Editor’s note: TravelQ, a series that documents travel through the eyes of stylish queers, returns this week with a new feature by Caroline and Erin, web designers, freelance photographers and writers for the travel blog Authentic Asheville.
The Florida Keys are a place of beauty, wonder, and adventure. If the winter has taken its toll on you, or you’re just plain overdue for a vacation, consider the Keys. You can sit poolside, snorkel the reef, go sailing in the Gulf, or lounge under a coconut tree. The options for fun are seemingly endless. And don’t even get us started on all the wonderful things to eat and drink. As always, we’ve also recommended our favorite places to stay and the two we’re writing about are absolutely stunning.
Though many opt to fly into Miami or Fort Lauderdale to access the Keys, we chose to drive our van. Our adventure started in Key Largo (Upper Keys) and after a few days continued south through the middle Keys en route to Key West.
The following is a guide on the best places to stay as well as the best things to see, do, and eat when visiting the Florida Keys. Thanks so much to our friend and Key Largo local, Lisa Giles, for helping us with this piece!
The Best Place to Stay in the Upper Keys
Kona Kai Resort, Gallery and Gardens | 97802 Overseas Highway, Key Largo
We fell in love with this place at first sight. Upon checking in, we were treated to a bright, light-filled art gallery that features original art from artists all over the world. A few minutes later, we were walking down a beautiful palm tree path, lined with plants of all colors of the rainbow, (the resort is also a botanic garden and signs are discreetly placed so that you can identify and learn about what you’re looking at) and opened the door to our room (we stayed in Mango). The sleep in our King sized bed was the best we’ve had in a very long time but nothing, not even an incredibly comfortable bed, could keep us asleep for sunrise. Why? Because the resort has a gorgeous dock with thatched roofs and lounge chairs, a beautifully groomed beach area and even paddle boards and kayaks just beyond the lap of the shore, all of which are complimentary for guests to use. On our last morning at Kona Kai we paddled out on glassy water and ended up seeing two dolphins! We highly recommend Kona Kai and are already eager to return.
The Best Things to Do in the Upper Keys
Glass Bottom Boat Tour at John Pennekamp Coral Reef State Park | 102601 Overseas Highway, Key Largo
We started our adventure here at John Pennekamp Coral Reef State Park. The park has almost something for everyone. There’s a great little beach to lounge around on, kayaks and paddle boards available for rent, an aquarium to check out, as well as SCUBA Diving Boat Tours, Snorkel Boat Tours and Glass Bottom Boat Tours. We went on the glass bottom boat tour and started oohing and aahing moments after leaving the dock. You’ll weave through some mangrove habitat and then in about fifteen minutes or so, you’ll start seeing the most exquisite turquoise color that you’ve ever seen. We were mesmerized by the color of the ocean and spellbound once we started catching glimpses of the reef through the bottom of the boat. (If you’re prone to seasickness, consider taking a Dramamine before you leave the dock!) There were two naturalists on-board and they were quick to point out the different marine animals that we were seeing. We can’t think of a better way to kick off your Florida Keys adventure than with this glass bottomed boat tour.
Theater of the Sea | 84271 Overseas Highway, Islamorada
You can swim with dolphins. Or sea lions. Or hang out with parrots. Read that again, it’s true. And it’s an incredible experience. We had the opportunity to interact with a sea lion named Malibu and it was unreal! We met our trainer at the dock and after a brief lesson on what to do and what not to do, we were wading into the water near Malibu and getting hugs and kisses from her. Her fur was so soft and she was so gentle with us. It was one of the coolest experiences of our entire trip. In addition to animal interactions, we also had a chance to go on a 4 hour snorkel adventure. The 30-foot boat held up to 6 guests, but the day we went there were only two others with us. We snorkeled two different patches of reef, went to two different state parks (Lignumvitae Key Botanical State Park and Indian Key Historic State Park) and even took a pit stop at Robbie’s marina where we saw some massive tarpon. All of the gear is provided and the fun is guaranteed. We’d do both of these adventures again without question.
The Best Places to Eat in the Upper and Middle Keys
M.E.A.T Eatery and Taproom | 88005 Overseas Highway, Islamorada
Anytime we hear about a good burger, we’ve got to try it for ourselves, especially when the tip is coming from a local. Just as we had hoped, this place more than delivered. Get yourself some of the house-made pork rinds to start (they’re served with a Lime Cilantro Aioli) and they’ll pop and crackle all the way up to your last bite. As for the burger, you can expect it to be tender, juicy and cooked to order. There’s a whole host of local brews to help wash everything down as well. After eating there, it’s no wonder that Diners, Drive-In’s and Dives (0n the Food Network) decided to feature it.
