Delight in a Classic Florida Vacation
What’s the attraction of a tropical island off the coast of Florida that is only 4 miles long and 2 miles wide? Despite its small size, Key West, Florida has a plethora of activities to enchant, entice and entertain visitors. Bordered by the Atlantic Ocean and the Gulf of Mexico, Key West boasts wonderful, soothing tropical breezes. Plus, this southern village offers an abundance of activities from a relaxed vacation to action-packed adventures on land and sea. Key West caters to all ages and interests for a classic Florida vacation.
Seeking a getaway, we’re off on a trip to the Florida Keys. Yes, even Florida residents enjoy vacations in our state. Florida’s national treasure is its 825 miles of sandy beaches along the Atlantic Ocean and Gulf of Mexico. Having visited beaches, towns, cities, and villages along Florida’s coastline, we find each brings its own unique charm. On our “bucket list” is to drive the Florida Keys Overseas Highway. The history of the Overseas Highway, from its beginning as the vision of millionaire Henry Flagler of the Florida Keys Over-Sea Railroad from Miami to Key West, has always intrigued me. We thoroughly enjoy the drive and picturesque scenery of the Over Seas Highway, its 42 bridges, aqua blue waters, enchanting villages and views of the remains of the original Over-Sea Railroad. Driving on weekdays and early mornings avoids traffic. Now to experience Key West!
ACTIVITIES ARE PLENTIFUL IN KEY WEST
Hop on a Trolley –“See the Best First”
Hopping on the Old Town Trolley, we are excited to experience and learn about Key West. Mr. Ed, our driver and tour guide, is terrific. He provides great information on this amazing island, its history, the variety of things to see and do, plus a lot of fun facts. With almost 25,000 residents on a 4 mile by 2 mile island, the downtown area of Key West is very congested with buildings nestled next to each other and narrow alleys. Mr. Ed explains that the early settlers realized that buildings close together avoids destruction by hurricanes. This prevents the wind from blowing them down. Another intriguing fact is that a defoliation occurs during a hurricane. So every tree is bare having lost ALL it leaves except for palm trees.
On the Trolley Tour in downtown we see and hear tales of Mallory Square, the Historic Waterfront, and Simonton Row. Ed points out Kermit’s Key Lime Pie Shoppe known for its famous “Key Lime Pie.” Even better the Trolley tour is entire island offering 13 stops to Hop On/Hop Off. Six of the stops are outside the main downtown area, allowing exploration on other portions of the island. Mr. Ed has lived in the Keys most of his life and doesn’t own a car. A bicycle is his mode of transportation. In fact, many residents don’t own a car.
As we tour Key West on the Trolley, Mr. Ed tells us to look out over the Atlantic Ocean. He spots a Coast Guard boat. Yes, Cuba is only 90 miles away. Mr. Ed say that Cubans continue to seek a better life in the United States by traveling the often dangerous water journey in man-made boats to Key West. Just stepping on U.S. soil allows them to stay. Yet, if caught in the water by the Coast Guard, they are sent back to Cuba. Later at the Mel Fisher Museum, we see The Marianna, a man-made vessel that had 23 men and one woman successfully make it to U.S. soil. This boat doesn’t look like it could even float but it made it to Key West.
Between Stops 9 & 10, Mr. Ed points out Smathers Beach, Rest Beach, & Higgs Beach. Key West doesn’t have any natural beaches. Keeping the tourist happy is a priority, so man-made beaches are created. We hop off at Stop 10 – The Casa Marina Resort & Beach House. On prior business conferences to Key West, I stayed at this beautiful old hotel. Built in the 1920’s the resort was once a hideaway for Old Hollywood elite. Today it is a terrific tropical resort that still captures the essence of its heritage. After a stroll on the White Street Pier, we decide to walk to Stop 11 – The Southern Most Point.
No visit to Key West is complete without a photo op at the Southernmost Point. Key West is the Southernmost City of the contiguous United States. From Southern Most Point, Key West is 159 miles southwest of Miami and 90 miles north of Cuba. Rounding the corner onto South Street, people are lined up on the sidewalk. WOW! It’s the line to get a picture by the oversized buoy landmark that represents the lowest spot of the map of the United States. Yes, with a cruise ship in town for the morning, it seems the cruise guests have packed all the main attractions. Bypassing the line, we just take a selfie with the buoy in the background. From here we hop on the Trolley and continue into downtown. On the way we hear tales of Mel Fisher, a boy growing up in Indiana, who becomes the World’s Greatest Treasure Hunter. His discovery of the treasures of the Atocha gave him world-wide fame. The Hop On/Hop Off is a great way to learn about Key West and it is easy to visit various special sights along the route.
