Two weeks in Italy is the sweet spot. It's long enough to soak in the country's absurd range — ancient ruins, Renaissance art, turquoise coastlines, and more carbs than you thought humanly possible — without feeling like you're sprinting through a checklist. You'll have time to linger over a three-hour lunch, get genuinely lost in Venice, and still hit all the highlights that made you want to visit in the first place.
This itinerary takes you from Rome up through Florence and Cinque Terre, across to Venice, and down to the Amalfi Coast before wrapping up in Naples. It's a well-tested loop that balances iconic sights with slower, more human-paced days. Here's the full day-by-day breakdown.
Before You Go
Trains are your best friend. Italy's rail network is excellent. Book high-speed Trenitalia or Italo trains between major cities — Rome to Florence is 1.5 hours, Florence to Venice about 2 hours. Book a week or two in advance for the best prices on Trenitalia's website. For shorter regional hops (like the Cinque Terre coastal line), you can buy tickets same-day at the station.
Money: Card payments are widely accepted in cities, but carry some cash for smaller towns, beach clubs, and market stalls. Tipping isn't expected, though rounding up or leaving a euro or two for great service is always appreciated.
Connectivity: Pick up a local SIM at the airport or grab an eSIM before you fly. Having mobile data makes navigating train schedules, Google Maps, and restaurant reservations dramatically easier.
When to go: May-June and September-October are ideal. You dodge the worst of the summer crowds and heat. July-August works but expect higher prices, packed attractions, and 35-degree days on the Amalfi Coast. For more on timing, check our guide on the best summer destinations.
Days 1-3: Rome
Rome deserves at least three full days, and even then you'll leave wanting more.
Day 1 — Start at the Colosseum and Roman Forum. Book skip-the-line tickets online (this is non-negotiable; the queues are brutal). Wander through the Forum, up Palatine Hill, and then walk to the Pantheon. In the evening, cross the river to Trastevere — it's the neighborhood that most people fall in love with. Narrow cobblestone streets, ivy-covered buildings, and some of Rome's best food. Grab dinner at Tonnarello for classic Roman pasta, or Da Enzo al 29 if you can snag a table (arrive early or expect a wait).
Day 2 — Vatican day. Hit St. Peter's Basilica first thing in the morning, then the Vatican Museums and Sistine Chapel. Book the earliest entry slot you can find. Afterward, walk to Castel Sant'Angelo and then slowly make your way to Piazza Navona for a late lunch. Try supplì (fried rice balls) from a street vendor — Rome's ultimate snack food.
Day 3 — Slow Rome. Visit the Borghese Gallery (reservations required), stroll through Villa Borghese park, toss a coin in the Trevi Fountain, and wander the Spanish Steps area. For your final Roman dinner, find a spot near Campo de' Fiori. Roscioli is phenomenal for cacio e pepe and their curated wine list. Also: do not leave Rome without trying a maritozzo (cream-filled brioche) from Regoli bakery near Termini.
Days 4-6: Florence & Tuscany
Take the morning high-speed train to Florence — you'll be there before lunch.
Day 4 — Drop your bags and head straight to the Duomo. Climb Brunelleschi's dome for the panoramic views (book ahead). Walk through the leather markets around San Lorenzo, cross the Ponte Vecchio, and explore the Oltrarno neighborhood on the south side of the river. Dinner at Trattoria Mario is a Florence institution — communal tables, handwritten menus, and Florentine steak that's been done the same way for decades.
Day 5 — Uffizi Gallery in the morning (again, pre-booked tickets are essential). Spend the afternoon at the Accademia to see Michelangelo's David, then wander up to Piazzale Michelangelo for sunset views over the city. Grab a lampredotto sandwich from a street cart — Florence's signature street food, and an acquired taste worth acquiring.
Day 6 — Day trip to the Tuscan hill towns. Take a bus to Siena for its stunning Piazza del Campo and Gothic cathedral, or head to San Gimignano — a tiny medieval town famous for its towers and surprisingly excellent gelato (try Gelateria Dondoli, a world championship winner). Return to Florence in the evening for a final Tuscan dinner. Il Latini does an outstanding bistecca alla fiorentina.
