You already have the list. Anyone who’s been to Italy has handed it to you… Rome, Florence, Venice, maybe Milan if there’s time. It’s the same list in every guidebook, and when you’re visiting Italy for the first time, it feels like the safe choice. You know these cities, so they must be the ones worth seeing.
The trouble is that when everyone follows the same list, everyone ends up in the same piazza at the same hour, waiting in line at the same restaurant that went viral last spring.
The cities that stay with people are rarely the famous ones. They’re the places where the barista knows your order by day three, where nobody rushes you through dinner, and where you’re the only visitor in the wine bar and nobody minds.
So we made our list a little differently. We’ve spent our lives uncovering this country’s hidden gems, and these are the eight places we’d send a friend to on their first trip. You’ll recognize a few, fall in love with the rest, and wonder why nobody told you sooner.
Key Takeaways: Planning Your First Trip to Italy
- Mix famous with unknown, and see fewer places. Choose one or two home bases for a week, or two or three regions for two weeks. Rome or Venice makes a great start or finish, and the smaller places on this list let you experience Italy like a local.
- Time it right. Crowds, weather, and prices change dramatically by season. Spring and fall give you the best of all three, from April through June and September into October.
- Regional differences matter. The North and South offer completely different experiences. Match the region to your interests, because food lovers, history buffs, and beach seekers each need a different itinerary.
Get To Know The Regional Differences
Italy has only been one country since 1861, and you can still feel it. Drive a few hours in any direction and the dialect changes, the pasta changes shape, and the butter on the table gets swapped for olive oil.
This means choosing your region matters more than any single city on your list. Here’s how the North, Center, and Southern regions compare, so you can match the Italy you’re dreaming of to the right part of the map.
Northern Italy
- Where it is: Milan, Venice, Verona, Lake Como, and the Dolomites.
- The vibe: Polished, fast-moving cities, with an alpine edge the closer you get to the mountains.
- Best for: Art and architecture, mountain scenery, and high-end shopping in Milan.
- Weather: Cooler and wetter than the rest of the country. Fall and winter can bring acqua alta, the seasonal high tides that flood parts of Venice.
- Food style: Risotto, polenta, and butter-based sauces, paired with Northern wines like Prosecco and Amarone.
This is home to our small group tour of Northern Italy, and our ultimate guide to Veneto goes deeper.
Central Italy
- Where it is: Rome, Florence, Umbria, and Le Marche, plus Abruzzo, which sits right on the line between the Center and the South.
- The vibe: Classic Italy — rolling hills, Renaissance art, and landmarks you’ve seen in a hundred photos. An hour off the main road, you’ll find hill towns where you hear more Italian than English.
- Best for: First-timers, history lovers, and wine country.
- Weather: Mild, with four distinct seasons. Spring and fall are the sweet spot.
- Food style: Pasta, olive oil, and Florence’s bistecca alla fiorentina. The wines change as you go: Chianti in Tuscany, Verdicchio in Le Marche, and Montepulciano d’Abruzzo just over the border.
Two of our tours live here, Umbria Undiscovered and Italy’s Epicurean Journey, and both start with a pickup in Rome.
Southern Italy
- Where it is: Naples, Puglia, and Sicily.
- The vibe: Slower days, warmer weather, and long lunches nobody rushes you through.
- Best for: Seaside towns, food-driven travel, and smaller crowds outside of August.
- Weather: The warmest part of the country, and beach season starts earlier than up north.
- Food style: Seafood, Neapolitan pizza, and tomato-based sauces finished with olive oil. In Puglia, add orecchiette and burrata to the list.
This is where you’ll find Passport to Puglia, and our locals’ guide to Puglia has everything else.
8 Best Places to Visit in Italy for First-Timers
Every place on this list had to pass one test: Would we happily spend our own day off there? The famous names that stayed earned their spot, and the others are our personal favorites.
1. Go To Ascoli Piceno or Marche For History & Culture
If Rome is on your list for the history, start here instead. The locals in Ascoli Piceno love to tell you their city is older than Rome, and they’re right. The Piceni people settled this valley centuries before Rome was founded, right on the Via Salaria, the ancient salt road that still runs through town. Today the whole city glows in travertine stone, and the piazzas fill up with Italians instead of tour groups.
Start at Piazza del Popolo, one of Italy’s most beautiful squares, with an anisetta at Caffè Meletti (Hemingway’s favorite café) and a plate of olive all’ascolana, the fried stuffed olives this city invented. Then peek at the Roman ruins beneath the Palazzo dei Capitani del Popolo, and save a day for nearby Fermo, home to what the city calls Italy’s largest Roman cisterns.
