For a city that’s known as Margaritaville to some, how can you honestly make a pub or bar crawl interesting? Well, that’s what I did when I went to Key West for the second time with Virgin Voyages, on the legendary Duval Street. On my last visit, I took a food tour that involved fish tacos, shrimp cocktail, lobster mac and cheese and of course, Key Lime pie. Since I’m always interested in the food and drink a place has to offer, I naturally gravitated to this, thanks to Key West Pub Crawls.

The only problem here? The amount I was going to drink at 10 AM or so. Now, I’ve done wine tastings around this same time out in California, and I’m just not used to day drinking, especially when I haven’t eaten anything except the digested breakfast from a few hours before. I also wanted to be mindful of how much I drank, because I’ve realized that I don’t do well when I’ve consumed too many alcoholic beverages, no matter what time of the day it is. Having several drinks early meant I didn’t want to have much on the ship later.

But as it turned out, the four drinks I did have (there were five altogether, and I opted out of the fifth one) were not too strong, except for one. We also had a great guide, Sarah, who has lived in the area for ten years and is a fitness instructor on the side. At each bar, we could get the signature cocktail, a two-part mixer like rum and coke, or a beer. I chose the cocktails.

Surly Siren

The first stop on the pub crawl was at this second-floor bar, which made me wonder how many patrons nearly fell or did fall down the stairs in an inebriated state. When you think of a Key West bar, you might envision something dive-y, with worn tables and chairs, high ceilings and dark wooden rafters, no air conditioning (because there are breezes that blow through the open entryways), and dollar bills stapled to the beams. That’s exactly what this place looked like.

Mermaid Lemonade was a welcome first drink, since it was about 90 degrees outside with nearly equal humidity. The cocktail consisted of lemonade, vodka, Sprite and blue curaçao, and it was naturally turquoise colored because of that last ingredient. Normally, I don’t like blue-tinged drinks, but I nearly chugged this down because I was so thirsty. It wasn’t necessarily because it was my favorite.

Rick’s Tree Bar/ Rick’s Downstairs

Ernest Hemingway – probably the most famous local resident along with Jimmy Buffett – supposedly would come to this outside watering hole and lean against the monkey pistol tree. What’s most interesting about this place is it’s an eight-bar complex that includes a live music venue called Durty Harry’s, an upscale room, a karaoke bar, a daiquiri bar, a dance club, a terrace bar and a gentlemen’s club. I suppose there is a bar here for whatever mood you’re in.

At both places, we could have the Key West Lemonade, which was very similar to the Mermaid Lemonade at the Surly Siren, just without the blue curaçao and Sprite and with triple sec. That gave the cocktail a pleasant citrus taste that was missing from the Mermaid, and it didn’t have the weird blue tint that can look like Windex window cleaner. For some reason, the last stop on the tour was Rick’s Downstairs, and I chose not to have their lemonade again, or the two-part mixer or beer, so I left the pub crawl early.

Irish Kevin’s Pub

All of us on the tour appreciated this cavernous bar because it was the only place with air conditioning. I think the dark interior also helped us cool off from the relentless heat and humidity outside. Another positive vibe was the live music already playing. Some people sang along and even danced after having a drink or two.

We had our first rum-based cocktail here, called the Green Gator. It also included blue curaçao, sour mix (citrus juices and simple syrup), orange juice and a Bacardi 151 rum floater. This last element alone made the drink stronger, but it was probably my favorite from the entire pub crawl because it was unique and had a great flavor. I thought I wouldn’t drink the whole thing, but just because I was generally overheated, I did just that.

Fogarty’s and the Flying Monkey Saloon

The fourth stop on the tour took us to the outdoor bar portion of this restaurant, which is housed in a white Old Florida-style mansion with two large porches on the first and second floors. We ordered from their open-air stand, with adjacent patio seating, fans and misters. Most drinks came from slush machines, so they were ready for easy serving.

Along with the Green Gator cocktail at Irish Kevin’s, I liked my option here, strangely called Pain in the Ass.  It was half a pina colada and half a rum runner (light and dark rum, grenadine, banana and blackberry liqueur, pineapple and orange or lime juice). Having this combined frozen cocktail, which I normally don’t like, hit the spot. I would recommend going on the Duval Street Pub Crawl, especially if you’re like me and foolishly go on a hot August day.