Planning a trip to Italy? Yeah, it can feel overwhelming—there’s just so much to see. After a handful of visits and helping friends plan their own adventures, I finally put together this two-week Italy itinerary. It captures the country’s magic but won’t leave you totally wiped out.
This route takes you through Rome’s ancient wonders, Florence’s Renaissance art, Venice’s dreamy canals, and the stunning landscapes of Lake Como and the Amalfi Coast. You’ll actually have time to enjoy each place, not just rush through it all.
Italy really rewards slowing down. I tried to balance the big sights with hidden gems and enough downtime for those long, lazy piazza lunches. You’ll get the major cities—Rome, Florence, Venice—but also some spots like Verona and Bologna that most tourists skip.
I mapped this route to cut down on backtracking, so you’ll spend more time soaking up Italy and less time shuffling luggage. I’ll share tips on trains, where to stay, and how to keep things stress-free. You can use this plan any time of year, though I’ll point out seasonal quirks to help you make the most of it.
Essential Italy Travel Planning Tips
Planning your Italy trip means making a few key choices that can really shape your experience. Over the years, I’ve realized timing, transportation, and where you sleep matter way more than you’d think.
Best Time to Visit Italy
Spring (April-May) and fall (September-October) just hit that sweet spot—good weather, fewer crowds. I visited Venice in early May and got sunny 70°F days and barely any lines.
Summer (June-August) turns up the heat, and the crowds and prices follow. Rome and Florence especially get packed. If you have to go in summer, seriously, book everything as early as you can.
Winter (November-March) has its perks—think Christmas markets and almost no tourists. But you’ll get rain, and some coastal spots basically shut down. Small-town hotels might not even open.
If you want a real cultural experience, try timing your trip for local festivals like Venice’s Carnival (February) or Siena’s Palio (July and August). It’s wild, in a good way.
How to Get Around: Trains, Cars, and Local Transport
I swear by Italy’s trains for city-to-city travel. The high-speed lines (Frecciarossa, Italo) zip you between Rome, Florence, and Venice in no time. Book on Trenitalia’s website a couple of months out for the best deals.
Driving only makes sense if you’re exploring rural Tuscany or the Amalfi Coast. Italian cities? Nightmare for parking, and those ZTL zones will get you fined fast.
In Rome and Milan, city buses and the metro work great. Venice is all about the vaporetto—if you’re staying more than two days, grab a multi-day pass.
Honestly, walking is the best way to see most Italian city centers. I always stumble on my favorite cafés and shops while wandering those tiny streets that buses can’t reach.
Booking Flights and Accommodations
I usually find the best flight deals to Italy about 4-6 months out. Venice Marco Polo and Rome Fiumicino are your main international gateways. Multi-city tickets (fly into Venice, out of Rome) save you time and hassle.
When I book hotels in Venice or Florence, I always pick central neighborhoods—even if they cost a bit more. San Marco in Venice or near the Duomo in Florence make all the difference. You’ll save so much time.
Airbnb can be a steal, especially for longer stays. Some of those apartments in historic buildings have so much character—chain hotels just can’t compete.
I always go for accommodations with free cancellation if I can. Plans change, trains strike, or you find out there’s a festival you didn’t know about. It happens!
Week One: Exploring the Heart of Italy
Your first week in Italy plunges you into the country’s deep history, art, and food. You’ll hit the iconic cities and get a real feel for what makes Italy tick.
Rome: Ancient Wonders and Vibrant Streets
Kick things off in Rome, where history just bursts out of every corner. I’d give yourself at least three days to soak up the Eternal City.
The Colosseum is a must. Go early if you want to dodge the crowds. I remember just standing there, blown away by how massive and old it is. Buy your tickets online—trust me, you don’t want to wait in those lines.
A short stroll away, the Roman Forum lets you walk right through ancient Rome’s daily life. I felt like I’d stepped back 2,000 years.
Don’t skip the Pantheon. That dome? It’s perfect. The light from the oculus makes the whole place feel magical, and it’s free to enter.
Make a wish at the Trevi Fountain—it’s cheesy, but hey, it’s tradition. Early mornings are best if you want it (almost) to yourself.
Spend an evening in Piazza Navona with a gelato, just people-watching. The Spanish Steps are another classic spot to just sit and soak up the city.
Florence: Renaissance Art and Tuscan Charm
Hop on a high-speed train to Florence, the Renaissance’s hometown. The city’s small enough to explore on foot, which I love.
The Uffizi Gallery has all the big names—Botticelli, Leonardo, Michelangelo. Buy tickets ahead and go early.