ENJOY A TOUR FROM AUTHORS TO PRESIDENTS TO BUTTERFLIES.
The Home of an American Legend – Ernest Hemingway
For us a “must do” is the Hemingway Home & Museum. Having read many of the Hemingway books and biographies, we are excited to tour the former home of this American legend. Arriving a little before 11:00AM, we are efficently signed up for the 11:15 AM tour. Our guide, Liz, provides a terrific tour of the home, as well as, giving insight into the life and times of Ernest Hemingway. We are immediately intrigued by both the home’s history and Hemingways life, especially in Key West. The Hemingway home was built in 1851 in a Spanish Colornial style. When Ernest and Pauline Hemingway acquired the home it was in disrepair. A massive restoration in the 1930’s created the home that we visit today. The high brick wall around the home was added to provide Hemingway privacy. We tour various rooms of the house from the living area, the dining room, bedrooms and more. Liz shares many details of Hemingway, his wife Pauline, his passion for adventure, and various loves, too.
In the dining room, Liz introduces us to Joe DiMaggio, a six-toed cat, asleep on the dining room table. Hemingway was originally given a white six-toed cat by a ship’s captain. About 60 six-toed cats live at the museum. A gene in the DNA is what creates the six-toed cat. Here Cats are King & Queen! This unique breed truly have the run of the house and grounds. We see them asleep under the pillows in Hemingway’s bedroom, in the Gardens, under trees, in flower beds and wherever they choose to go. In fact the six-toed cats here are actually protected. Liz states that the cats have better treatment and healthcare than we do.
At the pool outside the home, Liz tells the tale of Pauline spending $20,000 to build this massive pool in the 1930’s. This inground pool is an architectural feat. It required digging through solid coral to create a hole 24 feet wide, 60 feet long, 10 feet deep at the south end and 5 feet deep at the north end. A humours tale is Hemingway yelling to Pauline, “you spent all but my last penny and you might as well have that.” Then he tosses a penny on the ground. It is now sealed in a square near the pool. After the tour we stroll the grounds and gardens of the home. Numerous storyboards provide insight into Hemingway, his love for fishing, his friends, and his life on Key West.
A Tropical Retreat for a President –The Little White House
Having visited the Truman Library & Museum in Independence, MO, we look forward to a tour of the Harry S. Truman’s Little Whitehouse. Mary, our guide, explains how Truman initially came to Key West for health reasons. Arriving at this tropical island, the health issue cleared up. Here, Truman found a wonderful setting that allowed him to have a respite (he was still on duty) from the daily grind of living in Washington, DC. As we walk through the home, Mary points out that the house was previously two houses and was converted to one for the President. She also shares interesting stories and a few tales of various events, gatherings, and meetings that have been held at the Little White House. A fun tidbit is that whenTruman was diagnosed with a heart condition, he started a daily regime of a shot of Bourbon in the morning and a two-mile walk. We learn a lot about Truman, as well as, other leaders who have used The Little White House for getaways to serious meetings regarding issues concerning the United States. The house is beautifully decorated with many items matching its rich history under Truman. We better apprecate decisions Truman made that had major impacts on the direction of the United States. (Note: After visiting the Truman Library & Museum, I read Harry S. Truman by his daughter Margaret Truman, The biography gives detail and depth into Truman’s life. Margaret Truman provides back-up in letters, memorandums, etc.)
Enjoy the Beauty of Butterflies – Key West Butterfly and Nature Conservatory
Let’s see some butterflies. Recommended by a Trolley driver, we hop off to visit the Key West Butterfly and Nature Conservatory. UGH! The cruise passengers are lined up. Thankfully, the line moves and we are in a room to watch a short video that provides an education on butterflies their stage of life from the egg to the caterpillar to the pupa and finally emerging as a beautiful butterfly. The room also has an awesome display of a huge variety of butterflies. Great to see them individually.
The conservatory is so packed that it is one long line of people, thus we move at a snail’s pace. Due to the crowd, the butterflies are flittering everywhere and don’t stay in one place for very long. About the time I try to get a picture, it has flitted off to another place. They are beautiful! All types, colors, and sizes of butterflies are landing on plants, flying around, or sweeping over our heads. It is dazzling. Look! In trees we see exotic birds. Rhett and Scarlet the flamingoes are fun to watch, too. There is a display with pupa, the 3rd stage of the butterfly cycle. Here we actually see a few butterflies emerge from the pupa. This is a wonderful and impressive Butterfly and Nature Conservatory.