Sundowners | 103900 Overseas Highway, Key Largo
We arrived at Sundowners just as the sun was setting and managed to snag a table by the water. We sipped on a round of drinks, snacked on some conch fritters and enjoyed the evening for quite some time before deciding to order. This is a good place to visit upon arriving. It’ll help you settle into island time. When you’re ready to eat, there are tons of choices for you to pick from. We opted for the lobster and the hogfish (both were cooked perfectly and left us stuffed!) and though we were literally full to the gills, we went for the key lime pie which was good right down to the last bite.
The Florida Keys Brewing Co. | 200 Morada Way, Islamorada
For us, the icing on a perfect day is always a cold beer. But not just any beer. We like small batch craft beer. And we fell in LOVE with the Florida Keys Brewing Company. Head on over to Islamorada’s Arts and Cultural District and order up a round of beers. We recommend ordering a flight and then heading out back where you can enjoy the space (picnic tables, corn hole, random chickens – just good vibes all around). Can’t decide and not up for a sampler? Go for the Iguana Bait. Described as a “honey hibiscus kolsch made with local Keys honey and hibiscus” we found it to be as refreshing as it was unique. This is the kind of place we would visit regularly if we lived in the Keys.
Doc’s Diner | 99696 Overseas Hwy, Key Largo
On a budget? Choose Doc’s. Want some excellent pancakes or french toast? Choose Doc’s. Want a place where the locals frequent? Choose Doc’s. Need we say more? We both ordered the #2, which is cleverly named Four Pairs (2 large eggs, 2 bacon strips, 2 sausage links and 2 “Uncle Adrian’s Pancakes” or 2 french toast). For $5.99, we left full and happy.
Key Largo Fisheries Backyard Cafe | 1313 Ocean Bay Drive, Key Largo
Dockside dining with live music on Saturdays and a fun atmosphere the rest of the week (except for Sunday’s when they’re closed) this place is your go-to for lobster: lobster BLT’s, lobster bites, Caesar salad with grilled lobster…we enjoyed all three. The seafood comes fresh off the boat at the dock, so you can order off the menu or walk into the retail space and bring home fresh fish for dinner, along with house-made seasonings and dressings. The beer is cold and the staff is friendly. Hang out for a while after you’re done eating and if you’re lucky you might just see a manatee just beyond your picnic table. We did!
The Best Things to Do in the Upper and Middle Keys
Rain Barrel Artisan Village | 86700 Overseas Highway, Islamorada, MM 86.7
Keep your eyes peeled for a giant Florida Keys spiny lobster on the side of the road. When you see “Betsy” you’ll know you’ve arrived at the Rain Barrel Artisan Village. There’s a bunch of local art here (everything from really kitschy decorations to really beautiful jewelry) and is a good place to pick up a little souvenir or a cool Instagram photo.
Visit the Dolphin Research Center | 58901 Overseas Highway, Grassy Key
This non-profit marine mammal education and research facility has been teaching the community about dolphins since 1984. There are several programs a day that guests can sit in on as well as the option to swim with dolphins or even paint with them. If you enjoy learning as much as you enjoy being entertained, this is just the place for you. All of the dolphins work/interact/entertain as they much or as little as they want to. They are naturally social mammals, but the staff at the research center respect their desire to work or seek alone time. They live in natural sea water and are allowed to develop communities or pods as they would in a natural setting. We truly felt a sense of family between the staff and the mammals here.
The Best Place to Stay in Key West
Marquesa Hotel | 600 Fleming Street, Key West
Private. Quiet. Gorgeous. Exceptional service. Wonderful location (a block off of Duval Street). Literally everything has been thought of in advance at the Marquesa Hotel so that when you arrive, you can immediately shift to island time. We were taken care of from the moment we arrived. The view from our room overlooked a crystalline pool and though we were just a couple minutes from all the action downtown, the hotel was incredibly peaceful. It’s no wonder why it’s won awards from Conde Nast Traveler and Travel and Leisure Magazine, both of which have featured the Marquesa as one of the top places to stay in the world. Consider leaving your car in their covered garage and ordering bicycles thru drop-off service, which you can also keep in the garage. We didn’t drive our van for 4 days which is a huge departure from ‘normal life’ for us! (More about what we’re doing these days here.) Treat yourself and stay at the Marquesa. It’ll be worth every penny and then some. We hope to get back here as soon as possible.
The Best Things to Eat, Stay, and Do in Key West
Sunset Celebration | 400 Wall Street (Mallory Square), Key West
When’s the last time you made a point to watch the sun set? To just sit and enjoy the day’s end. If it’s been a while, the sunset celebration in Mallory Square is the perfect reason for you to change things up. You’ll see funky street performers, a psychic or two, musicians, food and drink vendors and top-notch people watching. (The experience itself is free but bring some cash to tip the performers.) The sun however is still the star of the show and all eyes are on it as it dips below the water, always right on time. This is a Key West tradition and one that you should experience at least once while you’re here.
