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I can’t believe it’s only July and I’ve driven the entire length of the Florida Keys three times this year.
Last year, the Florida Keys were one of my top most wanted destinations, mostly due to Bloodline. So in February Cailin and I planned a girls’ road trip from Orlando to Key West and back again. And oh, was that FUN. Especially Key West.
In fact, I enjoyed it so much that when Florida Keys Tourism invited me to return in July, I said hell yes.
But why would you go back to the same place so soon, Kate?
Lots of reasons. I did genuinely fall in love with the Keys, especially Key West, and I felt like my last trip ended sooner than I wanted it to. And when the opportunity came up to work on a campaign with a brand I love, that’s an excellent opportunity. Also, I hate to say it, but the older I get, the more I crave trips to closer destinations with short, ideally direct flights.
Complete Guide: Solo Female Travel in the Florida Keys
Plus, it’s amazing how much can change in a destination in just a few months. Several new properties have opened, including the fabulous Perry Hotel on Stock Island near Key West. Key lime pie-making classes are now a thing at the Key West Key Lime Pie Company. Key’s Meads is now open in Key Largo. And most significantly, Key West now has Uber and Lyft, which is a complete game-changer. (Also, Maragaritaville has reopened, so there’s that.)
But the #1 reason why I came back to the Keys was this:
As soon as I heard that my visit could potentially coincide with Hemingway Days in Key West, I knew it was a must for me! I’m not a die-hard Hemingway fan, but The Sun Also Rises is my favorite book of all time. And the idea of a Hemingway Lookalike Contest was just hilarious.
I was only here for the first night of the contest — and it was SO MUCH FUN that I came perilously close to changing my flight and staying another two nights! (Then I realized it would cost me upwards of $1000 and that was insane — so with a heavy heart, I flew back to New York.)
More on that beautiful contest later.
A Summer Road Trip From Key Largo to Key West
My trip this time began in Key Largo. Just a 75-minute drive from Miami Airport, starting in Key Largo is a relaxing way to start your trip. (Especially when you consider that last time I drove all the way from Orlando to Islamorada, which took seven hours with traffic and was not my smartest move of all time.)
I actually skipped over Islamorada this trip and made stops in Grassy Key, Marathon, and Big Pine before ending up in Key West. Visiting in July was different, too. It was extremely hot and humid everywhere, and it was hard to spend extended time in the sun, but it was incredibly beautiful and perfect weather for swimming in the Upper Keys.
Snorkeling with an All-Female Crew in Pennekamp State Park
I don’t dive, but I love to snorkel, and one of the best places to snorkel in the Keys is by Pennekamp Coral Reef State Park, just off Key Largo.
I’m probably the most spoiled snorkeler of all time — my only two real snorkeling experiences have been the Belize Barrier Reef and Western Australia’s Ningaloo Reef, easily two of the world’s top sites — but I really enjoyed the wildlife at Pennekamp. Seeing my favorite fish, the queen angelfish, is always a highlight for me.
And the Keys are most famous for the underwater Jesus statue! You might remember it from season one of Bloodline when Danny takes the guests snorkeling. Jesus is actually covered with fire coral, so we were instructed not to touch him.
One nice surprise was that we had an all-female crew on our trip! I’m fairly certain that that was the first time I’ve had an all-female crew on a boat. Sometimes you don’t notice gender inequality in certain industries until it smacks you in the face.
Either way, I loved getting to know the women who took us on our trip, and as a shipwreck survivor who still gets nervous on boats, I felt very safe in their hands.
Later on, I visited the Coral Restoration Foundation and learned first-hand about the devastation to the reefs in the Florida Keys. It’s harrowing stuff, you guys.
But here they are doing such good work. The volunteers showed me how they were regrowing coral and planting it throughout the Keys. You can volunteer with them if you’d like, and if you’re a certified diver, you can even join them on trips replanting the coral!
Sampling the Meads of Key Largo
On my first trip, I visited the Florida Keys Brewing Company in Islamorada to sample the local beers. This time, it was about something more concentrated — mead! Keys Meads is a new business selling meads with flavors of the Florida Keys.
