Begin the day early with cornetto (Italian croissant, often filled with cream or jam) and cappuccino, a classic Italian breakfast.

Climb to the top of the dome of Florence Cathedral (Duomo) for panoramic views over Florence’s terracotta rooftop. The dome also offers an immersive architectural experience.

Continue to the interior of Florence Cathedral (Duomo), where the vast scale and frescoed dome convey the grandeur of Renaissance Florence. Visit the nearby Baptistery of St. John, renowned for its glittering mosaic ceiling and bronze doors.

Optional add-on: Visit the Museo dell'Opera del Duomo to see original sculptures and artworks from the cathedral complex, offering deeper insight into the craftsmanship and history behind the monuments.

Explore the Uffizi Gallery, home to an extensive collection of Italian Renaissance art, including works by Botticelli, Leonardo da Vinci, Michelangelo, Raphael, as well as other master painters.

Pause for gelato and stroll through Piazza della Signoria, the historic political heart of the city, where sculptures in the open-air Loggia dei Lanzi create a museum-like setting.

Walk across Ponte Vecchio and browse the nearby jewelry stores and small artisan workshops that reflect Florence’s goldsmithing heritage.

Head to Piazzale Michelangelo for sunset with its sweeping views over the Arno River and the city’s skyline.

Enjoy dinner featuring local specialties, such as bistecca alla Fiorentina (grilled T-bone steak served rare), ribollita (stew of kale, beans, and bread), or pappardelle al cinghiale (wide noodles with a boar ragu), showcasing the rich, hearty flavors of Tuscan cuisine.

End the day with an evening walk along the Arno River, where the city lights reflect off of the water, creating a serene atmosphere.

Start the day with budini di riso (custard and rice tart) or bombolini (fried filled donut), before heading to Galleria dell'Accademia, renowned for Michelangelo’s David.

Continue to the Basilica of San Lorenzo and the Medici Chapels, which together showcase the Medici family’s influence through architecture, sculpture, and lavish tombs designed by Michelangelo. Requirements for respectful/modest attire apply at churches and other religious sites. Visitors should avoid disrupting religious observances and remain mindful of posted customs.

Optional add-on: Browse the San Lorenzo Market, where vendors sell leather goods and other types of souvenirs.

Visit Palazzo Vecchio, the historic seat of Florence’s government, which houses an extensive collection of Renaissance art and offers insight into the life and influence of the Medici family.

Continue to Basilica of Santa Croce, known as the burial place of notable figures like Michelangelo and Galileo, and admired for its frescoes and historical significance. Make sure to see the Pazzi Chapel, with its unique geometric design incorporating squares and circles.

Explore the Oltrarno district, Florence’s artisan quarter, known for traditional crafts such as marbled paper, bookbinding, leatherwork, and cornici (traditional gilded frames.

Stop at a wine window, such as the one at Babae, a historic way to enjoy a quick glass of wine served through a small street-facing opening. Enjoy dinner in the Oltrarno and end the evening with a wine tasting at a local enoteca (wine bar).

Head to Siena and visit Piazza del Campo, a unique shell-shaped square that serves as the heart of Siena’s civic life.

Optional add-on: Climb the Torre del Mangia for expansive views over the city and surrounding countryside.

Explore the Siena Cathedral, known for its striking black-and-white marble façade and elaborate decoration of its Piccolomini Library. Requirements for respectful/modest attire apply at churches and other religious sites. Visitors should avoid disrupting religious observances and remain mindful of posted customs.

Continue on to Santa Maria della Scala, a former hospital that contains frescoed halls, archaeological layers, and terraces with views.

Enjoy lunch in Siena before heading to San Gimigano.

Travel to San Gimignano, famous for its medieval towers and skyline. Explore the San Gimignano Musei, by climbing the Torre Grossa, offering panoramic views of the surrounding countryside and visiting the Palazzo Comunale, a historic civic building that reflects the town’s medieval governance and includes a pinacoteca.

Browse artisan shops in Piazza della Cisterna, known for local products and a picturesque setting, before returning to Florence. Consider making time for a stop at Gelateria Dondoli, an award-winning spot to pick up a gelato.

Travel to Pisa and visit Piazza dei Miracoli, home to the Leaning Tower of Pisa, known for its iconic tilt and elegant arcaded structure; the Pisa Cathedral, a defining example of Romanesque architecture with a striking marble façade; and the Battisero di San Giovanni, notable for its circular form and blend of Romanesque and Gothic styles.

Requirements for respectful/modest attire apply at churches and other religious sites. Visitors should avoid disrupting religious observances and remain mindful of posted customs.

Optional add-on: Walk through Piazza dei Cavalieri, a refined Renaissance square lined with historic palaces, then continue to the Lungarni di Pisa for a stroll with a stop at Santa Maria della Spina, a small Gothic church set along the river.

Travel to Lucca and visit Duomo di San Martino, known for its richly decorated façade and artworks. Stroll along Via Fillungo, the city’s main commercial street lined with historic buildings, on the way to take a café break at Piazza dell'Anfiteatro, a unique oval piazza built on the site of a Roman amphitheater.

Optional add-on: Climb Guinigi Tower, famous for the trees growing on its rooftop.

Rent a bike for a sunset ride along the Mura di Lucca, offering a scenic way to experience the city, before returning to Florence.

Head to Greve and explore Piazza Matteotti, where local shops offer olive oil, wine, and regional specialties.

Optional add-on: Stop at Antica Macelleria Falorni, known for high-quality cured meats and traditional Tuscan products.

Visit Museo del Vino to learn about wine-making history, featuring antique tools and artifacts and then head to local wineries and enotecas (wine bars), where tastings provide insight into Chianti wines and the region’s winemaking traditions. Options are available in Greve, as well as in the surrounding region.

Enjoy dinner at a vineyard, where meals are often paired with estate-produced wines and set within scenic countryside surroundings, before returning to Florence.

Visit smaller towns nearby, such as Panzano and Radda, that offer local shops, scenic streets, and a slower pace of exploration. If you choose to visit Panzano, Dario Cecchini in Panzano is one of Italy’s most famous butchers and has a restaurant called Solociccia that celebrates traditional Tuscan meat dishes.