Trip Itinerary & Cost Breakdown for 9 Days in Italy for Two
We just got back from a whirlwind trip to Italy with some of our closest friends — from left to right: Jerome, Ashley, Me, Bryan, Jordan. It was a jam-packed 9 days where we used every mode of transportation and spent no more than 2 nights in any one location. I say this upfront, because if you were looking for a super relaxing itinerary, this isn’t it.
Backstory: In July 2018, Bryan and I went on Kara and Nate’s Italy Vespa Tour. I think registration for the trip opened in October-ish 2017, and we ended up snagging a last minute spot in March 2018 when a couple unexpectedly dropped out. Bryan was in the midst of his busiest season at work and said, “I can’t comprehend what you’re asking me right now, but if you think it’ll be fun, just do it.” So I signed us up and crossed my fingers it would be worth it. We knew absolutely NO ONE going on this tour, but I felt in my gut that we’d regret it if we didn’t go.
There was a Facebook group created for each of the tour weeks, and by the time we were added to the Week 1 group the activity had died down (we were late adds, remember.) We spent time reading everyone’s posts from the last few months and decided to do a little stalking, as any good Millennial would do, before we spent a week with these strangers. Long story short, our stalking revealed that a couple going on the tour LIVED IN OUR SAME APARTMENT COMPLEX IN DALLAS. It absolutely blew our minds! We planned to play it really cool on the first day and let the facts unfold for them organically, but we were about as subtle as a sledgehammer. Bryan wore a Dallas t-shirt, and the first thing I said to them was “Do you live in XYZ apartment complex in Dallas? We do too.”
That couple? The lovely Ashley and Jordan of Keep Going Places. At the time they didn’t travel full time but were actively saving to do so!
We also met another one of our now dearest friends, Jerome, on that tour. If you’ve been following along for a little while, you’ll know we’ve made a concerted effort to keep up with this incredible human. He came to visit us in Dallas in 2019, we traveled with him to Kara and Nate’s 100 Country party in Nashville in January 2020, we visited him in Seattle in August 2021, and he visited us in Dallas a few months before we took this trip to Italy in 2022.
Now that you’re up to speed on how fate brought this crew of 5 together - let’s talk about our itinerary!
Itinerary Overview
Please note this trip was made possible and amazing by Ashley’s insane planning skills. She deserves all the credit for the trip we had. The only things that Bryan and I booked independently were our flights, our hotel in Rome on night one, and the AirBnB for the group on our last night in Rome.
Dallas (DAL) —> New York (LGA)
New York (EWR) —> Rome
Rome: One night
Positano: Two nights
Capri: One night
Ripatransone: Two nights
Rome: One night
Rome —> New York (EWR) —> New York (LGA) —> Dallas (DAL)
Days 1 & 2 - Travel Day + Night in Rome
Dallas to New York
We flew Southwest from Dallas to New York using points and planned an intentional, long layover in NYC to visit our friends and make the eventual airport transfer less stressful. (We flew United out of Newark for the long leg of our trip — more on that in a minute.)
Once we landed, we ubered to our friends’ apartment and walked to a cute brunchy/lunch spot on the Upper West Side called Community Food & Juice. After a lovely visit, we embarked on our public transit journey from NY to NJ to arrive at Newark. To uber from our friends’ apartment to Newark would have cost us about $100 - yikes - so, since we had the time, we opted for public transportation. We took the subway to Penn Station and bought train tickets for the NJ Railway that took us straight to Newark. We saved about $65!
TOTAL COST of our NYC pitstop: $156.57
Flights for two: $11.20 x2 = $22.40 for the taxes on our round trip flights from Dallas to New York
Lyft: $54.99 from the airport to our friends’ apartment
Lunch for two: $42.68
Subway: $2.75 x 2 = $5.50 to ride the subway to Penn Station
Train tickets for two: $31 from Penn Station to Newark
Once we made it to Newark, we were bummed to find out that the only Priority Pass lounge (a perk of our Chase Sapphire Reserve) was located in a different terminal. At Newark, you have to exit and go through security again if you change terminals, so we wandered around, grabbed a snack and some water, and killed time before our flight.
