Now three months removed from the shenanigans that were the Outspoken Groom’s Bachelor Party, we’ve had some time to sit back, sober up and reflect. Overall this was one hell of a destination to celebrate the demise of the Outspoken Groom’s life as a single bachelor. From Six-Toed Cats to Captain Joe’s Jolly Roger II fishing charter, the 7.4 square mile island has everything needed for a textbook bachelor party weekend.
Where to Stay. One of the few considerations I had in finding adequate lodging for the weekend were the location and accommodations (pool, beach, etc). The Pier House Resort is where we disembarked. This resort boasts the perfect location on Duval St. at a competitive rate. We spent most afternoons at the beach bar sipping well-mixed libations and watching multi-million dollar yachts cruise by. Runners up would include the La Concha and Westin Resort. Let’s just say that this group had no regrets.
Bars. As the former home of Hemingway, Key West knows how to party. With just a quick stroll separating Hog’s Breath Saloon, Irish Kevin’s, Fat Tuesday, Rick’s, and the infamous Sloppy Joe’s, these bars are a great foundation to kick off, or close out, the night. If you’re more of the day drinking crew, or if you just need to escape the touristy filled bars for a few hours, a great spot to drop in for an adult beverage (or four) is The Rum Bar. Bahama Bob, bartender and owner of this speakeasy style saloon, concocted some of the best drinks we had throughout the entire trip. And with a sign on the wall says that reads “If you’re lucky enough to be at the Rum Bar, you’re lucky enough,” you’ll usually find a few locals pulling up a stool on a hot afternoon. Be sure to ask about his special concoction: Bob’s Bark Juice. Honorable mentions for the cocktails of the island go to the Dark ‘n Stormy (especially for using real ginger beer), Rum Runner and Mojito.
Entertainment. We’re firm believers in having somewhat of a plan, but don’t overdo it. The perfect bachelor party weekend involves at least one dinner with the whole crew and a Saturday afternoon activity that you don’t have to be successful at to still enjoy. In Key West, invoke the help of the fire department. With a yearly average of 7 to 11 infernos, these guys have some free time on their hands. Our fishing guide, Captain Kyle of the Key West Fire Department and skipper of the Jolly Roger II was a winner. We hauled a solid catch of Mahi and Blackfin Tuna while sipping our domestic of choice. A quick word for the wise, keep it low key the night before (a.k.a. don’t get too shit-faced) since you have to be at the marina at 7:00 AM. While the previous evening’s cocktails can make for good chum, vomiting off the side doesn’t equal a successful trip!
Eats. Most of our days didn’t involve breakfast…you could call it happy brunch though. Wake up at 9:00 or 10:00, and head to Blue Heaven. I’ll say no more, just go and send us a thank you card. For dinner, we’ll call out Sloppy Joe’s where the local band kindly announced to the entire bar that our table had a unique resemblance to the Last Supper. Let’s just say that turned into the running joke of the weekend. Now if you’re going fishing, DO NOT miss having your fresh catch cooked up at Dante’s or the Conch Republic. If combing the island for some late night options during your stumble home from Duval Street, look no further than Amigo’s Tortilla Bar and Angelina’s Pizzeria.
I could go on all day. But this should be enough to wet your palate. If you’re in planning mode drop us a line. We’ll be your wingman anyday.
Cheers Gents.Hailing from Buckeye Country, Keith (Best Man to the Outspoken Groom) is a bean counter that enjoys a good French press at daybreak, takes his bourbon neat, and winds down many evenings with a bold tobacco product. His lovely wife thinks it’s all odd, but to him life could not be better.