Weekend Getaway to the Florida Keys

A string of islands at the base starting at the base of Miami-Dade County, the Florida Keys offer a tropical respite without having to leave the continental United States. Although Key West is the most well-known, don’t sleep on the other destinations before the southernmost point.

Key Largo

Where to Stay

Playa Largo Resort & Spa
Key Largo is underrated in my opinion. If you’re really looking to get away from Miami, the thought of going somewhere that’s less than an hour’s drive might not feel like a real vacation. But on the other hand, how nice is it that you can get away in around an hour? Playa Largo is a four-star resort with a pool and a man-made beach. Located on the west side of Key Largo, the sunsets here are outrageous. I didn’t stay here (sadly); I just stopped by for dinner at one of their restaurants, but the atmosphere was completely peaceful.

Where to Eat

Blackwater Siren
Blackwater Siren is a very funky, laid-back restaurant on Yacht Club Drive just off of Overseas Highway. It’s right on the water, so you can tie up your boat outside and go in for a bite to eat. As stated on their menu, the Harvey sandwich is somewhat of a Keys tradition with grilled mahi, lettuce, tomatoes and cheese with tartar sauce for dipping and a side of waffle fries. Or if you want something spicy, go for the Macho sandwich, which is basically the Harvey, but with blackened mahi and jalapeños.

Sol by the Sea
This is the aforementioned restaurant at Playa Largo Resort. Everything here is amazing: The food, the drinks, the sunset views. For starters, the spicy conch fritters with chipotle aioli and the tuna poke came highly recommended. For the entree I had the fish tacos, made with mahi mahi, pickled onions, coleslaw, jalapeños, mango and a rum crema all inside a corn tortilla. A light, yet delicious way to round out the day. To drink I started with the Island Spritzer, which is Sol by the Sea’s take on an Aperol Spritz. Sometimes I think that spritzes can be too bitter, but here it’s made with strawberry and lemongrass Grey Goose, Aperol, Prosecco, strawberry and sparkling water: Not bitter at all, but also not too sweet. To wash down the tacos and watch the sunset, I had a refreshing glass of rosé.

What to Do

Snorkeling at John Pennekamp Coral Reef State Park
Basically all the activities in Key Largo revolve around being on the water, which makes a day at John Pennekamp a one-stop-shop for all your watersports needs. Their main attraction is their snorkeling trips. A two and a half hour excursion, they take you to a reef that’s a 35 to 40-minute boat ride away. Once you’re there, they give you over an hour to snorkel around the reef, which sounds like a really long time, but it goes by in a flash when you’re captivated by all the marine life swimming around. I saw so many colorful fish, a stingray and THREE barracudas.

When you sign up, they’ll tell you to get their an hour to an hour and a half early, but you really only need to get their 30 minutes before the trip’s start time. There are also so many other things to do at John Pennekamp, like kayaking, paddleboarding and glass bottom boat tours.

Islamorada

Where to Stay

Cheeca Lodge & Spa
This four-star resort has so much to do, that you never have to leave the property if you don’t want to. There’s a beach, a pool, a spa, a fitness center, workout classes, six tennis courts and even a nine-hole golf course. Fishing is huge in the Florida Keys, so they have a long pier jutting out into the water and fishing poles to rent. This pier is also used for a number of the water sports available, like paddle boarding and jet skiing. Cheeca also offers snorkel trips, parasailing and sunset cruises.

There are a number of on-site dining options, like Mia Cucina and Nikai Sushi Bar & Restaurant (open for dinner only). There are also two tiki bars that serve food and, most importantly, cocktails. Atlantic’s Edge has indoor and outdoor dining. If you can, sit outside. Their patio has beautiful, unobstructed views of the water; it’s called Atlantic’s Edge for a reason.

I was at Cheeca Lodge for less than 24 hours, but I wish I had more time to lay by the pool and take advantage of all of the resort’s activities. I would definitely go back.

Where to Eat

Morada Bay
When I think of lunch in the Keys, I think of a casual cafe on the beach that serves cold drinks and fresh fish. And that is exactly what Morada Bay is. It’s not a trip to the Keys without having Key West shrimp, and their Thai Key West tacos don’t disappoint. Wash it down with a cold beer from a local brewery. For a more upscale experience, you can go right next door to Pierre’s.

Marker 88
Marker 88 is an Islamorada tradition. Located on one of the few natural beaches in the Florida Keys, this restaurant is famous for its sunsets. You’ll definitely want to get there early or make a reservation. If you don’t, you can sit at the bar and sip on their signature key lime pie martinis while you wait.

What to Do

Village Square at The Trading Post
The Village Square is quite literally a hidden gem. Right across the street from Cheeca Lodge and tucked behind the parking lot of The Trading Post grocery store is a miniature shopping center. There’s a boutique, craft store, restaurant and coffee shop packed into this quaint little village that can easily be missed if you’re zooming down Overseas Highway.

