Key West Bar/Golf Road Trip
Miami to Key Largo to Islamorada to Key West
Research by Fat Guy
The Florida Keys are a great destination no matter who you are. Partiers, chillaxers, outdoorsy types, bar flies, chaise lounge addicts, singles, families, young, old, straight, gay, bi, and everyone in between can find something about the Key West vibe that works for them.
Part of what makes The Keys great is the feeling of freedom (and dropping of hometown inhibitions) that comes from its' Caribbean aura and remote location. You can't get there without at least a 3 hour road trip across Route 1 Dixie Highway from Miami (or 8-plus hours from the Florida border and points north). Any road trip that takes you through Key Largo and Islamorada to a spot where you really shouldn't be during hurricane season is easily worth a week's vacation.
While a Florida Keys road trip is apt to be more about Rum Runners, key lime pie, Buffet tunes, and watching sunsets than it is about golf (there's only one 18-hole course in the Keys--Key West GC), you can still pair a couple rounds with a few days in paradise.
When To Go: It's hardly ever a bad time to head for Key West. Monthly temps average in the mid-70's in Jan/Feb, high 70's in Mar/Dec, low 80's in Apr/Nov, mid-80's in May/Oct, high 80's in June/July/Sept, and a tolerable breezy 90 in August. But beware that pesky hurricane season--technically from June 1 through November 30, but sharply peaking in late Aug/Sept. Partiers and hedonists will want to hit Key West during Fantasy Fest (www.fantasyfest.net), an eclectic celebration of Mardi Gras meets art festival meets biker rally meets Gay Pride week, which happens around the 3rd week of October annually.
If you're driving down from points north and have an abundance of vacation time, make this a two-week adventure and tack on TravelGolf.com's Florida Margarita Golf Trail on your way down to South Florida.
Key West Bar/Golf Road Trip Itinerary
First Stop: Miami
Miami is worth a week's vacay all by itself, for its uber-hot beach, Art Deco hotels, sexy pools, trendy restaurants, and world-class South Beach nightlife, let alone the great Miami golf scene. But it's a playground for the top 2% (both in looks and bank account), so for an Average Joe Key West road trip, it's just an overnight splurge for a great eye-candy-laden launching-off point.
For an affordable Miami round, play CRANDON GOLF AT KEY BISCAYNE. Per T&L Golf: "The perfect antidote to pricey resort golf, this affordable municipal course lies tucked away in a lushly tropical county park on Key Biscayne. The unspoiled natural setting—replete with palm trees, white and red mangroves and a dazzling assortment of waterfowl—belies its proximity to downtown Miami, a mere fifteen-minute drive away. A number of holes offer mesmerizing views of the city skyline across Biscayne Bay. Originally opened in 1972—the work of Robert von Hagge and Bruce Devlin—Crandon Park, the name commonly used for the course, hosted a Champions Tour event for years, entertaining the likes of Chi Chi Rodriguez, Lee Trevino and Gary Player. The layout received a thorough redesign (courtesy of von Hagge) in the early nineties following Hurricane Andrew. From the championship tees, it can play as long as 7,300 yards, with a whopping 145 slope, and includes a collection of par fives ranging from 555 to 638 yards. The layout features numerous doglegs as well as tons of sand and water. But the biggest challenge may be securing a tee time, as reservations are taken only five days in advance and discounts for Dade County residents make the course extremely popular."
For post-round drinks, Golf Digest says head for the Rusty Pelican. Enjoy the sunset views.
If you have enough time for a full night of hot South Beach nightlife, hit Mango's, recommended by my buddy Scott. He lost most of an evening there once. For something a little lower key (but still South Beach cool), hit my buddy Jeff's pick, The Clevelander Bar. Go low brow at Esquire fave Jimbo's, or hit local's hangout Automatic Slim's.
