My first trip to Italy followed the exact same route everyone tells you to take, Rome, Florence, Venice, checked off in order like a list rather than a country I was actually exploring.
It wasn’t until a second trip, when a friend suggested skipping a planned city day for a small hill town I’d never heard of, that I realized how much of Italy exists entirely outside that standard route.
This list is built for anyone planning their first real trip to Italy who wants a few genuine surprises mixed in alongside the classics, ten small towns across Tuscany, Puglia, Basilicata, and the Cinque Terre that are easy enough to reach even as a first-timer, but rarely make it onto a typical Italy itinerary, from cliffside villages wedged into rock spires to Renaissance towns small enough to walk in a single afternoon.
Each one below comes with exactly what you need to actually plan around it, how to get there from the nearest airport, where to stay on a first-time visitor’s budget, where to eat without overpaying for the view, how to navigate once you arrive, and safety tips worth knowing before you go.
If you’re mapping out the rest of your Italy trip alongside these small town stops, our 11 most beautiful places to visit on earth and travel checklist are both worth reading before you finalize your itinerary and book flights.
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Why I Would Add Small Towns to an Italy Trip
Rome, Florence, and Venice earn their reputations honestly, and I’m not suggesting a first-time visitor skip them.
What I am suggesting is that they only tell part of the story, and the part they leave out is often the part that ends up mattering most once you’re actually home and thinking back on the trip.
Big cities in Italy come with big crowds, and that’s true even in shoulder season. A small town like Pienza or Monteriggioni gives you the chance to actually stand in a piazza and take it in, rather than shuffling through it as part of a moving crowd.
That difference sounds small until you’ve experienced both back to back on the same trip.
Small towns also tend to reward a slower pace, which first-time visitors often don’t realize they want until they’re in the middle of a rushed, checklist-driven itinerary.
A town like Bevagna or Castelmezzano doesn’t have enough attractions to fill a full day, and that’s exactly the point.
There’s nothing to rush toward, which forces a kind of unhurried wandering that’s hard to replicate in a city with a dozen must-see landmarks competing for your afternoon.
Finally, small towns give you a version of Italy that feels genuinely local rather than built around tourism. Restaurants in these places serve regional food at regional prices, because most of their customers still are locals, not visitors.
That difference shows up in everything from the menu to the pace of service to the conversations you end up having, and it’s a version of Italy that’s much harder to access in a city where every interaction is at least partly shaped by tourism.
1. Cinque Terre (Manarola)
Five cliffside villages connected by hiking trails and a short train line, and Manarola is the one that stopped me mid-step the first time I saw it, colorful houses stacked above the water with genuinely no flat ground in sight.
For a first-time visitor to Italy, this is one of the easiest “wow” moments to actually reach without much planning experience required.
How to get there Fly into Pisa Airport (PSA) or Genoa Airport (GOA), both about a two-hour drive or train connection to La Spezia, the gateway town for all five Cinque Terre villages by local rail.
Where to stay Manarola itself has limited rooms, so many first-time visitors base themselves in La Spezia or Levanto, both well connected by the same local train line that links all five villages.
Where to eat Restaurants directly on Manarola’s small harbor charge a premium for the view. For better value, walk up into the village’s steeper streets, where smaller family-run spots serve the same fresh seafood and pesto-based dishes at noticeably lower prices.
How to navigate Cars aren’t practical here, use the local train between villages and hike the connecting trails where open. A Cinque Terre train pass, sold at any regional station, covers unlimited rides between all five villages for the day.
Things to do Walk the harbor for the classic photo, hike the connecting trail toward Riomaggiore if it’s open, and swim at the small rocky cove below the village.
Best time to visit: May or September, avoiding peak summer crowds while the weather still allows swimming.
Personal tip: Check trail conditions before hiking. Sections between villages close periodically due to landslides, so confirm at the station before planning your day around a specific route.
Safety tip Trail sections can be narrow with real drop-offs, so proper footwear matters more than the short distances suggest. Our 11 most beautiful places to visit on earth covers a few similarly dramatic coastal destinations worth comparing.
2. Vernazza, Cinque Terre
Vernazza is the village most photographs of Cinque Terre are actually taken in, a small stone harbor wrapped around a tiny bay with pastel buildings climbing the hillside behind it.
Arriving by train and walking straight down into the harbor, with almost no transition between the station and the water, made this one of the more immediately striking first stops I’ve had in Italy.
How to get there
Fly into Pisa Airport (PSA) or Genoa Airport (GOA), both roughly two hours by car or train to La Spezia, the main rail gateway into the Cinque Terre villages.
