibly special place and totally worth going to if you ever have the chance to do so. Every staff member we spoke to seemed to truly love working and San Pietro – it felt like a real family atmosphere. It’s so beautiful and romantic.

Other great hotels include Belmond Caruso (Ravello), Palazzo Avino (Ravello), Santa Caterina (Amalfi), Villa Tre Ville (Positano), Belmond Villa Margherita (Ravello), and La Sirenuse (Positano). Hotel Poseidon (Positano) is also nice and a bit more budget-friendly than the others on this list.

Q: Going for 2 weeks and just found out I’m pregnant! Will I be totally missing out because no wine? 

We loved all the wine during our time in Italy but you can always have great wine another time! There SO much to see, do, and EAT that it won’t affect your trip in the slightest!

Q: Favorite city? 

This question is almost impossible to answer! Every city we went to is different and offers something unique and special but if we HAD to choose just one from our trip, Positano was probably our favorite. It’s stunning, romantic, fun, and has tons of great food!

Q: Where did you fly into and where would you recommend flying into? 

A: We flew to and from Rome. I would recommend basing your decision on the cities you want to go to. It’s usually going to be cheapest to fly into the large hubs like Rome, Milan, Florence, etc. I’d recommend flying to one of these cities because your trip will likely include one of these large hubs or a city nearby. This will save you time and money.

Q: How do you travel throughout Italy? We are struggling to figure out transportation.

This can be very challenging but the first step is to finalize the cities you want to go to. Once this is decided, it’ll be much easier to choose an optimal route that will be most time and budget-effective. If we didn’t go to Cinque Terre, our transportation situation would’ve been much easier because most of our trip was in Southern Italy. It really requires a lot of research into trains, buses, flights, private transportation, boats/ferries, and rental cars. We did a mix of everything except renting a car and taking the bus. One helpful resource is rome2rio.com because it will give you an idea of what the most optimal route options are. Ultimately, only you know what’s going to be best based on your style of travel and where you’re traveling from. For us, admittedly, we occasionally opted for private transportation because it saved us a lot of time and hassle. One of the most overlooked but important things to do is figuring out how to get to your hotel/accommodation once you get to the city via flight/train/bus. If possible, ask your concierge or local host about the best way to get to where you’re staying.

Q: How did you get to Sicily? 

For us, it made the most sense to fly in and out of Catania and have our hotel set up transportation to and from the hotel.

Q: What is the best way to get to Positano from Rome? 

Great question, challenging answer. Check out our Rome Travel Guide here for more info!

Q: Do you need to book activities, train rides, and ferries in advance?

Absolutely, 100%. Make sure you figure out your transportation plans in advance for the best chance of having things go as well as possible.

Q: Was it easy to find taxis in Positano? 

Yes – we always had our hotel or restaurant set up our taxi for us. We also asked for the information of some of the drivers because we wanted to use them again. That way, they knew generally when and where they would be requested to go to and we would be rest assured that someone would be available when we needed a ride.

Q: How much luggage did you bring and was having checked bags hard to bring around? 

A: We started off with 2 large checked suitcases, 2 duffel bag carry-ons, and 2 personal items (1 backpack and 1 purse). We ended up purchasing an additional large suitcase halfway through our trip. If you have your transportation set up in advance (i.e. taxi, private transportation, rental car, etc.), it makes it significantly easier to get to your destination from the airport or train station (and they’ll help you with your bags!). For the most part, we were lucky enough to feel like it wasn’t too difficult even with all our luggage but we can see how it could get very challenging depending on where you’re going and how you’re getting there. For example, you might want to reconsider taking a bunch of luggage while also taking several forms of transportation from one city to another (taxi -> train -> switch train -> possibly switch train again -> taxi).

Q: Did you use a travel agent or did you plan everything yourselves? 

We planned everything ourselves. Andrew loves planning trips so he usually gets the ball rolling on this. Once we decided where we wanted to go, we planned out the transportation. From there we were able to make reservations for hotels, restaurants, and activities. If we weren’t able to get a reservation to a restaurant ourselves, we would have the hotel’s concierge help us and they were always so great and helpful.

Q: Do you need reservations at most restaurants and how did you make them? 

Like transportation, we HIGHLY recommend booking restaurant reservations in advance! Of course you always want to give yourself the option to stumble upon a hidden gem but at least make sure you reserve the places you absolutely need to try. We made reservations online for many restaurants and if we weren’t able to, we’d ask our concierge to help us. We also realized that even if you can make the reservation yourself, sometimes it’s better to reserve through the hotel because you might receive some perks. For example, we ended up being SUPER delayed at lunch one day and were over an hour late to our reservation. Because the concierge booked it for us, they saved the table the entire time even though the restaurant was packed! Had we made the reservation ourselves, there’s no doubt we would’ve lost the table and likely the chance to eat there (we had a boat tour scheduled for an hour later).