Florence’s Duomo dominates the skyline. If you can handle the climb, the view of Tuscany from the top is unreal.
Take a day trip from Florence to Siena. The bus ride through the Tuscan hills is gorgeous, and Siena feels like a medieval movie set.
Florence has the best gelato—my go-tos are Gelateria dei Neri and Vivoli. Try whatever’s in season; you won’t regret it.
The Ponte Vecchio bridge, packed with jewelry shops, is perfect for an evening walk. Watching the sunset from there as the Arno glows gold? Unbeatable.
Tuscan Gems and Medieval Towns
Tuscany’s all rolling hills, ancient towns, and food that’ll ruin you for anywhere else. I always find something new here, whether it’s art, history, or just the best meal of my life.
Siena and San Gimignano: Hilltop Marvels
Siena greets you with its shell-shaped Piazza del Campo, where the wild Palio horse race happens twice each summer. Climb the Torre del Mangia for killer views of the city and countryside. The cathedral’s marble floor is just stunning.
Not far away, San Gimignano rises with its medieval towers. I counted 14 left (there used to be 72!). It honestly feels like a fairytale, especially early in the morning before the crowds.
Both towns invite you to wander, sip local wine, and enjoy gelato in quiet corners far from the tourist crush.
Pisa and the Leaning Tower
The Leaning Tower of Pisa really is cooler in real life than in photos. Book your climb in advance—the 294 steps are worth it for the view.
But Pisa isn’t just the tower. The whole Piazza dei Miracoli is beautiful, with its cathedral, baptistery, and cemetery all together.
For a more local vibe, I crossed the River Arno and found some great student hangouts. Better prices, real Italian energy.
Charming Detours: Pienza, Umbria, and Perugia
Pienza charmed me with its Renaissance streets and valley views. Pope Pius II basically redesigned his hometown, and it shows. The local pecorino cheese? Don’t leave without trying it.
Once you hit Umbria, Perugia stands out with its university buzz and the annual Umbria Jazz Festival. Old meets new in a pretty cool way.
The underground city beneath Perugia fascinated me. I got in through the escalators at Rocca Paolina—suddenly you’re surrounded by ancient wells and ruins. It’s surreal.
Spiritual Escape: A Day in Assisi
Assisi perches on Mount Subasio, glowing pink at sunset. The Basilica of St. Francis blew me away with its Giotto frescoes.
Go early for a peaceful visit. Wandering those narrow streets, I stumbled on quiet corners and epic views.
Lunch was umbricelli pasta with truffles at a tiny family place. The owner told stories while I ate—honestly, it was the best meal of the day.
Before I left, I hiked part of the trail to Eremo delle Carceri. The forest and simple stone buildings felt worlds away from the crowds below.
Week Two: Northern Italy and the Italian Riviera
Your second week in Italy takes you north, where you’ll find Venice’s magic, Cinque Terre’s colors, and the style of Milan and Verona. Northern Italy mixes coastal beauty with history and a whole different vibe.
Venice: Canals, History, and Hidden Corners
Venice hooked me the second I stepped off the water taxi. It’s just unlike anywhere else. Give yourself at least 2-3 days to really get a feel for it.
Start with the biggies—St. Mark’s Square, the Basilica, and the Doge’s Palace. The €25 for the palace stings a little, but the art and history inside are worth it.
I stayed at Hotel Antiche Figure by the train station. You get canal views without the St. Mark’s price tag.
Definitely get lost in quieter neighborhoods like Cannaregio and Dorsoduro. You’ll find seafood pasta for half what you’d pay near the main sights.
Pro tip: The 48-hour vaporetto pass (€30) is a lifesaver. Unlimited water bus rides, and you see Venice from the water without dropping €80 on a gondola.
Cinque Terre and the Italian Riviera
Cinque Terre is the Italian Riviera’s showstopper—five fishing villages perched on cliffs. I’d base yourself in Monterosso al Mare or Vernazza for 2-3 days.
The hiking trails link all five villages, and the coastal views are unreal. The Via dell’Amore is the most famous, but sometimes it’s closed, so check ahead.
If you love the beach, Monterosso’s sand is your spot. Photographers, you’ll want to hit Manarola at sunset for those postcard shots.
Getting around is easy with the Cinque Terre Card (€16 a day)—unlimited trains between villages and access to the trails.
You have to try the anchovies, pesto pasta (a Ligurian thing), and the local white wines like Vermentino. Ristorante Belforte in Vernazza does incredible seafood with a view you won’t forget.
Side Trips: Verona and Milan
If you’re heading to or from Venice, you really shouldn’t skip these northern cities. They make fantastic day trips or even quick overnight stops.