New York to Rome
Once we made it on our flight it was relatively smooth sailing, minus the fact that we were in coach for the next 8.5 hours. We bought round trip tickets partially with points and partially out of pocket. Here was the cost breakdown:
Points Redeemed: 134,719
Dollar Value of Points Redeemed: $1,684.00
Amount Billed to Card: $1,057.34
Not too shabby for two round trip tickets during one of the busiest travel times in Europe! If we had more flexible dates, we probably could have gotten better seats for the amount of points we redeemed, but alas…any savings is a win in my book.
Once we made it to Rome and through customs, we took the Leonardo Express train from the airport to Roma Termini, about a 30 minute trip. I recommend buying these tickets online ahead of time. Even though you have to pick a specific departure time during the purchasing process, the ticket is valid all day regardless of the time selected.
If you wait to purchase your train ticket in person, you have to stand in one line to buy the ticket and a second to validate the ticket before you can go through the stalls to the train platform. The online ticket is prevalidated, which is why I prefer it over buying in person.
We stayed at the Hive Hotel for our one night in Rome, and it was about a 6 minute walk from Roma Termini - very convenient! It’s a simple, modern hotel that’s a 25 minute walk from major sites like the Trevi Fountain and Pantheon in the Campo de' Fiori area. That’s where we met up with our friends Jerome, Ashley, and Jordan and tried to beat the jet lag while enjoying fantastic cocktails and snacks on the rooftop of the 9Hotel Cesari & Terazza.
After drinks we walked to our dinner reservation at Clorofilla, a swanky restaurant with a ton of plants that served what I would call “creative Italian fare.” For example, Jerome and I both ordered a truffle carbonara ravioli, and they served an amuse bouche that looked like a raspberry in cream, but it was actually a caprese salad. They piped pureed tomato in the shape of a raspberry on top of whipped mozzarella with a basil garnish to look like a raspberry sitting on cream with mint. It was insane!
After dinner we ubered back to our hotel and slept like champs after a restless night on the plane.
TOTAL COST in Rome: $307.61
Hotel: $152.33
$140.09 room cost
$12.24 (6.00 Euros per person per night for 4 star hotels for the Rome Hotel City Tax)
Drinks for two (4 total cocktails): $66.03
Dinner for two: $71.30
Uber: $17.95
A few notes on cost and culture before we go on:
Requesting individual checks for each party in a group is kind of an American thing. In Italy they default to bringing one check to the table, so most of our restaurant and drink costs were split 5 ways on the trip. Since we all ordered similarly, this wasn’t an issue, but I wanted you to be aware. Also, tips aren’t expected like they are here, but a 5-10% tip is plenty if you’d like to leave one.
It’s customary to eat later (and longer) in Italy for both lunch and dinner. Where Americans eat lunch at 12:00 pm and dinner around 6:00 - 7:00 pm, Italians prefer a 1:30 to 2:00 pm seating for lunch and 8:30 - 9:00 pm seatings for dinner. Each meal lasts 2+ hours, and you should politely ask for your check if you’re ready to move on.
The exchange rate between the US dollar and Euro was practically 1:1 our entire trip — a rarity! That being said, I’m quoting everything in USD, since the exchange rate added only a few cents to each transaction. There were a few instances where cab drivers or coffee stands requested cash, but 90% of businesses accepted card.
Day 3 - Rome > Naples > Positano
Rome to Naples
The next morning we packed up our things and walked to the train station for an hour-ish long trip from Rome to Naples via train in First Class. It sounds super fancy, but it just translates to pre-selecting your seats and includes a beverage service (coffee, water, sodas, etc.), a snack, and a nice little table.
Once we arrived in Naples, we made our way to the metro station where things were nuts. Some of the ticket machines were down, so we waited about 30 minutes to buy tickets for the group and rode 3 stops to take us as close to the ferry port as possible. We had a reservation at La Larazza, a family run pizzeria that did not disappoint. (I ranked it in my top 3 meals of the entire trip, if that tells you anything!) Naples is the birthplace of pizza, so prioritize it! I went with a classic Margherita, and Bryan got Pizza Fritta - aka, a fried calzone.
Hot tip: Make all of your dining reservations well in advance of your trip if you plan to visit Italy in the summer. It’s not impossible to be seated without them, but for a group of 5 it was definitely worth it for peace of mind.