Q: How early do you recommend booking passes to museums? 

Similar to transportation and restaurants, we definitely recommend to book as soon as you know where and when you want to go!

Q: How long did you plan to stay and how long did you end up staying?

We planned to go for 21 days but then extended 2 more days so that we could get into a cooking class that we really wanted to try in Rome (Grano & Farina Cooking Class was amazing by the way!). We decided to extend again for an additional 3 days.

Q: What was the purpose of your trip? 

There were a couple reasons. Initially, we had started planning this trip years ago (back in 2019) as a vacation. Obviously the world shut down for a while so we were finally able to go this year. As some of you already know, I started my blog at the end of 2019. Towards the middle-end of 2020, I started seeing more traction and then it started to take off. As I was cooking more, I was really interested in the idea of learning more about cooking styles, specifically related to Italian food. Although this trip was a vacation for us, it was also a lot of work. We were constantly on the go and trying to gain as much knowledge about each city as we could – what to do, eat, drink, and see – so that we could bring the information back to share as a reference for anyone interested.

Q: Best bang for your buck on traveling to Italy on a budget?

Of the cities we went to on this trip, Cinque Terre was the best bang for the buck. It is relatively inexpensive and offers fantastic food and wine options, stunning natural beauty, and is just an overall amazing/fun experience. Rome was also great for this but you’ll have to sift through some of the pricier restaurants/hotels.

Q: Was everything very pricey? 

The quick answer to this is NO! Not everything was pricey but some things were. If you’re ballin’ on a budget, you’ll want to pick and choose where the best places to spend your money are. However, this won’t come at the cost of quality because some of the best restaurants are NOT Michelin star restaurants! Don’t be afraid to try something off the beaten path – ask the locals and they’ll usually lead you to the best spots that are very budget-friendly!

Q: Capri or Naples? 

Capri for the shopping, beaches, natural beauty and party time – Naples for the food and history, pizza heaven! 

Q: How to pack? Suitcase ideas, essentials, do you have a full list? 

I have everything listed out on my packing list here!

Q: Moving there? 

Not at this time but Andrew’s doing his best to convince me! We’ve definitely considered “moving” there for a few months to be able to explore and experience much more. 

Q: Did you purchase any wine and bring it back home? If so, how was the process? 

When we went to Mastrojanni winery in Tuscany, we purchased several bottles that were shipped back home for a fee. We also brought a couple bottles back in our extra suitcase.

Q: Should we plan a day trip to Florence? I booked a day trip to Tuscany – help! 

Florence is ALWAYS a great option! I would recommend it but not at the cost of total inconvenience. If it fits into your schedule, it’s well worth going to for even just one day.

Q: Would you go to Cinque Terre for a day trip from Florence? Worth it? 

Yes, Cinque Terre is definitely worth it! Though we’d recommend staying longer, if possible.

Q: Great spot to order Italian ceramic platters? 

We went to Pascal Ceramiche d’Arte in Ravello. Leo, the owner, was so kind and his work is incredible. They ship 

Q: Did you use laundry service? 

We tried not to use it too much because it gets VERY expensive very fast. Since we were there for almost a month, it was impossible not to. There’s always the option to find a laundromat yourself but the question comes down to if you have the time and if it’s worth the hassle. 

Q: Wondering if most places have washers? 

This depends on where you’re staying but for us, we had access to laundry at each of our hotels. The problem is it can be VERY expensive! There’s always the option to search for a laundromat or to wash your clothes in the sink/shower while letting them air dry.

Q: How was the language barrier during your trip? 

It was actually very easy in the places we went to. Many people spoke English which was SO helpful.

Q: How do you avoid the windy road on the Amalfi coast? 

Unless you take a boat into the Amalfi Coast, there’s no way to avoid the windy roads. I highly recommend having a local driver take you around (taxi, private transportation, bus, shuttle, etc.). I personally took dramamine with windy car rides. If you can’t do it the best option would be a boat. 

Q: What’s the best way to book ferries and boats? 

There are many different ferry and boat companies in each region. I would recommend that you ask your hotel concierge to help you plan your ferry/boat rides.

Q: How would you describe the different vibe of each city you visited? 

This is a great question – we recapped this in each of our city guides here.

