Explore with Me

Let me start by saying, I love Key West! Where else can you go in the U.S. that feels like you have traveled to a cool, laid-back tropical paradise? And what’s great about Key West are all of the ways to reach the southern-most tip of the U.S. Fly into Miami and drive via the Overseas Highway, the roadway originally built for trains a century ago. It’s a bit of a hike if you choose this route, a little over 4 hours from Miami, but the sights are fantastic as you drive across 43 separate islands and expansive bridges on the 127 mile stretch of highway.

If time is a factor, Key West also has their own airport with several major carriers, including American, United, Delta and JetBlue, flying smaller regional jets into this quaint island airport.

And last but not least, we witnessed, first-hand passengers unloading from the Celebrity Cruise to spend their day exploring the town. Several major cruise lines include Key West as a port of call including Norwegian, Disney, Royal Caribbean, Celebrity and Holland America. This is a great way to visit Key West and explore the Caribbean or Bahamas & Florida via a cruise at the same time.

We spent a week in Key West in January, considered part of the high season, which runs from December through April, however, except for cruise ship disembarkation day, we did not encounter significant crowds. Old Town Key West is very pedestrian and bike-friendly with narrow streets, making navigating and parking more challenging for vehicles. There are numerous rental shops offering bike and scooter rentals, which is a fun way to explore the historic district.

Or, if you are feeling more adventurous, consider biking the Key West Cycling Loop which is an approximately 10-mile paved loop that takes you around the entire island. We brought our own bikes on this trip and used them daily to explore the island and found it much easier to navigate than by car.

Things to do in Key West: Eat, Explore, Shop (& Admire Roosters)

The Chickens of Key West

Let’s talk about my favorite part of Key West first ~ the chickens! They are everywhere! Often called the “Key West Gypsy Chickens”, they are the descendants of domestic chickens and fighting roosters brought to the island by early settlers, particularly Cubans, in the 1800s. When cockfighting was outlawed, many chickens were set free and adapted to life on the streets. They are Key West’s unofficial mascot, and in addition to seeing live ones around every corner, you will have plenty of opportunity to shop for a replica rooster in many shapes and forms. Because of Key West’s affection and protectionism of their beloved wild chickens, there are steep fines ($5,000) and up to one year in jail if you torment or kill a chicken. Enjoy but don’t touch (or feed) Key West’s resident gypsies.

Shopping in Key West

There is no shortage of shopping in Key West with an eclectic and diverse mix of boutiques, souvenir shops, galleries and local eateries. You will find many of these options by strolling down Duval Street from one end of the shoreline to the other (about a 1 1/4 mile walk across the island). We made sure to stop at Kermit’s Key Lime Pie shop, which is a staple in Key West. Along this route you will pass Hemingway’s Home and Museum and, finally, find yourself at the Southernmost Point of the Continental U.S. As the crow flies, the Southernmost Point buoy is only 90 miles from Cuba. As the day goes on, the lines tend to get pretty long, so if you are wanting the best photo opp consider getting there in the morning, which provides the added bonus of adding a beautiful sunrise to your picture.

In the historic old town of Key West, there is a lot of activity in and around Mallory Square, where you will find a plethora of unique shopping options. This is where Key West’s quirky character really comes alive. Make sure to visit the Key West Sponge Market to take picture with the “Sponge Monster” and buy yourself a sea sponge. The Sponge Market has been around since the early 1900s and is an important part of the island’s sponge industry.

Exploring Key West

If you feel like taking a break from shopping, in this area you will also find the Shipwreck Treasure Museum and the Key West Museum of Art & History. We ducked into the Key West Museum for a quick reprieve from the heat. The museum explores in detail the renowned author Ernest Hemingway who made his home on Key West Island before deciding to relocate to Cuba in 1939. It was actually in Cuba, not Key West, where Hemingway wrote some of his most famous work The Old Man and the Sea and For Whom the Bell Tolls. He lived in Cuba for over 20 years. This was a great visit to learn about the history of this iconic storyteller.

On our strolls throughout the week we also encountered the Kapok Tree, the Key West Woman’s Club and beautiful architecture that exudes Southern charm.

Located on Whitehead Street, the Kapok Tree is a historic tree over 130-feet tall with roots spreading above ground. In Mayan culture, the Kapok tree is sacred. It is believed that the souls of the deceased climb its branches to reach heaven. It was planted in 1920 by a local horticulturist.

Located on Duval Street, the Key West Woman’s Club was established in 1915, founded to empower women to address community needs. It played a pivotal role in shaping the island’s social landscape.

These Conch-style houses are an example of the Victorian architecture that was so prevalent in Key West during the shipping boom in the late 19th Century. The open verandas and porches provided outdoor space to enjoy the breezy Key West climate and they are just beautiful to look at and wonder as to all they have seen over the years.

Dining in Key West

And, finally, our visit to Key West wasn’t complete without sampling several of the amazing restaurants and bars. Too many to name them all, I’ll highlight a couple of our favorites around the island.

Interestingly, there is a battle of the Sloppy Joe sandwich in Key West. There are two competing restaurants right across the street from each other that claim to be the original Sloppy Joe ~ Captain Tony’s Saloon, The first and original since 1933 – 1937 and Sloppy Joe’s Bar which started serving their sandwiches in 1937. We opted to try Sloppy Joe’s Bar, and while the outside looked unremarkable and we were concerned we had made the right choice, inside had a great atmosphere with live music, and the sandwiches and drinks were great.

While in historic downtown Key West, we also stopped for lunch at Amigos to try their square tacos. We sat outside and enjoyed people watching, as this was cruise port day. I won’t ruin the surprise on how you make a taco square, so consider making a stop here to find out for yourself.

We love beachside dining and enjoyed two wonderful venues with an ocean view. Salute! On The Beach was a fun surprise lunch stop during our 10-mile bike riding loop. Located on Atlantic Blvd, it sits right on Higgs Beach between White Street Pier and Casa Marina. We had a relaxing outdoor lunch and enjoyed our view.

We enjoyed breakfast at The Southernmost Beach Cafe, located on Duval Street, near, you guessed it, the Southernmost Point Buoy. We enjoyed our bottomless Mimosas with a gorgeous sunrise.

There are so many bars and entertainment to choose from. Every venue we passed had live music which contributed to the relaxed island vibe.

Why I Keep Coming Back to Key West

Key West is always one of my favorite visits. It’s easy to get to and makes for a great extended weekend trip. There’s something about the way the island mixes adventure with relaxation that makes it feel like the perfect getaway. Whether it was watching the roosters roam freely, biking around the island, or simply enjoying a fresh seafood meal while listening to live music, every moment felt like it belonged in a postcard.

I found myself slowing down and just taking it all in—the sunsets, the quirky shops, and the history around every corner. From the famous Southernmost Point to the little hidden gems off Duval Street, Key West offers so many experiences that make it feel like its own little world.

If you’re looking for an escape that lets you unwind, have fun, and truly experience a destination, Key West should be at the top of your list. I know I’ll be back, and I can’t wait to explore even more next time.

Marci@Sunningbythesea.com

(720) 803-7287

http://www.sunningbythesea.com

Your Premier Travel Agency