Italy, with its rich history, vibrant culture, and breathtaking landscapes, offers endless possibilities for an unforgettable trip. While five days may seem short for a country brimming with must-see sights, you can still experience many of its key highlights by focusing on its most iconic cities: Rome and Florence (with a little in between). Here’s the perfect five day Italy itinerary for an Italian adventure that balances culture, history, and leisure.
Day 1: Rome – The Eternal City
Morning/Early afternoon: Arrival & Ancient Rome
- Arrive in Rome and check get yourself checked into a centrally located hotel that makes the sites easily walkable. Here are a couple we recommend:
Explore other centrally located hotels in Rome
- Start your adventure with a visit to the Colosseum, the Roman Forum and Palatine Hill, all within a stone’s throw of one another. Because this is such a brief trip, you’re going to see this itinerary strongly recommend pre-purchasing tickets ahead of time. This ensures you are guaranteed entry to many of these popular sites, and just as importantly, have a local guide provide you with the history, context and stories of these incredible sites. A final tip, be sure to see all three. The Colosseum is iconic but the Forum really tells the history of ancient Rome.
Find a tour for the Colosseum, Roman Forum and Palatine Hill
Late Afternoon: Pantheon & Trevi Fountain
- After the tour, start to make your way towards the Pantheon. It’s by walking that you’ll experience the essence of Rome. Along the way, have a late lunch at a local trattoria. When you arrive at the Pantheon, you’ll likely notice a long line. But don’t worry, because you’ve read this article, you’ve pre-purchased skip the line tickets and can easily get quick access.
- After the Pantheon, Visit the nearby Piazza Navona and maybe visit a nearby caffee for an espresso if you’re starting to feel the effects of your travel.
Evening: Dinner in Trastevere
- In the evening, wander through Trastevere, a vibrant and energetic neighborhood known for its narrow streets and authentic Roman restaurants. Enjoy a romantic dinner at Trattoria Da Enzo al 29 and soak in the local atmosphere.
- Check out our tips for all you need to know when dining out in Italy
- To end your day, we recommend this time to be your visit to the iconic Trevi Fountain. It can be crowded during the day but less so later in the evening. Don’t forget to toss a coin in the fountain and make a wish to return to Rome.
Day 2: Rome’s Cultural Treasures
Morning: Vatican City
- Start your day early with a visit to Vatican City, the heart of the Roman Catholic Church. Explore St. Peter’s Basilica and admire the breathtaking art of the Vatican Museum and the frescoes in the Sistine Chapel, including Michelangelo’s famed ceiling. If you really want to see the Sistine Chapel, to guarantee entry and avoid wasting time in lines, it is strongly recommended you purchase tickets ahead of time.
- Find tickets for St. Peter’s, Vatican Museum and the Sistine Chapel.
Afternoon: Borghese Gardens & Spanish Steps
- Enjoy a relaxing afternoon in the beautiful Borghese Gardens. If you’re an art lover, don’t miss the Borghese Gallery, which houses works by Bernini, Caravaggio, and Raphael. Find tickets for the Borghese Gallery.
- End your day with a stroll to the Spanish Steps, where you can take in the lively atmosphere of the piazza and enjoy some shopping or a delicious gelato.
Evening: Piazza Navona & Dinner
- After your long day, make your way back to Piazza Navona for an aperitivo, surrounded by the square’s beautiful fountains and street artists. For dinner, enjoy a meal at Ristorante Santa Lucia, a charming spot near the square.
Day 3: Florence – Renaissance Art & Culture
Morning: Travel to Florence
- Take a high-speed train from Rome to Florence, a journey that takes about 1.5 hours. Check into a centrally located hotel. Here are a couple that we recommend:
Find other hotels in the heart of Florence
Afternoon: Duomo & Uffizi Gallery
- Begin your Florence exploration with a visit to the Duomo, the stunning cathedral topped by Brunelleschi’s iconic dome. Climb to the top for a panoramic view of the city. This is a very popular destination for people visiting Florence, so don’t be disappointed with having to wait in line or not gain entry at all and book your tickets to skip the line ahead of time.