Fun and Intriguing Activities at Key West
Sculptures, Entertainment, Sunsets, Wharf, Duval Street & More!
Strolling in Mallory Square, is the Sculpture Garden. Here we appreciate the magnificent sculpture “The Wreckers,” an 18 feet long and 25 feet high. This large sculpture captures the early spirit of Key West as a boisterous seaside town on the frontier of young America. In fact wrecking and salvaging were the life blood of the island. In the mid-1800s due to salvage fees from wreckage, Key West was the richest city per capita in the U.S. The Sculpture Garden has 36 bronze busts of notable men and women who had an impact on Key West. These include Ernest Hemingway, Tennessee Williams, and Harry Truman.
Cocka doodle doodle doo!
While the six-toed cats rule the Hemingway Home, feral fowl of roosters, hens, and chicks rule the streets of Key West. Whether walking along a sidewalk or enjoying a libation on a patio, we consistently see these hens with baby chicks and roosters. Hens are cute as they push their baby chicks along. Bright colorful wild roosters are seen and heard as they roam the streets and alleys. Yes, we must admit these “gypsy chickens” add to that off-beat charm of Key West.
Mallory Square
Richard on a prior visit to Key West, fondly recalls the entertainment at sunset on Mallory Square. So after a tasty dinner, we head over to check out the entertainment. A large crowd is packed around a young man, who is asking for participants to help him get on a unicycle. Whether this is a part-time job or his career path, Jase keeps us laughing as he explains the challenges and more of maneuvering to get on the unicycle. The crowd loves it. Timing is perfect, as Jase gets on and rides the unicycle just in time for the crowd to move over to the boardwalk to watch the sunset.
Be ready to do some jostling through the crowd at Mallory Square to view a sunset. It is PACKED! Some viewers arrive early to get a spot near the water, others are just strolling the boardwalk, and some are jockeying for position to find the “best spot.” We pick a spot that gives us a good view of the sunset and the crowd. Sadly the sun goes behind a cloud so it doesn’t have the fantastic colors that many were seeking. Mallory Square at sunset is still a scenic and fun experience.
The Wharf at A&B Marina
At the wharf just a short walk from Mallory Square, charter boats have just come in and are showing off the spectacular catch of the day. Additionally, there are several restaurants, bars, and eateries along the wharf offering a wide mix of dining options. After checking out the various options, we enjoy drinks at Alonzo’s Oyster Bar. Sitting at the bar, we are thoroughly entertained just watching the bartender making drinks for the restaurant. The restaurant is super busy and the bartender is constantly mixing and making a wide variety of libations including the popular Key Lime Martini. He is “a drink making machine.”
Key West’s Duval Street
Yes, we stroll Duval Street many times on this visit to Key West. On early morning walks to do sightseeing, Duval Street is quiet. Passing by Sloppy Joe’s in the morning, we easily take a photo of this large empty bar and statue of Hemingway at the bar. The daytime Duval Street is sedate with tourists checking out shops and dining, at night it is alive with visitors seeking drinks, entertainment, and excitement. Walking by Sloppy Joe’s, it is JAMMED! No room to move or even squeeze in as music blares from a band. Definitely wall-to-wall people. So we opt for drinks at a nearby bar with a quieter laid back setting and enjoy the singer/guitarist. Much more our style.
DINING AND LIBATIONS
It is easy to find a place for a refreshments in Key West with it’s many dining options, bars, and more. Definitely something for everyone from upscale to laid back. For us it’s a variety of eateries. We enjoy libations at Salty Frog’s Bar & Grill near Mallory Square while we watch a rooster strolling the street and patrons signing dollar bills to staple to the building. On a policeman’s recommendation, it’s tasty conch fritters with a tangy Margarita and fruit filled Mojito at Two Friends Patio Restaurant. Yep, another rooster roams the patio here. A cool wine bar is the Funky Rooster Coffee House and Wine Bar on Caroline Street.
A fantastic lunch stop near the Butterfly Conservatory is Key West Lobster Shack on South Street. This small eatery dishes up a traditional New England Lobster Roll. It is AWESOME! At Caroline’s Cafe, they make a unique Cuban Sandwich with bacon. We are surprised it was not on Cuban Bread like the famous Cuban Sandwich in Ybor City, Florida. For dinner, great seafood is found at Off the Hook Bar and Grill Key West. Initially, we selected it for its convenience to our hotel, but it definitely exceeds expectations with it fresh-off-the-boat seafood. Onlywood Grill dishes up tasty pizza. A scenic and pleasurable dining venue is 245 Bistro at the Opal Key Resort and Marina. Adjacent to Mallory Square, we have great views of the Atlantic Ocean just before sunset.