Naples to Positano
After lunch we walked directly across the street to the ferry port where we boarded a boat to Positano, about a 2 hour trip.
Ferry Travel Tips
Arrival: Ferry travel is a breeze, but plan to arrive about 30 minutes ahead of your scheduled departure time to get first dibs on seats for the longer rides.
Tickets & Bag Fees: If you’ll have luggage and a backpack (like we did), you’ll purchase a ferry ticket for yourself and pay a fee for any rolling luggage — typically around $3 for each piece. We purchased our tickets ahead of time, but bag fees are paid the day of (more reason to arrive early.) The ticket person was feeling extra generous and didn’t charge us for our rolling bags since they were all on the smaller side, but this wasn’t normal.
TOTAL COST in Naples: $191.39
Train Tickets for 2: $87.28
Metro Tickets for 2: $10
Lunch for 2: $35.65
Ferry Tickets for 2: $58.46
Positano
Once we arrived in Positano the crowds were insane but quickly dispersed as we made our way up the many stairs to our AirBnB. They have porter services if you’re staying at the tippy top of town or in a fancy hotel, but since we were staying just a couple of flights away from city center in an AirBnB, we opted to carry our bags. (…well, Bryan, Jerome, and Jordan did. Thanks pals!)
Our AirBnB was stunning and SO conveniently located to everything we wanted to do and see. It was the priciest place we stayed on our entire trip, but it was worth every penny. There were two bedrooms and a couch bed that worked well for our group of 5.
You can tell how low our AirBnB was located from the perspective of this picture, but we were still pretty winded once we reached the door of our apartment every day. Be aware that it’s not a forgiving city when it comes to physical capabilities.
We downed espresso, rested, and then got ready for the evening. We attempted to talk our way into the bar at Hotel Poseidon, an iconic hotel in Positano (and also the setting of One Italian Summer that I thoroughly enjoyed!)
Since we didn’t have a reservation, we were unable to be seated; however, the nice man at the front desk recommended Faro bar, a 3 minute walk up the hill from the hotel. It’s attached to Il Capitano and had gorgeous views. We were immediately seated in a cozy area with chairs and couches where we enjoyed cocktails and the view for almost 2 hours.
After aperitivo we made our way up more stairs to a restaurant called Da Gabrisa. Our table was outside with a cliffside view of the town and water, and we enjoyed stuffed zucchini flowers, delicious pasta, decadent tiramisu, and stellar conversation. Bryan and Jerome both ordered the seafood pasta, a must while you’re in the area!
Day 4 - Positano
On Day 4 we woke up to beautiful sunshine that was perfect for our planned beach day. We rented 5 chairs at the Arienzo Beach Club, accessible by boat from the ferry port where we came in the day before. This was a major highlight of our trip!
We rented chairs on the third row (the price point and options increase as you move closer to front row), and we were each provided:
A chair with mattress
A towel
2 drinks from the premium menu
A large bottle of water for each person
Individual appetizers and entrees at lunch
Dessert
Espresso or limoncello
The crowds were controlled because we pre-purchased tickets for limited spots on a secluded beach, the water was crystal clear, and you got to admire the town of Positano while you swam…what more could you ask for?
I mentioned earlier that we didn’t feel like things were insanely crowded during our stay even though we were visiting during the peak season, and that’s all thanks to the planning and research Ashley did ahead of time. Had we reserved chairs on the main beach, we definitely would have felt the crowds and congestion so much more than we did by opting for the secluded beach club.
Your chairs are rented for the entire day, so you have the freedom to come and go as you please. We arrived at the club’s opening time, 10:00 am, and stayed until around 3:30ish pm.
After the beach
We took showers and got cleaned up for our final evening in Positano. Similar to the night before, we didn’t make any reservations for drinks, so we did some virtual exploring on Google Maps and set out to find Al Palazzo. What. a. gem. We made the decision on a whim, and it was probably the most charming place we visited on our entire vacation. It was so…elegant? I’m trying to find the words…
I mean, look at the sign itself!
