Though I prefer the SL (if I can get a non-courtyard room) I have stayed at the Taormina before and have never had any issues with the room or housekeeping. I was perusing booking.com for my next trip in early April and I saw rooms at the Taormina for around $60 plus tax. Even with the new $10 guest fee (that I have not experienced yet) it is still a good deal.
I did end up booking this trip at the Castillo, primarily because I got a great deal on a king / balcony room with the all inclusive and I will save an additional $200 or so on round trip Jaco and airport transfer. I will probably visit the Taormina bar on occasion and would not consider walking back to the Castillo with a "date".
Despite what others have said, the hill does have a pretty considerable grade. Unless you are pretty young, you are going to be winded and your guest is really going to struggle in heels. Not a great way to start a romantic interlude.
Also, while relatively safe, after 9 pm or so you still have a few unsavory characters roaming around. Why take the chance for a couple of bucks.
Back in January, even getting overcharged, I usually paid 1000 CRC for a taxi back to the Castillo or the Sportsmens. Only one time after the Taormina bar was closed, did a guy say it was 2K (still less than $4) and I went ahead a rode with him just because I didn't want to wait. Just be sure you settle on a fare before you head out as very few taxistas will run the meter late at night for a short distance.
On the other hand, walking back to the Castillo from the Sportsmens is a no brainer. It's all downhill and a much shorter distance. You will also encounter a lot fewer characters on the street. And finally, the drivers out in front of the SL have a tendency to severely overcharge.
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