Travel: Is Key West on your Bucket List? You Should Go

By Sally Tippett Rains

Conde Nast Travel Magazine listed the “Four Best Places to Travel Without a Passport That Feel a World Away” and Key West, Florida made the list.  (Puerto Rico, Virgan Islands, and Alaska were the others.)

The interesting thing is Key West is the southern-most point in the United States, and  really only about 90 miles away from Cuba.  According to the magazine, “Fall and all the way through winter is an ideal time for a visit…” They point out the summer crowds have thinned  and encourage readers to “belly up to Sloppy Joe’s for a cocktail in Ernest Hemingway’s beloved watering hole.”

There are hotels from not-as-expensive to the Southernmost Beach Resort. Conde Nast cautions: “The fresh rooms and beautiful views make this hotel worth it, but factor in the so-so beach and resort fees when making your decision.” Southernmost Beach Resort, has undergone a  massive, $15 million renovation and is one of the most famous accommodations in the Keys.

Of Key West, the Miami Herald says “Key West, Florida is one of the top travel destinations in America.” If it’s on your bucket list, maybe it’s time to plan a trip.

Everyone raves about the sunsets in the Keys, but the sunrises are also beautiful.

According to the website,,  “Direct flights or connections to Key West International Airport are available from many cities. Please check with the airlines for the latest flight and route information.”

The website goes on to say, Visitors can fly to Key West International Airport via connections or direct flights from a host of Florida cities. The airport offers a host of ground transportation options, including local shuttle buses and rental cars. Getting around Key West is fun and easy!”

There are several other options for flying. Go to a city you like, such as Jupiter (when traveling to Spring Training), Orlando, Miami or there’s even a small airport in Marathon, Florida which is in the keys. All of the airports (including the very small Marathon) have a car rental so you could fly and then rent a car. If you are driving, don’t forget there are  Drury Hotels along the way and brand new one in Orlando. The chain has not yet reached the Keys so

We decided to take the trip but since we drive to Spring Training in Jupiter, Florida, our car basically knows the way so we drove.

Key West is about 6 ½ hours south of Orlando via US-1 N and the Florida Turnpike.

It is worth learning a little history of Florida when heading to the keys. If not for Henry Flagler building the railroad in Florida and connecting the Florida Keys to the rest of the country, tourists might never have found Key West.

According to Starting in 1905, at any given time, there were more than 4,000 men working to build the railroad. During construction, three hurricanes passed through the keys. The railroad was finally complete in 1912 and was called the eighth wonder of the world. The railroad remained in operation until the Labor Day hurricane in 1935 and then transportation began leaning towards the automobile and then airplanes.

Sometimes it’s hard to believe that the U.S. is such a young country that this all happened a little more than  100 years ago.

Henry Flagler was born in 1830 in New York, the same era as the Rockefellers and Vanderbilts. He met John D. Rockefeller and soon they were partners in their new business Standard Oil. They were living in New York but in 1878 his Flagler’s wife became ill so they moved to Florida, hoping the weather would help her.

Flagler built a winter home on  140-acre ocean-front property for his wife, but she ended up dying and he was left with his son to raise. .She ended up dying but he fell in love with Florida, and moved away from Standard Oil and concentrated his work on building a railroad so tourists could travel there. He also built hotels to have destinations for the tourists and pretty soon he was designing streets and cities in Florida.

When building a railroad there have to be stops to encourage people to ride, so he built some hotels along the way as he developed the railroad from Daytona to Key West. He enlarged his winter home on the oceanfront side of his 140-acre property to form the Palm Beach Inn (later renamed The Breakers in 1901. The Breakers still exists today as an upscale destination hotel in the Palm Beach area.

Flagler married again, a woman named Mary Lily Kenan and they moved into “Whitehall,” one of the great estates in America’s Gilded Age.. This exquisite 55-room marble palace on Lake Worth was built as a gift for Flagler’s bride. Today, Whitehall is known as the Henry Morrison Flagler Museum and it is open for the public to enjoy.

Flagler made a significant contribution to Florida’s economy through tourism and agriculture and was so important that many towns have a Flagler Street. If going to the Keys it is worth knowing about Flagler.