Where to stay
Vernazza has more rooms than some of the other four villages, small guesthouses and rooms above the harbor put you steps from the water, though summer books out quickly given how popular this specific village is.
Where to eat
Restaurants directly on the harbor charge a premium for the setting. For better value, head up into the village’s narrow side streets, where smaller trattorias serve the same regional seafood and focaccia at noticeably lower prices.
How to navigate
The village itself is walkable in minutes, cars aren’t practical or necessary here. Use the local train and a Cinque Terre pass to reach the other four villages, and check trail conditions at the station if you want to hike between them.
Things to do
Walk out to the small breakwater for harbor views, climb up to the Doria Castle ruins above the village, and swim at the small beach near the harbor entrance.
Best time to visit: May or September, when the village is noticeably calmer than peak July and August.
Personal tip: Arrive early or stay overnight if you can. Vernazza fills with day-trippers from cruise excursions by late morning, and the harbor feels completely different before they arrive.
Safety tip
The harbor’s rocks and breakwater get slippery when wet, so watch your footing if you’re exploring beyond the main paved area. Our travel checklist is a useful starting point if you’re organizing a first Italy trip around stops like this one.
3. Positano
Positano is the postcard everyone pictures when they think of an Italian summer, pastel buildings stacked up a steep cliffside above the sea, and for a first-time visitor, it’s genuinely one of the most rewarding stops to build a short trip around despite how famous it’s become.
How to get there Fly into Naples International Airport (NAP), then take a private transfer, ferry, or SITA bus along the coast, roughly 90 minutes to two hours depending on traffic. A morning transfer avoids the heaviest summer coastal traffic.
Where to stay Stay in town rather than on the outskirts if this is your first visit and you want to walk everywhere without needing a car. Rooms with a sea view book out months ahead for summer.
Where to eat Restaurants directly on the beach or main street charge a genuine premium for the location. For better value, climb a level or two up the town’s staircases, where smaller family-run spots serve the same fresh seafood and lemon-based dishes at noticeably lower prices.
How to navigate Positano is built almost entirely on stairs, so comfortable shoes matter more here than anywhere else on a first Italy trip. A car isn’t necessary and honestly isn’t recommended given how limited parking is, ferries and the SITA bus cover day trips well.
Things to do Walk down to the main beach, climb up to a quieter viewpoint for a photo over the town, and take a short ferry to nearby Amalfi or Capri for the day.
Best time to visit: Late May or September, avoiding peak summer crowds and heat while the water is still warm.
Personal tip: Pace yourself with the stairs. First-time visitors consistently underestimate how much climbing a single day in Positano actually involves.
Safety tip The coastal road connecting Positano to nearby towns has sharp blind curves, so if you’re on a bus or in a transfer vehicle, don’t be alarmed by the pace, local drivers are experienced with the route.
Our 12 cheapest islands to visit in 2026 is worth a look if Positano’s prices come as a surprise and you want a lower-cost coastal alternative.
4. Siena, Tuscany
Siena’s shell-shaped main square, Piazza del Campo, is one of the first places in Italy that actually made me stop and just look, no photo, no rush to the next stop, just standing there taking in the medieval brick buildings curving around the square.
For a first-time visitor, it’s a gentler, less overwhelming introduction to Tuscany than Florence.
How to get there Fly into Florence Airport (FLR) or Pisa Airport (PSA), both about an hour and a half’s drive or bus connection to Siena.
Where to stay Small hotels and guesthouses within the historic walls put you within walking distance of the Piazza del Campo and the cathedral, generally calmer and more affordable than comparable properties in central Florence.
Where to eat Restaurants directly on the Piazza del Campo charge a premium for the location. For better value, head into the surrounding side streets, where local trattorias serve genuine Tuscan dishes, pici pasta, wild boar, alongside Sienese specialties at noticeably lower prices.
How to navigate The historic center is entirely walkable, compact enough to see in a day. A rental car, arranged at either Florence or Pisa airport, is useful if you’re combining Siena with a wider Tuscany itinerary.
Things to do Sit in the Piazza del Campo and take in the square itself, climb the Torre del Mangia for panoramic views, and visit the cathedral’s striped marble interior.
Best time to visit: Spring or early autumn, avoiding both peak summer heat and the crowds of the Palio horse race in July and August.
Personal tip: Visit early morning before the tour groups arrive. The Piazza del Campo feels completely different with space to actually sit and take it in.
Safety tip The square and surrounding streets can get very crowded during the Palio horse race dates, so plan around those specifically if a calmer visit is the priority. Our 11 most beautiful places to visit on earth covers a few similarly iconic squares and historic centers worth comparing.