If you're liquid, an overnight stay at one of South Beach's stylish Art Deco hotels is a no-brainer. For us middle-class schmos trying to do a road trip on a budget, T&L Golf says hit Biscayne Blvd for the glorious ruin of seedier motels like New Deal, Mardi Gras, Vagabond, Sinbad, Starburst & South Pacific. Or, AOL Traveler ranked The Palms Hotel & Spa (www.thepalmshotel.com) as their #1 Best Budget Beach Hotel. "Normally this super sleek oceanfront resort just above the bustle of South Beach would cost a grip during the winter high season. But, it's a bargain for those who don't mind the steamy August through October weather. Rooms are a great size and mimic the colors of the sea scene outside with their brown, cream, and turquoise touches. And they come kitted with an iPod docking station, flat screen TV, and free WiFi. Outside, take a refreshing dip in the bathwater-warm ocean, lounge by the pool, or enjoy a potent Miami Vice at the Tiki Bar. But if you're like us, you'll find yourself relaxing atop an opium bed in one of the free cabanas -- a true rarity in these parts."
The Palms Hotel Pool & Tiki Bar
After a night of partying in Miami, chances are you'll have a decent next-morning hurang to get over before you can get on the road. The sands of South Beach are consistently rated as America's sexiest, so nurse yourself back to sober with a morning on the beach while checking out all the uber-hotties in barely-there bikinis.
South Beach possesses the largest collection of art deco buildings of any neighborhood in North America. For a full appreciation of this elegant Jazz Age school of design, accented in the Miami vernacular of pastel-hued and neon-emblazoned facades, take a guided walking tour offered by the Art Deco Welcome Center (305-531-3484, Tenth Street & Ocean Drive).
For a pre-departure lunch, sneak into the pool at the Fountainbleau Hotel. You may not realize it, but you remember this pool; it's the one from the pool scene in Scarface (it's also where Connery's Bond played cards with Goldfinger poolside). In addition to a great pool bar, the Fountainbleau's Lobby Bar was once a Rat Pack hangout.
For more Miami info, see also: Doral GR&S, Miami FL Golf Weekend
Second Stop: Ramrod
Per KeysVacations.net, hit Boondocks Grill and Drafthouse in Ramrod at Mile Marker 27 on the Dixie Highway. The bar is open air and dog friendly (the porch comes complete with water bowls and a kiddie pool for Fido to cool off). They also have the only mini golf in the Keys, glow (night) golf as well, and great 1/2-price happy hour specials. Peel & eat shrimp are only 49 cents on Tuesdays after 4PM.
Third Stop: Key Largo
You gotta stop at any place a Bogart movie was named after. Climb all the way out of the hurt locker with great Bloodys (made with Clamato Juice and spices) at Carribean Cafe (www.facebook.com/CaribbeanClub), a waterfront local's joint where Bogey and Becall filmed Key Largo. Play a few games of 8-ball with the local bikers, and then sing a tune with the band.
GolfChannel.com digs Alabama Jack's (1500 Card Sound Rd, 305-248-8741) out in the mangrove swamps, where locals, shrimpers, boaters and other odd assortments of castaways (including Jimmy Buffet) have been tilting a few for more than 50 years. You can get locally made Key West Lager and Sunset Ale to go with your conch fritters and steamed shrimp. Live music on weekends.
To soak up some of that booze with some great fresh seafood, FloridaTravelLife.com likes Fish House Encore (Mile Marker 102, www.fishhouse.com) for the great courtyard patio and a fun tiki bar.
Fourth Stop: Islamorada
Islamorada sounds like a Captain Jack Sparrow port o' call. True to form, the Florida Keys version is flush with waterfront tiki bars. Hit Islamorada's Holiday Isle Resort (www.holidayisle.com) for a cocktail or three, and you may as well get a room while you're at it... you won't want to leave the resort's friendly waterfront confines, or be in any shape to drive after hitting their 5 fun-filled bars.
Their original Tiki Bar claims to be where the Rum Runner was invented, and their Rum Rummers Island Bar is like a Swiss Family Robinson hideaway with a liquor license.
Or, you can't pass up Holiday Isle's Kokomo's (yeah I know, the Beach Boys tune is now stuck in my head too). Or hit the Wreck Bar, shaped like a shipwreck, or their Jaws Raw Bar for waterside casual seafood.
Golf Digest likes Islamorada's Lazy Days Oceanfront Bar for waterfront tables, excellent conch chowder, the fresh grouper sandwich, and the best Key Lime pie in the Keys.
FloridaTravelLife.com likes the dockside tables at Islamorada Fishing Company (behind Wide World Sportsman) for everything from coconut-crusted fish sandwiches to conch fritters.
