Travel Guide: 72 Hours in Southern Italy

I first discovered the Amalfi coast about 3 years ago on Instagram. I know, so romantic. But really, it was. A few summers ago I watched several gals I follow going to these beautiful coastal Italian towns that I had never seen before – specifically, Positano. Following along on their trips – even through social media – was a vacation in itself. I had one of those “aha moments” when you immediately make it a mental goal that one day, if given the opportunity, you will go there. Although I was determined and it was top of the list, I thought it would maybe happen years down the road, or on a honeymoon, should I ever get married. But to my surprise, it came sooner.

P.S. I’m sharing my travel notes from an incredible 10 days in Europe divided by three legs of travel – Italy, Mykonos and Santorini. I’ll be breaking down specifics, and it’ll be lengthy. For today, I’m just sharing notes from Italy. 

Back in November, on a whim,  a few friends and I were talking about places we’d want to travel to in Europe. We all agreed that Greece was on our list, was “cheap” and would be beautiful come summer. Also on a whim, we decided to check flights. My friend, cleverly played around and added “Rome” as a destination from Chicago, only to find that a roundtrip ticket would be more affordable at a suprising $600. Yeah, I know. So we basically decided that night we’d be going on this trip. We waited a little over a month. ended up paying $800, and never looked back.

The minute I heard we’d be taking a few days in Italy, I immediately knew I had to get down to this damn coast. Planes, trains or automobiles, I was going to find a way. While four of the girls decided they wanted to stay in Rome, my friend Ashley and I quickly committed to spending our 72 hours in Positano regardless of the hassle, cost or time lost on travel. And given that this town was the most beautiful place I’ve ever seen in my life, it was totally worth it and I’d do it over, and over, again.

Being a novice international traveler – but for real, I’d never left the country before, nor had my friend – I was nervous as hell to travel for a solid 24 hours, in a foreign country, catching 2 planes, 2 trains and car before reaching ever reaching destination. The logistics seemed impossible and the odds of something screwing up pretty plausible. I scoured travel blogs and itenieries to figure out train lines, timing and how the “hill” in Positano works. So in writing about my travels I feel it’s most helpful – and necessary – to include specific details – in  case someone out there is just as clueless as me. (Probably impossible, but just in case.) If you want to skip the logistics and are just looking for places to stay and eat, scroll down to my list of recommendations at the bottom of this post.

DAY 1 – Travel + Positano

10 hours on Air Canada flights is all it took for me to understand why everyone’s obsessed with Canadians. After landing for a layover in Toronto and musculuating the time change, we nearly missed our flight after realizing the “last call” being blasted for a fourth time was for our flight. Forgot your food at the counter? No worries, this sweet staff let us run back and grab it. We booked our flights on Priceline, and weren’t able to pick our seats  – and yet somehow 3 of us ended up in the same row. A few tiny bottles of free wine and one viewing of I, Tonya later, we each got a couple of ours of sleep before landing in Rome.

Once at the Fiumicino airport in Rome, the group split and my friend and I bought tickets for the Leonardo Express train that departs from inside the airport and goes straight to Roma Termini train station (Rome’s main train hub). This train runs every 15 minutes and costs about €14. Within 30 minutes we arrived and had 2 hours to kill until our train to Naples. (I realized after the fact that through Italia Rail you can buy some sort of pass to knock out both of these trains. Not sure how it works, but FYI for next time.) During our wait we decided to leave the station and crossed the street only to find the cutest pizzeria and deli. This is how I imagine a small, Italian mom-and-pop deli to be. We grabbed two big slices of pizza, a mini bottle of wine and devoured them while sweating in our travel clothes. It was amazing.

We then hopped on the Trenitalia Frecciarossa train to Napoli Centrale in Naples. These tickets vary in price and get more expensive as you get closer to the date (I know because I procrastinated…). You can also buy these at the station, and take a gamble on price. After an hour-long train, we hopped into a car we hired to take us on the 90-minute, gorgeous coastal drive to Positano. We used this service for €110 each way and they were amazing. On time, stopped for photos and kept us safe on the cliffs – let’s just say we’d never want to drive these ourselves.

