One of my lifelong goals has been to take my mom to Italy, just as a way to give back for everything she’s done for me over the years! Despite being 100% Italian, she has never been to Italy before (let alone Europe!), and has been dying to visit the places her family emigrated from in Sicily and explore other parts of the countryside. After I graduated college in 2016, we decided to plan the trip for her next milestone birthday in 2020. There were a few must-see destinations on our list that we had to incorporate: Sicily, Puglia, and the Amalfi Coast. As each year passed, we’d talk about this amazing trip and how it was quickly approaching. 

I began the planning process in November 2019, and within a few months had a full route mapped out for the two-week-long June trip. Then one morning we woke up to the news of coronavirus cases confirmed in Italy. I thought it was a nightmare. But sure enough, COVID-19 has steadily spread from country to country and halted virtually all travel across the globe. Although we won’t be able to visit Italy this summer, I am grateful and blessed that my family is healthy and safe.

The onset of this pandemic has put many travelers’ plans on pause, but it can’t and won’t stop us from dreaming of that next trip. That’s why I wanted to share my two-week southern Italy itinerary, to provide hope and inspiration for others that “this too shall pass.” The photos of Rome, Positano, and Capri were taken by me when I visited previously, but because I was unable to see the other destinations I used pictures from other photographers and provided source credit below the image. Let me know what you think and if you have any Southern Italy tips or recommendations! Our family will probably reschedule for June 2021, so it’s never too late to incorporate any suggestions. 😉

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Itinerary Overview

DAY 1: CIAO ITALIA

As I mentioned earlier, my mom has never been to Italy! Although our prioritization was the southern region, we planned to make a 2-day pit stop in Rome so our first-timer can see a few major monuments! Plus, it was much cheaper to fly in and out of the capital from NYC for a primetime, Friday night departure.

Once we landed in FCO around mid-morning, we’d take a taxi to our Airbnb in the Trastevere neighborhood. After settling in and assessing our jet lag, the plan was to grab lunch and explore the surrounding area throughout the afternoon. We could possibly do sightseeing at St. Peter’s Basilica and the Vatican if the family was up for it. I also thought it would be fun to take advantage of the time difference and check out the night-life, as midnight would be 6 PM back in NYC. This of course depends on how exhausted we are! I try to keep the first day flexible in case of travel mishaps and in order to acclimate to the new time zone.

DAY 2: ROME-ing AROUND

The bulk of our sightseeing was planned for today. We’d start out our morning with a skip-the-line tour of the Colosseum, Roman Forum, Palatine Hill, and Pantheon. Then we’d break for a leisurely lunch, followed by a visit to famous sites like the Spanish Steps, Trevi Fountain, and Piazza Navona. After freshening up in our Airbnb, we’d have dinner and then turn in early to rest up for an early morning Vatican tour.

DAY 3: MORNING AT THE VATICAN / AFTERNOON BY THE SEA

*Important Planning Tip: tours of St. Peter’s are unavailable on Sundays! So, if we were unable to make it to the Vatican on Saturday (due to travel delays or exhaustion), I made a back-up plan to go on an early morning tour that offered access to the Sistine Chapel and St. Peter’s Basilica before they opened to the public. After admiring the artistic and architectural beauty, we would grab our bags from our Airbnb and head back to the airport to catch our 1 PM flight to Sicily.

Once we arrived in Catania, we’d pick-up our rental car and make our way to Taormina. From there, we’d settle in and hit the beach during the afternoon, specifically making sure to check out the famous Isola Bella! As always, we’d commence our evening with a nice dinner and call it a night. We planned to stay at Villa Ducale, which has an amazing view of the city!