- Some of the greatest art the Renaissance has to offer, or that mankind has to offer for that matter, can be experienced at the Uffizi Gallery, home to masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo. To keep your itinerary on track, you can book your tickets before you arrive and even select a time that would work best for you.
Evening: Ponte Vecchio & Dinner
- As the sun sets, take a stroll across the historic Ponte Vecchio, the medieval bridge lined with jewelry shops. From there, a walk up to Piazzale Michelangelo offers one of the most breathtaking views of the city, with its iconic skyline featuring the Duomo, Ponte Vecchio, and rolling Tuscan hills. As the sun sets, the golden light bathes the city in a romantic glow, creating an unforgettable moment for visitors.
- On the way back, stop in at Osteria Antica Mescita San Niccolò and enjoy a traditional Tuscan dinner known for its rustic charm and excellent local cuisine. We recommend sitting downstairs in the old rustic cellar. You won’t regret it.
Day 4: Tuscan Day Trip – Siena & San Gimignano
Morning: Rent a Car and Drive into Tuscany
- Start your day by renting a car from a nearby airport or city rental service and set off on a scenic drive into the Tuscan countryside. We recommend renting at the airport location as it’s much easier to get out of the city from there. Italy can be confusing to drive in some of its older cities so getting your car at the airport can simplify things for you. It may not be necessary but it’s a good idea to get an international driving permit. As far as car rental companies in Florence, we’ve had good experiences with EuropCar.
- To see the beauty of Tuscany, make your way down SR222 (Strada Chiantigiana) and you’ll experience the most beautiful drive while finding a local winery in Chianti.
- Your first stop is the medieval city of Siena, famous for its stunning Piazza del Campo and Siena Cathedral. Take a leisurely walk through the narrow streets and enjoy the town’s rich history and charm. If it looks familiar, the James Bond pre-title sequence was filmed in Siena in the motion picture Quantum of Solace.
Afternoon: Explore San Gimignano
- After Siena, continue your drive to San Gimignano, a UNESCO World Heritage site known for its well-preserved medieval towers and breathtaking views of the rolling Tuscan hills.
- Stroll through the town’s charming streets, visit the Collegiata di San Gimignano, and enjoy a relaxing late lunch at one of the town’s trattorias while sampling local wines, including the famous Vernaccia.
Evening: Return to Florence
- After a day of exploring the Tuscan countryside, drive back to Florence in the evening.
- Enjoy a casual dinner back in the city, perhaps at Trattoria Sostanza, known for its hearty Florentine steak and welcoming atmosphere.
Day 5: Florence – Last Day of Italian Beauty
Morning: Galleria dell’Accademia & Florence Markets
- Start your final day with a visit to the Galleria dell’Accademia to see Michelangelo’s David, one of the most famous sculptures in the world. Once again, to ensure quick and easy entry, be sure to purchase your tickets ahead of time to get the most of your day.
- Afterward, spend some time at the San Lorenzo Market, where you can pick up local leather goods, souvenirs, and taste delicious Tuscan delicacies.
Afternoon: Leisure Time in Florence
- Take your final afternoon in Florence to relax and soak in the beauty of the city. Visit the Boboli Gardens for a peaceful walk, or explore the artisan shops in the Oltrarno district.
- Enjoy a final gelato from Gelateria dei Neri before heading back to your hotel to prepare for departure.
Evening: Departure
- Depending on your travel schedule, either enjoy a quiet dinner before heading to the airport or catch a late train back to Rome if you’re flying out from there.
Conclusion:
This 5-day itinerary perfectly balances city exploration with a scenic countryside escape, allowing you to experience the historical wonders of Rome, the artistic treasures of Florence, and the charm of Tuscany. By spending one day driving through Siena and San Gimignano, you’ll get a taste of the slower pace and beauty of rural Italy, creating a well-rounded and memorable trip.