5. Monteriggioni
Monteriggioni is a genuinely tiny walled medieval town, so small and so completely enclosed by its original fortress walls that seeing it from a distance on the drive in feels almost staged, like a film set rather than somewhere people actually live.
For a first-time visitor to Italy, it’s one of the easiest ways to experience a fully intact medieval town without much walking required.
How to get there Fly into Florence Airport (FLR) or Pisa Airport (PSA), both about an hour to an hour and a half’s drive to Monteriggioni.
Where to stay Monteriggioni itself has very limited accommodation, so most visitors base themselves in nearby Siena or the surrounding Tuscan countryside, both a short drive away with far more hotel and agriturismo options.
Where to eat The handful of restaurants inside the walls charge accordingly given the setting and limited seating.
For better value, eat in Siena or a nearby countryside agriturismo, where meals often come with a wider selection and genuinely excellent Tuscan wine at lower prices.
How to navigate The town itself is tiny and entirely walkable in under an hour, no car needed once you’re inside.
A rental car, arranged at Florence or Pisa airport, is essential for reaching Monteriggioni and exploring the wider Tuscan countryside around it.
Things to do Walk the full loop of the fortress walls, visit the small central church, and take in the views over the surrounding vineyards from the wall’s edge.
Best time to visit: Spring or early autumn, when the surrounding countryside is at its most colorful and comfortable for walking.
Personal tip: Combine this with a Siena day trip. Monteriggioni itself only takes an hour or two to see fully, so pairing it with a nearby stop makes for a better use of the day.
Safety tip The wall walk has minimal railings in places, so keep a reasonable distance from the edges, especially with children.
Our travel checklist is a useful starting point if you’re organizing a first Tuscany itinerary around stops like this one.
6. Verona, Veneto
Verona gave me an unplanned evening that turned into one of the more memorable nights of that whole trip, stumbling into an open-air opera performance at the ancient Roman arena without having any idea it was happening that night.
For a first-time visitor, it’s a genuinely easy, walkable introduction to Italy that most itineraries skip in favor of Venice just an hour away.
How to get there Verona has its own airport (VRN), or take a direct train from Venice, about an hour, or Milan, about an hour and a half.
Where to stay Stay within the historic center walls for easy walking access to the Roman arena and Juliet’s balcony, generally more affordable than comparable central accommodation in Venice.
Where to eat Restaurants directly near the arena or Juliet’s balcony charge a premium for foot traffic. For better value, head into the quieter streets near Piazza delle Erbe, where local trattorias serve genuine Veneto dishes at noticeably lower prices.
How to navigate Verona is compact and walkable, one of the easiest cities in Italy to explore without a car. Trains connect easily to nearby Venice and Milan if you’re combining stops.
Things to do Visit the Roman arena, check the current opera or concert schedule, walk to Juliet’s balcony, and wander Piazza delle Erbe.
Best time to visit: Late spring or early autumn, particularly if you want to catch the summer opera season in the arena.
Personal tip: Check the arena’s summer opera schedule in advance if you want tickets, since performances sell out and last-minute seating is limited.
Safety tip Piazza delle Erbe and the arena area get genuinely crowded during evening performances, so keep valuables secure in the busier crowds.
Our 11 most beautiful places to visit on earth covers a few similarly iconic Italian landmarks worth comparing.
7. Bevagna
Bevagna is a small, walled medieval town in Umbria that most first-time Italy visitors have genuinely never heard of, and that’s exactly what made it stand out, a real, functioning town rather than something built around tourism.
Wandering the main square on a quiet weekday afternoon, I didn’t see another visitor for nearly an hour.
How to get there Rome’s Fiumicino Airport (FCO) or Perugia’s smaller regional airport are the closest gateways, both roughly two hours by car to Bevagna.
There’s no direct train into the town itself, so a rental car is the most practical route.
Where to stay Small hotels and guesthouses within the walled center put you within walking distance of the main square and Roman ruins, generally more affordable than comparable towns in neighboring Tuscany.
Where to eat The town’s few restaurants center around the main square and are worth trying regardless, given how few tourist-priced options exist here compared to more famous stops.
Meals lean into genuine Umbrian cooking, wild boar, lentils, local olive oil, at prices well below anything comparable in Tuscany.
How to navigate The town is tiny and entirely walkable in under an hour. A rental car, arranged at Rome’s airport, is essential for reaching Bevagna and exploring the wider Umbria region around it.
Things to do Walk the main square and its Romanesque churches, visit the remains of a Roman bathhouse, and explore the town’s small artisan workshops if any are open.
Best time to visit: Spring or early autumn, when the town’s outdoor spaces are most comfortable to explore.