And finally, there's Lor-e-lei Cabana Bar (www.loreleifloridakeys.com), a tasty slightly-upperscale joint, hard by the water with a thatch roof bandstand, palm trees, and spectacular sunsets.
If you're looking for something a bit more upscale and theatrical, head for Pierre's Restaurant's Full Moon Parties (Mile marker 81.6, www.pierres-restaurant.com). Every full moon, they host a big beach party with bonfires in the sand, fire blowers, stilt walkers, and specialty drinks available at their indoor and outdoor bars. Think Caribbean beach party meets P.T. Barnum meets Eyes Wide Shut. If there's no full moon any time soon, they also serve outstanding gourmet food on the bayfront.
If you've got your golf widow along for the trip, it's time to pay the piper for her putting up with a vacation itinerary built around bars and golf courses. Splurge to crash at the most gorgeous (and pricey) resort in the Keys, Cheeka Lodge (Mile maker 82, www.cheeka.com). When she dreams of the perfect Florida romantic beach/spa getaway, this is what she pictures. They even have bathtubs on room balconies (this must be where they film all the Cialis commercials). Cheeka Lodge is picture perfect postcard, everywhere you look. The bonus for you: They also have a picture perfect tiki bar.
Cruise Over: 7 Mile Bridge
From James Bond flicks to Robert Redford’s Up Close and Personal, the Seven Mile Bridge is one of the country’s most photographed. Can't quite picture it? Think Jamie Lee Curtis' black dress downblouse cleavage shot from a helicopter while the bridge is being blown up in Schwarzenegger's True Lies.
Fifth Stop: Big Pine Key
FloridaTravelLife.com digs Big Pine Key's No Name Pub (Mile marker 30, www.nonamepub.com), the oldest in the Keys. It started as a general store in 1936 (and once housed a brothel upstairs) and has been serving thirsty travelers ever since. "Dollar bills hang from the ceiling at the No Name Pub. It may be hard to find, but the funky atmosphere of this tiny bar is known for its tasty pizza." Their slogan: "A nice place if you can find it."
Final Destination: Key West
Tee it up (finally!) at Key West GC. Per GolfChannel.com, "Rees Jones designed Key West Golf Club, the southernmost golf course in the continental United States and situated seven feet above sea level. Since real estate is at a premium in the Florida Keys, the golf course rolls out at 6,512 yards, short by today's standards, but it has plenty of scenery to keep you interested. Most golfers talk about the infamous "Mangrove Hole" -- the 143-yard, par-3 eighth that is a test for the best players. But the golf acreage includes dense foliage, tall palms, mangroves, lakes, rolling fairways, multi-tiered contoured greens and wildlife, including plenty of egrets. A recent renovation improved the golf course, rebuilt its 90 bunkers and improved its conditioning with newer salt-resistant Paspalum grass. The golf course was built in 1983 and has had numerous chances to improve. In 2005, Hurricane Wilma destroyed many greens and left little grass on many fairways. Today's bunkers include some with sand and some coral waste areas."
After the obligatory lost afternoon at Hemmingway's old hang, Sloppy Joe's (201 Duval St, www.sloppyjoes.com), Richmond golf writer and author of Blue Fairways Charles Slack says the current Sloppy Joe's is a tourist trap rebuild, and that Hemmingway's original hang is on Greene St and is now called Captain Tony's. My buddy Bo recommends Irish Kevin's (211 Duval, www.irishkevins.com) as a good spot for divorcee's on the prowl. Per Philly's Metro Paper, for other dive bars and live music, try Whistle Bar or Hog's Breath. For dance music and meat markets, go to Wax, The Copa, Rick's, or RumRunner's. For a killer happy hour, hit the Half Shell Raw Bar, which serves Key West's best conch fritters and cheap oysters. The Green Parrot and The Meteor boast awesome BBQ and ambience. Cowboy Bill's Key West Honky Tonk Saloon (www.cowboybillskw.com) is a great party spot with a little of everything for everyone... live tunes (country and otherwise) and dancing, a sassy scantily-clad Coyote-Ugly-style staff that dances on the bar, a mechanical bull, good food, and great happy hours. OR, for drinks at sunset, Travel Channel says try Billy Fish. A great spot for this Key West tradition, and the house specialty frozen Rum Runner ($8) comes with a test tube shot of dark Bacardi 151.