DAY 4: TAORMINA

The next morning, we’d enjoy a beautiful breakfast on our hotel’s terrace and then explore the Teatro Antico, an ancient Greek theatre in the heart of Taormina. After soaking up all the history, we’d have lunch and do a little shopping along Corso Umberto. Today’s pace would be a lot more relaxed and flexible after a busy start in Rome, enabling us to feel things out and be more spontaneous. In the late afternoon, we’d take our rental car and head south towards the Valle di Noto. We wanted an immersive experience, so we chose to stay at an organic winery and olive oil farm manor!

Joseph Recca

DAY 5: VAL DI NOTO

Today we planned to explore some of the surrounding towns in the Val di Noto! Our first stop was going to be Ragusa, where we could admire the beautiful old town (called Ragusa Ibla) and taste authentic cuisine. Most of this day will be spent wandering the quintessential narrow streets and really learning about the locals who live here. We also planned to take a cooking class that evening in the town of Modica, another nearby town, which is famous for its chocolate-making! The 3-course meal would be taught in the chef’s own family home, which has a beautiful terrace where the students can gather after class and eat the food they just prepared all together.

Sabrina Mazzeo

DAY 6: NOTO

Today we would’ve enjoyed our last breakfast at the manor and then drove to the baroque city of Noto to admire the Baroque architecture of its many churches and cathedrals. A highlight would’ve been enjoying the views of the sun reflecting off of the limestone buildings during golden hour! After exploring for a full day, we’d drive off to the island of Ortigia in Siracusa. We planned to stay here for the next two nights in an Airbnb that had gorgeous sea views.

Jacob Buchhave

DAY 7: SIRACUSA

Siracusa is the main attraction of our Sicily itinerary, as this is the place where my mom’s family is from. Our plan was to wander around the city streets, learn about history, and interact with locals at some of the famous food markets!

Hugo Zlotowski

DAY 8: PUGLIA

The next morning, we would drive up to Catania and catch a flight to Bari. From there, we planned to stop in Monopoli for lunch and see Polignano al Mare’s renowned Lama Monachile beach in the late afternoon. From there we’d head to Masseria Salinola as our base for the next three nights.

Massimo Virgilio

DAY 9: SALENTO

The plan for today was to enjoy breakfast at the Masseria, and then road-trip down to Lecce for the morning, which is about an hour away. The city is also famous for its baroque architecture, and is known as the “Florence of the South.” After walking around for a few hours, we’d drive out to the coast and relax by some of the famous beaches. We’ve had our sights set on diving off the edge of the Cave of Poetry! Depending on our level of ambition, we may try to make it out to the coastal town of Otranto, but otherwise, we’d head back to our Masseria and relax.

Giulia Gasperini

DAY 10: VALLE D’ITRIA

Another beautiful day in Puglia can only begin with another amazing breakfast at the Masseria. From there we planned to check out some quaint towns in the Valle D’Itria. Our first stop would be to visit Alberobello, a UNESCO World Heritage site known for its Trulli homes. Although this town is more touristy, I think it’s still worth a quick visit. We planned to make one or two other stops in some of the neighboring towns, like Martina Franca, Cisternino, or Locorotondo. Let me know if you recommend visiting one over the other because they all sound pretty amazing! We’d likely end up breaking for lunch in one of those towns before heading to Ostuni for the rest of the afternoon and dinner. The “White City” is set upon a hilltop not too far from our Masseria.

Giulia Gasperini

DAY 11: MATERA

The next morning, we planned to have our final breakfast at the Masseria before heading to the ancient town of Matera. I lumped this stop in with the Puglia leg of our journey, but it’s technically located in the region of Basilicata. After arriving in the morning, we planned to drop our bags at the Sextantio Hotel, where they give guests the opportunity to stay overnight in actual Sassi! To give some background information, the Sassi are ancient cave dwellings in Matera that have been inhabited since the Paleolithic time period. My family thought this would be a really unique experience, and didn’t mind roughing it in a cave for just one night! The plan for the rest of the afternoon was to walk around the town and marvel at one of the most unique landscapes in Europe.

