Italy is one of those rare countries that can be anything to anyone. Whether you’re dreaming of ancient ruins and Renaissance art, picturesque villages and mountain lakes, or coastal cliffs and culinary heaven, Italy delivers. The only challenge? Deciding how to make the most of your time there.
This comprehensive guide provides curated itineraries for trips lasting 5, 7, 10, 14, and 21 days. Each length includes three thoughtfully planned routes to suit different interests: a classic itinerary for first-time visitors, a cultural and historic path, and a more scenic, relaxed option for nature lovers or those returning to Italy.
How to Use This Guide
Start by determining how long you’ll be in Italy. Then, pick the itinerary that most closely matches your travel style or interests. These itineraries assume you’ll be traveling by train where possible, with optional car rentals in certain regions like Tuscany or the Amalfi Coast.
5 Days in Italy: Three Itinerary Options
Option 1: Classic Italy Sampler (Rome & Florence)
This itinerary is ideal for first-time visitors wanting a taste of Italy’s greatest hits.
- Days 1–2: Rome Explore the Colosseum, Roman Forum, and Palatine Hill on day one, then spend day two marveling at the Vatican Museums, St. Peter’s Basilica, and the Sistine Chapel. In the evening, toss a coin in the Trevi Fountain and enjoy dinner in the Trastevere neighborhood.
- Days 3–5: Florence Take a high-speed train to Florence. Visit the Duomo, Uffizi Gallery, and Accademia Gallery (home of Michelangelo’s David). Wander across the Ponte Vecchio and enjoy panoramic views from Piazzale Michelangelo. Consider a half-day trip to nearby Pisa or Fiesole.
Option 2: Culture and Ruins (Rome & Naples)
Perfect for history buffs and archaeology fans.
- Days 1–3: Rome Cover the same major Roman sights listed above. Add time for Capitoline Museums or the Baths of Caracalla if you’re especially into Roman history.
- Days 4–5: Naples and Pompeii Take the train to Naples, then spend one day exploring Pompeii or Herculaneum and another enjoying Neapolitan pizza, the National Archaeological Museum, and a stroll along Spaccanapoli.
Option 3: Romantic Escape (Venice & Verona)
Best for a slower-paced, charming getaway.
- Days 1–3: Venice Arrive in Venice and let yourself get lost. Visit St. Mark’s Basilica, Doge’s Palace, and the Rialto Bridge. Take a gondola ride if you like, or hop on a vaporetto to the islands of Murano and Burano.
- Days 4–5: Verona Take the train to Verona. Visit Juliet’s House, the Roman Arena, and walk along the Adige River. Don’t miss a sunset view from Castel San Pietro.
7 Days in Italy: Three Itinerary Options
Option 1: Italy’s Golden Triangle (Rome, Florence, Venice)
Ideal for first-time visitors who want to hit the iconic cities.
- Days 1–2: Rome Visit the Colosseum, Roman Forum, and Vatican. Enjoy dinner in the Jewish Ghetto or Campo de’ Fiori.
- Days 3–4: Florence Tour the Uffizi and Accademia. Walk the medieval streets and visit artisan shops in the Oltrarno district.
- Days 5–7: Venice See the main attractions in San Marco, then explore the quieter Dorsoduro and Cannaregio neighborhoods.
Option 2: Tuscany and the Heart of Italy
For those who prefer art, food, and countryside views.
- Days 1–2: Florence Dive into Florence’s Renaissance wonders.
- Days 3–5: Tuscan Hill Towns Rent a car and explore Siena, San Gimignano, and Montepulciano. Stay in a countryside agriturismo and enjoy wine tastings and home-cooked meals.
- Days 6–7: Val d’Orcia Visit Pienza, Montalcino, and Bagno Vignoni. Soak in natural hot springs and enjoy the scenery.
Option 3: South of Italy and the Coast
For a Mediterranean-flavored adventure.
- Days 1–2: Naples Discover Naples’ food and historic center. Day trip to Pompeii or Mount Vesuvius.
- Days 3–5: Amalfi Coast Base yourself in Positano, Amalfi, or Ravello. Hike the Path of the Gods or cruise the coast by boat.
- Days 6–7: Capri or Sorrento Take a ferry to Capri to see the Blue Grotto or explore Sorrento’s cliffs and lemon groves.
10 Days in Italy: Three Itinerary Options
Option 1: Classic Italy with a Twist
- Days 1–3: Rome Thoroughly explore the Eternal City, including Trastevere and Aventine Hill.
