Part 1 covered the highlights. Part 2 covered France. Now let’s talk about Italy.
We spent thirteen days exploring Italy using trains and buses for most of the travel starting in Venice and ending in Naples.
Travel Mistake Number 4: Confusing Business Addresses with Locations
In hindsight it is comical how many times we got turned around or lost due to this problem. In the moment there were a couple of instances where it lead to full emotional panic and breakdowns, especially when it kept happening from city to city. Let me explain.
We are each carrying about fifty pounds of travel gear strapped to our back and the shoulder straps of the backpack are cutting into our shoulders. We are tired from the trip to the city. It is night time with barely anyone else outside. Everything around us is a dimly lit alley making it feel like we are going to be mugged any moment from something in the shadows. Our cell phones barely have any battery left after a full day of use and the GPS is leading us to our lodging for the night. Our GPS shows us we have arrived but we are staring at a nondescript building with no windows and no signs of life. What now? How did we end up lost!!!? Where is our lodging!!!????
A travel tip we heard repeatedly about saving money on places to stay is to try and book directly with the owner of the property instead of a 3rd party website like hotels.com. Price searching online confirmed that in many cases this was in fact true and helped us save on our lodging expenses. What I failed to understand until we arrived in Italy is that in many of these instances the owners record different addresses on the invoices/receipts/booking confirmation emails that they sent to us compared with the address of the property we were going to be staying at. The result is that for almost every place of lodging we booked, we had the wrong address for the GPS coordinates of where we needed to be. My super-power for this vacation was the abysmal ability to map out our destinations.
GPS is a great tool but it is only going to send you to the place you tell it, not the place you intended. Triple check your lodging address before you strap fifty pounds to your back and start walking.
Travel Mistake Number 5: Venice Gondolas
Our trip began with an overnight stay in Venice. Despite the nightmare of not being able to find our lodging that first night, we eventually figured it out and got some rest. Venice really should have been a day trip for us. We toured St Mark’s Basilica and explored the city and had some great food, but we were underwhelmed with the Gondola ride. The Gondola ride was the only time in all of Italy I felt let we had fallen into a tourist trap. The ride was overpriced and short.
We enjoyed our guided tour of Venice St Mark’s Basilica & Doge’s Palace and after a day of walking around, over eating, and walking some more, we checked out of our room and boarded the train to Florence.
Travel Mistake Number 6: Not spending more time in Florence
We booked three days and two nights in Florence. The first day ended up being our favorite part of the entire trip: A Four to Seven Hour Electric-Bike Self-Guided Tour around Florence including a winery. The weather was perfect and we met some great couples to share a day with.
The second day was using Florence as a launching point for a twelve-hour Bus tour of San Gimignano, Siena and Pisa.
Travel Mistake Number 7: Train drama
Just take the train… is a mantra of European travel. What we thought would be a simple, easy way to travel did in fact prove to be simple and easy once you got onto the train with one huge caveat: you have to figure out which train company you are riding.
Europe has trains like America has brands of vehicles. Within a train station this is all easy to sort out and figure out, but attempts to decipher this from the US via online resources was a nightmare, especially buying tickets in advance. Many of these companies require SMS Text 2-factor authentication to complete ticket purchases but the automation systems don’t do international texting making it impossible to verify the accounts required to purchase tickets. We gave up on advanced ticket purchases from the US. When we arrived in Italy we activated our Holafly e-sim phone numbers thinking we would have a better experience but that failed to solve the problem. Instead we focused on finding which train station to show up at and in person took the “Cherish is cute; go charm a local into helping us figure this out” approach. That worked for us and I’m happy to say we never got lost once we got onto a train.
Trains were also a challenge for our travel backpacks, which are too big to fit in the overhead storage compartments of most of the trains we boarded. This meant our backpacks sat in our laps for many of these train trips which is not ideal. We ran into this same problem on the Flexbus and ended up needing to store our backpacks under the bus a couple of times.
Travel Mistake Number 8: Too much time in Rome
We spent four days in Rome. I think we would have been happier had we only stayed two days, but this was due in part to some travel drama.