Stand Up Paddle Board Yoga with Lazy Dog | 5114 Overseas Hwy #7, Key West
Lazy Dog has been featured in SUP Magazine as well as Outside so we knew were going to have a really authentic experience but what we weren’t counting on was how nice and patient our instructor was. We got a brief lesson on the basics of paddle boarding before we even left the dock and nothing but positive vibes the rest of the yoga class. The 2 hour session went by so fast and we left with that full body-mind relaxation that only yoga can give you. Bonus? Seeing two nurse sharks on the way back to the dock. All skill levels can access this class, even beginners. PS. There’s no shame in falling off your board, so don’t let your fear of perfection stop you from having a great time.
Sebago Key West | 205 Elizabeth Street, Unit 1, Key West
Sebago Key West has been taking people out to have fun on the water for 25 years! We signed up for the Island ‘Ting adventure: an all-day sailing, kayaking, and snorkeling that includes breakfast (quiche and fruit salad), lunch (fried chicken and peel & eat shrimp), fresh baked cookies, and beer, wine, and sangria! The crew was upbeat and extremely hard working. On our kayak excursion they taught us some interesting things like how the mangroves filter out salt, how the black cormorant can hold it’s breath for up to 4 minutes and dive down to about 150 feet for fish and how the body of water we were in was the third saltiest body of water in the world. We truly relaxed on the boat ride out and back from the dock and would take this trip again, for sure!
Air Adventures Helicopter Tours | 3471 S. Roosevelt Boulevard, Key West
It was my first time on a helicopter and I absolutely loved it! Your trip starts at the tiny airport on Key West where you’ll hop onto a golf cart that takes you out onto the tarmac and the pilot (who was a woman!) will give you a brief rundown of things and then you’re off, up, up, up until you’re whirring over the most gorgeous turquoises and blues that you’ve ever seen. We went up for a thirty minute flight and in that time we saw at least a dozen nurse sharks and stingrays. We also had a really great view of Key West itself and after a couple of days exploring the place, it was fun to pick out things we’d seen on foot or bike. I have to admit that while I was nervous at first, once we got underway I completely forgot about my fears. The ride is smooth and felt very safe. Go for it!
Fury Water Adventures | 241 Front Street, Key West
We went parasailing with Fury Water Adventures one afternoon and enjoyed it more than we expected. It was the first time for one of us and the peace and quiet way up there floating over the blue-green water was so relaxing. The crew, JP and Chris, were hilarious and had us laughing the whole time. They’ll take photos for you while you’re in the air and you can purchase a memory card with a couple hundred of photos and a video when you get back to the dock. The whole ride only lasted about ten minutes but it actually felt longer than that (and we mean that in the best of ways.) Oh and if you’re feeling super adventurous, they’ll dip your legs into the water once or twice. Don’t miss this!
Ernest Hemingway Home and Museum | 907 Whitehead St. Key West
The Nobel Prize winner lived on Key West for about 10 years and his house is open for touring. The grounds themselves are quite lovely but the rooms inside are worth a look-see as well. The furniture and his belongings have been left as if they are expecting him to return at any moment. Oh and for you cat lovers, there are about 40-50 polydactyl (six-toed) felines on the property. When we visited, one was even lounging on the writer’s bed!
Distillery Tour at Hemingway Rum Co. | 201 Simonton St, Key West
We headed on over to the distillery right after touring Hemingway’s home and took a closer look at the man who has inspired this super-premium rum company. We learned about his passion for exploration on both land and sea and tasted both the blonde, dark and sherry finished rum which have been crafted to reflect his thirst for adventure. All three of them were a treat to try and something we’ll be drinking long after we’ve left the islands.
Danger Charters Wind and Wine Sunset Sail | 245 Front Street, Westin Marina, Key West
There wasn’t a single thing dangerous about this sail. It was so fun! We were treated to nine different delicious wines (they’ll keep it coming until you say stop!) as well some hors d’oeuvres. The crew provides a healthy dose of humor and does all of the work on the historic schooner, so you don’t need any prior sailing experience. You can literally sit back, enjoy the view and relax. The hardest decisions we made the entire evening while underway was red wine or white.
Southernmost Point | Whitehead St & South Street, Key West
One of the most Instagrammed places in Key West is the big concrete buoy that marks the southernmost point in the United States. There’s often a line of people waiting to have their photo taken there so if you want it all to yourself, be sure to get there early.
