We begin our day with early morning shots at Piazzale Michelangelo, which offers breathtaking panoramic views of the city, the Arno River, and the Ponte Vecchio bathed in soft, golden light.

After, we’ll visit Sant’Ambrogio Market, one of Florence’s most historic markets. The market is an excellent place to have breakfast and focus on people photography. Florence’s markets are a vibrant part of the city’s cultural and commercial life, offering a glimpse into its rich history, local traditions, and the everyday life of Florentines. Located in the heart of the old city, this market has been a bustling hub for centuries, where locals and visitors shop for fresh produce, artisan goods, and unique souvenirs. Sant’Ambrogio has been serving Florentines since the late 19th century and is one of Florence’s most authentic local markets. The indoor section offers a wide range of fresh produce, meats, fish, and cheeses, while the outdoor section features vendors selling clothing, household goods, and fresh flowers.

After lunch, we’ll continue exploring the center of the city and the nearby neighborhoods, focusing on street photography, documentary portraits, architecture, and cityscapes. (B)

On day three, we depart for the medieval walled city of Lucca, just one hour west of Florence. From here, we will set out for a day of photography in this ancient yet stylish northern Tuscan city. Lucca is a city renowned for its well-preserved Renaissance walls—these walls offer elevated views of the historic center and distant hills. We’ll photograph the unique Piazza dell’Anfiteatro, a circular square built on a Roman amphitheater’s remains, offering a charming, enclosed space perfect for wide-angle shots. The Torre Guinigi, with its rooftop garden, provides a unique vantage point, while the Lucca Cathedral offers intricate Gothic architecture to explore with your camera. Lucca has become a favorite among many of our guests. In the evening we’ll return to our hotel in Florence. (B)

On day four, we depart Florence early for the rolling hills of southern Tuscany. We begin with a stop in San Gimignano, famous for its medieval towers. The town’s skyline, dotted with these ancient structures, is particularly photogenic, especially from a distance. We’ll wander through the narrow, cobblestone streets, capturing the rustic charm and the interplay of light and shadow among the stone buildings. The Piazza della Cisterna and Piazza del Duomo are key spots for architectural shots, while the surrounding countryside, with vineyards and rolling hills, provides beautiful landscape photography opportunities.

After lunch, we depart for Siena, the medieval heart of Tuscany. They say that Siena is a “State of Mind,” and perhaps they are right. It has an allure that grabs hold of you and has you returning for more. Siena dates back to 900 B.C. and is declared a UNESCO World Heritage site and one of Italy’s most visited cities. The Piazza del Campo is one of Europe’s most remarkable squares. The unique shell-shaped design of the square, with the towering Torre del Mangia and the historic Palazzo Pubblico, provide a dramatic backdrop. The Siena Cathedral (Duomo di Siena) is one of the most dramatic Duomos in Italy, with its intricate Gothic facade and richly decorated interiors. We’ll explore the winding streets that radiate from the piazza, each offering unique perspectives and intimate scenes of daily life.

After, we’ll settle into our hotel near the rural medieval city of Montepulciano. (B)

Today, we are up very early to explore Val d’Orcia and capture breathtaking landscapes, likely including the rolling fog that southern Tuscany is known for. This area is famous for its idyllic landscapes, rolling hills, cypress-lined roads, and isolated farmhouses that have become iconic images of Tuscany. The Cappella della Madonna di Vitaleta, a small chapel set amid the fields, is a must-photograph location, particularly at sunrise or sunset when the light enhances the serene beauty of the landscape. The Horti Leonini gardens and the Romanesque Collegiata di San Quirico church offer additional opportunities for capturing the historical and natural beauty of the area. We’ll have lunch in San Quirico d’Orcia, a small, picturesque town in the heart of the Val d’Orcia.

In the late afternoon, we’ll visit Montepulciano, known for its narrow, winding streets, which are a photographer’s delight. We’ll capture the charm of the cobblestone alleys, lined with stone buildings, artisan shops, and flower-adorned balconies. We’ll look for unique perspectives, such as doorways and arches framing views of the town or countryside. The interplay of light and shadow in these narrow streets, especially in the early morning or late afternoon, creates a dramatic effect in your photos.

The Piazza Grande in the heart of Montepulciano is surrounded by impressive buildings, including the Palazzo Comunale, which resembles Florence’s Palazzo Vecchio, and the Duomo (Cathedral of Santa Maria Assunta), both offering fantastic architectural photography opportunities. We’ll have dinner in Montepulciano. (B)

We begin our day with more southern Tuscan landscape opportunities. A morning stroll and early lunch in Pienza, a UNESCO World Heritage site and a gem of Renaissance urban planning. The town is perched on a hill overlooking the stunning Val d’Orcia, making it ideal for capturing panoramic views of the Tuscan countryside. The Piazza Pio II and the Pienza Cathedral offer beautiful examples of Renaissance architecture. The town’s narrow streets and charming squares, like Via del Bacio (Street of the Kiss), are perfect for capturing the romantic essence of Tuscany.

After lunch, we set out to discover Cortona, a small charming town in the Valdichiana, or Chiana Valley, in the province of Arezzo in southern Tuscany. The city, enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill about 600 meters (about 1968 feet) above sea level. This dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno.

Our afternoon and evening in Cortona will be spent inside and outside city walls, taking in all Cortona has to offer. In Cortona, we’ll enjoy a wonderful “Farewell Dinner” with our group. (B) (D)

After an early morning shoot, breakfast, and a review of our photos, we’ll check out of our hotel in Montepulciano and return to Florence for your departure. In Florence, you can catch a train elsewhere or depart from the city’s international airport.

We urge you to extend your stay in Italy or elsewhere in Italy and use all the wonderful photographic techniques you will learn on our amazing photo adventure. (B)