Days 7-8: Cinque Terre
Take the train from Florence to La Spezia (about 2.5 hours), then hop the regional train into the five villages.
Day 7 — Base yourself in Manarola or Vernazza (the two most photogenic villages). Spend the day hiking between villages — the Sentiero Azzurro trail connects all five, though not every section is always open. The Vernazza to Monterosso stretch is the most scenic. Cool off with a swim at Monterosso's beach afterward.
Day 8 — Visit the remaining villages by train (it's just a few minutes between each). Eat focaccia di Recco and freshly caught anchovies at a seaside trattoria. Ristorante Belforte in Vernazza, built into the old watchtower overlooking the sea, is worth the splurge. In the afternoon, take the train to Venice.
Days 9-10: Venice
Venice doesn't need a plan — it needs surrender. Put away the map and let yourself get lost. Seriously. That's the whole point.
Day 9 — Arrive and check in, then take a vaporetto (water bus) down the Grand Canal to St. Mark's Square. Visit the Basilica and the Doge's Palace, then wander into the quieter Dorsoduro and Cannaregio neighborhoods. For dinner, go to Osteria Alle Testiere — tiny, reservation-only, and some of the best seafood in the city. Order whatever they tell you to order.
Day 10 — Take the vaporetto to Murano (famous for glassblowing) and Burano (famous for being impossibly colorful). Back in Venice, do a cicchetti crawl — Venice's version of tapas. Hop between bars near the Rialto Bridge, grabbing small plates and glasses of local wine at each stop. Cantina Do Spade and All'Arco are excellent starting points.
Days 11-13: Amalfi Coast
Take the train from Venice back down to Naples (about 4.5 hours by high-speed rail), then a bus or ferry to the Amalfi Coast.
Day 11 — Settle into Positano. Walk the steep streets down to the beach, swim in the Tyrrhenian Sea, and have dinner at Da Vincenzo — family-run, unpretentious, and the kind of seafood pasta that makes you question every Italian meal you've had at home.
Day 12 — Bus to Ravello, perched high above the coast. Visit Villa Rufolo and its gardens, then walk the Path of the Gods (Sentiero degli Dei) — a cliff-side hiking trail with views that genuinely stop you in your tracks. It's about 4 hours one-way, so plan accordingly.
Day 13 — Day trip to Capri. Take the ferry from Positano or Amalfi. Visit the Blue Grotto (weather permitting), ride the chairlift up Monte Solaro, and have lunch in Anacapri, which is quieter and cheaper than Capri town. Le Arcate does a fantastic caprese salad — mozzarella this fresh should be illegal elsewhere.
Day 14: Naples & Departure
Head to Naples for your final day. Naples is raw, chaotic, beautiful, and home to the best pizza on Earth — that last point is not debatable.
Go straight to L'Antica Pizzeria Da Michele or Sorbillo for a margherita pizza. Visit the Naples National Archaeological Museum — it houses most of the treasures from Pompeii and Herculaneum, and it's one of the most underrated museums in Europe. Walk through the Spaccanapoli street, grab a sfogliatella (flaky pastry filled with ricotta) from Attanasio near the train station, and catch your flight home from Naples International Airport.
Budget Tips
Two weeks in Italy can be done on a range of budgets. For more detailed strategies, see our budget travel tips.
- Book trains early — high-speed fares can be as low as 9-19 euros if purchased 2-3 weeks ahead.
- Eat lunch as your big meal — many restaurants offer a pranzo (lunch) menu that's half the dinner price.
- Stay in apartments — especially on the Amalfi Coast, where hotel prices are steep. A small apartment with a kitchen saves a fortune.
- Free museum days — the first Sunday of each month, many Italian state museums offer free entry.
- Drink house wine — it's usually excellent and costs 3-5 euros a glass. No need to splurge on bottles.
Plan Your Italy Trip
Two weeks, five regions, and enough memories to fill a lifetime. If you're ready to start building out your own version of this itinerary, JourneyOutline makes it easy to organize your day-by-day plans, save restaurant picks, and keep all your transport details in one place. Start planning your Italy trip and customize this route to match your pace and interests. And if you're thinking about combining Italy with other European stops, our guide on how to plan a Europe trip has everything you need to get started.