Q: Can we please get a full itinerary of your trip? 

Each city guide includes an itinerary that we highly recommend. It’s not put together in a way that we actually did it but it’s done in a way that we feel is realistic with our favorite options. Hopefully this helps!

Q: What cooking classes did you take while you were there?

In Rome, we took Grano & Farina’s classes twice! You CAN’T miss them – they just added a few in the coming months so be sure to check them out (both in Rome and Sabina which is about an hour outside of Rome and BEAUTIFUL. It reminded us of Tuscany!) In Taormina, our favorite cooking classes were at Osteria Santa Domenica with the owner Gianluca, and at the Cooking Lab with Chef Pietro D’Agostino. In Gianluca’s class he also takes you around the city for a fun tour where you pick up produce at a great local market and taste granita – he is SO kind and it’s a lot of fun. We also took one in Tuscany at our hotel (Castello di Vicarello) with Chef Kevin Luigi Fornoni. 

Q: Can you share more details about the Rome cooking class!? Going in September and really want to do it! 

Yes – it was an absolute highlight of our trip and was the best decision we could have made. We ended up taking 2 classes, Docli Italiani and Pizza Making, and learned so much. The owner’s, Chef Pino and Sfoglina Julia, are absolutely amazing. They’re not only the most welcoming and kind people, but they also taught us so much in a short period of time. We loved that this was far from your typical showy cooking class geared towards tourist entertainment. You actually felt like you were in culinary school and they shared the most useful tips & tricks. We also have to mention that it was the best food we had in Rome… Be sure to check out all of the details on their website (linked here) because they provide a ton of information. It’s designed for adults only and they just added an Olive Grove & Gastronomy experience in Sabina that sounds incredible. 

Q: Which camera/tripod did you use to film videos while there? 

We use the Canon EOS M50 camera. We also took our Lume Cube mini tripod but didn’t really use it.

Q: What made you love Taormina? 

It’s such a special place. It’s very romantic, walkable, charming, historic, and has incredible food.The driver who picked us up from the airport to take us to our hotel gave us the best advice: “Get lost in Taormina.” That’s exactly what we did – It’s so easy to wander down quaint alleyways and stumble upon the most beautiful sights. Highly, highly recommend adding it to your travels! 

Q: Best cities for a honeymoon?

This is a tough one because everyone likes to honeymoon differently. If you want to kick back and relax, I’d recommend the Amalfi Coast or Tuscany. If you’re looking for a more adventurous trip, I’d check out Cinque Terre or Capri. If you want something more historical, Rome is your place. For a more romantic vibe, Ravello and Taormina are amazing. Of course, there are plenty of other cities in Italy that will fit the bill for any category, but these are just the best options from our trip.

Q: What was worth splurging on?

• Something that we personally felt was worth “splurging” on was our transportation. Like many people, we REALLY value our time so we were willing to pay a bit more for a more convenient and quicker option (e.g. hiring a private driver to take us from our hotel in Positano to our hotel in Ravello as opposed to taking two separate buses or a ferry + bus).
• If there’s something you’ve always wanted to do or see, do it! You never know when you’re going to go back to such a special place and you might as well enjoy the experience. You don’t want to go home and feel like you missed out on something that would’ve been really enjoyable just because it would’ve saved you a little bit of cash.
• One thing we HIGHLY recommend splurging on is the Early Access and Skip The Line Tour when it comes to major attractions like The Vatican. This will save you hours upon hours and will make for a much more enjoyable experience. 
• If you’re staying in a city that’s known for relaxing and you feel like there’s not that much to do, maybe consider the nicer option for accommodations. In a city like Rome, it’s nice to stay in a great hotel but if you’re constantly on the go and you’re barely at the hotel, it doesn’t really matter where you’re staying (as long as it’s close enough to the things you want to do). In a place like Positano, we found that it was worth splurging on a nicer hotel because even though we ventured out, a lot of our time was enjoying the resort and its amenities. 
• As some of you know, Andrew actually encouraged the Chanel handbag purchase in Rome. I truly never thought I’d see the day. Andrew and I both felt like it was a good investment to make because it was much less expensive in Europe than in the US (you can see our reasons for purchasing here). If there’s a luxury item you’ve always wanted, it might be worth purchasing while you’re abroad where you’ll pay a lot less than at home and have the option for a portion of the tax back.

Q: What was worth saving on?

