Ultimate 14-Day Italy Travel Itinerary

Ah, Italia! It’s one of the world’s favorite destinations in Europe, where countless travel opportunities await. How can you create a dream vacation in Italy? Focus on key elements that embody its essence: stunning architecture, warm-hearted people, rich culture, and delicious cuisine.

With a well-planned itinerary, you can explore Italy in just two weeks: spending three or four days in Rome, a week in the picturesque hill towns and the countryside of Tuscany or Umbria, and wrapping up with three days in the romantic city of Venice.

When it comes to flying, securing your plane tickets, hotel accommodations, and entry to popular tourist attractions should be done well in advance—ideally, six months prior. By planning early, particularly during mid-winter for a summer trip, you’ll likely find better prices and availability.

If you prefer warm weather but wish to dodge the summer crowds, the best times to visit Italy are between May–June and September–October. Additionally, prices are often lower during these months. Aim to book your lodging when you finalize your flight details. If a major attraction like the Uffizi Gallery in Venice is on your list—drawing around 10,000 visitors daily—it’s crucial to make reservations early.

Traveling between destinations is most convenient by car or train. If you decide to drive, check with your car rental company about the best booking times—earlier is generally better in Italy. For train travel, buying tickets upon arrival at each destination ensures you won’t miss a beat. Within cities, public transportation or taxis will get you around, while a car is often necessary for exploring the countryside.

Start in Rome: Day 1

Rome serves as an ideal starting point for your journey. It is accessible from most locations, and you may find that a car isn’t necessary. Dedicate at least three or four days to explore the city. For structured ideas, consider a detailed Rome travel itinerary to maximize your visit.

Opt for accommodations close to public transport to facilitate your exploration. Personalized service can greatly enhance your experience, particularly if it’s your first visit. A popular option is the Daphne Inn, where the English-speaking staff can assist in planning your days, suggesting restaurants, and providing a cell phone for any assistance you may need.

On your first day, allow yourself to wander, acclimatizing to Rome while mitigating jet lag. Choose an area nearby and simply explore, without the pressure of hitting every tourist site. For an overview, take bus number 110, which offers a tourist circuit from Termini Station.

Rome: Days 2–3

Dedicate one day to touring ancient Roman archaeological sites that punctuate the city’s rich history. Use the second day to explore the Piazza Navona, Campo de Fiori, Pantheon, Trevi Fountain, and the Spanish Steps—each offering unforgettable experiences at no cost. Delve into neighborhoods like Trastevere, the Jewish quarter, and Testaccio, perfect for indulging in authentic Roman cuisines.

Rome: Day 4

Consider dedicating another day for a visit to Vatican City, including the Vatican Museums, St. Peter’s Basilica, Sistine Chapel, and Castel Sant’Angelo. For a chance to see the Pope, schedule your visit on a Wednesday and acquire tickets well in advance. You can also make arrangements to request an audience with the Pope.

Tuscany or Umbria: Days 5–11

As your vacation unfolds, consider renting a house or an agriturismo (a renovated farmhouse) in Tuscany or Umbria. This way, you’ll have the opportunity to explore Renaissance and medieval towns, experience breathtaking nature, and immerse yourself in genuine Italian life. Make sure to plan this segment of your journey by finding lodging that’s conveniently located for day trips to various attractions.

Lodging

Choosing to stay in a house for a week often leads to cost savings, along with the benefit of shopping and dining like the locals do. Seek out accommodations with amenities like a washing machine to pack light and do laundry mid-trip. Embrace the experience of shopping at local farmers’ markets, preparing your meals, and eating at your leisure.

Book your lodging a few months in advance, opting for locations in small villages, cities, or the serene countryside. If you wish to visit specific cities, ensure that your house remains within a reasonable driving distance. In Tuscany, Le Torri vacation apartments offer an excellent midpoint between Florence and Siena, while the holiday houses at Il Fontanaro Organic Farm provide a convenient option for those wishing to experience both Tuscany and Umbria.

Italy’s train system is both affordable and efficient. Consider taking a train from Rome to a nearby city relative to your lodging. Upon arrival, pick up your rental car—already reserved—to reach your house. Booking a vehicle through reputable companies eliminates hidden charges. If your your stay is in a town, a car may not even be necessary.

Most house rentals operate from Saturday afternoon to the following Saturday morning. Since many shops are closed on Sundays, trying to stock up on essentials (like wine and water) shortly after your arrival is wise. Also, allow some time for leisurely exploration of your new surroundings.

Sightseeing

Tuscany and Umbria’s compactness makes visiting numerous places easy. If heading to larger cities like Florence, consider parking at a nearby train station and taking the train to avoid excessive driving.

Popular destinations in Tuscany include Siena, Pisa, San Gimignano, Lucca, the wine towns of Montepulciano and Montalcino, the Chianti wine region, and Cortona, famously portrayed in “Under the Tuscan Sun.”

In Umbria, explore Assisi, Perugia, Orvieto, Spoleto, and other charming hill towns, as well as Lake Trasimeno and Roman ruins.

Venice: Days 12–14

After a week at your country house, return the car and take the train to Venice—a stunning treasure on Italy’s eastern Adriatic coast.

Navigating Venice involves either walking or utilizing a vaporetto, a large passenger boat that functions like a public bus. Spending at least two to three days here allows for a comprehensive experience. Before leaving home, review a Venice sestiere map to select the optimal neighborhood for your stay. If your visit extends beyond three days, consider renting an apartment in a local neighborhood.

While in Venice, don’t miss the opportunity to visit San Marco Square, the Rialto Bridge, and the Grand Canal. Take some time to escape the crowds by exploring small back streets and canals, truly immersing yourself in the local culture. Before lunch, pop into a local bar for some cicchetti (traditional Venetian snacks) and a glass of wine, and consider indulging in a gondola ride for the quintessential Venetian experience.

As your journey comes to a close, you can fly back to Rome or take a train to Milan, potentially spending a night or two in the city or at scenic locations like Lake Como or Lake Garda. From there, flying back to the United States is a breeze.