Mead is honey wine. It’s one of the spirits making a comeback today. Think of it like port — you sip on small glasses of it. And the Keys Meads are delicious. One of my favorites was Holiday Spice, which tastes a bit like a boozy applesauce and is a perfectly Christmassy beverage. There’s an orange cream flavor that rocked my socks. And because this is the Keys, there are not one but two different key lime-flavored meads!
Also, they ship — so if you’re carrying on your luggage, you can get bottles sent to you at home.
Trading Bloodline Stories with Locals
You might recall that the reason why I visited the Keys in the first place was because I was obsessed with the Netflix series Bloodline (which has since wrapped its third and sadly final season). It’s a drama about a prominent family in the Keys and their dark secrets. As amazing as the cast is, the Keys are the true star of the show and the cinematography is stunning.
Every local in the Keys has a story about the Bloodline cast. My favorite was from a local woman who ate a meal at a bar next to Kyle Chandler. “He got up to leave and my friend grabbed me and said, ‘That’s Kyle Chandler,’ and I said, ‘Oh! I just thought he was a handsome man!'”
Oh! I just thought he was a handsome man! is totally going to be my excuse for everything.
Chilling at the Kona Kai Resort
The Keys are a funny little place — there is so little land that you see all kinds of businesses pushed up against each other, from ramshackle seafood shacks to luxury resorts. You never know what you’ll find when you see a driveway leading off the highway.
In Key Largo I pulled off the road, walked down a path, and discovered a wonderful little place called the Kona Kai Resort and Gallery. It’s home to just a few apartment-style rentals with a gorgeous, landscaped pool area. You will definitely spot some iguanas!
What I loved most about this place was the friendly and helpful staff (especially when they helped with a car issue), the beautiful outdoor area, and just how intimate it felt. If you don’t want to be in a pool with dozens of other people, this is an excellent choice. And the art gallery on site is a nice touch.
I loved my suite. It was gorgeous, airy, and about double the size of my apartment. Not to mention beautifully chilly thanks to a great air conditioning system!
If you’re looking for a small, friendly, local property in Key Largo, I wholeheartedly recommend the Kona Kai.
Dollar Dollar Bills in a Big Pine Pub
I happened to be road-tripping from the Upper Keys to Key West while Kristin and Scott of Camels and Chocolate were doing the trip in reverse, so we decided to meet in the middle! Our spot? The No Name Pub on Big Pine Key.
Kristin and I have been online friends for years, but we hadn’t met in real life until this trip! And what a place to meet.
The No Name Pub is a dive bar located a few miles off the main road in Big Pine, which feels like forever in a place as small as the Keys. It’s absolutely plastered with dollar bills. The three of us estimated that there might be $20,000 covering the walls of that pub. Just insane.
You’ll probably be looking for an interlude en route from the mid-Keys to Key West. This is a good spot. And for what it’s worth, their pizza smelled sensational.
You can read Kristin and Scott’s post about their Keys trip here.
Kicking Back at the Perry Hotel
In Key West I stayed at a brand new boutique hotel on Stock Island, just east of Key West: the Perry Hotel. It was gorgeous and modern and I loved all the stylistic touches. Much of the design is an homage to Stock Island’s history as a shipyard (old propellers are repurposed as giant flowers!). And the pool area was incredibly inviting.
Now…is staying on Stock Island worth it? You might recall that after my first trip to Key West, I wrote about how much I appreciated staying in downtown Key West, walking distance from everything. If it were a few months ago, I would not have wanted to stay on Stock Island. But times have changed. Now that Uber and Lyft have been available in Key West for a few months, it makes living without a car so much easier. Plus, the hotel has a free hourly shuttle to and from Key West and it takes about 15 minutes, though it does end at the early time of 8:30 PM.
Plus, a property with these amenities would be far more expensive in Key West itself. Either way, I just loved spending time here. I loved my room, the pool area, the decor, the giant glass of champagne they poured me upon arrival, the nearby Cuban coffee truck, and the fish tacos were extraordinary.