Some things to know before visiting Ascoli Piceno:
- Best for. History buffs, culture lovers, and foodies.
- Timing & weather. Give it 3 to 4 days minimum, in April or May, or September or October. That’s warm enough for long lunches outside without the scorching summer heat.
- Who should skip it? Anyone looking for a beach base or a party scene. The Adriatic coast is close, but Ascoli is a town of stone and piazzas, and nightlife here means an aperitivo that turns into dinner.
- First-timer tip. Take a guided walking tour. A local guide will show you the Roman layer hiding under the medieval one, and those are details you’d walk right past on your own.
Ascoli is our home base on Italy’s Epicurean Journey, with an orientation walk on your first evening and a private guided tour of the city the next morning.
2. Go To Urbino For Art & Architecture
Love the idea of Florence? Go to Urbino instead. In the 1400s, the Duke of Montefeltro filled this hilltop town with some of Italy’s most outstanding artists and scholars, and Raphael was born right here. Its historic center earned UNESCO World Heritage status in 1998, and its Renaissance architecture is still beautifully preserved. The difference is that you can stand in front of a Raphael without fighting a crowd for the view.
Spend a morning inside the Palazzo Ducale, one of Italy’s finest Renaissance palaces, where the Galleria Nazionale delle Marche holds works by Piero della Francesca and Raphael. Then visit the house where Raphael was born, climb to Parco della Resistenza for the best view of the city, and order a crescia sfogliata with melted caciotta tucked inside.
Some things to know before visiting Urbino:
- Best for. Art lovers, architecture fans, and first-timers who would rather skip the crowds.
- Timing & weather. Give it 2 to 3 days in spring or fall, when the weather is mild, and there are fewer day-trippers. Pack with our spring packing list, or read why fall in Italy is the best, especially when the truffle festival comes to nearby Acqualagna.
- Who should skip it? Anyone who isn’t interested in Renaissance art and history. Urbino is built around it, and that’s the whole point of the visit.
- First-timer tip. Leave time to wander beyond the main sights, because the narrow side streets hide some of the best architecture in town.
Urbino is a full day on Umbria Undiscovered, with a private guided walking tour of the historic center, and our local’s guide to Urbino has everything else, from where to stay to what to eat.
3. Go To Venice For Romance & Magic
Venice earns its spot on this list on one condition: you stay the night. Too many visitors arrive by train or cruise ship in the morning, shuffle through St. Mark’s Square with everyone else, and leave before dinner. They see the crowds and miss Venice. Stay at least TWO nights, and you’ll watch the city change once the last day-trippers head home — the canals go quiet, the bacari fill up with Venetians, and the palaces along the Grand Canal glow from the inside.
Cross the Grand Canal on a traghetto, the standing gondola ferry locals use, for a fraction of a gondola’s price. In the evening, do a giro di bacari through Cannaregio, with cicchetti and an ombra (a small glass of wine) at every stop.
Some things to know before visiting Venice:
- Best for. Romantic getaways, architecture lovers, and travelers willing to slow down.
- Timing & weather. Stay at least two nights, or three to four days if you can, in late spring or early fall. Between April and July, day-trippers pay the Venice entry fee on peak days, but overnight guests are exempt and only need to register for a free QR code.
- Who should skip it? Anyone hoping to see it in a day. If you can’t give Venice at least two nights, save it for another trip.
- First-timer tip. Sleep on the main island, not the mainland. Waking up in Venice is worth the price, and our picks for the best boutique hotels in Venice will help you find the right one.
See Venice off the beaten path on Northern Italian Delights, with a private day on the islands of Murano, Mazzorbo, and Burano. Our Venice travel guide has everything else you need to plan the perfect stay.
4. Go To Umbria For Wine Country Perfection
Dreaming of Tuscan wine country? Skip the crowds and go next door. Umbria has the same rolling hills, cypress-lined roads, and medieval towns on every hilltop, with a fraction of the tour buses. Spend a week here, cross the border into Le Marche, and you’ll taste wines most visitors have never heard of, poured by the families who make them. We break down the full comparison in our guide to Tuscany vs. Umbria.
Taste Sagrantino at a family-run winery around Montefalco, then learn to make pasta all’uovo at a farmhouse cooking class. Save time to wander Gubbio and Bevagna, two of Umbria’s most beautiful villages, and spend an afternoon among Giotto’s frescoes in Assisi.