He took us right to our hotel – the insanely gorgeous, perfectly located luxury that is Villa Rosa Positano… where I’m almost positive we stayed in the honeymoon suite. It was perfect and I wanted to cry.  It was easily the most beautiful view I’ve ever had at any hotel in my life (I mean, why wouldn’t it be right?!). We booked this 3 months in advance. And by that time, there were about 3 hotels left. We wanted something low on the hill and this view – with breakfast included – couldn’t be beat. It was our splurge of the trip, and well worth it. You can’t beat the location. A walk down to the beach is only 10 minutes, and for the “vertical city,” that’s nothing. We quickly got dressed, had a cocktail at Franco’s, met some new friends from England and joined them for a hilarious and welcoming dinner on the beach. We found the best gelato down there, too tucked right inside Buca di Bacco.

DAY 2 – Positano

We woke up to our first (and only) full day in Positano to a handsome Italian man delivering us breakfast on the terrace. I will probably never be more content than I was eating a platter of pastries and drinking coffee in a robe, outside, looking at this view. A true “pinch me” moment that will probably never be topped. and no, I’ll never get over the photos of this breakfast spread – I mean, look at it!

After breakfast, it was time for a beach day! Ever since I saw Jessica Sturdy’s  afternoon at Bagni d’Arienzo beach club, I knew whenever I made it here, I’d go. Although there’s a public beach in Positano, I heard recommendations that a beach club is preferred and now I get it. It’s so secluded and private and overall just feels more… Italian. You honestly feel like you’re miles away from everything, living in a Gray Malin print. But most importantly, the 5 minute boat ride to the beach club allows for the most stunning view of the city from the water. I’m forever thankful for the 5 minutes and those dozens of iPhone photos I snagged that will most definitely be framed. Well worth it. (Because Gray Malin prints are pricey, LOL.)

I can’t speak highly enough of this place. I made a reservation online a few weeks in advance – with the date, time of arrival (time you’ll meet the boat), time you’d prefer to have lunch  and size of party. After grabbing the club’s boat on the pier, you arrive with chairs and umbrellas ready for you. One thing to note is these Italian beaches aren’t sandy – but rather rocky. Like full blown rocks. Just walk with your sandals on and you’re good. Reservations for each chair were €14.

Once it was time for lunch, we headed up to the restaurant (right behind our chairs) and ordered the most incredible lemon ravioli that I’m determined to try and recreate it at home. The staff was so friendly and welcoming – you can tell this is a family-owned place that takes pride in sharing their little piece of this gorgeous coast with you. Oddly enough, after we were a couple of bottles of €20 rosé in, we realized we were sitting next to travelers from Texas on our left, Indianapolis on our right and Chicago directly behind us. How crazy that you can travel halfway across the world, on a tiny private beach, you find people from your own backyard.

After the beach, we showered up and did some walking before dinner to the cutest shops and markets all throughout town. We decided to head up the hill in search of some roadside restaurants we discovered on our drive in. We stopped at Il Capitano and sat on the most beautiful – and quiet – terrace! We shopped and wandered a bit more, made it back down to the beach for gelato and finished the night with some rosé on our terrace. It was the most perfect, most luxurious, Italian day.

DAY 3 – Rome

We woke up on our last morning in Positano at about 5 a.m.. Of course, we wanted to sneak in one last breakfast before we headed back to Rome. We booked the same car service en route back and they proactively pick you up from Positano three full hours before your train in Naples departs. Apparently, traffic on these hills can get pretty backed up during the summer months. To our delight, we were greeted by the owner of the company who’s a native of Positano but spends half the year in Orlando, FL. He had great stories, and even kindly stopped and bought us pastries and an espresso to kill time since we were early for our train. (Yes, we’d already had that entire platter of food, but still gladly snarfed down breakfast #2.) We took the same train back to Rome, then hopped in a cab to our hotel.