Personal tip: Time a visit around a weekday if possible. Even in peak season, Bevagna sees so few visitors that a weekday afternoon can feel almost entirely private.
Safety tip The town has minimal tourist infrastructure, so carry cash, since some smaller shops and restaurants don’t accept cards.
Our 15 places in Italy almost no one knows about shares this same spirit of finding towns most visitors overlook entirely.
8. Locorotondo, Puglia
Locorotondo sits just up the road from the more famous Alberobello, a small circular hill town of whitewashed houses that most first-time visitors to Puglia never even hear about, let alone visit.
Walking its perfectly round historic center at golden hour, with vineyards stretching out below in every direction, felt like discovering a quieter version of everything Puglia gets praised for.
How to get there Bari Karol Wojtyła Airport (BRI) is the closest gateway, about an hour’s drive to Locorotondo. Brindisi Airport works too, with a similar drive time.
Where to stay Small guesthouses and countryside trulli conversions just outside town offer a genuinely memorable, affordable stay, generally cheaper than the more famous trulli accommodations in Alberobello nearby.
Where to eat Restaurants near the main viewpoint charge slightly more for the vineyard views. For better value, head into the town’s quieter residential streets, where local trattorias serve orecchiette, fava bean puree, and the region’s crisp white wine at noticeably lower prices.
How to navigate The historic center is compact and entirely walkable, its circular layout making it genuinely easy to explore without getting lost. A rental car, arranged at Bari or Brindisi airport, is essential for reaching Locorotondo and exploring the wider Valle d’Itria region.
Things to do Walk the circular historic center, take in the vineyard views from the town’s edge, and visit nearby Alberobello’s trulli as an easy day trip.
Best time to visit: Late spring or early autumn, when the surrounding vineyards are at their most scenic.
Personal tip: Visit at golden hour specifically. The white buildings and surrounding vineyards catch the evening light in a way that’s genuinely worth timing your visit around.
Safety tip The town’s narrow streets can be tight for driving, so park outside the historic center and walk in rather than attempting to navigate the center by car.
Our travel checklist is a useful starting point if you’re organizing a first Puglia itinerary around stops like this one.
9. Castelmezzano
Castelmezzano is built directly into the cliffs of the Lucanian Dolomites, a small stone village wedged between dramatic rock spires that most first-time visitors to Italy have never heard of, let alone considered visiting.
Looking up at the village from the valley road below, I genuinely wasn’t sure at first whether it was built into the rock or grown out of it.
How to get there Bari Karol Wojtyła Airport (BRI) is the closest gateway, about two hours’ drive to Castelmezzano through increasingly mountainous terrain.
Where to stay Small guesthouses within the village itself put you right among the rock formations, generally more affordable than similarly dramatic mountain villages in northern Italy.
Where to eat The village’s handful of restaurants serve genuine Basilicata mountain cooking, hearty pasta, local cheeses, cured meats, and are worth trying without much concern for tourist markup given how few visitors actually make it here.
How to navigate The village itself is small and walkable, though genuinely steep given its cliffside position.
A rental car, arranged at Bari airport, is essential for reaching Castelmezzano and the winding mountain roads leading in.
Things to do Walk the village’s steep stone streets, take in the views of the surrounding rock spires, and consider the Volo dell’Angelo zip line if you want to see the village from above.
Best time to visit: Late spring or early autumn, when mountain temperatures are most comfortable for the walking involved.
Personal tip: Book the Volo dell’Angelo zip line in advance if it interests you. It’s genuinely popular for a village this size, and spots fill up on weekends.
Safety tip The village’s steep, narrow streets can be slippery when wet, so proper footwear matters here more than almost anywhere else on this list.
Our 11 most beautiful places to visit on earth covers a few similarly dramatic natural landscapes worth comparing.
10. Pienza
Pienza is a small Renaissance town in the Val d’Orcia, often called the ideal city for how deliberately it was planned and built in the fifteenth century, and for a first-time visitor, it’s one of the most rewarding stops in Tuscany precisely because it’s so easy to see fully in a single afternoon without feeling rushed.
How to get there Fly into Florence Airport (FLR) or Rome’s Fiumicino Airport (FCO), both roughly two hours by car to Pienza. There’s no direct train into the town, so a rental car is the most practical route.
Where to stay Small hotels and countryside agriturismi just outside town offer memorable stays with views over the Val d’Orcia’s rolling hills, generally more affordable than similar properties closer to Siena or Florence.
Where to eat Restaurants on the main street charge a premium for the view. For better value, head into the quieter side streets, where local trattorias serve Pienza’s famous pecorino cheese alongside genuine Tuscan classics at noticeably lower prices.
