AUTHOR’S NOTE:  For those of you just catching up, I’m documenting my recent trip to the Florida Keys from two weeks ago, so if you’ve missed the first installment, make sure to read “Part 1 – Islamorada” from last week!

Picking up where we left off last week, we finished up our Tarpon-feeding antics at Robbie’s in Islamorada and continued our travels southward over the Seven Mile Bridge, passing by “Fred” the tree (a rogue tree growing up out of the old bridge trestle on our right – the tree is internet famous and even has his own Facebook page) before taking a westward turn into Big Pine Key once we completed the span.  Our destination?  The No Name Pub, tucked deep on the back side of Big Pine Key.  We traversed acres of scrub pine and low palms, and the island’s famous key deer popped out of the brush along the road from time to time.  These small deer are only the a few feet high, and several bucks (with full miniature racks of antlers) scampered along the roadway to avoid our car as we slowly crept along, trying to avoid any literal “run-ins” with our rental transportation.

The No Name Pub was a typical dive bar that you want to find in the Keys.  Dark, out of the way, and the walls and ceiling were festooned with dollar bills left behind by previous patrons.  In fact, according to their count, there were over $75,000 in ones decorating the walls, and in some cases, probably holding the structure together.  We had a few cocktails and sampled lobster bisque, wood fired pizzas, and burgers before hitting the road again to head towards the end of Route 1.

Mile Marker Zero.

Key West, Florida!

We made our way down to the historic old town and traversed Duval Street, busy with pedestrians from the docked cruise ships, and found our B&B for the next few days, the Seascape Tropical Inn.  Tucked nicely in the middle of the island on a side street (just off of Duval), our poolside cabanas were small, but provided the quintessential “Key West” vibe we were looking for in our accommodations.  Fun fact, cruise ships have to be out of port before sunset, or else they get a hefty fine (for blocking the sunset views of visitors staying in town), so the crowds quickly dissipated in the late afternoon as the cruise liners left port.

After settling in, we headed out on foot to hit the first of countless drinking establishments and watering holes that make Key West a laid-back escape.  We first stopped into Mary Ellen’s, where the drink of choice was a frozen Irish coffee topped off with crumbled Oreo cookies.  Then we hit up the historic Green Parrot, a Key West institution that’s been around since 1890.  Here we had the first drink in a bar challenge known as the “Bar-muda Triangle”.  Drink the signature shot at three different bars and get a free beer koozie.  The shot here was a ‘root beer barrel’, a half-glass of beer in which a shot glass of root beer liqueur is dropped in and the entire thing consumed in one go.  Tasty!  We then ended up at Rams Head Southernmost for some appetizers and more cocktails, listening to one of the many live singers that perform at the bars and restaurants.

We then headed down for our obligatory picture at the Southernmost Point, a large concrete buoy that draws the tourists like flies, then made our way to the end of the island to watch the cruise ships light up the horizon as they disappeared off into the Atlantic night.  We ended our first day in Key West with a soak in the jacuzzi pool at our B&B before calling it a night.

For our fist full day in Key West, I was up early and headed down to Cuban Coffee Queen for a hot and strong cortadito, a double Cuban espresso with cane sugar and steamed milk.  I paired that with a Cuban bagel – fresh, hot-pressed Cuban bread slathered with cream cheese and topped with honey and “everything” bagel seasoning.  A great was to start off the morning.

Once everyone was up and moving, we began the day of bar crawling down on the waterfront at Schooner’s Wharf, where I had my first Bloody Mary of the trip.  We then headed over to the Half Shell Raw Bar, where I completed “round two” of the “Bar-muda Triangle”, an oyster shot with jalapeno vodka.  Here we also took the time to play some table-top shuffleboard while drinking beer in the mid-morning, a true sign we had embraced the Key West lifestyle.  We then headed over to Dante’s, where the bar included a massive pool with a waterfall.  Then it was on to the Conch Republic for lunch, where we sampled conch chowder and blackened fish sandwiches while watching the water-men return from their morning journeys and cleaning their catch at the docks.  One more stop at Island Dogs to complete the bar quest (this time it was a Key Lime pie shot), and with our hard-won koozies in hand, we headed back to our B&B for some power naps before taking on the evening.