The best first stop is for those who are members of AAA to head into their local AAA Travel Office and get the free help of setting up your trip. They still have the Trip-Tics, but the travel books are online. For no extra charge they will book your hotel and help you with ideas of what to do. For more on AAA CLICK HERE.

Key Largo

Key Largo is one of the first stops (the first key) on the way to Key West. For more detailed information on Key Largo  CLICK HERE.

It is the self-proclaimed Dive Capital of the World. and is home to the world’s largest artificial reef, the 510-foot USS Spiegel Grove, the John Pennekamp Coral Reef State Park and the African Queen.

The Caribbean Club bar is a famous bar. Opening in 1938, it served as a poor-man’s fishing retreat. The property originally included a small hotel, restaurant and the bar that remains today—making it the oldest bar in the Upper Keys. After Fisher’s death in July 1939, the Caribbean Club became a popular gambling establishment.

In 1947, Warner Brothers used the hotel and bar as inspiration when writing the screenplay for the Humphrey Bogart and Lauren Bacall film, Key Largo. It also served as a filming location for exterior shots in the film, a tradition that has carried on most recently serving as a filming location for the Netflix original series Bloodine. Today it appears to be more of a local spot, but worth the stop to those who liked the Bogart/Bacall movie.

Everglades National Park is just a short trip away from Key Largo for those who want to make the trip.

The Hampton Inn Key Largo, 102400 Overseas Hwy, Key Largo, FL 33037 is a great place to stay. One of the interesting things about the Florida Keys is that there are very few real beaches. Some areas have man-made beaches and the Hampton Inn has a sandy beach along with a swim pool.

For someone whho as never been to the Keys, yet dreams of the “romance” of it, they often picture themselves laying on a sandy beach in the sun. The sun is there but the water mostly just comes up to the shore. There may be water on both sides of you as you drive on the seven-mile-bridge, but not many beaches. Most beaches have been made for tourists to enjoy.

The beach at the Hampton Inn has paddle boards and kayaks on it and visitors can rent them out by the hour or half day. The water behind the hotel where the beach is located is very calm and full of manatees. Manatees are safe, friendly animals that won’t bother the tourists.

The water is the Gulf of Mexico but in this area it is as still and calm as a lake. With large boats moored nearby it is a safe place to try kayaking or paddle boarding.  The hotel has life jackets and paddles.

The Hampton Inn has a tiki bar out near the beach. Whether you are at the beach, at the pool, or you just want to sit under the tiki hut, there is music going and a bartender serving soft drinks and wine, beer and cocktails. Tiki bars are spotted all over the keys and add to the island charm.

The beach at the hotel is a perfect place to take in the sunset.  A few minutes before sunset, guests come out of their rooms with cameras in hand and it is a fun time for all as the sun puts on a grand display.

Fort Zachary Taylor is said to be home to the best beach in Key West, Fort Zachary Taylor State Park is also one of the top places to watch the sunset.

There is a great restaurant called Snook’s Bayside Restaurant (shown left) at 99470 Overseas Hwy, Key Largo, FL 33037.  They specialize in fresh seafood & tropical drinks.

It is outdoors with a beautiful view of the Gulf of Mexico.

At lunchtime there was live music playing. Many of the tables have umbrellas and some don’t so diners can choose being in full sun or the shade.

One interesting and unique thing were the floating tiki huts moored at Bayside’s dock.  Adventurous people can  rent the motorized floating huts and ride around the Gulf nearby. With the smooth water, riders can bring their drinks with them and possibly not even spill them.


Marathon, Florida

While Flagler’s crew was building the railroad around  the area of Marathon, they were working feverishly and long hours, and one was said to have uttered, “This is getting to be a real Marathon”– and the town of Marathon was named.

Marathon doesn’t have the notoriety that Key Largo has—largely due to the previously mentioned movie– and Key West has been made more famous  by the rich and famous including Ernest Hemingway, Tennessee Williams, President Harry S. Truman and  Jimmy Buffet. But Marathon is definitely a stop on a trip to Key West worth making. There is a lot to do there.

In Marathon you can interact with dolphins at the Dolphin Research Center, feed stingrays at the Aquarium Encounters, see turtles at the Turtle Hospital where they rescue the sea turtles and let visitors come to learn to appreciate them. There is the Crane Point Hammock and Nature Trail and Curry hammock State Park.