ACCOMMODATIONS
Kimpton Ridley House – in downtown Key West
Wanting to be close to downtown Key West, we select the Kimpton Ridley House, part of the IHG hotels. Location is fantastic as it is close to Duval Street, Mallory Square and the Wharf. The Ridley House was originally owned by Richard Kemp, a wealthy industrialist, passionate fisherman and celebrated naturalist. The house is tucked behand a white picket fence with overhanging palms. It has been carefully renovated to meet the needs of travelers while still maintaining its original charm. Each morning we delight in a complimentary breakfast in a tropical setting by the pool. Our room is #3 “The Library” on the first floor. Fitting its name, the spacious room has one wall of bookshelves filled with books, while the windows have shutters providing privacy. The large bathroom is updated with all the modern conveniences. Since parking is a major challenge in Key West and can be very expensive, we are thrilled to find the Kimpton Ridley Home offers parking a few blocks away at a sister property for only $20 a night. The Kimpton Ridley Home is terrific for a visit to Key West!
We thoroughly enjoy our getaway to Key West. While our visit was a bit more sedate than others might seek, it fit our desires for a tropical respite. From the Hop On/Hop Off Trolley to excellent tours of the Hemingway Home, The Little White House and the Butterfly and Nature Conservatory, it was both fun and educational. Of course Key West also offers an off beat vibe with its many attractions including Mallory Square and Duval Street. Food and libations are plentiful, too. Definitely a wonderful tropical paradise at the very tip of Florida. Check it out!
Travel Tips
- Time of Year to Travel – We visited during spring break in early March so it was very crowded and expensive. Summer months are less crowded and less expensive.
- Hop On/Hop Off Trolley – we highly recommend the trolley tour. Either stay on the entire ride to get a great overview of Key West or take advantage of the Hop On/Hop Off feature. On the Tuesday we toured the Trolley started earlier than the schedule. We assume due to cruise ship only being in port for the morning. Check their pricing schedule as some days are a bit lower price. This is also an indication it might be a less touristy day. When cruise ships are in town, the Trolley can quickly fill up. A few times we had to wait for the next Trolley. The staff does a great job of being in constant contact to assure passengers are only delayed a short time before another trolley comes along. Another reason to take the Hop On/Hop Off Trolley on non- busy days.
- Parking in Key West is a major challenge. Having done our research, we knew that the Kimpton Ridley House had offsite parking. Additionally, our back up plan was to park at the Key West Airport to avoid the high daily rate for parking in town. We didn’t need a car in Key West at all.
- Florida Keys Overseas Highway was a fun drive, scenic, and we are glad we did it. If we drove directly from Oldsmar, Florida (Tampa Bay Area) it is 428 miles taking 7.5 hours. To avoid this long drive, we made stops in Naples and then Key Largo before heading to Key West. This divided the drive into more reasonable portions plus we had fun stops at each. On the return we stopped overnight in Marathon then again stayed in Naples before the last leg of the trip to home. We are glad we drove the Overseas Highway and the stops added to our enjoyment. Driving in on Sunday afternoon, we avoided heavy traffic. Then leaving early in the morning helped avoid high traffic times. Now that we’ve “been there, done that” should we return to Key West we will fly or take the boat from Fort Myers.
- Tours – when touring houses or homes in Key West, we recommend arriving early. The exception being early is when cruise ships are in port the attractions are busiest. On our visit the cruise ship was in town only for the morning, so the afternoon was not as crowded. Check with the Visitors Bureau and they can probably assist with best times for touring main attractions.
- The Florida Keys & Key West has a wealth of information for planning a trip to the Florida Keys and Key West. Be sure to check it out.
While we did not do any adventurous activities (snorkeling, scuba diving, fishing) there a wide-variety to do so check out your preference. We do recommend doing some preplanning as some things get filled quickly.
A memory from Charlene’s first visit to Key West:
My first visit to Key West was in the early sixties. My father had a four passenger Cessna airplane at that time and delighted in taking the family on flying adventures. One Sunday morning Dad says, “let’s go to Key West.” We were a family of seven, three teenagers, a seven year old and a baby. That was seven people in a four passenger plane. This was at a time when many Cubans were seeking to escape to Florida. Once we landed, we were quickly greeted by airport security. Dad, attempting to be funny, said, “We just flew in from Cuba. ” Big mistake! Much time was spent with security going through all the records on the airplane and documents. Thankfully, all was resolved and we enjoyed a fun day in Key West before flying home to Plant City, Florida.