This Is Not a "Best Of" Key West List

Like most, we hit the Google search bar before planning an adventure… scouring the “must-see-must-do” lists and looking for the hidden gems along the way. So, if you’ve found this reflection while doing your own research, keep reading! 

Our overall agenda was pretty simple - eat all the key lime pie, drink all of the mojitos, and try to score standby seats on the ferry to Dry Tortugas National Park.

 While we didn’t make it to the park, we learned a lot about how to make the most of a Key West adventure. The connections we made along the way helped to redirect our plans, like local photographer, Lindsay Pinto. We met Lindsay during a rousing game of poolside blackjack. She loaded us up with advice and fun ideas from a local perspective. Our adventures are always better once we make local friends!

Island Geography

Key West is a small island - only 4 miles long and 2 miles wide. If you are an active adventurer, this distance in either direction will not scare you. That’s easy biking/walking/hiking mileage. Because of this, we booked our accommodations on the eastern side of the island and decided against renting a car. Big mistake! 

While, yes, you can walk or bike should you choose to do so, it is not an enjoyable journey from east to west. You travel along a highly (auto) trafficked roadway. Even when traveling by car, it feels like a much longer drive from one side of the island to the other. 

We arrived during an approaching tropical storm so we couldn’t depend on a bike or scooter due to the heavy and consistent rainfall. The Uber charges were piling up and we broke down and rented a car on Day 2. One of us insisted on a convertible Mustang, which, admittedly, was a lot of fun to run around in.

Additionally, the eastern side of the island is what we refer to as a “Chili’s Vortex.” It is home to all of the commercial restaurants and fast food joints. There is not much to enjoy if you are looking for a true Key West experience. All of the action and local eats are in Old Town on the western side - with one exception… we enjoyed very tasty conch fritters and Cuban sandwiches at Kim’s Kuban, not far from where we were staying. We recommend it.

When we return to Key West in the future, we will stay in Old Town Key West to be near all of the local amenities and attractions. You can definitely get by without a car if you are staying in Old Town. If you are staying on the eastern side, make plans to rent a car. You will be so glad that you did. Interestingly enough, in Key West, it was much cheaper to book a car through a rental company, rather than Turo! 

Beaches

We researched and mapped out where the beaches were around the island. It wasn’t clear to us that Key West isn’t home to spectacular beaches - the photos seem to communicate otherwise! 

Surprisingly, Smathers Beach was at the top of every list we found. We pulled up to Smathers on Day 2 - an overcast day - and walked onto the “beach.” It was bad. It was really bad. It reminded us of the small island beaches of the Atlantic coast or maybe a pile of sand next to the shore of a local lake… dark, rocky sand, shallow shoreline depth, thick seagrass.

But we were determined to enjoy what was there. We settled in to a couple of rental chairs and within minutes, the skies opened and our beach day was washed out! We sought shelter at the Margaritaville Beach Club (hello, Chili’s Vortex!) and tried to wait out the rain. 

Unfortunately, it. never. stopped. And so ended our first Key West beach day…

After a failed attempt to board the Dry Tortugas National Park ferry on Day 3 (more on that to come), we decided to visit some of Key West’s other beaches. After hopping around to a few, we finally landed at the beach at Fort Zachary Taylor State Park. It was beautiful and serene! We arrived early - around 9 am - and the beach was just waking up for the day. We enjoyed a few hours of quiet time before the crowds showed up. It was a perfect spot to snorkel! There were beautiful schools of fish and even a manatee! No matter what the lists tell you, this is Key West’s best beach.

While the weather was uncooperative for most of the week, we went back to the beach for a few hours before boarding our departing flight just to get in a little more time. It was later in the day and packed with visitors! If you prefer a quiet beach, be sure to arrive earlier in the day.

Food… The Good, The Bad, and Our Favorites

We ate a lot of good food. A lot. And some not-so-good food, too. We never waited for a table for the entire duration of our trip. It was truly remarkable! And our service was incredible everywhere we went.

