2-Week Italy Itinerary: 5 Amazing Ideas For First-Timers

Planning a trip to Italy? Good luck narrowing it down. Between Rome’s ruins, Venice’s canals, Milan’s style, Florence’s art, and Sicily’s everything, Italy’s like a buffet you can’t possibly finish. No wonder crafting an itinerary feels like solving a delicious puzzle

To help you out, this article offers five takes on the perfect two week Italy itinerary, each tailored to a different travel style and taste.

2 Week Italy Itinerary: Map

Before we get into the details, the two week Italy itinerary map below offers a handy overview of where each route takes you

Now read on to compare all the itineraries in detail, pick the one that speaks to you the most, and start planning your Italian trip!

This itinerary covers Northern Italy’s greatest hits, from Cinque Terre’s cliffs to Venice’s canals, with stylish stops like Milan and Lake Como in between.

Day 1-3: Milan and Lake Como

Milan makes a stylish starting point for your Northern Italy two week itinerary. This fast-paced metropolis is known for global events like Fashion Week and Design Week, but it’s also packed with cultural heavyweights—the Duomo Cathedral, Leonardo da Vinci’s Last Supper, Sforza Castle, and the artsy Brera district. Just an hour away by train, Lake Como offers a dreamy contrast: alpine views, elegant villas, and postcard-perfect towns. It’s one of Italy’s most breathtaking escapes.

Want help planning your three days in Milan and Lake Como? This guide breaks it down. 

Day 4-7: Cinque Terre

Monterosso, one of the five villages of Cinque Terre (literally “five lands”), is just a 3-hour train ride from Milan. You can leave the city at 8 am and get there in time just in time for brunch. 

The five villages of the Cinque Terre—Monterosso, Manarola, Vernazza, Corniglia, and Riomaggiore—are basically the heart of the Italian Riviera. Each one’s got its own vibe: dramatic cliffs, colorful houses, quiet harbors, and steep hillsides. A local train zips between them in minutes, making it easy to explore. Ferries cost more, but the views from the water are worth it at least once.

For more details on how to organize your 3 days in Cinque Terre, check out this post.

Day 8: Portofino Day-Trip

Just up the coast from Cinque Terre sits Portofino, the former fishing village turned high-fashion postcard. These days, it’s all designer boutiques, glossy yachts, and Aperol spritzes with a view. If you’re day-tripping from Cinque Terre, swing by for a stroll through its narrow lanes, sip something bubbly at a waterfront café, and climb up to Castello Brown for a panorama that’s pure Riviera drama.

Day 9: Cinque Terre to Venice

To reach Venice from Monterosso, you’ll need to backtrack to Milan first, then catch a direct train east. It’s about six hours start to finish—so if you’re tackling this on day nine, set that alarm early and pack snacks.

Day 10-14: Venice

Your two-week Northern Italy adventure ends with a showstopper: Venice. Ask anyone who’s been: this floating city is in a league of its own.

Spend your five days soaking it in. Start early at St. Mark’s Square before the crowds, snap the Bridge of Sighs, and treat yourself to zaleti or a bigné from a tucked-away pastry shop. Wander to Rialto Bridge, duck into the Frari Basilica, and people-watch over a tramezzino in Campo Santa Margherita. Don’t miss Libreria Acqua Alta, where books spill out of bathtubs and gondolas.

On your final day, hop a vaporetto to San Giorgio Island, climb the campanile, and take in one last, sweeping view of Venice—because yes, it really is that beautiful.

Love hiking and alpine views? This two week Italy itinerary is your ticket to the country’s most stunning trails and lakes. Starting in Milan, swinging through Venice, and heading into the jaw-dropping Dolomites: it’s Italy, elevated.

Day 1-2: Milan and Lake Como

With its international airports and fast train links, Milan is a natural launchpad for any Northern Italy itinerary. After a day of city sights, hop a train to Lake Como for a change of pace. The Greenway trail—an easygoing 10 km walk from Colonno to Cadenabbia—serves up lake views, charming villages, and enough postcard moments to fill your camera roll.