We booked a tiny hotel in the Trastevere neighborhood where our four other friends were staying. I’m assuming this area came to us by recommendation, but we were delighted by how gorgeous and lively this area was. By the time Ashley and I arrived it was nearly noon and the neighborhood was bustling with locals drinking, eating and literally just spending time with each other out on the street. Because we didn’t see much of the city, I can’t speak of all of, but here, there was either a restaurant or gelateria every few feet – pizza and ice cream, basically, my dream!

I know we’ll get a lot of eye rolls for this – but because we were in Rome for only about half a day, we skipped hitting the main attractions and historical monuments. Had we had more time, and not chosen to hike it to the Amalfi Coast, this would’ve happened. But, the minute we landed in Trastevere, we fell in love with it’s charm and just wanted  to sneak in with the locals and enjoy the Saturday as they would. Never once did we take the suggestion of our hotel host – instead we wandered and took a gamble on a cute corner restaurant with shaded seating on a street in the heart of the neighborhood. While Im confident that you probably can’t go wrong with any of those restaurants, this one served the best bruschetta and pasta I’ve ever ever had. I can’t explain it – but the tomatoes here are a totally different fruit. They say it’s the sandy soil. Add in a bottle of wine and next thing you know we’ve been at lunch for three hours. Whoops.

We finished the evening doing more exploring and splitting a bottle of rosé at a piazza – basically a “square” to people watch and listen to live music. We loved the idea that everyone brings their own booze and gathers on the steps of this piazza to listen to live covers of American songs. After that, we took a stroll down on the riverwalk. There’s a ton of bars, restaurants and vendors who set up shop along the river. I stumbled upon the most incredible stand selling these gorgeous hair wraps/scarves for €7. I bought two – which I wore repeatedly over the following week in Greece. If ANYONE – yes, anyone – is planning a trip to this part of Rome soon, please let me know and I’ll Venmo you in exchange for a few more of these. I’ve scoured the the riverwalk’s website, and Facebook, but I’ve yet to find her contact information. But, I haven’t given up yet!

We then grabbed gelato (are you seeing a trend here?) and then headed to bed before waking at 4 a.m. to meet the girls and head to Mykonos. But before we even got there, we just kept saying, “I can’t believe we have another country. It feels like we’ve been gone forever.” I don’t think we’ll ever be able to wrap our heads around the incredible beauty that is Positano – Rome, too! I feel so fortunate that we were able to make a visit to the Amalfi Coast a reality so early in our lives – even if it was only two days. (And Rome less than 24 hours.) It was magical, and I’m pretty confident that won’t be the last time either of us visit.

Since there were three legs to this trip: Italy > Mykonos > Santorini, I thought it’d be helpful, and less overwhelming to create posts around each destination of the trip. I’ll be posting abut our two stops in Greece soon – which isn’t short of any wild stories. Ciao!

Recommendations: Positano

• Villa Rosa Positano – The best location, service and views; I would stay here again and again
• Franco’s Bar – No food, just booze and the best view (and the best olives that are free)
• Chez Black – Dinner down on the beach is a must at least once and the pizza and wine here was great; They’re open late, too
• Gelateria Buca di Bacco – The. best. gelato. Seriously, of the entire trip and it’s convinitely located on the beach
• Il Capitano – Gorgeous dinner views with a peaceful, serene terrace
• Mandara Car Services – To transfer you to and from

Recommendations: Rome

• Relais Casa della Fornarina – A tiny hotel in the heart of Trastevere and within perfect walking to distance to restaurants, bars, the river, etc..
• Piazza Trilussa – A fun piazza, or square, to hang out, drink, watch live music
• Lungo il Tevere – The Riverwalk in Trastevere with vendors, bars and restaurants