Some things to know before visiting Umbria:
- Best for. Wine lovers, foodies, and slow travelers.
- Timing & weather. Give it 4 to 7 days in April, May, September, or October. Spring turns the “green heart of Italy” its greenest, and fall brings the harvest, plus some of the best food festivals in Umbria.
- Who should skip it? Fast-paced travelers who need constant stimulation. Umbria rewards long lunches and slow afternoons, so if you need a new sight every hour, this isn’t your region.
- First-timer tip. Pick one home base and let the day trips come to you. Most of Umbria’s hill towns aren’t on the train line, so plan on a car or a local host to get around.
Experience it on Umbria Undiscovered, 10 days across Umbria and Le Marche from a single home base near Gubbio, with hosts who live here. Our ultimate guide to Umbria covers everything else.
5. Go To The Coast of Conero in Le Marche For Iconic Coastal Beauty
If the Amalfi Coast is on your list, cross it off. We never recommend it, because it’s become Disneyland for adults.
Instead, head to the other side of the country: the Coast of Conero in Le Marche. White limestone cliffs drop straight into turquoise Adriatic water here. The villages on top still belong to the people who live there, and some of Italy’s best beaches are tucked along this stretch.
Take a boat from Numana’s harbor to Spiaggia delle Due Sorelle, a wild beach you can only reach by sea, then hike trail 302 to Passo del Lupo for the view from above. Save another day for a long seafood lunch on the Bay of Portonovo and a sunset stroll through Sirolo, the Pearl of the Adriatic.
Some things to know before visiting the Coast of Conero:
- Best for. Beachgoers, scenic-drive lovers, and small-town travelers.
- Timing & weather. Give it 3 to 4 days in May, June, or September. The water is warm enough to swim, the trails are cooler, and you’ll miss the August rush when half of Italy heads to the beach.
- Who should skip it? Travelers who want resort-style beaches and nightlife. The most famous beach here has no facilities.
- First-timer tip. Stay in Sirolo or Numana rather than right on the beach. You’ll be steps from dinner, and your evenings will end with a passeggiata through the piazza.
We spend a full day along this coast on Italy’s Epicurean Journey, from the medieval hamlet of Torre di Palme to a seafood lunch on the Bay of Portonovo and the clifftop views of Sirolo. Our guide to exploring Le Marche through culinary tours has more to offer.
6. Go To Puglia For Southern Italy’s Authentic Secret
Giovanni’s parents are from Giovinazzo, and he spent his childhood summers at the family home on this coast, so we’ll be honest.
Puglia isn’t the secret it used to be, and in summer its most famous towns fill up fast. Come in spring or fall, though, and the locals take their towns back. You’ll find whitewashed villages, olive groves older than most cathedrals, and some of the country’s best food, served by families who have been making it for generations.
Tour the UNESCO-listed trulli of Alberobello with a local guide, then see Polignano a Mare’s sea caves from the water before a long seafood lunch. Save a day for Lecce, the “Florence of the South,” and another for watching a multi-generational cheesemaker turn fresh milk into burrata.
Some things to know before visiting Puglia:
- Best for. Food lovers, beach seekers, and travelers who want to see how locals live.
- Timing & weather. Give it 5 to 7 days in April through June, or September or October. It’s warm enough for the beach without the scorching heat, and you’ll miss the summer crowds.
- Who should skip it? Travelers who need famous landmarks and big museums. Puglia’s treasures are its villages, olive groves, and long lunches.
- First-timer tip. Base yourself in the Valle d’Itria, between the trulli towns and the coast, so you only unpack once and every day trip stays short.
Passport to Puglia gives you 8 days from a single home base in the Valle d’Itria, with the two of us as your hosts.
7. Go To Le Marche & Eastern Italy For Italy’s Best-Kept Secret
You’ve already met three of this region’s stars on our list, with Ascoli Piceno, Urbino, and the Coast of Conero, and the rest of Italy’s east is just as good. Between the Apennine mountains and the Adriatic Sea, Le Marche and its southern neighbor Abruzzo are full of hilltop villages, family-run wineries, and kitchens that have cooked the same recipes for generations. Most visitors to Italy never make it here… which is exactly why we call Le Marche Italy’s best-kept secret.