- Days 4–5: Florence Add visits to Boboli Gardens and day trips to Pisa or Lucca.
- Days 6–7: Venice Visit art museums like the Peggy Guggenheim Collection and take a sunset ride down the Grand Canal.
- Days 8–10: Milan or Lake Como Choose Milan for fashion and The Last Supper, or Lake Como for lakeside villages like Bellagio and Varenna.
Option 2: Italy for Food and Wine Lovers
- Days 1–2: Bologna Explore Bologna’s markets and indulge in tagliatelle al ragù. Don’t miss a food tour.
- Days 3–5: Florence & Chianti Visit Florence, then head to Chianti for wine tastings and rolling vineyard views.
- Days 6–7: Rome Sample carbonara, cacio e pepe, and gelato.
- Days 8–10: Naples or Amalfi Coast End with authentic pizza, seafood, and lemon desserts.
Option 3: Natural Beauty and Charm
- Days 1–2: Milan Visit the Duomo and Brera district.
- Days 3–4: Lake Como Cruise the lake and relax in lakeside towns.
- Days 5–6: Dolomites Stay in a mountain lodge, hike alpine trails, or drive through scenic passes.
- Days 7–10: Venice and Surroundings Wind down in Venice, with a day trip to Torcello or Padua.
14 Days in Italy: Three Itinerary Options
Option 1: Grand Tour of Italy
- Days 1–3: Rome Hit the Vatican, ruins, and less-visited neighborhoods like Testaccio.
- Days 4–5: Florence See Michelangelo’s David and enjoy wine in Chianti.
- Days 6–7: Tuscany Road trip through the Val d’Orcia.
- Days 8–9: Venice Stroll along canals and visit the outer islands.
- Days 10–11: Milan & Lake Como Blend city culture with lake tranquility.
- Days 12–14: Cinque Terre or Amalfi Coast End with sea views and coastal hikes.
Option 2: South-Central Italy Adventure
- Days 1–3: Rome Mix major sights with hidden gems.
- Days 4–6: Naples & Pompeii Dive deep into southern Italian culture and archaeology.
- Days 7–9: Amalfi Coast Relax in Positano or hike through Ravello.
- Days 10–12: Matera Explore the ancient cave dwellings of the Sassi.
- Days 13–14: Puglia Visit Alberobello or Lecce for baroque beauty.
Option 3: Northern Italy and the Lakes
- Days 1–2: Milan Explore museums, shops, and parks.
- Days 3–5: Lake Garda & Verona Combine Shakespearean romance with lake scenery.
- Days 6–8: Dolomites Go hiking or simply enjoy alpine towns like Ortisei.
- Days 9–11: Venice Add a food or rowing tour to your visit.
- Days 12–14: Bologna & Modena Sample balsamic vinegar and fresh pasta.
21 Days in Italy: Three Itinerary Options
Option 1: Ultimate Classic Italy (North to South)
- Week 1: Milan, Lake Como, Venice Shop and see art in Milan, relax by Lake Como, and wander Venice’s alleys.
- Week 2: Florence, Tuscany, Rome Dive into Renaissance art, drive through Chianti, and see the Eternal City.
- Week 3: Naples, Amalfi Coast, Capri Experience southern Italian culture and seaside relaxation.
Option 2: Hidden Gems + Famous Cities
- Week 1: Rome, Orvieto See top sights, then escape to a cliff-top town.
- Week 2: Assisi, Perugia, Siena, Florence Explore spiritual and medieval towns before arriving in Florence.
- Week 3: Bologna, Verona, Lake Garda Discover Italy’s heartland and relax by the lake.
Option 3: Coastal & Island Escape
- Week 1: Rome & Naples Start with ancient history and big-city energy.
- Week 2: Amalfi Coast & Capri Soak up the sun and coastal charm.
- Week 3: Sicily Visit Palermo, Taormina, and Mount Etna. Enjoy beaches, temples, and volcanic landscapes.
Final Tips for Planning Your Italy Trip
- Best Time to Visit: April to June and September to October offer pleasant weather without overwhelming crowds.
- Train Travel: Efficient between major cities. Book in advance for high-speed routes.
- Car Rental: Recommended in Tuscany, Umbria, and the Amalfi Coast.
- Flights: Consider open-jaw tickets (e.g., fly into Rome, out of Milan) to maximize your time.
- Pace Yourself: Don’t try to do everything. Leave time for a lazy lunch or a spontaneous detour.
Italy rewards those who wander but also respects those who plan. With the right itinerary, your trip will feel like a perfectly composed opera—rich, varied, and unforgettable.