Key West: Eternal

Key West, the Conch Republic has played host to rum runners, pirates, Ernest Hemmingway, fishermen and all those seeking to escape from the norms of life. Living in Tampa, it’s only about an hour’s flight from me, but depending on where you live, it may be a higher level of effort. However, it is absolutely an experience that you should have. This being my fourth trip down, I was lucky enough to spend five days there last week, it was something to behold.

 

Key West Offshore Fishing

Our first day fishing out of Ocean’s Edge Resort and Marina aboard a 24-foot Yellowfin.

 

 

After we caught bait, we ran offshore to the reef for some mangrove snapper action. There were mangrove snappers galore and we certainly caught more than enough for a great lunch. These shallow reefs play host to a variety of snapper species, sharks, mackerel, jacks and barracuda. If you head out to the bluewater, tunas, dolphin, wahoo, amberjacks and sailfish can be common catches.

Becoming bored of the constant snappers, we ran inshore to try to put a tarpon in the air – we found a super fishy canal that was home to cubera snappers, sharks, tarpon and even the rare Key West snook.

 

I did manage to feed the elusive Key West snook, which broke me off in the trees, and I also played around with some cuberas, but after a while, we decided that it was time to head in for lunch.

 

 

 

 

Key West Inshore Fishing 

My primary goal upon coming down was to try to catch a bonefish on fly. Sadly, on this day, the weather was truly horrific. We had an hour window in the morning where we snuck out and Captian Jared Cyr worked as hard as any guide could ever work for their client. I had about seven shots at tailing bonefish, but couldn’t manage to get one to eat. After this, the weather got even worse and we headed in early, lest we get caught in a monsoon of wind and rain.

 

Just because I couldn’t make it happen doesn’t mean that you can’t. Jared and his brother Brandon are two of the best guides in all of the Keys. If you are looking for a bonefish, tarpon or permit, call them.

 

Key West Attractions

Now that the fishing is over and done with, here are some places for you to plan your itinerary around.

 

1. The Hemmingway House:

   You will see the descendants of his famous six-toed cats sleeping, grooming and scurrying about the property. Don’t worry, they are very well taken care of by the on-site staff. No reservations are necessary and adult tickets are only $18.

From left to right: Personal letters from Hemmingway. The original copy of “A Farewell to Arms” and Hemmingway’s study where he wrote many works (also pictured, cat).

 

2. The Southernmost Point:

Yes, this is the southernmost point in the continental United States. Is it a tourist destination that requires you to stand in line just to take a photo? Yes. Is it worth it? I will let you decide that.

 

 

3. The Pappa’s Pilar Distillery:

Of the many things synonymous with Key West, perhaps none are greater than Hemmingway and rum. Hemmingway was referred to as Papa by his family and close friends, his boat was named the Pilar, so the distillery founded by his descendants aptly named their rums “Papa’s Pilar”. You can tour the facility, have a tasting (both by appointment), or just go to the bar and hang out. If you’re a whisky lover, I encourage you to try the old-fashioned made-with rum, I think you’ll be pleasantly surprised. A cool note – this organization is very active in giving back to the oceans and community. 

 

 

4. Nightlife:

Pretty simple, go do Duval Street. You would never think that you could find so many bars in such a small stretch of land. Recommendations include Hog’s Breath Saloon, Irish Kevin’s, Captain Tony’s Saloon, Rick’s, Sloppy Joe’s and more. Many bars feature live music, cheap drinks and all the fancy, fun, touristy cocktails that you could want.

Another great place that is as divey as dive bars come and is off the beaten path is The Chart Room. This tiny bar is hidden within the Pier House Resort and is famous for playing host to a variety of legendary Key West fishermen over the years. The walls are adorned with photos of past patrons alive and dead, there is a popcorn machine that has seen better days and they have sports on TV. What’s not to like? If you want to beat the crowds and actually hear the person next to you, go here.

 

5. Food:

Key West has some excellent restaurants, here are my recommendations.

1. Blue Heaven: Great for breakfast, lunch, or dinner. At breakfast, try the lobster benedict, for dinner, they have a great seafood scampi. Here you will find inside dining upstairs and outdoor dining that features live music.
2. A&B Lobster House: You’ll feel as though you’ve gone back in time with the classical music and turn of the century decore. Try any of their lobster dishes. This spot is located at A&B marina and has many other bars and live music venues a stone’s throw away.
3. Hot Tin Roof: Located at Ocean Key Resort and Spa, this is an upper-class, drop-some-cash-type dinner. However, you won’t be disappointed, the food is amazing and they offer perhaps the best sunset view in Key West. My menu recommendation: anything. This place is spectacular.
4. The Docks: This technically isn’t in Key West, it’s on Stock Island, but it has the freshest seafood anywhere in the greater Key West area. You will notice a difference between the seafood here and other places, it’s THAT fresh. I recommend the figs in a blanket and also a secret non-menu item, the lobster mozzarella sticks. Both these appetizers will blow your mind.

 

6. Forts:

Fort Jefferson and the Dry Tortugas are incredible. Tickets for the ferry are $200 a piece, but it is a great experience. The 70-mile trip takes place aboard an air-conditioned, 110-foot catamaran-style ferry that serves both food and drinks. Upon arrival, you can tour the fort, swim and snorkel in some of the clearest waters that you’ve ever seen. I think it’s worth it.

Fort Zachary Taylor is a fort that can be accessed without needing to get on a boat or spend hundreds of dollars. Despite being surrounded by water, Key West isn’t a very beachy place, but Fort Zachary Taylor exists on one of Key West’s only public beaches. The beach is beautiful and the fort has a lot of cool history.

 

 

Lodging: 

We stayed at The Perry Hotel in Stock Island, this was my one regret of the trip. While the hotel and staff, restaurant, pools, bar and overall ambiance were great, it was just too far from all of our activities. There is a shuttle that runs to Key West, but most days we were taking an Uber ride to get where we wanted to go. If you have no desire to go into Key West proper for more than a one-day trip or fly and don’t rent a car, I wouldn’t recommend staying here since it is about 20 minutes from all of the places and activities that I mentioned above.

I recommend staying at the Pier House Resort or Ocean Key Resort and Spa if you want to spend your days in Key West proper. If you drive down, or rent a car and can simply drive into Key West, then you’ll be ok. Again, I want to reiterate, that The Perry Hotel is a great place to stay, it was just a bit far from 90 percent of what we wanted to do while on the trip.

 

In Conclusion 

I named this article “Key West Eternal” because of the rich history of the island and all the memories that it holds. I saw people from all over the world on vacation, the classic dollar bills stapled to the walls of various bars with names of happy couples just married or bachelorette parties.Thinking of my own memories here at a friend’s bachelor party and it made me pensive. This place has played host to so many people over the years, from pirates to Hemmingway, to fishing guides, lobstermen and all those who came down here for an escape. I thought of how their experiences were so unique and yet how that tradition and those same memories will continue to be made today, next week, month year and forever. They’ll never die. Key West Eternal.

Until next time, tight lines.