Upon arriving, we headed to Old Town to track down lunch. A lot of the info we found online recommended Two Friends as a local must-do - as did our Uber driver. After an order of mahi tacos and mojitos, we left unimpressed. Hurricane Hole is another spot that left us feeling disappointed.

Our favorite seafood dinner came from Alonzo’s Oyster Bar on the wharf. We both ordered the seafood boil and it was so satisfying and fresh. We also loved Moondog on Whitehead. It was the perfect spot for clean eating. We ate there more than once because it was so, so good!

Other restaurants that we really enjoyed included: Blue Heaven, Cuban Coffee Queen, Clemente’s Pizzeria, The Koffie House, and La Grignote.

The Best Key Lime Pie and Mojitos

Key West is said to have the best key lime pie on earth. We didn’t really have vast experience to compare it to; however, our favorite didn’t make it to the top of any of the “best of” lists that we perused.

Our absolute favorite was from Moondog (we went back twice!). Not only was it the most delicious, it was also incredibly beautiful! We did enjoy the key lime pie at Blue Heaven, a Key West staple. We found Kermit’s disappointing. It was even handed over in a plastic container, which didn’t make the experience any better. We also tried the pie at Sloppy Joe’s - it was okay… nothing to write home about.

However, our favorite mojito was the Hemingway from Sloppy Joe’s. It was more refreshing than others we had. Our second favorite was from Seaside Cafe at the Mansion (delicious lobster pizza!). They garnished our drinks with rock candy, which was a fun touch. Ranking again at the bottom was Two Friends. The key lime mojito was bad… so bad.

Attractions

The rainy weather started shortly after we arrived in Key West. The front (that turned into Tropical Storm Alex) kept us running and ducking under cover throughout our week. In between rain showers, we managed to visit the Hemingway House and the Key West Butterfly and Nature Conservatory. Both visits were WONDERFUL. Definitely worth the hype! 

As previously mentioned, our only firm plans for Key West included vying for two standby seats on the ferry to Dry Tortugas National Park. This is one national park visit that actually requires advance planning - not our forte! We arrived at the ferry terminal at 5:30 am to wait in line for the standby list. Only one party of 2 was ahead of us so we felt fairly confident that we were going to make it. Alas… everyone showed up to claim their bookings so we didn’t make it on the boat. We will be returning with reservations within the next year!

Because our ferry ride didn’t happen, we seized the opportunity to join a sunset cruise and were rewarded with a gorgeous sky! Most of these cruises market live music and all you can eat/drink on board. Not surprisingly, the food was all fried (chicken fingers, potstickers, egg rolls) - proceed with caution when mixing with cheap alcohol! Having said that, the music was great and the company was fun. We had a great time on the boat.

We also… stood in line for our photo at the Southernmost Point. Pro tip: there is no prop for your phone or camera so you’ll need to make friends in line. We wandered around Mallory Square and Duval Street, ducking in and out of shops and bars. We tried kava for the first time. We dodged congregations of iguanas at the Key West Cemetery. We melted at Fort Zachary Taylor. In other words, we packed in everything we could to experience the island!

We have plans to return to Key West within the next year to visit Dry Tortugas, but we likely won’t stay as long. We’d like to fly into Miami and drive the 100-mile bridge across the Florida Keys. We gathered quite a few tips from people we met along the way, such as the “middle” keys have the nicest beaches and some Key West boutique hotels have a 7-night minimum but more affordable pricing. They won’t even show up in search results if you’re searching for fewer than 7 nights. Definitely good intel!

What We Missed

There are so many wonderful attractions and experiences that have been recommended to us since authoring this post! We will definitely be making a return trip. Here are some suggestions:

• Ghosts and Gravestones was highly recommended, but we couldn't fit it in during the time we had.
• Judy Blume owns and operates Books & Books in Key West and can sometimes be found behind the desk. The tween in me is grieving over missing out on this!
• The Reach by Hilton has a gorgeous natural sand beach.
• The grounds of Casa Marina feature beautiful reflecting pools. 

Tell us - have you been to Key West? What was your favorite memory/tips/tricks/pie from your adventure?