My family has been going to Key West since the 70’s and a lot has changed but so much remains the same. It is a laidback, fun place to go with plenty of water activities, great food, great weather, flowing cocktails and loads of entertainment.

When you decide to visit Key West, the only way to get there is via US 1 or Overseas Highway. The drive is about 4 hours from Miami but, once you cross over the bridge to Key Largo, you will feel like you’ve left the US of A and entered some tropical island getaway.

The island is only 2 miles x 4 miles so the best way to see it, and absorb all the quirkiness, is by bike. Now you can walk it, but can’t cover as much ground, or rent a scooter or electric car, but they cover the ground a little too quickly. We much prefer bikes. Yes, I do mean the kind you have to peddle yourself! Then we spend the day leisurely traversing the island, enjoying the soft island breezes, blue skies and, of course, cooling off with our favorite beverages and a dip in a pool.

Here are a few pictures that I hope convey the fun, laidback vibe & total uniqueness of the “Conch Republic”. Conch Republic? Well, that’s a story for another time.

HOUSEBOATS - Comfortable & floating - what a way to live!

To get yourself in the spirit, turn on some Jimmy Buffett, you know him, the famous singer/songwriter who moved to Key West in the 70’s, and developed his laidback beach bum style, with songs like Cheeseburger in Paradise and Changes in Latitudes, Changes in Attitudes.

SMATHERS BEACH – is the largest public beach on the island. It has a half mile stretch of beach, plenty of activities and some good restaurants nearby, one of our favorites being Salute on the Beach.

SOUTHERMOST POINT – is a concrete monument that marks the southernmost point in the continental US and is located 90 miles north of Cuba. Actually 94 miles but who’s counting. In truth, the actual southernmost point is located just west-southwest of the buoy but is on US Navy property and inaccessible to tourists.

SOUTHERNMOST HOUSE –is one of the most historic Key West bed and breakfasts on the island. You must be 18 years or older to stay there due to the museum and historic pieces contained inside. Famous presidents, royalty and Ernest Hemingway have relaxed and unwound on the premises.

FORT ZACHARY TAYLOR - is an historic state park featuring a fort built in the mid-1800s. It hasn’t aged very well but it is interesting to visit. This fort helped defend the SE coastline during both the Civil War and the Spanish-American war.

HEMINGWAY HOUSE (POOL) –is nestled in the heart of Old Town and was home to Ernest Hemingway, a well-known author. He lived there for 10 years while writing books such as A Farewell to Arms and Death In The Afternoon. He was a huge boxing fan, loved to fish and, of course, visit the local bars. His favorite being Sloppy Joes (now known as Captain Tonys). The pool in this picture was built by his wife while he was away, replacing his boxing ring. That went over real big!

KEY WEST LIGHTHOUSE – The original lighthouse was destroyed in 1846 by the Great Havana Hurricane and was rebuilt in 1848. It originally stood 50 feet tall but as vegetation and taller buildings were built they raised in to a height of 100 feet. It was decommissioned in 1969 and is now part of the historical society.

VINO WINE BAR – We stopped for a sip in this cute little wine bar. Get a load of that ceiling!

You could also add the cemetery to your itinerary, which looks like any old cemetery would, but they do have a few unusual headstones. My favorite has to be the headstone that says “I told you I was sick”.

A CUTE SIDE ALLEY – There is always something interesting in the little side alleys. Here we found a neat little pizza joint and, on another, a neat little jazz bar.

MM0 – or as the non-islanders call it, Mile Marker 0, is the start of US Highway 1 that runs from this point to Fort Kent, Maine, some 2,369 miles away.

TRUMAN LITTLE WHITE HOUSE – was initially a naval station during the American-Spanish War as well as World War 1 & 2. In 1946, it became the winter White House for President Truman. Later presidents also made use of it as a site for the Cold War response. It is now owned by the state of Florida and run, on private donations, as a presidential museum.

BLUE HEAVEN – an iconic landmark in Key West, was opened by a pair of free spirits. Chickens, roosters and cats roam free as you dine under the sails in the courtyard. Over the past hundred years, the house has been a dance hall, bordello, billiard hall, playhouse, as well as hosting cock fights, gambling and boxing matches refereed by Hemingway himself.

Sign at BLUE HEAVEN – part of the whimsy of Key West.

BULL & WHISTLE BAR WITH GARDEN OF EDEN ON TOP FLOOR – A well-known open-air bar that still retains its Old Town heritage. The walls are hand painted murals of people, events and places around Key West that you can peruse as you enjoy a cocktail and live entertainment. This building also features the Whistle Bar on the second floor, with a great balcony for catching the wackiness on Duval St, and a rooftop bar known as The Garden of Eden, a clothing optional bar. Enter if you dare!

KEY WEST HOUSE – one of the lovely old houses, full of charm, that grace the streets of Key West.

CUSTOMS HOUSE – was built in 1891, and served as a courthouse, post office and government center during Key West’s heyday when wrecking made it the richest city per capita in the US. Now it is owned by the historical society and run as a museum. Have some fun with the lifelike statues that are situated around the exterior. Place yourself beside them and become part of the scene for a great photo op.

SHIPWRECK MUSEUM – is a great place to learn about the 400-year history of Key West’s notorious past. Founded on shipwreck salvage, some of which they helped along, wreckers would watch from the observation tower or patrol in their boats, and await a possible shipwreck. On average, this happened at least once a week, leading to a population of wealthy salvagers (which some still call pirates to this day).

CAPTAIN TONYS –is a famous Key West bar, built around the infamous Hanging Tree , and originally named Sloppy Joe’s bar. On most nights you could find Ernest Hemingway sitting on one of the stools. Now, when the landlord raised the rent $1 a month, the owner up and moved the bar to what is now Sloppy Joe’s current location. Captain Tony’s was later bought by a local charter boat captain and stands with his name today. Jimmy Buffett got his start here in the early 70s, writing his song Last Mango in Paris, and was often paid in tequila. Love that fact! When famous patrons visit the bar they get their own bar stool painted with their name on it. Here you will find stools for well-known writers, such as Ernest Hemingway & Truman Capote, musicians such as Jimmy Buffett and presidents John F Kennedy and Harry Truman.

HOGS BREATH – a famous laidback key west bar,nestled back from Duval, with one of the most popular sayings in the islands – Hog’s Breath is better than no breath at all! Gotta love 'em!

ROAMING ROOSTERS – Don’t touch the roosters and free-range chickens or they will call foul (sorry, couldn’t resist the pun). They are protected under the law.

SCHOONER WHARF – a bar with rustic charm, outdoor dining and great entertainment all day long. Not to mention the great view of the harbor, especially from the second-floor deck.

DANTES –Time for a dip! This restaurant is a great place to get lunch, dinner or drinks and you get free use of their pool.

BOS FISH WAGON – You would think this place was condemned and falling apart, well maybe that part is true, but they have some of the best fish sandwiches on the island.

BEST BAR SIGN – Drinking Mandatory

MALLORY SQUARE SUNSET CELEBRATION – Every night Key West celebrates their beautiful sunset over Florida Bay & the Gulf of Mexico with a big party. Street entertainers and musicians line Mallory Square and show off for tips while artisans show off their wares as everyone awaits the sunset.

The perfect end to an idyllic day.

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