So yes — I would absolutely stay on Stock Island for a property as good as the Perry!
Kayaking After Dark
One of the cooler activities I did in Key West was “nightboarding,” or kayaking after dark with lit glass-bottomed boats. Not only was the sunset incredible beforehand (that is an east-facing photo above! East-facing!!), but we got to enjoy being out on the water in peaceful darkness.
Paddling at night allows you to see a lot of creatures you wouldn’t see by day. We saw live sea cucumbers spurting out water (which….let me just say is a sight), and jellyfish floated through the water. I even saw a lobster shimmy underneath my boat!
I think what I enjoyed most was the quiet and the darkness. The polar opposite of Key West’s famous sunset celebration in Mallory Square.
Learning About Truman at the Little White House
After my hedonistic first trip to Key West in February, I was shocked that the highlight of my trip this time around was a visit to the Truman Little White House. Seven presidents from Taft to Clinton have used this residence as a retreat during and after their presidencies, but Harry Truman was the president who loved it the most. He spent a total of 175 days in Key West and loved the island fiercely.
I loved this tour — I enjoyed it far more than I thought I would! The house is styled as it was in 1949, down to the rare upholstery, and while it was cutting-edge at the time, it’s so simple that you shake your head at how different life is today for the president.
That above is actually the President’s bedroom. I think we can all agree that Trump wouldn’t be caught dead staying there.
I loved learning tidbits about Truman — he loved to play poker with his Cabinet and the Chief Justice, but gambling was still seen as a sin in America back then, so they had to keep it under wraps. Truman only had a high school education but chose to be an intellectual — he played Chopin on the piano by memory, he read every book in the library of Independence, Missouri, and he and his wife Bess would write each other love letters debating the merits of Shakespearean plays. And the reason why he had such low approval ratings at the end of his presidency was because he was pro-Civil Rights and most of America wasn’t at that time.
This visit really inspired me to learn more about Truman, and the staff suggested I pick up David McCullough’s Truman, as it’s regarded as the best Truman biography. (Fun fact: I did a project on Truman in the fifth grade. It’s nice to come full circle 22 years later!) If you’re in Key West, I urge you to stop by for a visit. I bet you’ll love it.
Also be sure to check out the Truman Annex, the neighborhood surrounding the Little White House. It’s neat and stately with some of the prettiest houses in Key West.
Even More Key Lime Pies — and Making My Own!
Back in February, Cailin and I basically lived for eating key lime pie across the Keys. This time I didn’t find any life-changing pies, but the one at Fish House in Key Largo was especially delicious, especially when it comes to crust.
But on this visit I got to make my own pie! The Key West Key Lime Pie Company has recently started offering classes. Their pie is a frozen variety, so you get to build your own personal pie, let it freeze overnight, then pick it up the next day. (They give you a slice to eat afterwards, too — they’re not torturers!) Do know that it’s more of an “assembly” class than a cooking-from-scratch class, but it’s fun and interesting and you get to do piping!
Also notable? This class is only $20, making it one of the best bargains in Key West.
I ate a ton of key lime pie on this trip to the Keys as well, but there was only one pie that I repeated from my first trip. I went to Mrs. Mac’s in Key Largo and took a slice to go to enjoy in my air-conditioned suite at the Kona Kai. Mrs. Mac’s is still my favorite.
Hemingway Lookalike Contest
THIS CONTEST. Did it ever live up to the hype! I’m a sucker for crazy festivals (dancing all night long with Vikings in Shetland, setting everything on fire in Valencia, joining a city-wide water fight in Bangkok) and it broke my heart that I could only be here for the first night of the contest.
They’re called the Hemingway Lookalike Society. They call their idol Papa. And every year they throw celebrations to celebrate their favorite author’s birthday, culminating in a lookalike contest.
Every Papa wannabe goes up on stage and has 15 seconds to make his case to the judges for why he should be the next Papa. The contest is judged by the previous winners of the contest, who are called the Papas, which makes things a bit more confusing.
