Spend six days visiting historical sites, eating delicious food, and relaxing in Italy. Start in Tuscany for a wine tour of the Chianti region and admire the beautiful villages of the Italian countryside. Catch a high-speed train to Rome and explore the Eternal City with visits to the Vatican City and Colosseum, then round out your trip with a food tour of the city's famous markets and gelaterias.

Highlights

  • Explore Vatican City and St. Peter's Basilica
  • Sample Rome's favorite treats, like suppli and gelato
  • Dive into history of the Roman Empire at the Colosseum & Roman Forum
  • Go on a wine tasting tour in the Chianti region of Tuscany
  • Visit the Bistecca alla Fiorentina "steak poet"

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Florence, Transfer to Radda in Chianti Radda-in-Chianti
Day 2 Full Day Chianti Tour: Winery & Steak Poet of Fiorentina from Radda Radda-in-Chianti
Day 3 Radda in Chianti to Rome by Train, Walking Tour Rome
Day 4 Guided Food Tour of Testaccio & Trastevere Rome
Day 5 Vatican, Colosseum, & Roman Forum Tour Rome
Day 6 Goodbye Italy  

Detailed Itinerary

Day 1: Arrive in Florence, Transfer to Radda in Chianti

Typical village home in Radda
Typical village home in Radda

Welcome to Tuscany! Arrive at Florence Airport, then transfer to your accommodations in the peaceful town of Radda in Chianti. After the 1-hour trip, check in to your hotel and enjoy some downtime to settle in and unpack. 

The commune of Radda in Chianti dates back to the 9th century, and the town's medieval stone fortifications and narrow streets serve as a reminder of a time when the city was the main defensive and financial capital of the Chianti region. In the countryside outside the town, endless fields of vineyards supply the wine grapes for the region's famed Chianti wine. 

The remainder of the day is free. Rent a bike to explore the city's hilly streets, or head out of town to spend the afternoon cruising around winding country lanes through the peaceful Tuscan landscape.

Day 2: Full Day Chianti Tour: Winery & Steak Poet of Fiorentina from Radda

The perfect glass of Chianti
The perfect glass of Chianti

Hit the road today with your private guide to explore the romantic region of Chianti. This large region is located between Florence and Siena and is famous for its unparalleled beauty and peaceful countryside. Each part of this incredible region is full of vineyards, wineries, medieval towns, and winding rural roads. 

The Chianti region is renowned for producing the delicious red wine of the same name, and the region's unique characteristics and local climate have made the region unfavorable to most crops but ideal for growing wine grapes. The Chianti wine, made primarily of Sangiovese grapes, is the local staple. 

Visit the famous Castello di Verrazzano (birthplace of the famous explorer), and spend the morning learning about the winery touring the cellars and vineyards, then enjoy a wine tasting accompanied by a delicious Tuscan lunch of pasta, cured meats, cheeses, and local desserts. 

From here continue to another authentic Tuscan experience: a visit to the legendary butcher Dario Cecchini, nicknamed the "world's best butcher." The 8th-generation butcher of Antica Macelleria Cecchini is known as the "Poet of Fiorentina"—the famous Tuscany T-bone steak—and you'll find him behind the counter of his butcher shop in the heart of Chianti, in Panzano, every day of the week including Sundays.

The walkway behind the counter is raised, so Dario looks much like a large, smiling giant, a benevolent and friendly man who loves entertaining locals and visitors with his recitations of verses of the Divine Comedy. For a real taste of the butchering process, taste his Chianti Butter (lard cream flavored with herbs and spices), and the Sushi of Chianti (thinly sliced raw meat). 

Afterward, return to your hotel in Radda. 

Day 3: Radda in Chianti to Rome by Train, Walking Tour

Colosseum at sunrise
Colosseum at sunrise

Enjoy a leisurely breakfast, then pack up and head to the Florence train station to catch a high-speed train to Rome. Italian trains are fast and comfortable and make multiple daily trips between major cities, which makes them an excellent choice for travelers. The ride to Rome takes you through beautiful countryside, so kick back and enjoy the smooth ride and beautiful views! 

Arrive in Rome and transfer to your accommodation in the center of the city, then settle in and head out for your first look at the Eternal City. Grab lunch at one of the city's many streetside cafes and restaurants, then meet your tour guide for a private walking tour of the Roman squares. 

The tour will take you to Rome's top historical and cultural sites, winding through narrow streets and wide piazzas as you explore the city. You'll learn about Rome's role as Italy's political capital, as well as the city's importance as the cradle of Catholicism. 

