West Tampa Sandwich shop had the best Cubans in Tampa. Good enough for Obama to stop by for lunch while he was president and visiting Tampa. I've eaten at all 5 of the top contenders and WTSS is the clear winner. Columbia in ybor is a good option too, mainly for the atmosphere.
Ybor, and Sparkman wharf for nightlife. A free trolley travels between those two night spots. 10-15 min ride.
About an hour north of Clearwater is Weeki Wachee Springs. Beautiful, Crystal clear water, very refreshing that time of year. You can rent kayaks, paddle down river and then be driven back t