Key West Caricatures

Located in Mallory Square for the Sunset Celebration, this caricature artist makes fast, great-​looking artwork. The prices on-​site are cheaper than listed on the website ($ 20 per person for a color portrait; I forget how much it was for black and white), and the artist, Terry Riley, was super friendly.
I got a caricature taken with my girlfriend, and he was able to get everything done extremely fast. The scenery around the pictures is fun, and it looks like he always tries to incorporate the feeling of Key West somewhere into the portraits, whether it’s a sign or the Southernmost Point marker. One downside: the characters don’t really look too much like us (you can’t expect much more with caricatures, I think), but it really could be a picture of two random people — not us.
That being said, the overall experience was great. If you’re heading to the Sunset Celebration, I’d definitely suggest stopping by his stand and getting a caricature done.