How would I plan your trip to Lecce
1) June and September are the best periods, then July and August
2) take a plane to Brindisi, after having booked a car. You will get the car at the Brindisi Airport.
3) Lecce is far about 40 minutes from the Airport. A number of good hotels are in Lecce, which might satisfy any need in term of confort and budget. However, you might also choose to book a room in small towns near the sea. I would suggest Otranto and its surroundings. As an alternative to the hotels, it is quite easy to find B&B offers, cheap and in most of cases in very nice places in the country. In an hour by car you can cross the country from one opposite to the other: do not mind much about the distances in choosing the place where to stay.
4) Your stay should not last less than 7 days. More than 15 could be too many, except the case you like a lot sea life.
5) make sure the rented car has air conditioned, ..then just go around, discover places, discover hidden restaurants, funny shops, small towns and their funny inhabitants which in most of cases will look at you as if you are just landed from Mars.
6) Otranto and Ostuni deserve a visit. Other nice places are Castro and Gallipoli. However, my suggestion is: not much planning. Just go around.
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