DAY 12: POSITANO

Assuming we are well-rested after our night in the Sassi, it’s time to begin the last leg of our journey bright and early: the Amalfi Coast. I had previously visited this area for a weekend while studying abroad in Florence during September 2014, and was so eager to return while not “ballin’ on a budget.” Our plan was to drive from Matera to Pompeii for the morning, and then drop off our rental car in Naples before transferring on a bus to Positano. We chose to base ourselves in a gorgeous Airbnb here for the remainder of the trip. After completing 2 PM check-in, we would probably relax and soak in the dreamy views of the beach. There are so many great places to eat in town, and we were still sorting through the options before our planning was halted. Definitely pass along any must-go restaurants!

DAY 13: CAPRI

Our plan today was to live life on the luxurious side and take a private boat tour of Capri. Here we’d get to see all the breathtaking sights around the island, like the famous Blue Grotto, and bask in the sunshine. Our family loves going on boat rides, so this experience would have definitely been a highlight! After a full morning of swimming and working on our tan, we planned to disembark on the island in the afternoon for lunch and walk around town, eventually making our way up to Anacapri for the views. After a day on the island, we’d head back around sunset and have a more casual diner in Positano.

Nellia Kurme

DAY 14: LA VITA È BELLA

There are so many places to explore on the Amalfi Coast that it’s hard to stay put in one place! My thought for today was to either check out the town of Amalfi or potentially embark on the Path of the Gods hike! The possibilities are endless. The only thing set in stone for today was to dress up for a fancy birthday dinner at La Sponda for my mom!

Kevin McMahon

DAY 15: RAVELLO

Our last full day in Italy! It feels bittersweet writing this even though I haven’t even started the trip, and probably won’t do so now for over a year! The plan was to hit Ravello in the morning, visiting the gardens at Villa Rufolo and Villa Cimbrone. From there, we made a reservation for lunch at the Belvedere hotel. I’ve seen way too many pictures of that hotel’s infinity pool and needed to check it out with my own eyes! Not sure if they’d let us sneak a swim but it would be worth a shot! After lunch, we’d head back to Positano and enjoy our final afternoon in this magical country.

DAY 16: ARRIVEDERCI

Ahhh, here is where the logistics planning shines through. Waking up in the morning in Positano and getting to Rome FCO airport by 12 PM is no simple task. I hadn’t exactly ironed out this detail fully just yet, but have a few ideas:

• Instead of dropping the rental car off before the Amalfi Coast, we would keep it parked at a nearby lot (mentioned by our Airbnb host), and then depart straight to FCO via car and return the rental in Rome (about a 3-4 hour drive)
• Take a bus from Positano to Sorrento and then to Naples, train from there to Rome, and then transfer to an airport shuttle to get to FCO (would probably require a VERY early wake-up time to give extra cushion)
• Hire a private transfer for either the full or partial journey, likely adding significant cost

I am currently leaning towards using a combination of public and private transport. Based on my past travel experiences in Italy, there were a few occasions where public transit workers went on strike and left travelers delayed for hours… some even missing their flights! This is something we cannot afford to risk, especially for our main long-haul journey back to the United States. My thought is to hire a private transfer from Positano to Naples. From there, we would take the train to FCO. With Naples being the largest hub in the south, there are multiple methods of transportation that we can take (including a taxi as the last resort) in the event of any unforeseen or out of the ordinary disruptions. After getting through security, we’d take our 2:30 PM flight back to NYC and revel in the memories of this incredible, once in a lifetime trip. 

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So, that’s a wrap! Once June comes around I will definitely start living vicariously through this blog post. You could probably spend months on end getting lost in each of these provinces, but our goal was to get a taste of three major destinations in this region and cover a lot of ground in a short amount of time. I thought this itinerary nicely balanced sightseeing and relaxation without spreading ourselves too thin. With so much in flux we haven’t rescheduled anything yet, so let me know what your thoughts are and if you would do anything differently! I appreciate any and all feedback!

xx

Kristen