Drag Show at La Te Da | 1125 Duval Street, Key West
Christopher Peterson is the star of this show and we were so excited to see it. It was to be the highlight of our trip but a transformer blew about ten minutes in and the show was cancelled. Still, we saw enough to know that Christopher is a master of impersonations and that he is HILARIOUS. The entire show is live and he does all of the vocals himself. We were laughing from the minute he began and are eager to see him perform again as soon as possible.
The food at La Te Da was one of the best meals we had on our trip. We started by sharing an Island Passion Salad (mixed greens, goat cheese, mango, berries and toasted almonds tossed with passion fruit vinaigrette) that delighted our taste buds and then moved onto the main course: the catch of the day (grilled grouper with broccolini and rice) and baked crab cakes with tender lump crab meat served with a citrus beurre blanc and over orzo with basil cream and grilled asparagus.
Bagatelle | 115 Duval Street, Key West
If you have a thing for architecture and great food, hop on over to Bagatelle. The house was built in 1884 and has a wraparound balcony that overlooks Duval Street. Our server was really knowledgeable about the menu and steered us towards some great wine as well as entree choices (Caroline opted for the whole fish and I had the grilled lobster.) The vibe at our outside table was both romantic and lively. We could hear music and laughter from the bars below and yet somehow we were able to maintain an intimate bubble at our table. If you’re planning on going out after dinner, this is a very good place to start.
Hot Tin Roof | 0 Duval Street – Located at Ocean Key Resort & Spa, Key West
Al fresco dining, great food and incredible ocean views, what more could you ask for? If you want to add a little romance to your Key West Adventure, Hot Tin Roof will provide the perfect backdrop: candlelight, water views, attentive but not hovering servers and a great food and drink menu. Their menu is unique and offers small plates as well as entrees. We opted for seafood of course: the butter poached Florida lobster with grilled pineapple and chervil salad with star anise gastrique and the yellowtail snapper with jicama slaw and citrus romesco sauce.
Blue Heaven | 729 Thomas Street, Key West
After exploring the town on bikes for most of the morning, we set off in search of lunch and ended up at Blue Heaven. It wasn’t really by accident. A local, the same one who suggested we visit M.E.A.T, suggested that we visit this place. The food was on point (we had the black bean salad and the caesar with fresh snapper) the beer was cold and the atmosphere was fun – live music and chickens roaming around. If you’re looking for a quintessential Key West dining experience, you’d be well served to pick Blue Heaven.
DJ’s Clam Shack | 629 Duval Street, Key West
This place is a must-do. Located right in the thick of things on Duval Street, you can eat your food at a bar that literally hangs out over the sidewalk or in their back patio area. They don’t have a ton of options but what they do have is so well done that you won’t even wish they offered more. Caroline ate a Grilled Garlic Shrimp Roll and I had a Lobster Roll and both of them were literally conversation stopping and finger-licking good. We’re already trying to figure when and how we can get them again.
Cafe Marquesa | 600 Fleming St, Key West
It should come as no surprise that Cafe Marquesa has excellent food, especially since we’d already had a wonderful experience at the hotel. And because it is Zagat’s highest rated restaurant in Key West. However, it literally exceeded our already high expectations. We ordered the Pan Seared Grouper (blue crab, baby squash and leeks served over a tomato beurre blanc) and Pan Seared Scallops (Israeli couscous, citrus fume’, sundried tomatoes and asparagus. The dishes were not only beautiful in presentation but an absolute delight to enjoy. If you are looking for an incredibly delicious meal to remember your time in the Keys, we highly recommend you make a reservation at Cafe Marquesa.
The Florida Keys are very much open for businesses! Though Hurricane Irma did an incredible amount of damage, the locals have done an enormous amount of work to bring their homes and businesses back. Tourism is huge here and though almost everyone and everything has been impacted by storm, there is a spirit here that says “can do.” If you didn’t know there was a storm, you’d be forgiven because many of the places have made a full recovery and are as beautiful and beckoning as they ever were. There is no reason NOT to plan a trip here.
We have done a good bit of traveling over the past two years and this was hands-down one of our most favorite adventures. If you have a weekend, take it. We recommend at least a week, though. All of the businesses listed above are LGBTQ friendly and were, in our experience, more than welcoming to an affectionate lesbian, bi-racial couple.
Come to the Keys, as you are, and get ready to have a wonderful time. Who knows, maybe we’ll see you there – we’re already planning our return trip!
About the authors: Caroline and Erin are freelance web designers, photographers and writers for the travel blog Authentic Asheville. When they’re not on the road, they hang their hats in Asheville, North Carolina. Follow their adventures on Instagram at @e.mcgrady + @carolineperdue + @authenticasheville