(As I was looking up the website for this place, I learned this was a Michelin star restaurant, and now I’m cracking up that we were so surprised at how beautiful it was and how delicious the cocktails were.)
Once we pulled ourselves away from the most gorgeous bar of all time, we made our way to dinner at Da Vincenzo. I’ll be honest, I was hesitant to make this reservation because they place a $200 hold on your card a few days beforehand to guarantee your reservation. It seemed kind of ridiculous, but I’m so glad we did it because the atmosphere and food were both insanely good. We had more stuffed zucchini flowers, delicious sourdough bread, and I ordered the zucchini pasta — another must-try dish when on the coast in the summer.
While we were in Positano, Italy was celebrating Ferragosto on August 15th. It’s known as the feast of the Assumption, the day when Catholics believe the Virgin Mary ascended to heaven, body and soul, at the end of her earthly life. There was a band playing in front of the church in the early evening, bells ringing from the tower, and a beautiful fireworks show at midnight over the the water. This celebration also explains why things were a little busier than usual!
TOTAL COST in Positano for 2: $968.30
Drinks for 2 on night one: $52.97
Dinner for 2 on night one: $114.49
Breakfast and coffee for 2 on day two: $6
Arienzo Beach Club experience for 2: $236.31
Drinks for 2 on night two: $35.04
Dinner for 2 on night two: $95.75
AirBnB Cost for 2 nights: $427.82
Day 5 - Positano > Capri
We caught the ferry from Positano to Capri for a ~24 hour experience on the luxurious little island. We hopped off the boat and into a taxi that had to have been from the 60s. The seats of the old convertible (with a cute little striped, canvas top) reminded me of the cadillac seats in my parents’ really old car from the 90s. We were thrilled not to be driving on the skinny cliffside roads, too, which made the whole experience even better.
We were dropped off in the piazza area of Capri and schlepped with our suitcases through town until we arrived at our hotel that operated much more like an AirBnB. We were a bit early for our check in time and were asked to leave our bags in the lobby area until they were finished cleaning.
We did a little backwards lunch and grabbed gelato on the way to our lunch spot in Ana Capri that was tucked away in a lemon grove, and Restaurant La Zagara was a hit! If you visit, order a caprese salad and anything with lemon as the star of the dish.
You’re seated under a TON of lemon trees - it’s gorgeous!
After lunch we quickly changed and made our way back to the main port area to meet our guide for a 3 hour boat tour. We booked it through AirBnB Experiences, and it had glowing reviews both online and from Ashley and Jordan, since they’d done the tour before.
Our experience was a little lackluster, primarily because of the weather. The water was insanely choppy, so we couldn’t visit the famous blue grotto (or any grotto for that matter), and mine, Ashley, and Jordan’s motion sickness was off the charts. My eyes were closed a majority of the time, but when they were open it was beautiful. I made myself take in the iconic rock formations and then went back to my horizontal position with eyes closed to make it through the rest of the tour.
After being on land for a few hours, we were all feeling much more alive and enjoyed dinner at the stunning Panorama restaurant. While it’s traditional to eat on the later side once the sun has set, throw the rules out the window and make an early reservation here so you can take in the views. We were all exhausted by the end of the day and called it a night after we enjoyed well-earned gelato.
I’m sad to say that Jerome experienced some really disappointing acts of discrimination during our short time in Capri. There are good and bad people everywhere, as with any country, but our experience on the island was a clouded by those interactions and the way they made our friend feel.
TOTAL COST in Capri: $747.79
Cab costs for two (~4-5 rides): $42.78
Hotel: $350.67
Boat Tour for two: $124.14
Lunch for two: $110.82
Dinner for two: $119.38
Day 6 - Capri > Naples > Ripatransone
This day was arguably our most stressful, but it was totally worth it to make it back to the place we all met in 2018, Ripatransone.
We packed our things and opted to take the funicular (a really slow, downhill train) to the bottom of the island to reach the ferry port. We then took the hour-ish long ferry ride to Naples, grabbed a cab to the airport where we picked up our rental car, and then started our 4 hour journey to Ripatransone in the Marche region.
Jordan was our fearless driver! Things were pretty intense leaving the Naples airport, but once we made it to the highway things were smooth sailing. (They drive on the same side of the car and road in Italy that we do in the US, just in case you were curious.) We stopped briefly in Caserta for lunch, but we tried not to waste too much time, since it was a pretty long drive.
