5 Days of Florence, Tuscany, and Isola Elba Itinerary

Begin your second day with a visit to the historic Palazzo Vecchio, Florence's town hall that dates back to medieval times. Next on your itinerary is an engaging experience: join the Florence Street Food Tour with Local Expert Guide to sample some of Florence’s best street food while learning about its culinary history. Breakfast can be enjoyed at Caffè Gilli, one of Florence’s oldest cafes.

In the afternoon, delve into literary history at the Dante House Museum (Museo Casa di Dante). This museum provides insights into Dante Alighieri’s life and works. For lunch, head over to All’Antico Vinaio, renowned for its mouth-watering sandwiches. Afterward, visit Basilica of Santa Maria Novella (Basilica di Santa Maria Novella), an exquisite example of Gothic architecture.

Conclude your day with an exploration of Florentine art at the lesser-known but equally fascinating Orsanmichele Church and Museum (Chiesa e Museo di Orsanmichele). Dinner awaits you at Trattoria Mario, celebrated for its authentic Tuscan flavors. Cap off your evening with a nightcap at The Fusion Bar & Restaurant, known for its innovative cocktails.

Kick off your third day by visiting one of Florence’s most famous landmarks: The Accademia Gallery (Accademia Gallery (Galleria dell'Accademia)), home to Michelangelo’s David. Enhance this experience by opting for an exclusive tour: join the  Accademia Gallery and David Skip-the-Line Entry Ticket to avoid long queues. Breakfast can be savored at Café Scudieri with their delightful pastries.

Spend your afternoon exploring another iconic site: The Pitti Palace (Pitti Palace (Palazzo Pitti)). This grand palace houses several museums filled with Renaissance art treasures. For lunch, dine at Gustapizza for some delicious wood-fired pizza. Post-lunch take time to wander through The Boboli Gardens (Boboli Gardens (Giardino di Boboli)), offering lush landscapes and stunning sculptures.

As evening approaches make sure not to miss out on visiting Piazzale Michelangelo (Piazzale Michelangelo), which provides panoramic views over Florence – perfect spot during sunset! Enjoy dinner nearby at La Loggia del Piazzale Michelangelo with spectacular vistas complementing Tuscan cuisine perfectly; end night relaxing stroll back along Ponte Vecchio (Ponte Vecchio)

Start your day with a relaxing visit to the Emilia-Romagna Euroterme Resort thermal pool Ticket. These thermal baths are renowned for their healing properties and provide a serene environment to unwind. Enjoy a leisurely breakfast at La Terrazza del Chiostro, which offers stunning views of the Tuscan countryside.

After your morning relaxation, head to the charming village of Montalcino. Explore the historic Montalcino Fortress (Fortezza di Montalcino), which offers panoramic views of the surrounding vineyards. For lunch, dine at Osteria Osticcio, known for its delicious local cuisine and excellent wine selection. Post-lunch, take a stroll through the picturesque streets of Montalcino and visit some of its quaint shops.

In the evening, make your way to Pienza, another beautiful Tuscan village. Visit Pienza, famous for its Renaissance architecture and stunning views over Val d'Orcia. Enjoy dinner at La Bandita Townhouse Caffe, which offers a delightful menu featuring local ingredients. End your day with a relaxing walk through Pienza's charming streets.

Begin your day with a visit to one of Tuscany's renowned wineries. Join the Tuscany Vineyard Wine Tasting with Cheese & Cold Cut Meats tour, where you can sample some of the region's finest wines paired with delicious local cheeses and meats. For breakfast, enjoy fresh pastries and coffee at Pasticceria Nannini.

After your wine tasting experience, head to the medieval village of San Gimignano. Explore its historic center and visit the impressive Basilica of Santa Maria Assunta (Duomo di San Gimignano). For lunch, dine at Le Vecchie Mura, which offers breathtaking views over the Tuscan countryside along with traditional Tuscan dishes.

Conclude your day in Siena by visiting its iconic landmarks such as Piazza del Campo and Siena Cathedral (Siena Cathedral (Duomo)). Enjoy dinner at Osteria Le Logge, known for its exquisite Tuscan cuisine in an elegant setting; end night savoring gelato from nearby Gelateria Kopakabana while strolling around illuminated streets