We arrived by train and promptly walked to the wrong building thanks to that property address problem I mentioned previously. If there’s one pet peeve that drives Cherish insane it’s back-tracking of any kind. Getting off a crowded train to traverse hoards of visitors on their way to the Vatican only to discover you’ve walked to the wrong building is bad enough, but finding out the location is on the opposite side of town back past the hoards of tourists and the train station you’ve just departed is ninth-ring of hell territory for Cherish. I did not like it either, but it’s the kind of travel stress that puts a sour mood on things. As before it got sorted and we calmed down and cooled off but then we got word that our guided tour of the Colosseum was changed. We had booked the Underground tour and our tour company ended up not getting tickets due to some type of new lottery system. We would still get to go inside, but not underground. We shook off the bad news and went in search of the Trevi fountain and some good food.
The next morning we took a three-hour guided tour of the Vatican & Sistine Chapel. I’ve had a print of Raphael’s painting “School of Athens” framed and hanging on the wall of every house I’ve owned since the college art class where I first saw that painting. Knowing that the painting is the size of a wall in real life does not sink in until you are standing in front of it, which for me was a bucket list item that we got to check off the list. Overall the tour felt rushed and we would have enjoyed having more time inside the Vatican.
We loved our guided food tour in Trastevere! We loved all of our food tours so much that have declared that these are now a permanent future vacation-must-do for us. At the end of the food tour, as we walked back to the Erreggi Luxury Rooms we commented on how much we enjoyed walking around Trastevere failing to realize that the next day we would be swapping rooms and coming back to stay at the Trastevere Glasshouse. Unfortunately the Trastevere Glasshouse apartment was a disaster. Locating the lockbox and even the front door to the apartment was difficult. WhatsApp is the only means of communicating with the owner of the property but it didn’t matter because no one ever responded. The overall run down conditions of the room made this the worst place to stay of the entire trip (well until Naples, more on that later). We didn’t think it could get worse until we heard the sounds of drunken idiots yelling and screaming at all hours of the night. We loved touring Trastevere and would recommend eating there, but trying to sleep there was horrible.
The next day was the Colosseum tour. It’s surreal to be inside this place and I still have a hard time wrapping my head around the idea that they used to flood it and have sea battles. I’ve never wished harder for a functional time-machine to see this thing in its prime.
The next day was our last day in Rome and we reserved it for the all important task of doing laundry. This was actually our second laundry day of the trip. That morning I rushed over to the only laundry mat nearby as soon as it opened. It had 4 washing machines and I was able to snag the last one available. We had our hearts set on Taverna Trilussa for dinner that night but Google failed to mention the restaurant is closed on Sundays. Always have a backup restaurant plan.
Travel Mistake Number 9: Not enough time in Positano
It took us just under seven hours to travel from Rome to Positano. An Uber to a Bus to a train to a Van to the Hotel Alcione. We stepped onto the balcony of our hotel and were stunned at the beauty. This was the perfect location to celebrate Cherish’s birthday.
While in Positano we saw our first volcanic sand beach. Bryan discovered his new favorite cocktail: A Bramble. We bought some art work for our house and some glassware for our bar. We window shopped and we enjoyed the best hotel of the vacation.
We hiked the Path of the Gods starting in Bomerno and after a wrong turn at some point on the way back discovered the joy of climbing a few thousand stairs.
By this point we were entering the final days of our trip. We loved this place so much we said to hell with the travel budget and tried to secure the hotel room for a few more nights and blow off Naples, but it wasn’t meant to be. Begrudgingly we said our goodbyes and began our final stop in Italy: Naples.
Travel Mistake Number 10: Thinking Naples was a good place to visit after Positano and that it was worth spending 3 days in
First and last impressions can make or break a vacation and I messed this one up. Much like Cherish’s first impression of France was marred by a long car ride to a no frills hotel room in an old castle, and had to be reshaped by our time in Paris, our final impressions of Italy were marred by leaving the beauty of Positano for the dump that is Naples. The proper order would have been to skip Naples entirely and end the vacation in Positano, but that’s not what happened.
