Key West: Home to Hemingway, Wild Roosters, Cuban Cigars and Famous Sunsets
- Gail McElroy
- Dec 30, 2022
- 7 min read
Updated: Mar 19, 2023
It’s 11 p.m. and the streets are crowded with noisy tourists who came to experience a perpetual spring break-like party atmosphere. The cigar smoke is as heavy and pervasive as the humidity hanging in the air. A mix of music – both live and recorded – blares from the bars that line the main street.
Intoxicated tourists – weaving to avoid the wild roosters roaming the streets – carry their drinks from place to place in open containers as they pass the still-open souvenir shops trying to entice the sweaty revelers to pop into their air-conditioned stores to purchase politically incorrect t-shirts and other novelty items that dominate the shelves.
This is Key West’s Duval Street every night of the year.
Happy to be out of the fray, my husband and I are sitting at a table on the deck of our hotel’s rooftop bar, watching the rebel rousers parade by.
We weren’t there to party (those days are behind us) but rather for the experience of driving the overseas highway, standing at Mile Marker 0 and watching the sun rise and set while standing in the same spot.
As the southernmost point in the contiguous United States and home to author Ernest Hemingway, Key West has long been on my travel bucket list.
My research, along with friends who had been there, informed me about the party atmosphere and that Key West was not the most beautiful of the 800 Florida Keys. I also knew to book a hotel off the main drag, so the street noise didn’t keep us up at night. What no one warned us about were the roosters that would crow almost non-stop from 4 a.m. on. The roosters are everywhere!
We chose a boutique hotel from the Marriott Bonvoy collection that was two blocks away from Duval Street but still centrally located. The Saint Hotel ended up being our favorite hotel during our nearly three-week Southeast road trip.
The street front of The Saint Hotel is unimpressive (and, honestly, a little brothel-like). It also looks deceptively small, but the compact property packs a big punch with its funky, artsy décor, red and blue ambient lighting, and unique amenities. Once through the lobby and the long, narrow bar area (lit up in red), the property opens to a small veranda and beautiful pool area, surrounded by rooms with patios and balconies.
We opted for one of the larger rooms (most rooms are tiny) with a private patio in a building located near but not facing the pool. The property also had a shortcut path and gate to access Duval Street. This is also where the rooftop bar was located.
After checking in, we rested from our long drive from Fort Lauderdale that morning. We hit a ton of traffic, which we expected, but thought would be better going out to Key West on a Sunday when most traffic would be headed the opposite direction, leaving the Keys. The only plus side of the traffic was having plenty of time to gawk at the eclectic public art sculptures and uniquely designed residential mailboxes, as well as the breathtaking views of the turquois water.
Rested and ready for dinner, we asked the gal at the front desk for restaurant suggestions where we could watch the sunset. When she found out we didn’t have any reservations, she politely said there were plenty of places to eat along Duval Street. (Apparently, I missed the memo that sunset view dining required restaurant reservations months ahead of time.)
She said we could take our chances with Salute! On the Beach, so we ordered an Uber ride to take us there. (We probably could have walked there, but it was hot, and we both have bad knees.) On the way, we asked our Uber driver to stop at Mile Marker 0, so we could take a pic. After waiting in a short line (we got lucky) and getting the shot, our driver took us to the restaurant.
The manager took our name and said he would try to squeeze us in when he could and asked us to be patient. We took a walk along the beachfront, getting some sunset photos, and
returned to wait it out in the bar area. It wasn’t long before we were seated at a small table on the patio where there was no lack of entertainment.
We ordered the local Stone Crab claws that everyone raved about and sat back to take in the scene. On the beach in front of us a sand volleyball game was underway by buff guys and bikini-clad girls. To the right, a band played on a gazebo stage. To the left was a woman performing fire dances to the beat of the music, which got more dramatic as dusk gave way to darkness.
