Italy Travel Guide: 6 Small Towns Not To Miss on an Italian Road Trip

Road-Tripping was never my favorite way to travel - as a former (and still in my heart) New Yorker, driving is no longer my first instinct and I didn't even own a car for almost a decade. However, in the last couple of years of full-time traveling, I have fallen in love with Road Trips. The freedom, the ability to stop at any and every little thing that looks interesting, the snacks and playlists, the questionable "roads" that Google Maps always seems to send us down. We have spent quite a bit of time since we started traveling driving through Nova Scotia, French wine country, and South Africa - but our first big road trip had to be Italy. Brandon's mother is from Italy, and he has always felt a very strong tie to the country. For our first Italy trip, it was never going to be enough to just stop in one or two major cities and then leave - he needed to see the country, to talk to local people, to really feel it.

Of course we had to stop in the big hitters - Milan, Rome, Florence, and Positano, but along the way we found some incredible gems. Some stops were planned, and some were just towns we spotted from the highway and decided to wander through. Italy is one country that is truly deserving of slow travel - the amount of history, art, culture, and architecture packed into one country is overwhelming. The cities are iconic, but every village we passed was also full of castles, storybook scenes, and some of the most incredible food we have ever experienced. We drove for three weeks, spanning half the length of the country, and there are still so many more areas to explore!

In planning your Italian road trip, here are six areas to add to your list, from north to south.

1. Parma

Famous for more than just ham and cheese, the area of Parma has been inhabited for thousands of years, and the city dates back to Roman times. It is home to the University of Parma, one of the oldest universities in the world, and the city center is lined with cobblestones, ancient streets, and churches, buildings, and monuments that are hundreds of years old. Parma is a direct drive from Milan, and a great stop on the way to Cinque Terre.

Eat: Definitely do not miss the Prosciutto di Parma or Parmesan Cheese, in the town that made them famous.
Do: Take a Food Tour here - it's an amazing place to deepen your understanding of Italian Cuisine.
See: The Teatro Farnese, a stunning theatre from the 1600s, and the Cattedrale di Parma
Stay: We stayed right in the heart of the city center at Condo Hotel Palazzo Dalla Rosa Prati and loved it! Search for more hotel deals here.

Where to stay

• Palazzo Dalla Rosa Prati: Stay beside Parma’s cathedral in the central palazzo we loved on our original trip.
• NH Parma: A modern option beside the railway station with a restaurant, gym, and convenient arrival by train.
• Grand Hotel de La Ville: A polished hotel by the Barilla Center, within walking distance of the historic center.

Tours and activities

• Parmigiano and Parma ham production tour: Visit local producers to see how Parma’s famous cheese and cured ham are made, then taste them.
• Parma food and sightseeing walk: Combine a walk through the city with tastings of its regional specialties.
• Parma city walking tour: Get oriented among the city’s squares and historic monuments with a local guide.

2. Monterosso al Mare

Monterosso al Mare is one of the five villages of Cinque Terre, and it is not to be missed! The old town and the newer Fegina area are connected by a pedestrian tunnel. The beach at Monterosso had crystal-blue water and was the most stunning I saw in the area, with plenty of space to settle in for a beach day.

Eat: The Liguria area is famous for pesto - don't miss it here! Either at the local restaurants, or stop by a grocery and make your own pasta to feel extra-authentic.
Do: I cannot emphasize enough how the beach here is by far the best in Cinque Terre. Head down to the beach club, and rent an umbrella and chairs for a day of swimming & Italian sun.
See: Explore the local vineyards and wineries, wander the streets of the old city,  and take the train from here to travel to the other 4 towns in Cinque Terre - it is by far the best way to travel between them.
Stay: We stayed up in the vineyards above the main city at a small Airbnb which we absolutely loved (the above was our balcony view.) That stay is a memory from our original trip; check current accommodation options and availability for your dates.

Where to stay

• Hotel Porto Roca: An adults-only clifftop hotel with a seasonal pool and sweeping coastal views.
• Hotel Margherita: A central base with a terrace, within walking distance of the beach.
• Hotel Palme: Stay near Fegina Beach and the railway station, with a garden for relaxing between outings.

Tours and activities

• Monterosso kayak and snorkeling tour: Paddle from Monterosso with a guide and stop to explore the coast from the water.
• Cinque Terre e-bike tour: Ride the hills above the villages, with a meeting point at Agriturismo Missanega rather than the beach.

3. Assisi

By far my favorite stop in Italy! The town of Assisi looks like a fairytale - every corner we turned down was even more beautiful and storybook-like than the last. I spent my birthday here, and it was a complete dream. 

Eat: The hotel restaurant, then called EAT, was one of the absolute culinary highlights of our trip to Italy. We loved the sunset views, home-grown produce, and unusual dishes (I believe we tried both pigeon and rabbit here), and Brandon is still talking about his Bistecca alla Fiorentina. For a visit now, the hotel’s restaurant is Benedikto, serving contemporary Umbrian cuisine; check its current menu and reservations.
Do: Explore the Basilica of Saint Francis of Assisi, an iconic Church built in the 13th century.
See: Ancient Roman ruins, Renaissance art, medieval villages - just wander the town and experience thousands of years of history in front of you.
Stay: If you take one piece of advice from this blog, check out Nun Assisi Relais & Spa Museum - one of the most incredible and special hotels I have ever stayed in. Built in a renovated nunnery from the 13th-century,  which itself was built on an ancient Roman amphitheater, the hotel's history is incredible - but the rooms and restaurants are stunningly modern and minimalist. The underground spa is built out of ruins of ancient Roman baths, and some pieces of the 2,000-year-old structures and walls are still intact. Seriously, treat yourself to a night or two here, and you will not regret it. 