Robbie’s
There is a lot to do at Robbie’s. There is an open-air market where you can buy clothes, jewelry and other souvenirs. You can rent boats and jet skis, or dine at their restaurant. And humans aren’t the only species eating at Robbie’s. One of the main attractions here is feeding the tarpons. For just a few dollars, you’ll get a bucket of fish and access to the pier, where there are dozens of giant tarpons swarming. Either toss a fish into the water and watch the feeding frenzy, or hold one just above the surface and wait for a tarpon to jump up and eat it right out of your hand. Tarpons don’t have teeth by the way, so you won’t be risking losing a finger.

Florida Keys Brewing Company
If you didn’t try a local brew at Morada Bay, this is your chance. Florida Keys Brewing Company has an overwhelming amount of beers on tap, so I recommend getting a flight to sample as many as possible. And their beer garden offers a relaxing spot to drink them. The best part is that the brewery opens at 11 a.m. Hey, it’s five o’clock somewhere.

Key West

Where to Stay

Marquesa Hotel
The best word I can think of to describe the Marquesa Hotel is “quaint.” From the street, it looks like a regular home in the Key West Historic District. But once you pass through the “lobby,” you’ll find an expansive courtyard with two pools and rooms surrounding them. Walking distance from Duval Street, the Marquesa Hotel is in a prime location. They also recently finished an expansion project, the Marquesa 4-1-4, a 14-room addition less than a block away from the original Marquesa.

Where to Eat

Old Town Mexican Cafe
I’m basically always craving Mexican food, so when I found Old Town Mexican Cafe while walking down Duval Street, I had to check it out. Their portions are large, so you don’t need to order that much food. The nachos were my favorite, made with chips, a blend of cheeses, beans, guacamole, sour cream, jalapeños, veggies and the option to add ground beef or chorizo. Their tostadas are also very good and you can choose between bean, veggie, chicken, steak or shrimp. Obviously the star of the show was the margaritas. They have just about every flavor of margarita you can imagine, plus an entire menu dedicated to all the different types of tequila they serve.

La Crêperie French Café
Just off of Duval Street, La Crêperie French Café is a quiet spot with an excellent breakfast menu. I’ll never pass up an opportunity to have a Croque Madame (a Croque Monsieur with a sunny side up egg on top) and a café au lait. They also have croissants, omelettes, quiches and, like any good French restaurant, assorted cheese plates.

Willie T’s
Willie T’s is a classic Duval Street restaurant and bar. It serves casual American bar food and they have drink specials every night of the week. If you can’t decide what to drink, get a mojito – they have 30 different flavors. They also have live music literally all day every day from 11 a.m. to 1:30 a.m.

Southernmost Beach Cafe
The Southernmost Beach Cafe is part of the Southernmost Beach Resort, but it’s open to the public as well. Located right on the beach with waterfront views, it’s a great spot for a casual breakfast or lunch. They have a daily selection of fresh local fish, so their fish tacos are outstanding.

What to Do

Stroll Down Duval Street
This may be a no brainer, but sometimes we get so caught up with having a planned itinerary or a concrete destination that we don’t leave any time to just wander the streets and explore. There are so many things to do and see on Duval Street – like a woman with size J (or bigger) breast implants driving a golf cart. True story. It’s called Key Weird for a reason.

Go on a Sunset Cruise
Once you set sail in Key West, you’re surrounded by nothing but water. And with no land masses obstructing your views, it’s the ideal place to go on a sunset cruise. There is a seemingly endless amount of boat charter companies that offer sunset cruises, and I chose the Appledore Star. Docked in the Historic Seaport, the sailboat is the last Chesapeake Bugeye to have ever been built.

The one thing I look for when booking any kind of boat trip is an open bar – and the Appledore Star did not disappoint. They kept the drinks coming while pointing out notable Key West landmarks that we sailed past.

Take a Jet Ski Tour
Located inside of the Waldorf Astoria Casa Marina Resort is Barefoot Billy’s. Fortunately, you don’t have to be a guest of the resort to take advantage of all the water sports they offer, like a two-hour guided jet ski tour. If you don’t have your boater’s license, you’ll have to get there early to take a quick test that certifies you to operate a jet ski. The tour goes all around Key West, gliding over water so clear you can see to the bottom.

The best part, in my opinion, was the open ride portion where they set the boundaries and let you drive as fast as you want around it. After the open ride session, you slow things down as you pass through Cow Key, named after the large population of manatees – also known as sea cows. Barefoot Billy’s also offers boat charters, snorkel trips and kayak and paddle board rentals.

Dante’s Pool Bar
Not going to lie, I didn’t go to Dante’s during my most recent trip to Key West. If I were going to get Covid anywhere, it’d be Dante’s. But if you’re vaccinated, go for it. Dante’s is basically one giant pool party. Surrounding the massive pool are two tiki bars to keep the drinks flowing all day long. It honestly might be even more of party than Duval Street – at least during the day.

Southernmost Point
Going to the Southernmost Point is one of those touristy things that you just kind of have to do to say you did it. You can’t actually see Cuba, but at least you can cross being in the southernmost point of the United States off your bucket list.