• One area where you can really save is on booking certain tours. Don’t get me wrong, having a guided tour is totally valuable but if you don’t want to spend money on it, you can always download the Rick Steves Audio app for free! Once it’s downloaded, you don’t even need wifi to get the guided tour of the area you’re going to – but of course, be sure the app offers the tour before you pass on a guide!
• As you may already know we LOVE good wine BUT that doesn’t mean it has to be expensive. Some of the best wine we’ve had was the house wine at a local restaurant. When we were in Capri, we ventured off to a less frequented area to go to a restaurant that was highly recommended by locals. Instead of ordering a wine from the menu that had a name and description, we opted for the house wine that is produced onsite. It was the cheapest wine on the menu, came in a labelless bottle, and it was delicious!
• Somewhere you can really save in Italy is on THE FOOD. Some of our absolute favorite bites were the least expensive. The street food there is unmatched and although fine dining is a great experience, it’s not at all necessary if you’re on a budget. We found that the best gems were local, low-key eateries (for example, Casa Manco No.4 and Dar Poeta in Rome for Pizza). In my opinion, that’s one of the things that makes Italy so beautiful!

Q: What are the COVID protocols? 

When we went, we didn’t need any paperwork or COVID test to get into Italy. Whenever we were in a place of public transportation within Italy (i.e. bus, train, airplane, etc.) we needed to wear a mask. The only time we needed any documentation was when we were coming back to the US. We needed proof of a negative COVID test but we heard this rule changed a couple weeks after we got home.

Q: I have heard that Italians dress up more than dressing casually, is this true? And will I stand out if I go casual? 

It definitely depends on where you’re going but for the most part, that’s very true. For example, Rome and Positano were more dressy than Cinque Terre which was much more casual. But, you won’t see any locals in athleisure or jeans. For women, “casual” looks are usually light and airy dresses or skirts. For men, pants and a linen button down – shorts are usually more of an American thing. 

Q: What cities are walkable?

The most walkable towns were Ravello and Taormina. You could easily get from one side of town to the other because it’s made for pedestrians to walk! For the most part cars either aren’t allowed or aren’t able to access most of the streets of these two towns. Capri town was very similar to this but if you wanted to get to other parts of the island, you’d need to take different forms of transportation. Cinque Terre is also pretty walkable and you can utilize the train to easily get around to each village. 

Q: How long is the train ride from one end of Cinque Terre to the other?

Cinque Terre is made up of 5 little towns/villages. Monterosso al Mare and Riomaggiore are on opposite ends with Vernazza, Corniglia, and Manarola in between. The train stops at each town and to get from Monterosso to Riomaggiore (and vice versa), it’s about a total of only 15 minutes!

Q: Most romantic cities? 

Ravello and Taormina felt the most romantic to us because of the beauty and feel of the charming little towns. Positano was also very romantic but it’s also a much more popular destination with more people around – it’s a good balance between romance and liveliness. 

Q: Anywhere you visited that you felt you could have skipped?

There were a lot of questions about which city we would’ve skipped if we had to choose one. It’s impossible to say because they’re all unique and have their own great qualities. It really just depends on what you’re looking for/what you want to do. If you love the beach and history/architecture doesn’t interest you, the Amalfi Coast or Cinque Terre could be the place for you. If you love trying a ton of restaurants with all sorts of pasta while sightseeing, maybe consider going to Rome over Lake Como which is a bit more low key. 

Q: How long do you need in each city? Planning for November. 

The first time we went to Italy back in 2015, we spent 2 nights in Venice (leaving early on the 3rd day) and 2 nights in Florence. We left feeling like we did nothing but see some of the tourist attractions. We didn’t get the chance to immerse ourselves within the culture of each city and that really bothered us because it felt like we missed an opportunity to get a real authentic experience. Since then, we’ve decided to do our best to stay longer in each city we visit. Although a few nights is almost never enough to enjoy a city, I would recommend at least 3 nights wherever you go (if possible, more depending on how much you’ve been wanting to go).

Q: Best season to visit? 

Back in 2015, we traveled in the middle of the summer. Although we loved Italy no matter what (how can you not!?), it was also unenjoyable to feel like a sardine due to all the tourist crowds. Along with that, we dealt with some pretty bad heat waves. This year, we traveled in early to late May. We started and ended our trip in Rome and it was really interesting to see how just 3 weeks could make such a big difference in how crowded the city was. In early May, the weather was occasionally a bit cold at night and in late May there were some pretty warm days – for the most part, the weather was great! We’ve also heard September is one of the best times to go.

Q: Was the Vatican too crowded to enjoy? Any tips? 

