Key West Sunset at Mallory Square
Mike's Meanderings Where is Parker Parked

Where Is Parker Parked? (Volume #6)

When the calendar barely reads November and the temperature in my home state is already struggling to reach 20 degrees F, it’s time to think about a warm weather winter vacation destination. If you don’t want to leave the U.S., your December to March options are somewhat limited. But in a recent survey, this small, 7 square mile island city had more bartenders per capita than any other city in the United States. I guess that almost guarantees that your insides will be staying as warm as your Speedo-clad exterior (or sand-covered derriere!)

Key West Airport
Welcome to Conch Airlines. Hope you had a shell of a flight!

The crazy culture of this place smacks you between the eyes the moment you step off the plane at this quaint little airport. The top of the airport terminal welcomes you to the Conch Republic. While the term for the people of this laid back area stemmed from protests that were brought about by a frustrating U.S. Border Patrol roadblock in the early 1980s, the nickname has hung on to this day in a more tongue-in-cheek capacity.

Key West cruise ship docked
This may not be the Love Boat, but Mallory Square sure is a beloved spot come sundown!

Probably the most well known area of the Conch Republic’s stomping grounds is Mallory Square. The town square type space on the waterfront is not only the docking port of cruise ships, but it’s also surrounded by an enormous selection of shops, restaurants and bars. And best of all, a couple of hours before sunset (yep, that amazing sunset that was this story’s cover photo) it also becomes a great performing stage. Stop down here to check out an unpredictable group of jugglers, comedians, musicians, unicyclers, and a variety of other talents you can only imagine.

Key West waypoint signs
Sittin’ on the edge of a world of water, you could go almost anywhere from here. But why leave?

When the show is over, walk down to the end of the Sunset Pier. What awaits is a crossroads that beckons you to sail away to anywhere your boat, or your long-distance imagination can take you. Not ready to leave this place? At least take a selfie!

Parker at Key West Lighthouse
For almost 150 years, this lighthouse (now fully restored) has been winking at nearby ships from the comfort of Whitehead Street.

Of course every coastal town needs a lighthouse. The funny thing about this town’s namesake lighthouse is that it’s not located right on the coastline. It actually sits more than a couple of blocks inland. But when you climb the 88 steps, spiraling all the way to the top, you’ll discover a full 360-degree bird’s-eye view of the entire island. (Plus you’ll be much closer to the famous first-of-its-kind Fresnel lens that eventually became commonplace design in lighthouses across the nation.)

Walk a few blocks to the north of the lighthouse and you hit the famous cat-filled house of 1954’s Nobel Prize for Literature winner, Ernest Hemingway.

Buoy at the Southernmost Point in Key West
Not only the Southernmost point, but also the “Selfi-most” point in the city.

Walk a few blocks in the opposite direction of the lighthouse and you hit the Southernmost point of the continental United States. If you could walk on water, you could keep walking – 90 more miles south to find some really good cigars!

Historic Key West Seaport Harbor Walk
Dive into plenty of food, drink and fun!

Speaking of walking, back on the north end of the island is a well-known historic seaport harbor walk that is filled with marinas, rental vendors (jet skis, glass bottom boat/snorkeling tours, sunset cruises, etc.), plus a bunch of those bartenders we talked about earlier. It’s no Duval Street when it comes to drinking establishments, but don’t worry, there are plenty of great choices to wet your whistle along the boardwalk.

Waterfront Brewery in Key West
There’s plenty of fun and great taste galore on tap at the Waterfront Brewery!

One of those such places is the Waterfront Brewery. The pub teeters close enough to the water’s edge that you may want to exit the back side of the building following the sampling of their signature beers. There’s 3 standards, Crazy Lady, Lazy Way IPA, and Island Life Lager, plus a rotating selection of other favorites. I’d suggest finding a new favorite … one beer flight at a time!

Flock of Seagulls of Key West
Hopefully I won’t be a one hit wonder but … I stand, I stand so close today … to this Flock of Seagulls

Speaking of flights, the area is filled with seafaring birds. Pelicans are very prominent along with the seagulls. You know what they say. When in Rome, do what the Romans do. Well, this isn’t Rome, but I still must have been suffering from “Pier” pressure when this picture was snapped!

Dry Tortugas National Park Ferry Boat with Parker Flatly
Hop aboard the Yankee Freedom and motor out to one of the most remote National Parks in the United States.

Also located in this north harbor area is the ferry boat tour to Dry Tortugas National Park. The park is located about 70 miles out into the Gulf of Mexico and is only accessible by tour boat, personal boat, or floatplane. Find out more about this interesting national treasure on this previous Park Yourself Outdoors blog post.

Although the National Park is miles offshore, Fort Zachary Taylor State Park is tucked away right on the tip of the island. It may be a bit hard to find, but it is a beautiful place to swim and picnic away a sunny day.

Harry Truman's Little White House in Key West
I elect Truman’s Little White House as one of my favorite tours in this crazy city!

As you’ve probably noticed, history abounds on this 4-mile long by 1.5-mile wide island. One of the most interesting historical places is Truman’s Little White House. In 1946 President Harry S. Truman was having some medical issues. His doctor prescribed a reduction of stress and an upgrade in temperature during the winter months. President Truman gladly obliged, retreating to this southern oasis (formerly the navy’s command headquarters during the Spanish-American War, World War I and World War II.) During the rest of his term, the President made repeated visits to this warm weather oval office alternative. He even started referring to it as his Winter White House.

Truman’s Little White House has since been turned into a popular museum that offers daily tours for a modest fee. If you have the time, it’s definitely worth a visit.

Key West Aquarium
I had all of those fish and aquatic creatures eating out of my hands!

Even though you probably came here to soak up some rays, it’s not always sunny in these parts. When it does rain, you can find a different type of rays by sticking closer to Mallory Square. The local aquarium is an interactive attraction that allows you to get up close and personal with a variety of aquatic creatures. Hand feed stingrays. Visit the touch tank and get a feel for giant hermit crabs, sea stars, conchs, and other common creatures. Or just watch the alligators, jellyfish or sharks from a safe distance. The aquarium experience is a great alternative when the weather doesn’t cooperate.

Key West drinking sign with Parker Flatly
Parker wants a Cocktail, too! And with over 350 bars located within a 1.5 x 4 mile radius, I don’t think there will be a problem finding one!

Have you figured out where Parker is parked yet? If you haven’t, you won’t find the KEY to this puzzle north, south, or even east. It’s entirely a direction of its own. And that place of conch shells, day drinking, relaxed atmosphere and mostly warm, sunny winter weather is KEY WEST, Florida. Check below for handy links to learn more about a variety of the places mentioned in this blog.

Have you ever been to Key West or somewhere else in the Florida Keys? We’d love to hear about your favorite hangouts in the comments box below, or feel free to email us at

Wondering where Meandering Mike and Parker Flatly are going to park themselves next? Find out as soon as their latest post hits the Web by signing up for email notifications here!


Mallory Square

Key West Lighthouse

The Ernest Hemingway Home & Museum

Southernmost Point

Waterfront Brewery

Fort Zachary Taylor State Park

Truman’s Little White House

Key West Aquarium

2 Comment

  1. Another great blog post! I hope you’re planning a trip for this winter; you need new material for your blog, right? 😉

    1. Terri Leonard, we’re hoping to get away for another short warm weather trip this winter. But our main focus is on a late spring/early summer trip out east to a destination that will be blogged about later!

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