Start at Piazza Navona, one of Rome's most well-known squares. It sits on top of the former 1st-century Stadium of Domitian which once hosted chariot races and other competitive athletic events (the stadium could even be flooded to recreate naval battles!) The modern-day piazza follows the curve of the stadium's original outline, and traces of the original walls still stand on the outskirts of the piazza. The 17th-century Chuch of Sant’agnese in Agone, designed by Borromini, marks the spot where the Christian martyr St. Agnes was murdered in 304 CE. 

In the center of the square stands the Fountain of the Four Rivers (Fontana dei Quattro Fiumi), which was designed by Gian Lorenzo Bernini, a leading Italian sculptor. 

A short walk from the square brings you to the Pantheon, ancient Rome's most complete surviving building. Nearby, St. Peters Church dominates Rome's skyline. The church is a central location for Catholicism and is the burial place of Raphael and the first kings of a united Italy. 

Your next stop is the Trevi Fountain, where travelers throw coins into the water to ensure a return to Rome. From here walk to the Spanish Steps, then round out your tour with a stop at the neighborhood gelateria for the perfect cone of gelato. Find a quiet bench in the piazza and enjoy a relaxing evening of people watching before making your way to a family-owned pizza shop for dinner. 

Day 4: Guided Food Tour of Testaccio & Trastevere

Perfect place for an afternoon coffee
Perfect place for an afternoon coffee

Spend the morning exploring Rome's famous food scene and tasting all the different flavors and ingredients that make Italian cuisines famous around the world.

Start the tour by meeting with your local food guide, then enjoy a nice stroll through the quieter neighborhoods of Testaccio and Trastevere. Start in Testaccio to see traditional markets, restaurants, and coffee shops. Sample the local foods from fried artichokes, codfish, and zucchini flowers to delicious porchetta and Supplì rice-balls. 

From here, continue to a very different area, the former working-class neighborhood of Trastevere, whose name literally means "across the river". Nowadays the neighborhood is a quiet bohemian haven with picturesque squares, peaceful narrow alleyways full of potted plants, and small coffee shops with one or two tables to linger at during the afternoon. The area is now a fashionable residential area with a wealth of great restaurants and bars. 

Enjoy a relaxed stroll to see the area's churches and palaces, including the Basilica of Santa Maria, Basilica of Saint Crisogono, and Basilica of Santa Cecilia. 

After some sightseeing, enjoy a light lunch and drinks out on the town. Round things off with an afternoon cappuccino or espresso at a local caffeteria, then head to a gelateria and choose from an incredible variety of flavors, each made with the finest ingredients from all over Italy. Pistachio from Sicily, nuts from Piedmont, and lemons from Sorrento make for a mouth-watering selection. 

If you're still hungry, try a Roman pizza, accompanied (as always) by a chilled glass of prosecco or spumante. In the afternoon, visit some of Rome's iconic museums, such as the Capitolini Museum or the Galleria Borghese, on your own. 

Day 5: Vatican, Colosseum, & Roman Forum Tour

Rome at sunset
Rome at sunset

Today you will visit the Vatican City museums and Sistine Chapel, as well as other top sights for an exclusive guided tour of the city's incredible art and history. Start at the Vatican to see the Pio Clementio Museum, Gallery of the Candelabra, Gallery of Tapestries, and Gallery of the Geographical Maps

Continue to see the magnificent Raphael Rooms, ending in the breathtaking Sistine Chapel to see Michelangelo's Genesis ceiling frescoes and his Last Judgement altar fresco. Continue to St. Peter's Basilica and Square and experience the magic of Renaissance art as you learn about the secret details and untold stories of the masterpieces. 

After lunch in the city center, continue your day with a dive into the history of the Roman Empire with a guided walking tour of the Colosseum, the world's largest amphitheater. You'll explore the main complex as well as the Belvedere, the recently opened third ring with a view of the arena and the Imperial Forums up to the fourth and fifth rings. 

Walking through the ancient amphitheater is like taking a trip back in time to the days of the Roman Empire. At its prime, the Colosseum held 50,000 spectators and was the central venue for gladiator fights. Learn about some of ancient Rome's most famous citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian Emperors who built the Colosseum. 

From here, continue to the Roman Forum and Palatine Hill, built between 46 BCE and 113 CE. Walk along the ancient Roman street Via Sacra to see the Temples of Vesta, Antonino, and Faustina. See the ancient Basilica Julia and Aemilia and experience the grandeur of the Roman Empire.

Day 6: Goodbye Italy

Little details of life in Rome
Little details of life in Rome

After one last cappuccino over breakfast, head to the airport for your connecting flight home. Have a good trip!