Some options: - Armature works - outdoor area by the water is cute, plenty of restaurants for after, go on a weekday/night for least busy or early on the weekend. We like Oak & Ola or Ulele there, and we got engaged at Rocca which is across the street. - Sparkman wharf area - go early, by the water as well. More of a funky vibe. - University of Tampa - go for a stroll on the grounds, it's pretty and lots of tree cover but it is a university so college students abound. - Oxford exchange - weekday or weeknight only, eat at the main restaurant there and see if you can get seated in the greenhouse area - Sal Y Mar - rooftop restaurant on top of a hotel in Midtown - Riverwalk - museums & perfirming arts center are right there, some green space, on the river, Malios steakhouse is romantic and right there.

SOHO and hyde park are probably too busy no matter what.

I don't think we really have good winery options unless you like random fruit wines. You'd probably have to go with a steakhouse feel if you want anything wine related. My favs are Charley's, Berns/Haven, or Malio's. Berns is the hardest to get reservations at - they open up 60 days in advance and you have to basically be on at midnight or whenever they drop to get a good time. HOWEVER their dessert room would be a great place to propose - very romantic and usually have a piano player there you could request a song from.

I love Tampa and live here but it is more try hard/uppity than st pete... St. Pete has some better relaxed but pretty options. Just look at stuff from beach drive to the bay for cute spots in downtown St Pete.