Ripatransone
Once we made it to the familiar little medieval hill town, we all took a collective sigh of relief. There’s something about the town that just makes you slow down, and we all needed it after the whirlwind trip we’d had so far.
We were pleasantly surprised by our AirBnB. The pictures on the listing just don’t do the place justice! The views were perfect, the location was right in the heart of the town, and the hosts were extremely accommodating and visited with us for a while during the check in process.
That evening we enjoyed a true Italian dinner (4-ish hours long) with locals, Bob and Gina, who played an integral role in planning the Vespa tour experience in 2018 that we all cherish. We enjoyed lots of fried olives, pasta, wine, and fantastic conversation at Barone Rosso before we hit our pillows around 12:30 am.
Total Costs from Day 6: $231.04
Funicular tickets for two: $4.40
Ferry and bag fees from Capri to Naples for two: $33.10
Our portion of the rental car fee: $182.45
Lunch in Caserta for two: $5.09
Dinner was so kindly paid for by our friends: $0
Day 7 - Ripatransone & Montefiore
The next morning we slept in for the first time on the trip, sipped coffee made from a moka pot on our quaint little balcony, and visited with each other for a little while before venturing into town for sightseeing and gift shopping. After bee-bopping around town, we hopped in the car to visit a neighboring hill town, Montefiore, for lunch. We ate at Osteria 5 Colli where we indulged in more fried olives and pasta. The restaurant was really cozy with an arched brick ceiling and wine cellar, but the airflow was limited - you’ve been warned!
After lunch, we quickly stopped by our place to pick up the gifts we bought for Bob and Gina and made our way to their house to help prep for the evening’s pizza party. They have a fancy outdoor pizza oven that overlooks their vineyard, and the views are just <chef’s kiss>. We enjoyed more great conversation, sipped on pecorino and rosato made from the grapes in their vineyard, caught up with another fantastic local, Enza, and her husband who also helped with the tour 4 years ago, and we were able to meet one of Jerome’s co-workers and his girlfriend who both live in Rome!
Day 8 - Ripatransone > Rome
On our last day in Ripa we spent a majority of our time with Bob and Gina. They were kind enough to host us again, and Gina made some exceptional cacio e pepe served with salad and more of the “house wine” before we made our way back to Rome, about a 2.5 hour drive.
Our final AirBnB in Rome (not linked intentionally) was in some sort of state when we arrived. It felt like the pictures on the listing were taken the day before anyone had stayed there, and they hadn’t done any maintenance since. A bathroom light didn’t work, one of the toilet seats was broken, there was no hot water, the freezer was leaking and the doors were frozen shut. It was…interesting. We contacted the host, and he said he’d come look at everything AFTER we checked out the following day. Since he was no help, we ended up contacting AirBnB and got a partial refund on our stay — better than nothing.
TOTAL COST for Day 2 in Ripa & our last night in Rome: $686.09
Our portion of the Ripa AirBnB for two nights: $401.35
Lunch in Montefiore for two: $43.78
Coffee in Ripa: $3.67
Local art souvenir: $100
Our portion of the Rome AirBnB for one night: $137.29
Day 9 - Rome > Dallas
Bryan and I were up for like 24-25 hours straight on our crazy day home. Our flight from Rome to Newark left at 11:00 am, and we landed in New York at 2:30 pm local time. It took virtually no time at all to make it through customs, so we quickly grabbed a Lyft to take us to LaGuardia in order to make our connecting flight home. The 19 mile drive took us and hour and 20 minutes in the city traffic — lol. We had a few hours to kill before our flight home, so we ate salad and drank some green juice after a full 8 days of pasta, and did our best to stay awake until we pulled in front of our house around midnight.
Total Cost of our Travel Day home: $222.58
Train tickets from Termini to FCO: $36.10
Breakfast and coffee in the Rome Airport: $16
Lyft from EWR to LGA: $91.80
Dinner and coffee in the NY Airport: $44.57
Lyft from DAL to home: $34.11
TOTAL COST of our vacation for two for 9 days in Italy: $4,568.71