Day 3-6: Venice

Just three hours from Milan by train, Venice is non-negotiable. We’ve said it before: spend four days soaking up gondola glides, Byzantine domes, and Renaissance charm. Start at St. Mark’s Square, cross the Rialto Bridge, and let the city’s centuries-old beauty do the rest. It’s romantic and unforgettable.

Day 7: Venice to Dolomites

From Venice, rent a car and drive 2 hours north to Cortina d’Ampezzo, your base for exploring the Dolomites. This mountain range spans the regions of Veneto and Trentino-Alto Adige, with road signs often in German due to its proximity to Austria. A car is essential for reaching trailheads, lakes, and scenic villages. Prefer public transport? You can also take a train to Calalzo di Cadore, then transfer to a local bus to Cortina. Cortina is great for both summer hikes and winter sports.

Day 8-14: Dolomites

The Dolomites are all about getting outside. You’ll want to hike, drive, and stop often. Lake Braies is a must, but go early to beat the crowds. Tre Cime di Lavaredo is the classic hike: dramatic peaks, well-marked trails, and views all the way. Lake Carezza is a quick stop with unreal colors. Seceda ridge walk is simply unforgettable. We’ve mapped out the best places to see in the Dolomites and the top hikes worth your boots, so you can plan your days without the guesswork.

This two-week Italy itinerary takes you from the rolling hills of Tuscany to the Renaissance streets of Florence, and finally into the heart of Rome. In Tuscany, expect scenic drives past sunflower fields, hilltop towns, and vineyards serving world-class wine. Florence offers art, architecture, and easy day trips. Then it’s on to Rome: history, pasta, piazzas, and everything in between. 

Day 1-4: Florence

Florence is the beating heart of the Renaissance, packed with masterpieces by Michelangelo, Brunelleschi, and Botticelli. The Uffizi Gallery is a must, but so are the streets, with cobblestones, piazzas, and architecture that turns every corner into a photo op. The city’s compact size makes it perfect for walking, and its energy is young and vibrant thanks to students and creatives. Spend your time museum-hopping, shopping for leather goods, sipping Chianti, or joining a guided walking tour to get the full story behind the stones.

Day 4-6: Tuscany countryside 

Florence sits in the heart of Tuscany, a region known for its vineyards, hilltop towns, and postcard-perfect countryside. If you’re heading out of the city, make Val d’Orcia your target, especially places like Pienza or Montepulciano. South of Florence and Siena, this area is the Tuscany you’ve seen in photos—rolling hills, cypress-lined roads, sunflower fields, and stone villas. It’s ideal for a scenic drive, a wine tasting stop, or just soaking in the views.

Day 8-14: Rome

From Florence, Rome is just two hours by train: easy, fast, and worth every minute.

Once you arrive, prepare for sensory overload: ancient ruins, world-class art, and food that’ll ruin you for pasta anywhere else. Hit the big landmarks—Colosseum, Trevi Fountain, St. Peter’s Basilica—but leave time to wander. Rome is an open-air museum, and every piazza has a story.

If you’re after a romantic Italy itinerary, this one nails it. Start in Rome, walk ancient streets, eat too much pasta, and soak up the history. Then head south to the Amalfi Coast, where cliffside towns and sea views do the rest. It’s a perfect mix of culture and coast, ideal for couples who want both city buzz and beach time.

Day 1-7: Rome

You’ve already met Rome previously in this article. Our advice is the same here: spend your days exploring ancient landmarks like the Colosseum and Roman Forum, wandering through Baroque piazzas, and getting lost in neighborhoods like Trastevere. Don’t miss Via Margutta for galleries and antiques, and leave time to just roam: Rome rewards curiosity. 

Day 8: Rome to Amalfi Coast

Getting to the Amalfi Coast takes a few steps, but it’s worth it.

The easiest budget-friendly route is a high-speed train from Roma Termini to Salerno, then a direct SITA bus to Amalfi. If you prefer comfort, take the train to Naples and book a private transfer from there: faster, less hassle, and more scenic. Either way, plan ahead, especially in summer when routes fill up quickly.

