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Once you arrive, rent a car. While you can reach some of the major towns by train, having your own vehicle makes a significant difference in Puglia. It allows you to stop at a small village, pull over for a coastal view, visit a masseria or change your plans completely when you discover somewhere that looks interesting. Note: Be sure to book your car in advance, specially during high-season. When to Go I prefer late spring and early fall, particularly May, June, September and early October. The weather is generally well suited to sightseeing, outdoor dining and spending time along the coast, without the intensity of the peak summer season. July and August are the busiest months and can be very hot. If you are planning long days at the beach, summer obviously has its advantages, but if you want to explore Lecce, Otranto and the smaller towns comfortably, I would choose the shoulder seasons. September is particularly appealing. The sea remains warm, restaurants and hotels are still operating at full pace and the atmosphere is noticeably more relaxed. What to Avoid The biggest mistake in Puglia is trying to cover too much territory. It is tempting to create an itinerary that includes Bari, Alberobello, Ostuni, Lecce, Otranto, Gallipoli and Santa Maria di Leuca in just a few days. You can do it, but you will spend much of the trip in a car. Instead, I would divide the region into sections and give each area enough time. Also, avoid treating the historic towns as quick photo stops. Lecce, for example, deserves several hours of simply walking, stopping for coffee and looking at the architecture. The same applies to Otranto and the smaller villages. And don’t underestimate the importance of lunch. Puglia is a place where a meal can easily take longer than you planned.