Fortunately not for us. The first factor is that we went in May and not July/August when it’s likely to be the most crowded. But the main reason is because we chose to take an early access + skip the line tour. Although there were still quite a few people, we didn’t have to worry about waiting or feeling completely packed in a room. Our tour guide said that had we not chosen to opt for the early access/skip the line, the tour would’ve taken significantly longer and would’ve probably felt like a poor experience. Oh and make sure you get a tour guide for the Vatican because it’s WELL worth it!

Q: Best tours in Rome? 

We loved our tour guide, Davide! He is incredibly knowledgeable and so much fun. Our only regret is that we didn’t take a general city tour with him because he was so great! You can contact him on IG @davidebelloguide (he works with a great company).

Q: What is the dress code when visiting The Vatican/other cathedrals? 

We were told by our hotel concierge that we should wear clothing that covers the knees and upper arms/shoulders while visiting the Vatican. I’m not too familiar with the dress code for other cathedrals but my thought is that it’s safer to be a bit more conservative just in case.

Q: Which town was your fave? If you could only go to 2-3 cities, which would you prioritize? 

This is a VERY difficult question to answer because every city we went to during our trip was great in their own way. Positano was arguably our favorite and if we had to choose 2 more, it would probably be Rome and Taormina. We also loved Capri but due to its proximity to Positano, you could always do a day trip from Positano to Capri if you could only stay in 3 cities.

Q: How did you feel it seemed for traveling with kids? 

I’ll preface this by saying that I obviously don’t have kids and therefore I don’t have experience traveling with them. However, we definitely noticed a lot of parents with kids in Cinque Terre. I think it’s definitely doable almost anywhere you go but it also depends on how well you think they’ll do going through different forms of public transportation like planes, trains, buses, etc. As you’ve probably experienced countless times, you might have to sacrifice seeing “it all” so that you can stop for extra bathroom breaks/snacks. I think with kids, especially over 10 years of age, it’s such a beneficial experience.

Q: Any not so glamorous moments?

There were quite a few!

• One that I mentioned on IG stories was when we were stuck on the side of the highway for 3 hours in the heat. Something hit the gas tank at the bottom of the car which caused a major leak. We were driving from Cinque Terre all the way down to Positano and it happened when we were about 40 minutes east of Rome. By the time we got to our hotel, Il San Pietro di Positano, we were exhausted and starving!
• Another thing I mentioned in stories was when I had an allergic reaction. I always try to be as careful as possible when it comes to mosquitos because when I get bit, I get severe reactions (large welts and feeling sick). I decided to combat the possibility of being bit by using a “little” deet during our trip which I NEVER do. I opt for the all natural options but felt it was best to not take any chances with those Italian mosquitos haha. I would spay down with 40% deet and sometimes even 100% deet to be on the safe side… By the time we got to Capri, I started noticing little red bumps all over my body, especially my legs. I realized that I was having a reaction to the deet! After several days of spraying only all natural bug spray, I finally started to feel better. Gotta love travel adventures! The only thing I would add here is bring all of your “in case of emergency” items and be prepared for the unexpected. 
• Because we were constantly on the go during our trip, we’d get back to our hotel room and knock out – sometimes even as early as 7pm. Since we still had to work after getting content all day (edit videos, post stories, write captions, do voice overs, keep up with everyday essentials, etc. we’d wake up a couple hours later and stay up through the night. On many occasions, we’d be running on just a few hours of sleep.

Overall, there was nothing significant that went wrong. We are very thankful that things went relatively smoothly and safely!

Q: How safe did you feel overall and did you notice any pickpockets? 

Overall we felt very safe. We were very aware of our surroundings and fortunately we didn’t run into any incidents of pickpockets. We noticed a few people here and there that would try to distract random people especially near the Spanish Steps in Rome. Best advice is to BE AWARE and to always have your items securely stored away. I wore a crossbody bag and had my hands on it all the time. We didn’t spend time in Naples but have heard that this is a bit more common there so just be aware and alert. 

Q: What was your experience purchasing a Chanel bag in Europe and with customs back in airport in US?

It was great. We know that the cost of the handbag was definitely cheaper than if we had purchased it in the US. If you make any big purchases, just make sure you get your tax refund stamp/verification at customs before you leave Italy. You can go to the kiosk at the airport before the security check or in some places, they have a station that you can go to in the city before you even head to the airport. If this is available for you, I’d definitely recommend it because it will save you time and hassle.

Q: If you have to choose where to visit North or South? 

Right now, we would choose the South because we LOVED it. That being said, we have not explored the North nearly enough to truly answer this question. We would love to go and compare it one day. 

Be sure to check out all our Italy travel guides here!