Bring your walking shoes for this itinerary, perfect for first-timers in Florence. In less than a week, you'll meander all over the city, exploring the finest art and architecture, elegant gardens, hip neighborhoods, and food markets. You'll also take two incredible day trips to Tuscany (for medieval hill towns and wineries) and the Cinque Terre (for coastal hiking trails and seafood), returning each night in time for predinner "aperitivos."


  • Snap photos of Florence during a peaceful stroll around Boboli Gardens
  • Spend a day exploring Renaissance art and architecture with a self-guided tour
  • Enjoy the views as you drive to Tuscan hill towns and Chianti wineries 
  • Learn new pasta-making techniques to take home during a private cooking class
  • Hike between gorgeous cliffside villages on the Mediterranean Sea 

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Florence, Explore Florence
Day 2 Florence Self-Guided City Tour Florence
Day 3 Tuscany Day Trip: Siena, San Gimignano, Monteriggioni & Chianti Florence
Day 4 Local Cooking Class in Florence Florence
Day 5 Day Trip to Cinque Terre Florence
Day 6 Depart Florence  

Detailed Itinerary

Day 1: Arrive in Florence, Explore

Stretch your legs upon arrival with some fresh air at Boboli Gardens

Welcome to Florence, the capital of Italy's Tuscany region! Upon arrival at the airport, transfer to the city center and check into your hotel. Once you've had time to rest and settle, step outside and begin exploring the charming, pedestrian-friendly streets at your own pace.

Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, a terracotta-tiled dome that's impossible to miss, and the Galleria dell'Accademia, which displays Michelangelo's 'David' sculpture. To start, you might consider heading to Studio Artesia, located steps away from the Ponte Vecchio, to learn more about ancient fresco painting techniques. Alternatively, walk through the peaceful Boboli Gardens to see an oval-shaped island called Isolotto, surrounded by various sculptures and greenery.

In the evening, make your way around the historic L-shaped Piazza della Signoria, located in front of the Palazzo Vecchio, for some people-watching, followed by dinner and drinks in the hip Sant'Ambrogio neighborhood.

Day 2: Florence Self-Guided City Tour

Florence's compact historic center is easy to explore on foot

Wake up refreshed and start the morning with breakfast at your hotel. You'll want plenty of energy before you spend the day strolling the streets of Florence on a self-guided tour. There's no rush, and you can take your time to enjoy the sites along the way for a full-day experience. Start at the iconic Duomo, the Cathedral of Santa Maria del Fiore, one of the world's largest churches. Entrance into the main sanctuary is free, and keep in mind the modest dress code (no bare arms or legs). There is often a line to get in, so give yourself an hour to visit this architectural marvel. 

From here, make the short walk over to the Mercato Centrale on the second floor of the Mercado di San Lorenzo, where you'll be able to meander through the stalls of local goods and grab a midmorning pastry and espresso. Give yourself an hour or two to soak in the sights and smells and buy traditional leather goods as souvenirs. Next, head to the nearby Piazza della Republica, the perfect place to soak in the atmosphere of Florence's city center and the incredible architecture that embodies it. 

Then take a moment to pass through Piazza della Signoria, where replicas of famous statues line the square, before stopping for lunch nearby. Across this same piazza, you'll find the entrance to the Uffizi Gallery. Even if you decide not to make a stop to peruse the expansive art collection, you can cross through its courtyard, Piazzale degli Uffizi, to make your way to the Ponte Vecchio. This famed bridge is now dotted with jewelry shops and is an iconic sight in the Florence cityscape. Walk along the bridge, admiring views along the Arno River

End your day with a visit to Piazzale Michelangelo. Getting here requires a bit of an uphill climb, or you can take a short taxi ride. Either way, you can watch a sunset overlooking a spectacular viewpoint of the city before heading to Piazza Santo Spirito for some predinner aperitivos

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Day 3: Tuscany Day Trip: Siena, San Gimignano, Monteriggioni & Chianti

Your Tuscany tour begins at the walled hill town of San Gimignano

You'll head into the beautiful countryside this morning to explore Tuscany on a full-day tour. Your first stop will be the medieval village of San Gimignano, a UNESCO World Heritage Site located an hour from Florence. This quintessential village is most famous for the 13th-century walls that encircle it, as well as its medieval plazas, churches, and stone towers dominating the skyline. Spend the morning exploring the streets before taking a break in a terraced café for lunch. 