For those interested in the history of the building of the railroad there is the museum at Pigeon Key Island.

As far as restaurants go, it will be hard to find a more “islandy” restaurant in the entire keys than the Island Fish Company, 12648 Overseas Hwy, Marathon, FL 33050. The food is great, atmosphere just what you want it to be. Look to the West and you can see the sunset.  There are many outdoor eateries and that is one reason tourists flock to the keys. The sunsets are gorgeous and water is all around.

Island Fish Company has the tiki hut vibe, and along with the sea breezes and music playing it makes for a great atmosphere.

They are open most days of the year and on holidays they add to their menu serving turkey on Thanksgiving, ham on Christmas and corned beef and cabbage on St. Patrick’s Day.

There are many other fnu restaurants in Marathon.

For more on Marathon, visit their visitor’s website: CLICK HERE.

Key West

Key West is known as the “Southernmost Point in the Continental U.S.A.” There is a famous marker, shown above that has long lines of tourists waiting in it to get their photo. The tour busses and trolleys all drop the visitors off so they can experience the thought of being ninety miles from Cuba.

Speaking of Cuba, there are cigar stores around Key West. We noticed there were more ash trays set out than one normally sees. At the Rodriguez Cigar Factory in Key West, Florida, the oldest on the island, you can take a tour that includes trying your hand at hand-rolling a cigar. There’s a shot called Holt’s that has a  walk-in humidor, bar (beer and wine only) and a smoking lounge. Key West has many places with outdoor seating that allow cigar smoking, though it really wasn’t very noticeable.

Some Activities to do in Key West:

To find more, CLICK HERE.


Because of the large coral reefs around the keys there are hundreds of shiprecks– ships left in the waters that could not make it to safety There are so many wrecked ships there is a museum dedicated to it.


DUVAL STREET listed Duval Street as the  #1 attraction  in Key West. When someone says they are going to Key West, others who have been there, say “there’s nowhere like it.” You may wonder what that means–until you get to Duval Street. The closest thing to describe it would be Bourbon Street or even Beale Street, but there really is no place like Duval Street. During the day it is bustling with people taking tours. Once the sun goes down the party is started. For some the party goes all day.  Duval Street is full of Entertainment and Nightlife, cafes and shopping.
A native who grew up in Key West said, “just because it’s expensive doesn’t mean it’s good and just because it’s cheap doesn’t mean it’s bad”– and it is true on Duvall Street.
Searching for a “Hawaiian shirt” to lounge around in? The prices run between the $80 Tommy Bahama shirts to the $15 shirt found in one souvenir shops. There were shops with “Everything is $5” and shops with expensive art. Key West really does have “something for everyone.”
Mallory Square, located around 400 Wall St. is a popular shopping destination and everyone who has been there will tell you they have the best sunsets. There are many restaurants and be sure to plan your “sunset” out so you don’t spend too much time trying to get into the perfect restaurant and miss the magnificent view.
According to Mallory Square has always been the hub of Key West’s social and commercial life from the time of the city’s beginning in the early 1820’s. It is where master wrecker Asa Tift’s ships’ laden goods from the shipwrecks would dock and then be stored in his warehouses on the waterfront.
It is where the town folk would come to exchange news, gossip and shop. Fast forward a century-and-a-half and you will find that Mallory Square is still the center of Key West with restaurants, shops, theater, museums, live entertainment and the most spectacular sunsets to be found anywhere.
Probably the most famous bar in Key West is Sloppy Joe’s Bar, 201 Duval St, Key West, FL 33040.
The official beginning of Sloppy Joe’s Bar, the famous and infamous Key West Saloon beloved by Ernest Hemingway, was smack in the middle of the Depression, December 5, 1933, the day Prohibition was repealed. But the bar was destined to go through two name changes and a sudden change of location before it would become today’s Sloppy Joe’s Bar seen by millions of visitors to Florida’s southernmost outpost.
For those who prefer a more “low-key” Key experience, the Benihana has a beautiful view with it’s outside dining. Benihana, located at 3591 S Roosevelt Blvd, Key West, FL 33040 is in walking distance from the Hampton Inn, Key West, which is a nice hotel. The Hampton Inn offers a tiki bar next to the pool with live music and two free drinks in the afternoon. They are also one of the Trolly stops and they have their own shuttle downtown.
Benihana had great seafood and the hibachi shrimp is a nice choice.
Sunset in Key West is one of the things they make their money on. There are special points of interest to watch the sunset from and Mallory Square is always the one people point to as they make quite a deal out of sunset– every night.
Sunset Celebration is a nightly arts festival at Mallory Square Dock in Key West, Florida. The participants of this Key West attraction consist of arts and crafts exhibitorsstreet performersfood cartspsychics and of course the thousands of tourists from around the world who visit this Key West art show. Each night around two hours before sunset masses of people, both locals and tourists alike, flock to the water’s edge to experience a multicultural happening and to watch the sun sink into the Gulf of Mexico.
While Malory Square is a sunset destination, there are other ways to see the sunset and one is by boat.
“We did the Sunset Sail and the Shark and wildlife viewing when we were there,” said travel adviser Dixie Haggard of