From the moment we exited the Naples Train Station Cherish had this look on her face like we had just entered a third world country. The Taxi ride to the Hotel Villa Elisio Hotel Spa did not improve Cherish’s facial expressions. This city is filthy and I think Cherish was quietly praying the taxi driver wasn’t taking us to alley to be murdered.
We arrived at the Hotel to find the Spa was closed for renovations as was the hotel bar, which was less bar and more counter space with drinks stored on top. The city shuts down between lunch and dinner so getting a good lunch was not an option but I convinced Cherish to go for a walk to hunt down some type of snack and she agreed, but only because it was daylight. We found a small shop that was open. I think it might have been considered a grocery store by some, but to us it felt more like a 7-Eleven in an abandoned town that had already been picked over by scavengers. They had sodas and a couple of factor assembled ham sandwiches. I was so hungry I bought one. Back at the hotel we Google’d for a simple place to eat dinner and settled on a pizzeria. We got lured in by a 4.2 star rating. The pizza was terrible, but edible. We laid in the hotel bed watching TV and slept.
We woke up to find our legs were on strike from the hike through the Path of the Gods. I’m talking barely able to stand kind of shooting pains for both of us. We had no formal agenda for the day but the thought of walking around outside freaked Cherish out. At this point our flight to London was another 24 hours away but we hated this city so much we called British Airways to find out about changing our flights to leave. It would have been $1,000 in rebooking fees, something we just could not stomach paying. So we pulled out the travel massage gun and no joke, we spent the next 5 hours laying in bed trading the massage gun back and forth trying to convince or legs to start working again while we watched American re-runs in Italian.
By that afternoon our stomachs over-ruled our leg cramps and we forced ourselves to venture farther away from our hotel in search of a good meal. We struck gold at Il Salone Del Centro “Gino Natale” and had a fantastic lunch. The wine and amazing food re-energized us and we walked for a bit around the city mostly around the Castel Nuovo. We stopped at San Giuseppe for a drink on the way back to the hotel then grabbed a few snacks and headed back to the room for more massage therapy.
Travel Mistake Number 11: Not booking an overnight in London
Nineteen days is a long time to be away from home. Our final three days in Italy only made us more homesick, but coming back to my earlier point about us booking non-fundable airline tickets before we had settled on our final destinations really locked us into a couple of bookends to the trip that we did not want to pay to change. We should have skipped Naples and spent the 3 days in London.
Our flight out of Naples was a 9:15 AM flight to London. This would give us five hours before flying back to Georgia. The plan was to land at Heathrow, mad dash to a taxi, and drive over to see Big Ben and Parliament then turn around and head back. Since returning I’ve debated this plan with several locals who live in the London area and they are convinced that if we had attempted this we most likely would have missed our flight home. But Napels had other plans for us, delaying our flight to London by three hours. This had the domino effect of not only squashing our trip to see Big Ben but it also left us in a mad dash to scarf down some food and make it to our gate for our flight home. We didn’t even have time for tacky UK souvenir shopping for the family from the Heathrow gift shops.
Our flight back to Georgia was uneventful (as it should be). My parents had been dog-sitting for us and had brought Milo back home so he could greet us upon our arrival. A dog’s unconditional love was exactly what we needed after the long commute back home.
We absolutely loved our trip and despite the mistakes we’ve shared here, had an amazing experience.