Day 9-14: Amalfi Coast and Capri

Spend your final days of this two week Italy itinerary soaking up the Amalfi Coast, with cliffside towns, lemon groves, and endless sea views. Start in Positano for postcard-perfect streets, then head to Praiano for a quieter vibe. Stop at Furore to see Italy’s only fjord, and explore Amalfi’s historic center. Don’t miss Ravello up in the hills, because Villa Cimbrone and Villa Rufolo are worth the climb. Capri is just a short ferry ride away: dramatic cliffs, chic shops, and the famous Blue Grotto. Plan your days around views, swims, and slow lunches.

For more details on how to organize your 5 days in the Amalfi Coast, check out this post.

If you’ve done Rome, Florence, and Venice, or just want something different, Sicily hits differently. It’s raw, sun-drenched, and full of character. Think Mediterranean island vibes with ancient ruins, volcanic landscapes, and food that’s bold and unforgettable. Start in Palermo and wrap it up in the Aeolian Islands, where the pace slows and the sunsets steal the show.

Day 1-3: Palermo

Start in Palermo, Sicily’s gritty, sun-soaked capital. It’s loud, layered, and full of life. Arab-Norman churches sit next to crumbling Baroque facades. The Ballarò and Capo markets are messy, crowded, and unforgettable: grab a panelle or arancina and just wander. The streets smell like citrus and grilled meat, and scooters zip past like nobody’s watching. When you need a breather, Mondello beach is 20 minutes away: turquoise water, soft sand, and cold beer.

Day 4-6: Zingaro Reserve and Scopello

Leave the city behind and head west—Zingaro Natural Reserve feels like a different planet. No roads, no noise, just a rugged coastal trail with cliffs, coves, and turquoise water. Hike the 8km stretch, stop for swims at hidden beaches, and pack snacks because there’s nowhere to buy anything inside the reserve.

Just up the road, Scopello is worth a detour. It’s tiny, quiet, and home to the old Tonnara—once a working fishery, now a backdrop for every dreamy Sicily photo you’ve seen.

Day 7-9: Cefalù

Cefalù’s got that easy mix of beach and old town. The sand runs right up to the edge of the city, and the streets feel like they were built to get lost in. Grab a granita, sit by the water, and let the day drift. It’s slow, warm, and exactly what you need halfway through the trip.

Day 10-14: Aeolian Islands

Leave Cefalù early and head west to Milazzo—about 90 minutes by car or train. From there, catch a ferry to the Aeolian Islands. These volcanic islands sit off Sicily’s north coast, scattered across the Tyrrhenian Sea. 

Pick one to sleep, then island-hop by boat.

Lipari’s the hub with easy ferries, good food, and a mix of locals and travelers. Panarea is all style: whitewashed villas, aperitivo views, and yachts bobbing offshore. Stromboli and Vulcano bring the drama with active craters you can hike at sunset. Salina’s slower, greener, and full of good wine and quiet charm. If you want off-grid, head to Filicudi or Alicudi—no crowds, no noise, just sea, sky, and time.

Italy Itinerary Q&A

How many days do you need for an Italy itinerary?

Two weeks is the sweet spot. It gives you enough time to explore multiple regions without rushing through train stations or skipping meals. With 14 days, you can comfortably fit in a mix of cities (like Milan or Florence or Rome) plus a coastline, and/or countryside. If you’ve only got 10 days or less, stick to one or two areas max. Trying to do it all will leave you exhausted and missing the point. Italy rewards slow travel.

What’s the best time of year to visit Italy?

May to early June and September to mid-October are ideal. You’ll get warm days, cooler nights, and fewer crowds than peak summer. July and August can be brutally hot, especially in the south, and many locals leave cities for the coast. Winter has its charm, especially in places like Venice or the Dolomites, but expect shorter days and limited ferry service in coastal areas.

Should you travel Italy by train or rent a car?

It depends on where you’re going. Trains are fast, reliable, and perfect for city-to-city travel—Rome, Florence, Milan, Venice, all well-connected. But if you’re heading to Sicily, the Dolomites, or rural Tuscany, a car gives you freedom to explore small towns, scenic routes, and places trains don’t reach. Just be ready for narrow roads, limited parking, and some chaotic driving in southern regions.

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