Forage with a local truffle hunter and their dogs in Le Marche’s truffle country, then taste Pecorino and Rosso Piceno in the hilltop village of Offida. Cross into Abruzzo to climb the fortress of Civitella del Tronto, and snack on the region’s street food along the way, from fried stuffed olives to arrosticini lamb skewers.
Some things to know before visiting Le Marche & Eastern Italy:
- Best for. Off-the-beaten-path travelers, food and wine lovers, and anyone who wants to avoid the crowds.
- Timing & weather. Give it 5 to 7 days in May, June, September, or October. Pack a swimsuit for the beaches in early summer, and come in fall for the harvest.
- Who should skip it? Travelers who measure a trip by famous landmarks checked off. The magic here is in the people, the food, and the pace.
- First-timer tip. It’s easier to reach than you’d think. Fly into Rome and head east, and you’ll be sitting in a piazza in Le Marche by dinnertime.
Italy’s Epicurean Journey spends 10 days across Le Marche and Abruzzo, with a truffle hunt alongside one of Jamie Oliver’s truffle hunters, lunch at a family farm, and a home base in Ascoli Piceno.
8. Go To Northern Italy For Lakes, Mountains & Food
Northern Italy is where the Alps meet the vineyards. You’ll find polished cities like Milan and Verona, lakes framed by mountains, and the jagged peaks of the Dolomites, plus a kitchen built on butter, risotto, and polenta instead of olive oil.
Most first-timers head straight for Lake Como. We’d point you to Lake Garda instead. It’s Italy’s largest lake and, in our experience, far less touristy than Como, with shores lined in lemon groves, olive trees, and Bardolino vineyards.
Spend a few slow days hopping between towns on Lake Garda by ferry, or visit Lake Como’s villages on a weekday outside of peak summer. Then hike the Dolomites, see an opera at Verona’s 2,000-year-old Roman arena, and sip Prosecco in the UNESCO-listed Prosecco Hills before digging into the Veneto’s food and wine.
Some things to know before visiting Northern Italy:
- Best for. Mountain lovers, lake lovers, and foodies.
- Timing & weather. Give it 5 to 7 days in May, June, or September. If hiking the Dolomites is the goal, plan for summer into September, when the mountain lifts are running.
- Who should skip it? Beach seekers and budget travelers, since Milan and Lake Como come with big-city prices.
- First-timer tip. Choose one lake or one valley as your base instead of trying to fit Como, Garda, and the Dolomites into a single week.
Northern Italian Delights takes you through the Veneto beyond Venice and Verona. You’ll explore the UNESCO Prosecco Hills and Palladian villas, spend a private day on the islands of Murano, Mazzorbo, and Burano, and cook with a local chef in his family home.
Still Stuck? Here’s How to Choose Where to Go in Italy
Eight places, one first trip… we know it’s a lot. Start with what you want most out of your time in Italy, and the right place usually picks itself.
If this is your first time and you’re overwhelmed. Book a tour with us and let us plan everything, from the home base to the dinner reservations and logistics. Then add a famous city on your own, either two or three days in Rome or two nights in Venice before or after your tour.
If you want authentic Italy without the crowds. Skip Rome, Florence, and Venice and head to Umbria, Le Marche, or Abruzzo. Puglia works too, as long as you go outside of summer and know the right spots. You’ll come home with better stories.
If food and wine are your love language. Go to Umbria, Le Marche, or the Veneto. Cook with a local chef in the Prosecco Hills, hunt for truffles in Le Marche, and taste olive oil straight from the mill.
If you need beaches and sunshine. Skip the Amalfi Coast and head to Puglia. Here’s how the two compare. Or try the Coast of Conero, with kayaking, cliffside hikes, and beaches you can only reach by boat.
If you’re looking for adventure. Try the Dolomites, Abruzzo’s mountains, or the Coast of Conero, and bring your hiking boots.
Don’t Forget To Factor In The Weather
Where you go matters, but when you go can make or break your first trip. Here’s how Italy’s seasons play out, so you can match the place to the weather. For the bigger picture, see our guide to the best time to visit Italy.
Spring (April-May)
This is the sweet spot for almost everything. The weather is mild, everything is open, and the summer crowds haven’t arrived yet. Umbria is at its greenest and covered in wildflowers, Puglia is warm enough for long lunches outside, and Rome is comfortable for walking (just plan around the Easter crowds). Plan with our April and May weather guides.
Summer (June-August)
Summer is made for the mountains and the sea. Hike the Dolomites while the lifts are running, or swim off the Coast of Conero in June before the August rush. Rome bakes, Venice is packed, and around Ferragosto on August 15, many family-run shops and restaurants close as Italians head on vacation. Our July weather guide covers how to handle the heat.