Verona totally charmed me with its Roman arena and, of course, Juliet’s balcony (yeah, the one from Romeo and Juliet). The city center feels compact and is super easy to explore on foot.
I only spent a day here and honestly, I wish I’d had more time. Those medieval streets and the restaurants are just begging for a longer visit.
Milan, on the other hand, brings a totally different vibe—sleek, stylish, and buzzing with energy. You can’t miss Leonardo da Vinci’s “Last Supper” (just a heads up, you need to book tickets months ahead) and the incredible Duomo cathedral.
- Galleria Vittorio Emanuele II (luxury brands)
- Brera district (boutiques and designers)
- Navigli area (vintage shops and Sunday markets)
If you love football, or even if you just want to see what all the fuss is about, catching an AC Milan or Inter Milan match at San Siro stadium is something you’ll remember.
Unforgettable Italian Experiences
Italy just hands you magical moments—sometimes when you least expect them. On my two-week trip, I stumbled into experiences that blended food, history, and those dreamy coastal views. The country really knows how to stick in your memory.
Italian Food: Gelato, Pizza, and Regional Delicacies
Honestly, you can’t go to Italy and not dive into the food. Authentic Italian cuisine is unforgettable.
I still think about the creamy gelato I ate in Florence. Artisanal shops like Gelateria dei Neri serve up flavors made from whatever’s in season. Always look for the word “artigianale”—that’s the good stuff.
Pizza in Naples blew my mind. The crust is thin, a little charred, and the toppings are simple but top-notch. At L’Antica Pizzeria da Michele, I watched the pizzaiolos work their magic and turn out perfect Margheritas in under 90 seconds.
Every region brings something different to the table:
- Northern Italy: Risotto in Milan, truffles in Piedmont
- Central Italy: Bistecca alla Fiorentina in Tuscany, carbonara in Rome
- Southern Italy: Fresh seafood pasta by the coast, cannoli in Sicily
Take your time at meals. Italians linger over dinner, and honestly, it’s one of the best parts—conversation flows right along with the wine.
UNESCO World Heritage Sites Worth Visiting
Italy has 58 UNESCO World Heritage Sites. That’s more than anywhere else on the planet.
Walking through the ancient ruins of Pompeii just left me speechless. I wandered streets that have been frozen since 79 AD. You can peek into bakeries and bath houses and really feel that connection to the past.
Florence’s entire historic center is UNESCO-listed. I spent hours staring up at Brunelleschi’s dome at the Cathedral. That thing is a Renaissance marvel and still rules the skyline.
Ravenna doesn’t get the crowds, but wow—the Byzantine mosaics are breathtaking. These mosaics are 1,500 years old, yet the gold leaf and colors look almost modern.
Try to hit these sites first thing in the morning or later in the afternoon. You’ll dodge the crowds and the worst of the heat. Some places offer guided tours that really help you imagine life back then.
Hiking Adventures and Scenic Trails
Italy’s landscapes are so much more than just the cities you see in travel guides. The Dolomites in the north gave me my most jaw-dropping mountain views—those jagged peaks and wildflower meadows feel straight out of a storybook.
Cinque Terre has this coastal path that links five colorful fishing villages. You’ll burn off some of that pasta while soaking in those Mediterranean views. The Blue Trail (Sentiero Azzurro) is the most popular, but sometimes sections close for repairs.
Even if you’re near a big city, you can get into nature pretty quickly:
- Path of the Gods above the Amalfi Coast
- Monte Ceceri near Florence (Leonardo da Vinci tried out his flying machines here)
- Parco degli Acquedotti just outside Rome
Before you go, always check the trail conditions. Spring rains can make some paths pretty slippery.
The Amalfi Coast and Coastal Escapes
Honestly, the Amalfi Coast blew me away. Those vertical towns grip the cliffs so tightly, you almost wonder how they don’t tumble into the Mediterranean. I spent three days in Positano, and I still think about those pastel buildings tumbling down to the curve of the beach.
Riding the SITA bus along the coast road? Wild experience—my knuckles turned white, but the views made it all worth it. If you’d rather skip the adrenaline, you can catch ferries between Amalfi, Positano, and Ravello. The ferry ride feels much more laid-back.
You should check out Ravello’s Villa Rufolo gardens. They hang over the coast, and the views are unreal. Richard Wagner found inspiration here, and you can see why—there’s something magical about that spot.
If you can swing it, aim for May or September. The weather’s just right, and you’ll dodge the worst of the summer crowds and high prices. Even during the busiest times, you can find peace by heading out early or losing yourself a few streets away from the main drag.