Key west is about 4 miles long and 1 mile wide. It is easily walkable if you can stand it in the heat. We are wimps, so we rented a golf cart (the preferred mode of transportation) for a half day to explore the island on Day 2. (We had a car, but it was parked in an offsite lot because parking is limited around the island.) There are several golf cart rental companies, all with similar pricing, so pick the one that is most convenient for you.
We drove through the streets (avoiding busy Duval Street), zig-zagging through residential areas and, eventually, driving around the circumference, stopping for lunch at The Stoned Crab at Ibis Bay Resort. The resort is located on Highway 1 near the bridge that connects Key West to other Keys. If you are looking for a resort that is outside the fray of the southern end of the isle but with lots of activities to choose from, this might be a good option (especially if you have a family).
After lunch, my husband dropped me off at the Hemingway Home and Museum on his way to return the cart. As a writer and American Lit fan, this was a must-see for me (not so much for him). The line was short (but can be long, so be prepared).
When I got to the booth to buy my ticket (general admission is $17), I forgot they only take cash (which the website clearly states) and my wallet only had plastic that day. I asked about a nearby ATM machine, and the kind women told me there is one on the property near the gift shop and let me in. Once at the ATM, I realized I could tour and see everything I wanted without going back to pay for my ticket, but I am a rule-following honest person, so that wasn’t an option. I did, however, tour the home and took all my pictures while I was inside the gate and paid on my way out.
If you are in Key West and a Hemingway fan, don’t miss out on this gem. My favorite was his writing room over the garage, which back in his day was connected by a bridge from the second floor of his home. Seeing his typewriters and original manuscripts was also a thrill.
Across from the Hemingway Home, is the Key West Lighthouse, which I toured briefly then headed back to our hotel on foot via Duval Street. Once back at the hotel, I joined my husband by the pool for a relaxing afternoon.
Our mission that evening was to join the famous Sunset Celebration at Mallory Square, where people pack the square to watch the sunset over the ocean. People start lining up for a front row seat along the cement wall two hours (or more) before sunset. We got there about 45 minutes in advance and were among the last to get a front row (standing room only) along a fence.
Once there, we learned quickly you do not leave your spot for any reason! My husband made the mistake of standing two feet away to take a picture of me, and I literally had to fight off the amoeba-like crowd wanting to immediately fill the void. When I yelled at my husband to get back to his spot as I elbowed the woman trying to take his place next to me, she rudely said, “calm down, it’s not like you own the space!” Other than that encounter, people were jovial and kind, many offering to take photos in exchange for the same. By the time the sun set, the entire square was a mass of shoulder-to-shoulder people.
I guess it was worth it to say we did, but living on the California Coast, I’ve seen prettier sunsets. If I had to do it over again, I would book a table at one of the exclusive waterfront restaurants to enjoy the scenery from a table instead of being packed in like sardines. But you literally need to reserve the table months in advance, and it’s not cheap.
We headed to Miami the next morning, our final destination of our 16-day Southeast road trip. If we had one more night in Key West, I would have booked a day trip to the Dry Tortugas National Park to explore the 19thcentury fort and snorkel in the crystal-clear water.
On our drive back on the Overseas Highway, we stopped to take pictures at a place where we could see under the bridge and view the original railway track that connected the islands. Many of the keys are far more beautiful and scenic than Key West, with prettier water and views. It would be far more relaxing to stay on one of the less crowed islands and drive into Key West for the day (which was suggested to us, but I stubbornly insisted we stay in Key West).
We stopped in Key Largo for lunch at Sundowners. The bonus of this stop was watching the large tarpon fish swimming near the water’s surface while we ate. Key Largo was also our go-to lunch spot on the way to Key West. We ate at Snooks Bayside Restaurant and Tiki Bar, where we tried Conch (pronounced with a hard “K” sound by Floridians, like “Conk”). Snooks was by far the better food and ambience of the two.
As we drove off the last of the Florida Keys toward Miami – which went far smoother than the drive down three days prior – I mentally checked Key West off my travel bucket list, satisfied to be winding up another successful road trip.
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