So many of the guys gave long, rambling explanations, but my favorite was short and succinct from a Danish man: “Because I got off the plane and the immigration officer said, ‘Welcome to Florida, Mr. Hemingway.'”
It’s a strong community and lots of them look forward to reuniting every year. One sad thing is that three Papas passed away this year, and many tributes were given in their honor.
In between rounds, they auctioned off Hemingway merchandise, including old Life magazines with Hemingway on the cover. Proceeds go to the Hemingway Scholarship Fund, which supports students studying writing in the Florida Keys.
And my Danish favorite was actually chosen as a finalist! (He’s third from the right in the back row, the sliver of the face.) Here are all the finalists chosen from the first night, including a Young Hemingway on the right, which is fairly rare.
And, um, for those of you who were asking about Sexy Hemingway…he’s the guy in the black shirt. And I would.
This year’s winner was Richard Filip, who actually sailed a replica of Hemingway’s boat from Houston to Key West. That’s commitment! I asked him for this selfie because I had the feeling he was going to win. Richard has been a runner-up in the contest many times, as you can see by his medals, and he donates a lot to their scholarship fund. Between that, the boat, and his Hemingway looks, it’s not surprising to see why he was the Papa of 2017.
(Also, Paula Deen’s husband competed this year and apparently she was in the audience the same night as me!)
Finishing with SUP Yoga
If you’re flying out of Key West in the afternoon, I highly recommend booking a SUP (paddleboard) yoga course with Lazy Dog for the morning. It’s a great way to enjoy the outdoors and be good to your body before your flight.
If you’ve never done yoga on a paddleboard before, don’t worry — it’s not as scary as it seems. All levels are welcome, from beginners to experts, and Kyla will take you to a smooth spot where you can balance easily.
I loved paddling out into the mangroves and enjoying the scenery before zoning out in yoga. I have to say that the Keys have now beaten the Croatian coast for the most scenic place I’ve done outdoor yoga!
Where to Eat in the Keys
There’s a wide variety of restaurants in the Keys, from low-end to high-end. My big recommendation is to enjoy the fresh seafood, especially hogfish, which is local to the area. Mahi is a good choice, too. But not all of the seafood is local year-round, so I recommend you ask your server what’s local and delicious.
Here are some of the standouts of my most recent trip, from east to west:
Fish House in Key Largo was a highlight — it’s a mid-range place, and everything I had was delicious. Guy Fieri filmed an episode of Diners, Drive-Ins and Dives here and I had two dishes he featured: the smoked fish dip and the hogfish Matecumbe-style, topped with fresh tomatoes, fresh basil, shallots, capers, olive oil, and lemon juice, then baked. That hogfish rocked my world and I loved finding a healthy dish that was still mind-blowingly good.
And their key lime pie is one of the best I’ve had in the Keys.
Sol by the Sea at the Playa Largo Resort in Key Largo was home to my favorite cocktail of the trip: the dragonfruit mojito! So pretty and so tasty! (And the worst cocktail of the trip was the margarita at Margaritaville. Once you’ve gotten yourself used to plain tequila-lime-and-salt margaritas, sour mix wreaks havoc on your body.)
The Playa Largo is a gorgeous resort and having dinner at Sol by the Sea allows you to enjoy the beautiful sunsets. I loved their gingery tuna poke appetizer; the fish curry, though, was not remotely spicy despite me asking for spice. I think they might be used to catering to weak palates. They also have a nice frozen key lime bar.
When locals heard I was going to Tarpon Creek in Marathon, every single person told me I had to try the watermelon and feta salad. They were right — it was fabulous, especially with added shrimp. They had a nice conch chowder that was actually spicy, too!
This is the take on smores at Matt’s Stock Island Bar and Kitchen at the Perry Hotel. As a lifelong camper who took her first steps in a tent, I think I have the authority to say that no, these are not remotely smore-like — they are chocolate chip cookies with torched fluff.