Refreshed and re-energized, we hit the town again, this time heading down to Mallory Square to take in the Sunset Celebration, a daily occurrence in Key West.  Tourists, street performers, and vendors congregate at the central square along the waterline, all there to gaze at the evening sunset.  Although clouds on the horizon dampened this night’s view, the air was festive as singers, contortionists, and a unicyclist entertained the crowd.  Sailboats and catamarans dotted the water with sunset cruises, and music could be heard everywhere across the plaza.  This is truly a must-see event for anyone visiting Key West.

 It was then time to resume our bar activities, so we stopped into the Hog’s Breath Saloon to kick things off.  We then headed up to the Bull & Whistle, a three-story bar complex about halfway up Duval.  The Bull is the bar on the first floor, while the Whistle is the bar on the second floor, complete with a balcony that wraps around the building – just perfect for sipping on a drink and people-watching the pedestrians on Duval below.  The third floor of the establishment is a special treat.  Known as the Garden of Eden, it is clothing optional.  Cell phones are banned, and of course we went up to take a look.  Yes, there were several people either partially undressed or completely naked, and I admire that kind of self-confidence (although our party stayed fully clothed).  There was even a DJ who was pumping out energetic dance music, and several au-natural patrons were sweatily enjoying the dance floor.  With enough excitement, sights, and alcohol for one day, we retreated to the B&B for another pool soak before bed.

The next day I was again up bright an early for another Cuban coffee run, and once everyone else was awake, we headed over to Blue Heaven for breakfast.  With an island vibe and lush setting (including plenty of free-range live poultry), we sipped more coffee and dined on omelets, fresh fruit, and I had a wonderful steak and lobster Eggs Benedict.  Keeping things a bit low-key for the morning, we stopped in to the Key West Butterfly Conservatory, an enclosed tropical garden with over 50 species of butterflies freely flying around the space.  There were between 1000-1500 butterflies flittering about, along with small tropical birds and a pair of flamingos (Rhett and Scarlett).  It was enchanting.  We then headed down to Louie’s Backyard, a Victorian house-turned-restaurant that had an ocean-side bar where we sat, had a morning drink, and felt the hot breeze on our faces before heading back for yet another power nap.  I awoke early and slipped down to Kermit’s Key Lime Pie for a slice of island goodness, and also stopped into Old Town Tavern for an afternoon cocktail before everyone else awoke from their afternoon slumber. 

It was time for one last night of pub crawling.  We deduced that Key West is much like Las Vegas – about three days is all the body can take at one time – so we were determined to make the most of our last night.  We started out at Captain Tony’s, another Key West institution.  A dark and vintage watering hole, I tried to toss a coin into the giant grouper’s mouth over the entrance (I missed) before we headed up to Rick’s Tree Bar, where I learned how to make the perfect Bloody Mary by watching their bartenders over 25 years ago.  To my surprise and delight, they still make them the exact same way, and we left Rick’s to go across the street to Sloppy Joe’s.  After more cocktails (and some appetizers), we headed over to the Tiki House, where we sipped on ‘Zombies’ and ‘Singapore Slings’.  Then it was off to Irish Kevin’s, where Irish Kevin himself was providing the house entertainment.  He had the entire bar in the palm of his hand, having the audience join in for raucous drinking sing-a-longs, chants, and other shenanigans as he strummed his guitar and brought patrons up on stage to have them chug pints or to pour shots of Tequila or Irish whiskey down their gullets.  It was a great and entertaining way to finish off the evening, and after countless pints of Guinness, we headed back to the B&B for bottled water, aspirin, and some much-needed sleep.

I commend you, Key West – you have lived up to your storied reputation.

NEXT WEEK:  Join me for the final installment of my vacation adventure, as we take on Marathon and the Middle Keys!