One place that we ended up doing happy hour at (twice) was Half Shell Raw Bar and I was pleasantly surprised at how good it was. I've done HH at the bar here a good few times (sampled their 50c oysters - but I don't know if they still run this deal) and always enjoyed it - however that was before I liked Buffalo Shrimp.
Now I love Buffalo shrimp so I lapped up their HH while sitting at one of their bench tables in the super atmospheric main dining area which is right out at the water on the bight. We also ordered beer steamed shrimp, conch and lots more. With friendly staff, great food and good drinks there is nothing to not like this place!
A couple of afternoons we ended up at First Flight on Whitehead Street during HH as it was convenient to the attractions we had just visited (Little White House and Custom House museum). They do great HH drinks and Ciaran partook in tasty Margarita's both days. On one of the days we sampled a sliders option from the HH menu. Two beef sliders with cheese for $7. Tasty little bites but I think Ciaran may have eaten his in two bites and thought it was small. I thought it was perfect!
First Flight was where Kelly's formerly was (previously owned by actress Kelly McGillis) and it is a historical building as it was the original Pan Am office in Key West. See here for further info.
On this Key West trip I visited The Saint Hotel on Eaton Street for Happy Hour as I heard really good things about their cocktails and also their HH burger which is raved about. Their happy hour uniquely starts at 4.17pm as this their address! Very clever indeed!!
The Burgundy Bar is to the right as you enter the lobby and it is very salubrious and darkly lit, the perfect place for a special date.
The cocktail list is very cool - it is based on the 7 deadly sins. I had the "Wrath" which was a rum based cocktail which was very good indeed and was 40% off for Happy Hour. The cocktails here are top notch as they use top shelf liquors which always makes me a fan!
After most Happy Hours we ended up back in The Green Parrot listening to brilliant live music. This is a great chilled out joint full of locals and tourists having a great time. I reckon it is my favourite bar......I think it may also have a happy hour but am not sure what time it is on for and because they don't do food it is just drinks specials.