I actually missed taking a picture of my favorite dish: the snapper tacos. They were absolutely sensational. Delicious grilled snapper, orange jalapeño slaw, avocado polao crema, pickled onions, corn tortillas — and it’s enough for two people. Probably my favorite dish of the entire trip.
Hogfish Bar and Grill on Stock Island was my final meal in the Keys: fried hogfish tacos and a Hogfish beer by the Florida Keys Brewing Company. After that paddleboard yoga class, it hit the spot.
Bookmarked for the Next Trip
Even with two trips to the Keys this year, I still haven’t done everything that I want to do. At the top of my list? A boat trip to Dry Tortugas National Park, west of Key West; staying at The Moorings in Islamorada, which plays the family’s guesthouse on Bloodline; and a stop on Bahia Honda Key, which is home to a beautiful state park. And did you know that Judy Blume owns a bookstore in Key West? How have I not been there?!
But most of all, I want to come back for Fantasy Fest. It’s a multi-day Halloween celebration in Key West with different costume themes each night! Key West + my favorite holiday + rewarded creativity? HELL YES. I’ll make that my own personal Burning Man.
More on the Keys
Best Time to Visit Key West
Solo Female Travel in the Florida Keys: Complete Guide
Key West, You Are My New Favorite
Miami is Nice, So I’ll Say It Twice
Essential Info: On this trip, I flew into Miami and out of Key West. That’s definitely efficient, since it’s a 3.5-hour drive from Miami Airport to Key West, but keep in mind that a one-way car rental will be more expensive than a return trip — it may be cheaper for you to fly in and out of Miami or even Fort Lauderdale, which is still close.
In Key Largo I stayed at the Kona Kai Resort and Gallery, which I enjoyed very much and recommend. Rates from $219 per night. Find more Key Largo hotels here.
John Pennekamp Coral Reef State Park in Key Largo offers two kinds of snorkeling trips: 2.5-hour trips for $29.95 and 4.5-hour extended trips for $38.95; rental equipment is available for both. I felt perfectly happy with the 2.5-hour trip, which is entirely by the reef with the Jesus statue. Entering the park costs $4. You can visit the Coral Restoration Foundation and learn about their efforts or volunteer yourself.
Keys Meads is open to visit — no appointment necessary during opening hours. It looks like it’s in an office park; don’t worry, you’re in the right place. Be very careful and limit your consumption to just a few small sips if you’re driving. They ship bottles, too.
In Key West I stayed at the Perry Hotel, which I enjoyed very much and recommend. Rates from $237 per night. Find deals on Key West hotels here and see all Key West Airbnbs here.
Ibis Bay Paddle Sports offers 1.5-hour night boarding tours in Key West for $59.95. You can choose between paddleboarding and kayaking, but if it’s windy, they’ll recommend kayaks.
Visiting the Truman Little White House requires a guided tour; tours cost $15. No photography is allowed.
The Key West Key Lime Pie Company offers pie-making classes for $20.
Paddleboard yoga classes at the Lazy Dog cost $30; private lessons are $75 per person.
The sun is super strong in the Keys — be sure to wear sunscreen and reapply often, even on days when you’re just strolling around Key West. Sunburn can sneak up on you quickly here. Use coral-safe sunscreen when snorkeling. Also, be sure to hydrate. There was one point where I felt dizzy and nearly fainted out of the blue because I hadn’t hydrated enough that morning.
Watch Bloodline on Netflix before going to the Keys — you’ll appreciate your trip so much more! The show is a slow burn; give it a few episodes if you don’t click with it right away.
Be sure to buy travel insurance for your trip to the Keys. Whether you cut yourself and need to go to the hospital for stitches, or your phone gets stolen at a bar, or an injury means you need to cancel all or part of your trip, travel insurance will help you out in your time of need. I use and recommend World Nomads as travel insurance for trips to the Florida Keys.
This post is brought to you by Florida Keys and Key West, who hired me to work on this campaign. They also covered my travel expenses for this trip, excluding alcohol and incidentals. All opinions, as always, are my own.