Last February, my connecting flight to SJO got delayed and did not arrive until around midnight. Thankfully, customs didn't take long. I would highly recommend getting the airport transfer with Sportsmen's as the front desk closes at midnight. They made sure the late night security guard was prepared to sort of half check me in and have my room key. The driver was a good sport for having to wait two extra hours. Once you are checked in, or at least have your key, you can come and go as you please. This was a Saturday night and I was a bit surprised the place was totally shut down except for the night security. If you plan to check in fast, you could even check with the driver and he might be willing to take you over to Taormina
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