Italy is one of those countries where every town and city seems to offer something incredible, making it incredibly difficult to narrow down the best spots to visit—especially when you only have two weeks. After visiting more than 20 cities across the country, I’ve had the privilege of experiencing Italy’s diverse culture, art, history, and landscapes. While it’s impossible to see everything in such a short time, I’ve put together this itinerary with my favorite towns and cities, focusing on the must-see places that give you a well-rounded experience of Italy’s charm, beauty, and rich heritage. If you’re like me and want to see as much as possible in two weeks, here’s what I’d recommend.
Florence – 3 Nights
Florence is a must-see city, brimming with Renaissance art, stunning architecture, and rich history. It’s a perfect place to start your Italian adventure.
Where to Stay in Florence: Hotel Orto de’ Medici – A cozy, well-located hotel offering easy access to Florence’s top attractions.
See my recommendations on what to do in Florence here.
Day Trip: Cinque Terre
While in Florence, take a day trip to the stunning Cinque Terre, a collection of five colorful seaside villages. Explore the charming streets, relax on the beach, and hike the coastal trails that offer breathtaking views of the Ligurian Sea.
Siena – 3 Nights
Next, head to Siena, a beautiful medieval city in the heart of Tuscany. Known for its Piazza del Campo and rich history, Siena is the perfect base for exploring the Tuscan countryside. Find my recommendations on what to do in Tuscany here.
Where to Stay in Siena: Grand Hotel Continental – A luxurious, historic hotel located in the heart of Siena, offering elegance and comfort.
Day Trip 1: Cortona, Volterra & San Gimignano
Take a drive through the Tuscan hills and visit Cortona, a town with panoramic views; Volterra, known for its Etruscan heritage; and San Gimignano, famous for its medieval towers.
Day Trip 2: Montalcino, Montepulciano & Pienza
On your second day trip, visit Montalcino, the home of Brunello wine; Montepulciano, a hilltop town offering amazing views; and Pienza, renowned for its Renaissance architecture and pecorino cheese.
Positano – 5 Nights
Positano, on the stunning Amalfi Coast, is where you’ll find dramatic cliffs, colorful houses, and breathtaking views of the Mediterranean. It’s a place you won’t want to leave. I love this area!!!
Where to Stay in Positano: Villa Gabrisa – A family-run hotel with stunning views, located just a short walk from the beach.
Day Trip 1: Ravello & Amalfi
Spend the day visiting Ravello, famous for its beautiful villas and gardens, and Amalfi, where you can explore its historic cathedral and charming streets.
Day Trip 2: Sorrento
Take a day trip to Sorrento, a coastal town with incredible views, lovely cafes, and boutique shopping. Don’t forget to try the famous limoncello! Try to spend an evening here, enjoying dinner and taking in the ambiance of this town that is even more charming at night!
Day Trip 3: Capri
Visit the luxurious island of Capri, famous for its upscale shops, the famous Blue Grotto, and stunning coastal views.
Day Trip 4: Pompeii
Explore the ancient ruins of Pompeii, preserved by the eruption of Mount Vesuvius in 79 AD. Wander through Roman homes, temples, and baths, and discover stunning mosaics that offer a glimpse into ancient life.
Rome – 3 Nights
Finish your journey in Rome, a city full of ancient history, iconic landmarks, and vibrant culture. From the Colosseum to the Vatican, Rome is an essential stop on any Italy itinerary. See my 3-day Rome itinerary here.
Where to Stay in Rome: Hotel Indigo St. George – A modern boutique hotel near all of Rome’s top attractions, offering a relaxing stay after a day of sightseeing.
With this 2-week itinerary, you’ll visit some of the best towns and cities in Italy, each with its own mix of history, culture, and natural beauty. From the art-filled streets of Florence to the coastal charm of Positano, and the ancient sites of Rome, your first trip to Italy will be full of unforgettable experiences.