Where to stay

• Nun Assisi Relais & Spa Museum: Our original splurge is a converted convent with a spa built around ancient Roman remains.
• Fontebella Palace Hotel: Stay in the historic center with a garden and views over the Umbrian valley.
• Giotto Hotel & Spa: A central hotel with terraces and a spa, a short walk from the Basilica of Saint Francis.

Tours and activities

• Assisi and Saint Francis Basilica walking tour: Explore the medieval town with a local guide, checking the selected tour’s basilica access arrangements for your date.
• Pasta-making class with Mamma: Learn to make fresh pasta in a hands-on class near Assisi.
• Organic winery tour and tasting: Explore an organic winery and taste local wines in the Umbrian countryside.

4. Spoleto

We stopped by Spoleto on a whim as we were driving to Rome, and found one of the most adorable cities we had visited. On our visit in late August, the streets felt wonderfully quiet. Ancient walls, Roman remains, and medieval buildings layer thousands of years of history into the town. I may be a little obsessed with just how much history there is to explore in Italy!

Eat: The sandwiches we got at the above Salumeria were honestly one of the best I have had in my life (extra truffle spread, please!)
Do: Walk through a still-intact Roman Nobleman's home at the Roman House of Vespaia Polla, and explore the parks and countryside just outside of the city.
See: The stunning Spoleto Cathedral, the majestic Ponte delle Torri Bridge (how is it possible that this was built centuries ago!), and of course, the classic village streets.
Stay: We didn't spend the night in the city, but now I wish we had spent more time here - search the best hotel prices here.

Where to stay

• Hotel San Luca: A historic hotel with a courtyard for a relaxed stay in Spoleto.
• Palazzo Leti: Choose a historic residence with a garden and terrace near the cathedral.
• Albornoz Palace Hotel: A practical option outside the oldest streets with parking, a gym, and a seasonal pool.

Tours and activities

• Countryside pasta cooking class: Head into the countryside for a hands-on cooking class and a meal with wine.
• Spoleto-Norcia railway e-bike tour: Explore part of the old railway route by e-bike with a guide.
• Private Spoleto walking tour: Discover Spoleto’s medieval streets and major monuments with a private guide.

5. Sorrento

While Positano is absolutely stunning, don’t miss Sorrento on the other side of the Sorrentine Peninsula, with views across the Bay of Naples toward Mount Vesuvius.

Eat: Being so close to Naples (the original home of pizza), the pizza here was amazing. And don't miss the limoncello liqueur; I'm generally not a fan of Digestifs, but I fell in love with Limoncello here.
Do: Swim in the Bagni Della Regina Giovanna (Queen's Baths), a stunning inlet with ancient history, view the ruins of Il Vallone dei Mulini from the public overlook, walk through the main town Piazza.
Stay: We stayed at the incredible Excelsior Vittoria Sorrento, which could be described as more of a palace than a hotel (see more from this hotel here.)  For more budget-friendly options, search for hotels here. 

Where to stay

• Grand Hotel Excelsior Vittoria: The hotel from our original stay combines a central Piazza Tasso location with views over the bay.
• Grand Hotel La Favorita: A central hotel with a rooftop pool for a sunny break between sightseeing stops.
• Hotel Antiche Mura: Stay close to Piazza Tasso with a garden and swimming pool.

Tours and activities

• Capri boat trip: Explore Capri by boat with island time, with any optional Blue Grotto visit dependent on conditions and extra admission.
• Pompeii guided tour from Sorrento: Travel from Sorrento by train and explore Pompeii’s archaeological site with a guide.

6. Amalfi

While the Amalfi Coast is truly iconic, don’t overlook the town of Amalfi itself. We found some amazing gems here; for a visit now, expect a popular coastal destination, particularly in summer.

Eat: Seafood is big on the Amalfi Coast; try a seafood pasta dish.
Do: Trek inland for the ruins, greenery and waterfalls of Valle delle Ferriere , Drive the winding and stunning Amalfi Coast, Take a boat tour of the entire Amalfi Coast - we used Blue Star Boat Tours for ours and had an absolutely incredible day.
See: The Stunning and ancient architecture and ornate decor of the Chiostro del Paradiso, the Cathedral of Sant'Andrea
Stay: Amalfi hotel prices vary widely by season and room type; compare current rates for your dates.

Where to stay

• Luna Convento: Stay in a historic former convent with a terrace and an easy walk into Amalfi.
• Hotel Marina Riviera: A sea-view hotel with a rooftop terrace and pool close to Amalfi’s beach.
• Hotel Floridiana: A central three-star option near the cathedral with breakfast included.

Tours and activities

• Amalfi Coast and Positano boat tour: See the coast from the water with swimming stops, selecting the Amalfi departure when booking.
• Farmhouse cooking class: Visit a local farmhouse and prepare a meal in a hands-on cooking class.
• Amalfi Coast kayak and snorkeling tour: Paddle along the coast with a guide and explore the water on a snorkeling stop.

Get Inspired:

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