Billy Fish 
OR, tourists and Parrotheads alike love Jimmy Buffet's Margaritaville (500 Duval St, www.margaritaville.com/keywest ), big on live bands and Buffet's famous laid back island party style.
A U.S. couple who has traveled Mexico and the Caribbean extensively and now lives in Playa del Carmen recommends:
Schooner Wharf Bar, 202 William St., Key West, Florida.
Not technically a "beach" bar, but an island bar overlooking the water of Key West's historic harbor. Friendly, funky and relaxed best describe this place. The large bar is palapa covered, the kitchen serves excellent seafood, and best of all Key West's own storyteller/ songwriter/ crooner/ comic/ rogue, Michael McCloud, entertains most afternoons. The crowd is eclectic to say the least: spring breakers out to party, elderly tourists from cruise ships, locals, celebrities, undercover spies and pirate wannabes. This is the perfect place to spend a long afternoon sipping margaritas and starting that tropical adventure, or perhaps meeting that mysterious stranger you've dreamed about. Key West is the southernmost edge of the continental United States and the Schooner Wharf is on the edge of Key West. Anything can happen at the end of the road!
Here's Travel Channel's take on the perfect Key West pub crawl:
The southernmost city in the United States, Key West is a stretch of land 3 miles wide by 5 miles long. It was a home to Hemingway, the beginnings of Jimmy Buffett and is still the destination of serious fishermen. Duval Street is home to it all -- legendary bars, live music and ice-cold drinks. Pull up a bar stool and order a pint -- this is the Florida Keys bar crawl experience.
Turtle Kraals
Proving that, on a bar crawl, slow and steady wins the race are the Friday night turtle races at Turtle Kraals. The starting line is crossed at 6 p.m., so grab a ticket from the bartender when you order your first round. Place your bets and watch in excitement as a handful of box turtles slowly make their way down a shuffleboard table. At sunset, by which point the turtles should have crossed the finish line, head upstairs to the rooftop bar overlooking beautiful Key West.
Finnegan's Wake
If daiquiris and margaritas aren't your drinks of choice, hit up the $5 pints of Smithwick's offered at Finnegan's Wake on Grinnell Street. Live music provides a lively and festive atmosphere indoors, and outside there's a secluded backyard pub with ample seating. This Irish hideaway has happy hour specials. Check the website for more information.
Hogfish Bar and Grill
Just over the Cow Key Channel Bridge on tiny Stock Island is Hogfish Bar and Grill. Follow Front Street until you stumble upon the historic and iconic watering hole. This noisy haunt is nestled on Safe Harbor Marina, rumored to have been the base of operations for the Bay of Pigs Invasion. Strong drinks go hand in hand with the "Killer" sandwich: hogfish served smothered with Swiss cheese, onions and mushrooms served on fresh Cuban bread. Sure, it's not technically Key West, but Hogfish is the real deal.
Captain Tony's Saloon
Back in Key West proper is the authentic Captain Tony's Saloon. The smoky joint is full of regulars with "back in the day" and "remember when" stories. Before cruise ships lingered in the harbor, Hemingway supposedly drank, reveled and even wrote here. There's a friendly, yet heated, rivalry between Captain Tony's and Sloppy Joe's as to which bar was Hemingway's home away from home. However, Sloppy Joe's can't lay claim to Captain Tony's immortal mention in Jimmy Buffet's "Last Mango in Paradise."
Sloppy Joe's
The other side of the Hemingway debate, Sloppy Joe's is a classic bar still featuring its original early 20th-century wooden ceiling and cracked tile floor. Sloppy Joe's opens in the morning when mimosas and Bloody Marys are served with breakfast, making it the perfect spot to start your Key West pub crawl. Live entertainment is served with lunch and these good vibes continue through the late afternoon and long past sunset.
Durty Harry's
A Key West bar with a lively party atmosphere, Durty Harry's features live rock bands almost every night. Listen in the balmy Key West night air at one of the outdoor bars or head upstairs to Rick's, an indoor/outdoor dance club that heats up later in the night. Also located near Durty Harry's and Rick's is the Red Garter, a small strip club where the bouncers remind couples that the "family that strips together sticks together." This is clearly the place to go when you're feeling rowdy.