In the afternoon, you'll visit nearby Siena, a medieval city with important historical sites. You can't miss the great main square, Piazza del Campo, which the Gothic Pubblico Palace surrounds, the Tower of Mangia, and the Gaia Fountain. From here, walk over to the 13th-century cathedral, Duomo di Siena, which dominates the city's skyline. The town comes alive with festivities in the summer months, as the Palio takes place in July and August. This exciting horserace, held twice a year in the main square of Siena, ignites the town in fervor. 

Finish the day with a visit to the medieval fortress town of Monteriggioni. The intact castle walls surrounding this town perched on a hillside are a sight to behold. Then continue to the Chianti Classico wine region to visit a typical Tuscan winery (with tastings!) before returning to Florence for the evening.

Day 4: Local Cooking Class in Florence

Learn How to Make Traditional Italian Pasta
Learn how to make traditional Italian pasta and enjoy a meal

Enjoy a leisurely morning in Florence with breakfast at your hotel and a relaxed stroll through the historic center. Some highlights that you may not have had time to see yet include the sprawling 15th-century Pitti Palace and the world-famous Uffizi Gallery, which houses work by artists like Michelangelo and Leonardo da Vinci. Be sure to purchase your tickets to the Uffizi online to avoid disappointment.

In the afternoon, you'll meet your host near the center of Florence for a traditional Italian cooking class. He or she will first welcome you with a glass of prosecco as you begin the three-hour experience with an appetizer of Italian cheeses and other local products.

Next, you'll roll up your sleeves and learn to cook four regional Italian dishes from recipes passed down through generations. Observe the chef's different tricks and techniques involved in cooking Italian family recipes. In the summer months, you might be able to use the small vegetable and herb garden in the courtyard where zucchini, tomatoes, and herbs are grown. The best part comes at the end when you and your hosts will sit down and enjoy your freshly-made dinner together. Buon appetito!

Day 5: Day Trip to Cinque Terre

Stop for lunch in Vernazza during your Cinque Terre tour

Today you'll embark on another beautiful day trip—this time to the Cinque Terre, a section of the Italian coast famous for its five medieval villages situated on stunning cliffs over the Mediterranean Sea. If that's not enticing enough, the villages are strung together via beautiful hiking trails, so be sure to wear some good walking shoes.

Start in Riomaggiore, where you'll walk along the beautiful Via dell' Amore (Lover's Pathway) to enjoy exhilarating views of the coastline and sea. From here, continue to the town of Monterosso al Mare for some free time. The city's medieval center remains nearly perfectly preserved, with its ancient tower houses and network of carrugi (narrow alleyways that lead from the sea to the cliffs above the town). Monterosso is also renowned for having the best gelato in the Cinque Terre (make sure to try some!), as well as breathtaking views of the sea.

Next is Vernazza, a small resort town located at the mouth of a river and naturally protected from wild sea swells by a rocky promontory. This natural wave break protects the harbor, making it the only major docking point in the Cinque Terre. Enjoy lunch on your own time as you explore the local cuisine and savor regional delicacies. After the day's sightseeing, follow your nose to the neighborhood bakery to taste the local focaccia with pesto for a delicious snack you won't find anywhere else. In the afternoon, transfer back to Florence.

Day 6: Depart Florence

Until next time, Florence!

Say goodbye, or ciao, to Italy for now! Take advantage of any free time this morning with one last walk through the streets of Florence. At the appointed hour, you'll transfer to the airport to catch your flight home or to your next destination. Safe travels!

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Map of Highlights of Florence - 6 Days
Map of Highlights of Florence - 6 Days