Fall (September-October)
Fall is harvest season, and our favorite time to be in wine country. Temperatures stay warm without the summer heat, the vineyards come alive from the Veneto down to Puglia, and the cities cool off enough to explore on foot. Beach towns start closing for the season in October, so plan your coastal days early. See our September and October guides.
Winter (November-March)
Winter is quiet, cozy, and made for the cities. You’ll find Christmas markets in the mountain towns of the north and white truffle season in full swing, and you’ll have the museums almost to yourself. Many coastal towns shut down for the season, and the Dolomites are for skiers only. Our November weather guide will help you pack.
How Long Should You Plan To Stay In Italy?
Every first-timer asks this, and our answer is always the same: longer than you think, in fewer places than you planned. Italy rewards the people who slow down, so plan your trip around home bases, not checkmarks.
How To Spend One Week in Italy
With seven days, choose one or two home bases at most and let the day trips come to you.
Here are some things to keep in mind:
- Pair a city with a region. Spend two or three days in Rome, then settle into Umbria or Le Marche for the rest of the week.
- Go deep in one region. Base yourself in the Valle d’Itria to explore Puglia, or in Ascoli Piceno for Le Marche and Abruzzo, and unpack once.
- Don’t chase a new city every day. You’ll spend your vacation on train platforms instead of at the table.
How To Spend Two Weeks in Italy
Two weeks gives you room for two or three regions, plus a few buffer days for the long lunches and lazy mornings you didn’t plan.
- The classic route. Start in Rome or Venice, then spend a week in a region like Umbria or the Veneto, and keep a few days free.
- The deep dive. Skip the famous cities entirely and split your time between two lesser-known regions, like Le Marche and Puglia.
- The food lover’s route. Use one city to get your bearings, then give two food-and-wine regions enough time to taste everything.
Most people try to see too much on their first trip. Pick fewer places, stay longer, and you’ll leave Italy already planning your next visit.
Give Yourself Permission To Skip What Doesn’t Fit
It’s okay to skip some of Italy’s most popular places. Your first trip should fit the way YOU travel, not the photos everyone else posts.
- Skip Venice if you can’t give it at least two nights, crowds wear you down, or you’d rather spend your budget on long dinners than a hotel on the canal.
- Skip the Amalfi Coast if you’re traveling in winter (much of it shuts down for the season), crowds and high prices drain you, or you came to Italy to see how locals live.
- Skip Rome if big cities overwhelm you, ancient ruins don’t excite you, or you want quiet, slow days.
Where To Travel In Italy?
Your first trip to Italy only happens once, so make it the one you’ll be talking about for years. Go where the locals still outnumber the tour groups, stay long enough to have a favorite café, and let the long lunches run as late as they want.
The famous sights will always be there for your second trip (and trust us, there will be a second trip). For this one, pick the Italy that feels like it was waiting just for you.
Still not sure? Our small-group tours take the guesswork out. We’ve planned the itinerary, chosen the destinations, and built in the experiences — all you have to do is show up excited to get to know Italy!
FAQs About Visiting Italy for the First Time
How many cities should I visit in Italy in one week?
One or two. Pick a region, settle into a single home base, and let the day trips come to you. Unpack once and travel deep instead of wide.
Is Italy expensive to visit?
It depends on where you go. The famous cities cost the most, and the closer you sit to a major landmark, the more you’ll pay for a mediocre plate of pasta. Step a few streets back, or head to the smaller towns, and the prices drop while the food gets better.
Do I need to speak Italian?
No. You’ll find English in hotels, restaurants, and shops across the big cities, and plenty of Italians will switch the moment they hear your accent. In small towns it gets thinner, and that’s where a few words go a long way. Say buongiorno when you walk in, grazie on your way out, and permesso when you squeeze past someone.
What should I wear?
Comfortable shoes first, because cobblestones are hard on new sneakers and even harder on heels. After that, pack layers you can add or peel off as the day warms up, and keep something on hand to cover your shoulders and knees. Churches across Italy expect it, and they can turn you away at the door.
What is the best city to fly into?
Pick the airport closest to your first stop. Rome Fiumicino and Milan Malpensa are two of the country’s busiest long-haul hubs. If you’re starting in the Veneto, Venice Marco Polo puts you right at the door, and Bari is the gateway to Puglia. Flying in close saves you a full day of travel.
