Here's an ideal itinerary for 5 days in Pisa:

Day 1: Arrival and Exploring the City

• Arrive in Pisa and check into your hotel
• Take a stroll around the city center and explore the charming streets and alleys
• Visit the iconic Leaning Tower of Pisa and take some fun photos
• Enjoy a delicious Italian dinner at one of the many restaurants in the area

Day 2: Discovering Pisa's Art and Culture

• Start your day with a visit to the beautiful Piazza dei Miracoli, home to the Leaning Tower, the Cathedral, and the Baptistery
• Explore the Museo dell'Opera del Duomo, which houses some of the most important works of art from the Piazza dei Miracoli
• Visit the Palazzo Blu, a stunning palace that hosts temporary exhibitions of contemporary art
• End your day with a relaxing walk along the Arno River and enjoy the sunset over the city

Day 3: Day Trip to Lucca

• Take a short train ride to the nearby town of Lucca, known for its well-preserved Renaissance walls and charming historic center
• Walk or bike along the top of the walls for stunning views of the city
• Visit the beautiful Piazza dell'Anfiteatro, a unique oval-shaped square that was once a Roman amphitheater
• Explore the many churches and museums in the city, including the Cathedral of San Martino and the Museum of Villa Guinigi
• Return to Pisa in the evening for a delicious dinner and some gelato

Day 4: Wine Tasting in the Tuscan Countryside

• Take a guided tour of the beautiful Tuscan countryside, known for its rolling hills, vineyards, and olive groves
• Visit a local winery and taste some of the region's famous wines, including Chianti and Brunello di Montalcino
• Enjoy a traditional Tuscan lunch at the winery, featuring local specialties like pasta with wild boar ragù and pecorino cheese
• Return to Pisa in the evening for a relaxing dinner and some more gelato

Day 5: Shopping and Departure

• Spend your last day in Pisa shopping for souvenirs and gifts in the city's many boutiques and markets
• Visit the Mercato delle Vettovaglie, a bustling food market where you can sample local cheeses, meats, and wines
• Take a final stroll around the city center and say goodbye to Pisa before departing for your next destination.