Lecce

14 days in Lecce will give you plenty of time to explore this charming city and its surroundings. Here's a suggested itinerary for your trip:

Day 1: Arrival in Lecce

• Check into your accommodation and take a leisurely stroll around the historic city center
• Visit the iconic Basilica of Santa Croce and the Roman Amphitheatre
• Enjoy a traditional dinner at a local trattoria

Day 2: Explore the Baroque Architecture

• Spend the day admiring the stunning Baroque architecture of Lecce, including the Cathedral of Santa Maria Assunta and the Church of San Matteo
• Visit the Palazzo dei Celestini and the Castle of Charles V
• Relax in one of the charming cafes in Piazza Sant'Oronzo

Day 3: Day Trip to Otranto

• Take a day trip to the coastal town of Otranto
• Explore the beautiful Otranto Cathedral and the Aragonese Castle
• Relax on the sandy beaches and enjoy a seafood lunch by the sea

Day 4: Cooking Class and Wine Tasting

• Take a cooking class to learn how to make traditional Salento dishes
• Enjoy a wine tasting tour at a local vineyard in the countryside
• Indulge in a delicious dinner featuring local specialties

Day 5: Visit Gallipoli

• Explore the charming seaside town of Gallipoli
• Visit the historic Old Town and the stunning Cathedral of Sant'Agata
• Relax on the sandy beaches and enjoy a seafood dinner overlooking the sea

Day 6: Day Trip to Alberobello

• Take a day trip to the UNESCO World Heritage site of Alberobello
• Explore the unique trulli houses and visit the Trullo Sovrano
• Enjoy a traditional Apulian lunch in a local restaurant

Day 7: Relaxation Day

• Spend the day relaxing at one of the nearby beaches, such as Porto Cesareo or Torre Lapillo
• Enjoy swimming, sunbathing, and water sports activities
• Have a leisurely dinner at a beachfront restaurant

Day 8: Visit the Salento Countryside

• Explore the picturesque countryside of Salento
• Visit the charming towns of Specchia and Presicce
• Enjoy a traditional lunch at a Masseria (farmhouse) and taste local olive oil

Day 9: Explore the Grottoes of Castellana

• Take a day trip to the Grottoes of Castellana
• Explore the stunning underground caves and rock formations
• Enjoy a picnic lunch in the surrounding countryside

Day 10: Visit Brindisi

• Explore the historic port city of Brindisi
• Visit the Roman Column, the Swabian Castle, and the Cathedral of San Giovanni Battista
• Enjoy a seafood dinner at a waterfront restaurant

Day 11: Wine Tour in Manduria

• Take a wine tour in the town of Manduria, known for its Primitivo wine
• Visit local wineries and vineyards for tastings
• Enjoy a gourmet dinner featuring local wine pairings

Day 12: Visit the Ionian Coast

• Spend the day exploring the beautiful beaches and crystal-clear waters of the Ionian Coast
• Visit the town of Porto Selvaggio and the Natural Park of Porto Cesareo
• Enjoy a seafood dinner at a beachfront restaurant

Day 13: Shopping and Souvenirs

• Spend the day shopping for souvenirs and local handicrafts in Lecce
• Visit the artisan workshops and boutiques in the historic city center
• Enjoy a farewell dinner at a traditional restaurant

Day 14: Departure

• Take one last stroll around Lecce and soak in the atmosphere of this beautiful city
• Enjoy a leisurely breakfast at a local cafe before heading to the airport for your departure

I hope this itinerary gives you a good idea of how to spend 14 wonderful days in Lecce! Let me know if you need any more recommendations or tips. Safe travels!