Green Parrot Bar
Green Parrot Bar is the proud home of great drinks and bad art. The walls are adorned with works of local artists -- and not all of them are talented. The bar has been a landmark since 1890, and its open-air set-up is home to friendly bartenders, cold beers and tasty cocktails. While the drinks are delicious, Green Parrot's jukebox is legendary, featuring Chicago, Memphis, Texas and Delta blues.
Best of the Bars Scavenger Hunt
Sign up for Best of the Bars' whirlwind tour of Key West's Duval Street bars combining the fun of drinking with a competitive scavenger hunt. However, you won't be scouring the streets for mundane or weird objects; instead you'll have to solve clues and riddles that will take you to Key West's best bars and hot spots. The tours are normally scheduled every Friday, Saturday and Sunday nights and last about 3 hours. Winners will be announced at the last mystery location and prizes awarded, including dinner gift certificates, bar tabs, free drinks and Key West souvenirs.
See also: Fat Guy's Hemmingway's Favorite Bars Golf Tour
Where To Grub: Dining in Key West can get expensive in a hurry, so for a lower budget, listen to Rachael Ray from the Food Network's $40 A Day show. She recommends the Crack'd Conch, a local diner for over 30 years. They serve a very affordable lunch, and be sure to try the Key Lime Pie ($3) made fresh from Key Lime trees in the restaurant's backyard. OR, local artists love Blue Heaven. The building has been a bar & restaurant for 120 years, with plenty of lore to go with it. The top floor once housed a bordello, and Hemmingway boxed in the courtyard here on Friday nights (figures Pappa was DOING Fight Club 30 years before Fight Club was written). Blue Heaven is eclectic & colorful, with an outdoor courtyard featuring a thatched-roofed bar, ping-pong, and a rope swing. Try the jerk chicken tortilla ($10). OR, for dinner hit Bahama Mama's, owned by 5th generation locals (called "Conchs"). House specialties include Conch fritters, hush puppies, plantanes, and a Must Try is the curried conch ($16), served with their shrimp hashcake, which has 34 ingredients and is "out of this world."
Per Philly's Metro paper, nothing eases your morning-after suffering like M&M Laundry, a combination laundry and eatery specializing in Cuban sandwiches and cafe con leches. Golf Digest digs Hogfish Bar and Grill, where the specialty is the Killer Hogfish Sandwich. A combination of diver-caught hogfish, Swiss cheese and onions on Cuban bread, the dish turned out much better than the other operation masterminded right there at Safe Harbour Marina: The Bay of Pigs Invasion, in 1961.
Where To Stay: While there are a few chain hotels here for those of you with hotel points to spend, most folks go the B&B or small quaint hotel route on Key West. There are dozens of great little places with idyllic courtyards, ocean views, and serene pools. KeysVacations.net recommends The Blue Lagoon on Roosevelt Blvd. Affordable at $119 a night in February, decent rooms, a pool, hard by the ocean, and walking distance to the Bayside Bar & Grille (also on the water, with good food). The caveat: It's a short drive to Duval Street.
Tip: Duval Street's bars party so deep into the night, you may be hard pressed to get any sleep in a room anywhere along Duval. In case that actually matters to you.
For an on-the-cheap lodging alternative, bring a tent. My old boss used to frequent the Keys during his adventurous 20's, and used to camp at the Key West Naval Air Station (www.livestrong.com/article/263752-camping-at-key-west-naval-air-station/).
What To Read On The Beach: The Garden Of Eden by Ernest Hemmingway. Erotically-charged, and somewhat off Pappa's normal beaten path; Fight Club by Chuck Palahnuik; Blue Fairways by Charles Slack for a golf road trip tale; or Tales From Margaritaville by Jimmy Buffet.
Tip: My friend Danielle recently spent a March weekend in the Keys and offered this advice for your return trip to Miami: "It's a looong drive from Key West all the way back to Miami, plus you'll be way hungover, and there's a lot of traffic on the Dixie Highway, especially heading back north on a Sunday. Take an extra day off for a leisurely return travel day, and book a stay on Key Largo on your last night to make the long drive back to Miami a lot more tolerable."
[Fat Guy Note: I have not taken this trip or explored any of these courses/locations. As always, proper research and reservations are required. I'm just the idea guy on this one.]