Complete Itinerary for Italy
| Day 0: Saturday, May 11 | 7:15 PM – Arrive at Venice Airport Take Water Taxi from Airport to Venice. Ride the Orange Line to the 3rd stop then walk 10 minutes Check-In Al Portico Guest House in Cannaregio
 Address for GPS is Hotel Cannaregio 2357 Cannaregio, Corte del Volta Santo 2357, 30121 Venezia VE Italy. Find light dinner / bar to relax |
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| Day 1: Sunday, May 12 Venice, Italy | Agenda: Welcome to Venice! Explore the city and find a Gondola to ride in Find a Gondola to ride – Overrated and Expensive, not worth the effort. Breakfast: Lunch: Trattoria Bar Pontini – 5 minute walk from the hotel. Ask hotel about reservations. Dinner: |
| Day 2: Monday, May 13 Venice, Italy | Agenda: Tour St Mark’s Basilica then travel to Florence Breakfast: 8:00 AM – Walk 30 minutes from Hotel to Meeting place for the tour. 9:15 AM – 3-hour guided tour for Legendary Venice St Mark’s Basilica with Terrace Access & Doge’s Palace Museo Correr, P.za San Marco, 52, 30124 Venezia VE, Italy Meet at Correr Museum (Museo Correr) in Piazza San Marco under the portico just outside the entrance of the museum. Your guide will be holding a Walks sign. Tour ends in St. Mark’s Square (Piazza San Marco). Walk back to hotel to get luggage Walk 12 minutes to Venezia S Lucia Station Buy Trenitalia Train ticket to Venice Mestre (Stazione FS) Board Trenitalia Train 3638 and get off at the first stop Exit the Train Station and meet at the FlixBus stop (use the app to find the location) Take FlixBus from Venice to Florence (3.5 hours) FlexBus drop off is at a small building with a Tram. Buy a Tram ticket from the ticket machine, get on the Tram and ride it 14 stops to the city center. Exit the Tram and walk 15 minutes to the Hotel della Signoria located at Via delle Terme 1, 50123 Florence, Italy |
| Day 3: Tuesday, May 14 Florence, Italy | Agenda: Welcome to Florance! Take an E-Bike Tour of Florence to visit the AGRITURISMO POGGIOPIANO- B&B con PISCINA PANORAMICA vineyard in the town of Fiesole 10:00 AM – 4-7 hour SELF-GUIDED E-Bike Tour via viator.com Meet at Bike Shop Via S. Gallo, 97R, 50129 Firenze FI, Italy |
| Day 4: Wednesday, May 15 Florence, Italy | Agenda: 12-hour Day Tour of Italy to visit the cities of San Gimignano, Siena, and Pisa with lunch at a winery 6:30 AM – 25-minute walk to Train Station Piazzale Montelungo, Firenze FI, Italy for the Trip Advisor Pisa, Siena and San Gimignano 12-hour Day Trip with Lunch & Wine Pairing Dinner: Pack up for next day early morning checkout |
| Day 5: Thursday, May 16 Florence, Italy | Agenda – Travel Day to Rome with a visit to Trevi Fountain at night 8:00 AM Check-out of Hotel 15-minute walk to Firenze Santa Maria Novella Train Station 9:04 AM Train to Rome Termini (3.5 hour Train Ride) 1:15 PM Arrive in Rome Buy Metro Ticket and take Metro A Red Line toward Battistini, exit at Ottaviano then do 6 minute walk to Via Germanico 107 Lunch: Dinner: 3:00 PM Hotel Checkin at Erreggi Luxury Rooms. You need WhatsApp to communicate with this location in order for them to meet you at the door to let you into the locked gate, walk to the 2nd story of the building, then unlock the door to enter the rooms. We stayed in Room #4 which faces a restaurant that is very loud until midnight. We recommend asking for Room #5 or #6 facing the opposite side of the building to avoid this. Note WiFi is terrible here: 2MB download speeds. Fridge Snacks and Breakfast are awesome. Go see Trevi Fountain |
| Day 6: Friday, May 17 Rome, Italy | Agenda: Welcome to ROME! Vatican & Sistine Chapel & St Peter’s Basilica Tour followed by a dinner food tour. See Tickets for meeting details Breakfast: Included at Hotel 10-minute walk from Hotel to Meeting Spot for Tour 8:15 AM – The Tour Guy’s Private Vatican Tour with Sistine Chapel and St Peter’s Basilica 3 hour tour, felt rushed, wish we had more time to spend inside the Vatican. Lunch at Emma Dinner: 4:15 PM – Food Tour – Twilight Trastevere Rome Food Tour |