How to navigate The historic center is entirely walkable, small enough to see fully in a few hours. A rental car, arranged at Florence or Rome’s airport, is essential for reaching Pienza and exploring the wider Val d’Orcia countryside.
Things to do Walk the main street for views over the Val d’Orcia, visit the cathedral and central piazza, and try the local pecorino cheese the town is famous for.
Best time to visit: Late spring or early autumn, when the surrounding countryside is at its most photogenic and temperatures are comfortable for walking.
Personal tip: Pair this with a countryside drive through the Val d’Orcia. Some of the best views on this entire trip came from the road leading into Pienza, not just the town itself.
Safety tip Countryside roads in this region are narrow and winding, so drive cautiously, especially around blind curves near hilltop towns.
Our travel checklist is a useful starting point if you’re organizing a first Tuscany itinerary around stops like this one.
Practical Tips for Visiting Small Italian Towns
A few things I’ve learned after building an entire trip strategy around towns like these instead of the usual big-city checklist.
- Rent a car for most of this list. Public transport connects Italy’s major cities well, but reaching towns like Pienza, Bevagna, or Castelmezzano genuinely requires one, and it’s the single biggest logistical difference between this kind of trip and a standard Italy itinerary.
- Book accommodation early, even in tiny towns. Several of these places have very limited lodging, sometimes just a handful of guesthouses, so availability disappears faster than the town’s size might suggest.
- Eat a street or two away from the main square or viewpoint. This held true across nearly every town on this list, restaurants directly on the best view charge a premium, while local trattorias a short walk away consistently serve the same or better food for less.
- Pair a smaller town with a nearby larger one. Places like Monteriggioni or Locorotondo only take a couple of hours to see fully, so combining one with a nearby city like Siena or a bigger Puglia stop makes for a better use of a single day.
- Pack proper walking shoes regardless of destination. Cliffside and hill towns like Castelmezzano, Positano, and Manarola all involve steep, uneven streets that are more demanding than they appear in photos.
- Carry cash for smaller towns. Several of these places have minimal card infrastructure, especially the more remote stops like Bevagna and Castelmezzano, so don’t rely entirely on card payments.
- Build slack into your itinerary. The best moments on a trip like this tend to happen in the towns you didn’t rush through, so resist the urge to pack too many stops into a single day.
FAQ
What is the best time of year to visit small towns in Italy?
Late spring (April to June) and early fall (September to October) offer the best mix of mild weather and smaller crowds.
Summer brings heat and heavier tourist traffic, even in lesser known towns.
Do I need a car to visit these towns?
For most of them, yes. Towns like Monteriggioni, Castelmezzano, and Bevagna have limited or no train access, so a rental car gives you far more flexibility.
Coastal towns like Positano and Manarola are easier to reach by train or ferry.
Are these towns walkable, or is a lot of driving involved between stops?
Once you’re inside each town, they’re very walkable, often on foot only due to narrow streets and stairs.
The driving comes in getting between towns, so it helps to group nearby ones together, like Orvieto and Civita di Bagnoregio, or Monteriggioni and Siena.
How many days should I set aside to see a handful of these towns?
Plan on at least one full day per town if you want to actually experience it rather than rush through.
A week to ten days is realistic for covering four or five towns without feeling hurried.
Are these towns suitable for first-time visitors to Italy, or better for a second trip?
They work well for first-time visitors too, especially paired with a few days in a major city like Rome or Florence.
Mixing in small towns actually helps first-timers get a fuller, more balanced picture of the country.
Final Thoughts
Ten small towns, and every single one taught me the same lesson from a slightly different angle: the version of Italy most first-time visitors get sold, Rome, Florence, Venice, and not much else, is real, but it’s only a fraction of what the country actually offers.
Cliffside villages wedged into rock spires, medieval towns so small you can walk the entire historic center in an hour, a piazza quiet enough to actually sit in without a crowd, none of these require advanced planning skills or a second or third trip to Italy to access.
They just require being willing to rent a car, drive a little further than the train tracks go, and trust that the smaller stop is sometimes the better one.
If this is your first trip to Italy, I wouldn’t recommend skipping Rome or Florence entirely, they’re famous for good reason.
But building in even two or three of these ten towns turns a fairly standard itinerary into something that feels genuinely yours, full of the kind of quiet, unhurried moments that are increasingly hard to find in the country’s most photographed cities.
Pick whichever of these ten speaks to you most, whether that’s a cliffside village, a walled medieval town, or a Renaissance square built to be walked slowly, and let it anchor a day or two of your trip. That’s usually where the best memories from an Italy trip actually come from.