“I can give readers of  an exclusive discount if they use this link and book it before Dec. 6, 2023.  You don’t have to take the trip by then, just book the activities.”

She offers  this link: CLICK HERE, and this promocode:  EMT10

If it is past that date you can use this link: CLICK HERE.

Haggard can be reached at She is an authorized  Disney vacation planner so if you are headed to Orlando she can help you.

Other sights to see in Key West:

KEY WEST MEMORIAL  SCULPTURE GARDENS A lasting tribute to the most famous and influential residents of Key West, the Key West Historic Memorial Sculpture Garden is an oasis shared by all who live on the island. There are busts of Ernest Hemingway, Asa Tift, Harry S. Truman, Tennessee Williams, and others.

Two people with Missouri ties are remembered in various places in Key West. One is President Truman and the other is Tennessee Williams.

There is a destination called the Harry S. Truman Little White House.


The Harry S. Truman Little White House is the State of Florida’s only presidential site.

Originally, it was constructed in 1890 as naval officers housing. Important visitors have included extended stays by inventor Thomas Edison and scientist Edward Hayden and it has been used by six American presidents. Its most important usage was as the winter White House of Harry S. Truman who spent 175 days of his presidency here from 1946 through 1952. Harry Truman faced the rebuilding of Europe, the Palestine question, issues of Civil Rights and labor unrest changes in foreign policy and our response to the Cold War.

TENNESSEE WILLIAMS THEATRE 5901 College RoadKey WestFL 33040 3052961520  The Tennessee Williams Theatre is more than just a theatre. It is a performing arts center, a civic center & a community center. Conferences, parties, fundraisers, workshops or great performances. We have it all!\\

THE KEY WEST BUTTERFLY & NATURE CONSERVATORY Walk through a tropical paradise with hundreds of butterflies and exotic colorful birds from around the world. Let nature surround you as you enjoy a spectacular experience you don’t want to miss.

THE OLDEST HOUSE MUSEUM 322 Duval StreetKey WestFL 330403052949501 

The Oldest House is open 10am-4pm daily except Sunday & Wednesday, the store is open every day. Admission is $10-adults, $9-seniors, children under 12 are free. See original furnishings, period pieces & allow docents to share the history of the house.

DRY TORTUGAS NATIONAL PARK AND FORT JEFFERSON FERRY100 Grinnell StreetKey WestFL 330408006340939 3052947009 

Visit a historic, remote eco-treasure 70 miles from Key West. Enjoy snorkeling, birding, pristine beaches & tour Ft. Jefferson. Limited availability, reserve your day trip today!

FURY SUNSET CRUISE, SNORKEL, JET SKI, PARASAI 241 Front StreetKey WestFL 33040 Voted Best Watersports Company 10 Years Running! Celebrate Fury’s Decade of Excellence with Our Limited Time 10X Promo Code For Xtra Savings Up To $30!

*If you have a special place in the Florida Keys you think we should add to this article, please email us at:

If planning a trip to the Florida Keys– or anywhere else, for that matter– AAA Travel can help you. For more information on AAA, CLICK HERE.

About stlsportspage 2465 Articles
For the latest news and features in St. Louis Sports check out Rob Rains, Editor.