T-Minus 72 Hours (10 AM Arrival in the Keys)
Take the 15-minute drive from Key West International Airport to your oceanfront hotel at 1 Duval St., Pier House Resort & Spa. Check into your 1,200 square foot two-bedroom suite and let the Bachelor party begin! You and the guys will have a sweet setup with two King-size beds, two bathrooms, a wet bar, and a waterfront balcony.
T-Minus 70 Hours (12 PM The Most Kickass Food Stand Ever)
Start soaking in the casual atmosphere of Key West with an I-can’t-believe-this-came-from-a-food-stand lunch at Garbo’s Grill. With one look at the menu, you’ll realize that this is no typical taco shack. Chow down on the Kogidog (1/4 pound national deli all beef hot dog, house made kimchi, sesame mayo, fried cheesecabbage, scallions, carrots, daikon, citrus soy dressing, and sriracha) or a few Yum Yum Shrimp Tacos (with mango ginger habanero glazed shrimp).
T-Minus 68 Hours (2 PM Snorkeling/Diving Trip)
Take the hour-long scenic drive up Historic Route 1 to Hall’s Diving in Marathon, where you’ll have access to the largest sheltered coral reef system in the United States. If you’re set on snorkeling, book a private excursion to the Sombrero Reef Lighthouse. Scuba more your style? This is one of the best places to go reef and wreck diving. Hall’s also offers certification for new divers.
T-Minus 63 Hours (7 PM Dinner and Drinks)
After returning to your hotel to shower and change and take a why-the-hell-not shot, head to dinner Fogarty’s. This place serves up super generous portions of pretty much everything (classic American dishes, BBQ, fresh never frozen burgers, Key West staples like conch fritters, Asian and Italian inspired dishes, and fresh seafood with an island twist). We recommend the Bahamian Conch and Clam Chowder and the Pecan Encrusted Mahi-Mahi.
After dinner, be sure to stop by the Flying Monkeys Saloon for a frozen pregame drink. You could take it easy and pace yourselves, or you could add a floater…
T-Minus 61 Hours (9 PM Duval Street)
Duval Street is to Key West as Bourbon Street is to New Orleans, especially the last week of October during the annual Fantasy Fest (a crazy themed 10 day festival that’s been called “Mardi Gras on steroids”). Even if you can’t make it to the All Hallows Intergalactic Freak Show (this year’s Fantasy Fest theme), you’ll find that the real party starts right here, right now.
As always, we’ve got the best places for drunken debauchery all scoped out for you…
With 8 different bars (including a dance club and a strip club) Rick’s Bar Key West is pretty much your one-stop shop for a night out (i.e. no matter how many shots you have, you won’t get lost going to the next place). Your alcohol and live music needs are fully covered. Rick’s is also home to the best Gentlemen’s club in the Florida Keys, The Red Garter Saloon, which has two full nude stages, four poles, six private champagne rooms, and too many exotic dancers to count.
Sloppy Joe’s Bar has been a Key West favorite since 1937. The bar offers live music every night and a separate area (Joe’s Tap Room) for watching premium sports channels on HD big screens. During Fantasy Fest, Sloppy Joe’s hosts its Annual Toga Party and other themed events. They also throw a pretty huge NYE party. And of course, if you get hungry, you can order a delicious Sloppy Joe. It’s a bachelor party; you can get a little (or a lot) sloppy.
T-Minus 47 Hours (11 AM Screw Hangovers)
You’ll want to get up for “Breakfast With the Roosters” at Blue Heaven (don’t worry, breakfast is served until 2 PM). This place is self-proclaimed as “one of the most causal Key West restaurants,” so you may not even have to change out of your pajamas (use some discretion guys…) to dig into your BLT Eggs Benedict. Yeah, it’s breakfast, but save room for the Key Lime Pie topped with condensed milk and a ridiculous quantity of baked meringue. *Note: we’ve been notified that some people are afraid of chickens. Please make fun of anyone in the party who freaks out when a chicken runs by.
T-Minus 44 Hours (2 PM Hemingway House)
Today, we’re keeping it classy (for the most part). Soak up some brilliance in Ernest Hemingway’s Key West home turned museum. However, you’re definitely going to want to leave the marriage advice to us (the guy was married four times). You can book a private tour of the grounds to learn about the legendary Novel Prize winning author. Keep your eyes out for six-toed cats, descendants of Hemingway’s beloved pets. *Cash only.
T-Minus 42 Hours (4 PM Rum)
Hemingway may have said that “wine is the most civilized thing in the world,” but I think we can all agree that’s not the goal here. Rum is more on par with the bachelor party vibe, so head over to Key West First Legal Rum Distillery for a drink of history and an actual drink… or two or three. You know, whatever floats your boat.
After touring the distillery, go across the street to Rum Barrel for happy hour (2 for 1 drinks and bar food like wings, cheese steak eggrolls, and Philly style baked potatoes for $5). You’ll have your pick of 150 different rums and a large variety of craft beers.
T-Minus 38 Hours (8 PM Night Boarding)
Ibis Bay Beach Resort is the only place in the Keys where you can rent LED stand-up paddleboards. Not feeling confident in your ability to balance on a floating piece of wood? You can also rent a glass bottom LED lit kayak. Try not to capsize.
T-Minus 36 Hours (10 PM Serious Seafood)
Hopefully you’ve worked up an appetite because you don’t go to The Stoned Crab for a light meal. Start with a few Seafood Towers (each has enough Florida lobster, stone crab claws, Alaskan king crab legs, seared ahi tuna, local shrimp, sea scallops, New Zealand mussels, panhandle oysters, and littleneck clams for four people) followed by Lobster and Crab Mac & Cheese or Chef Tami’s Famous Specialty (scallops, shrimp, mussels, clams, lobster, today’s catch and stone crab in a roasted fennel, garlic, fresh herb and tomato broth).
T-Minus 24 Hours (7 AM Daytrip to Dry Tortugas National Park)
Get up and get going onboard the Yankee Freedom III, a high-speed ocean catamaran that will take you the 70 miles from the Key West Ferry Terminal to Fort Jefferson in Dry Tortugas National Park. On the boat, you’ll enjoy the beautiful scenery of the Marquesa Islands and Boca Grande, as well as have an opportunity to see wild turtles dolphins. The turtle shaped island (hence, the Spanish “tortuga” meaning sea turtle) is a favorite Key West destination with secluded beaches and shallow waters perfect for snorkeling and skin diving. Your trip also includes a guided tour of For Jefferson, breakfast, lunch, and snorkel gear.
T-Minus 16 Hours (6 PM Mediterranean Dinner)
Once you’re back from the island, sit down to dinner at Azur Key West, an award winning restaurant whose menu is inspired by the unexpected combination of Italian and Hungarian cuisines. We recommend the house-made gnocchi with braised beef rib and mushrooms. The lavender crème brûlée is also a must try.
T-Minus 12 Hours (10 PM Take Your Pick)
The Porch is a favorite local beer haven that has 18 beers on draft that change weekly, over 50 more in bottles, and about 20 big bottles to choose from (in addition to wine, mead, and bubbly). On the other side of the same house turned drinking hole, you’ll find a craft cocktail bar by the same owner Chris Shultz appropriately named The Other Side. There’s always something fun going on and the bartenders have a great sense of humor. You’ll feel right at home. It’s the perfect place to just kick back and chill for a few hours while you do some congratulatory drinking. Cheers to the groom!
For More information on the Florida Keys, head over to www.fla.keys.com.
Written by Ariel Guterman