| Day 7: Saturday, May 18 Rome, Italy | Agenda: Tour of the Colosseum followed by a hotel swap. Breakfast: Included at Hotel Checkout of hotel Walk to new hotel: Trastevere Glasshouse which turned out to be 5 minutes from where the food tour was the night before. It wasn’t a hotel, it’s a small apartment that included 2 towels and a bar of soap. Can’t check in until after 3:00 so we had to walk a block and store our luggage in a travel luggage storage bin. Never ever stay here. Terrible communication from the host, terrible check in process, area is filled with drunks each night yelling at all hours. 1:15 PM The Tour Guy Colosseum Underground Tour with Roman Forum and Palatine Hill. It’s a 3 hour tour was changed to not include the underground. Walk back from Colosseum to Gelato place from previous night. |
| Day 8: Sunday, May 19 Rome, Italy | Agenda: Go shopping along the Via Del Corso Laundry place a block away opened at 9:30 – get there early to snag 1 of 4 machines to do laundry. Hang out for an hour. Original plan was to to Piazza Venezia and Via Del Corso but it turns out we had already done this, so we did it again. Eat Lunch at Ristorante Abruzzi Coffee shop: Tazza D’Oro (best espresso in Rome?) Dinner option: Taverna Trilussa is closed on Sundays. Ate elsewhere. Pack for hotel checkout next morning |
| Day 9: Monday, May 20 Positano, Italy | Agenda: Travel to Positano and visit the beach 8:00 AM – Uber to Bus Terminal 9:25 AM – Board Train at Rome Termini to Napoli Centrale Termini (1.5 hours) 11:00 AM – Eat Lunch 12:50 PM – Shared Van (DayTrip.com) from Naples to Positano (arrives at 2:38 PM) 10 minute walk to Hotel Alcione Residence 10 minute walk to the beach: Positano Spiaggia, Italy Dinner: |
| Day 10: Tuesday, May 21 Positano, Italy | Agenda: Happy Birthday Cherish! Celebrate by hiking the Path of the Gods 7:15 AM – Private Transfer to Bomerano – Path of the Gods via GetYourGuide.com (make sure you install the app on your phone) 
Booking reference GyGBLKWZGNBX Pin a=xxD&5X Note Path of the Gods is poorly marked and many of the markers are confusing, install the AllTrails App on phone and use the AllTrails trail map to follow the path properly. There are 2 food / drink stops on the path – bring Euros if you plan to partake of them. Original plan was to go to beach but weather was not great and beach wasn’t a beach in the traditional sense so we went down and hung out at the beach bar. |
| Day 11: Wednesday, May 22 Positano, Italy | Agenda: Travel Day back to Naples to check in at Hotel Villa Elisio Hotel Spa 9:00 AM – Walk 7 minutes for Breakfast at Casa e Bottega, Viale Pasitea, 100, 84017 Positano SA, Italy 10:00 AM – Check out of Hotel Alcione Residence 12:45 PM – Meet driver at Mandara Parking for shared Van ride (DayTrip.com) to Naples Train Station. Driver ran late so pickup ended up being 1:15 PM. Take Taxi from Naples Train Station to Hotel. Check in to Hotel Villa Elisio Hotel Spa. Address: Via Luca Samuele Cagnazzi, 29, 80136 Napoli NA, Italy – discovered Spa is closed for renovations. Town has Lunch hours and we missed them so everything was closed. Everything! Dinner hours don’t start until 7:00 PM. Dinner at Pizzeria Oliva da Carla e Salvatore. Google rating is 4.2 stars but it was horrible, it was also cash only. |
| Day 12: Thursday, May 23 Naples, Italy | Agenda: So happy this day had NO Plans. Legs killing us from hike, city is terrible, we literally laid in bed for most of the day watching Italian TV wishing it wasn’t going to cost $1,000 to change our flights and fly home sooner. Breakfast: Lunch: Dinner: |
| Day 13: Friday, May 24 Naples, Italy | Agenda: Travel Day: Fly to England, quick tour of central London then back to ATL 9:15 AM – Fly British Airways Flight 427 from Naples to London Heathrow (2 hour flight) Flight delayed by 3 hours. 5-hour layover in Heathrow turned into 1.5 hours. 4:15 PM – Fly British Airways Flight 227 from London Heathrow to Home (9 hours-15 minutes) |