Getting comfortable in our little South Florida Miami nook, we sometimes forget that magical escapes are just a few hours away. Whether you’re venturing north or south, our surrounding cities are a treasure trove of cultural gems waiting to be explored. Earlier this month, we took our Culture Crusaders crew down to Islamorada for a sun-filled weekend and we’re still feeling the good vibes.

Escaping the drink-heavy avenues of Key West, Islamorada is its slower, more charming sister. It’s the land of bougainvilleas and iguanas, where historical shacks are as breathtaking as the water views. Somehow Islamorada has managed to retain the slow pace of a sleepy beach town while still offering eclectic happenings within its small borders. This mix opens up the floor for friendly conversations, turning smiles into life stories within minutes.

Keep it Fresh.

When making your trip down south, taking US-1 might seem like the path of least resistance but it’s the other options that come with the best rest stop choices. Start your trip bright and early with a milkshake or fresh fruit smoothie from the one and only Robert Is Here fruit stand. A spot so famous all of Miami is glad to take a trip down to Homestead without a second thought.

Founded in 1959, the mini market, fruit stand, and miniature zoo is packed to the brim with local delicacies of every variety. You might even see Robert himself behind the counter, dishing out suggestions and personally cutting fruit for customers. Even if you’re just going to ‘gram the brilliant sunflowers, the family-owned and run spot is a perfect way to start your Islamorada adventure.

A Friendly Coffee Home.

Cutting up a drive to make time for fun stops is what we’re all about. So when you’re heading down south, make sure to hit up Cafe Moka while you’re passing through Tavernier. It’s a cozy coffee shop with a natural understanding of the important things in life: good food and a great atmosphere. The light-filled, charmingly wooden coffee house is everything you need from a neighborhood go-to. It all makes sense when you meet the friendly and passionate owners, Pierre-Marc and Alex Bellion. To them, “a coffee shop is a place where people live. It’s the heart of the community” and Cafe Moka hits that out of the park. Don’t snub the almond croissant or coffee flavorings, and make sure to get comfy because you’ll want to stay all day.

Stretching our legs, we took a turn around Florida Keys Brewing Co. where we were met with the wonderful owner, Cheryl McBay. The place is so beloved by locals, they just recently moved from their small bar in the brewery to a larger cottage complete with a beer garden out back. It might be new, but the homey charm we all know and love still remains. Tie dye, handmade bottle cap art, mermaids, and surf documentaries fill the walls while reggae sways softly in the background. The brewery hugs the Morada Way Arts and Culture District, home to Islamorada’s monthly bustling art walks.

What strikes us most about Florida Keys Brewing Co. is their dedication to local pride. Not only do many of their beers feature locally-sourced fruit, but the tap house has become a destination for local music and congregation. Tie dye parties, AfroRoots concerts, and iguana sightings are regular here. The Iguana Bait (honey hibiscus kolsch) is their most popular beer–just as light, sweet, and refreshing as McBay herself. Her husband, Craig is the mastermind behind their recipes, with a fleet of brewers working from 3:30am – 8pm every day. It takes a village to make something work, and these guys have it down. Be sure to skip over to Portside Gallery, their backdoor neighbors, and say hi to Valerie Perreault. Her tropical and witty linocut prints will make you smile, paired thoughtfully with the works of emerging local artists.

A Nice Stay With a Side of History.

We had the delicious pleasure of staying at Cheeca Lodge during our trip, a much-needed escape. Originally built as one of the very first inns in Islamorada, the lodge boasts the freedom of a resort without the loud crowds. Tucked away along the highway, a lush, tropical entrance seduces you onto the historical property. You’ll pass luxurious villas and a Jack Nicklaus-blessed golf course on your way to the main house to check in.

When awestruck at Cheeca, the first thing that comes to mind is: oasis. The water sport-friendly haven even comes equipped with a saltwater lagoon and the longest dock in the Keys. The Lodge is an adventure in itself, where stumbling upon a pioneer cemetery is the norm and jamming to live music under a tiki hut is a daily pleasure. It’s easy to get lost in the greenery at Cheeca Lodge, where palms, waterfalls, and tiki torches reign supreme. It replaces walkways with wooden bridges, bathroom wallpapers with ocean views, and one eatery with three options–all equally delicious. Follow the white sand trails around the resort, you might be surprised by what you find hidden around the bend.

Artists and Artisans are Welcome.

Although it was hard to leave the confines of our simultaneously quaint and luxurious hideaway, the town was calling. We took our adventures to The Village Square across the street, an oasis of bougainvilleas, curated boutiques, and mouth-watering Mexican fare. While swooning over the selection of succulents and housewares, we dug into Bad Boy Burrito and their juicy fish tacos and steak burritos. Mirroring the art-filled sanctuary is the Rain Barrel Artisan Village just down the way. It’s the kingdom of tchotchkes and handmade creations, where each maker has turned their own colorful cottage into their studio and store.

Perfectly encapsulating the Islamorada “vibe” is the bay front shack, Lorelei. Ask anyone who’s been to the key and this spot will be on all of their lists. It’s all you need from a fish shack, complete with twinkling tribute bands, a delightful sea breeze, smiles and cheap happy hour specials. We planned our trip around the Morada Bay full moon party, which is famous across the state. The low-key eatery boasts its own private beach where families and quiet travelers converge. Gather around a decadent fish fry and a breathtaking view of the water.

Peep the full photo album by FujiFilm Girl here.

The Breakdown:

Eats & Drinks:

Robert is Here – Strawberry banana or coconut milkshake, Tupelo Honey, and homemade guac.
Cafe Moka – Almond croissant, rose flavored lattes, and their (heated) nutella pastry.
Florida Keys Brewing Co. – The seasonal Belgian Tripel Tail for heavy, the Iguana Bait for light.
Bad Boy Burrito – The baja fish tacos, any of their burritos, and the chipotle red chili sauce.
Lorelei Restaurant and Cabana Bar – The coconut shrimp and the half-frozen, half-regular margarita: frotharita.

Sights & Stays:

Portside Gallery – Say hi to Valerie!
Morada Way Arts and Culture District
The Village Square – Pop into Miss Munroe’s for dreamy shopping.
Cheeca Lodge – Use the adult pool for a quiet swim, use the bougie bathtubs, and watch the dock light up at night.
The Rain Barrel Artisan Village – Sniff the hand-poured candles and peep at the trees.
Morada Bay – Indulge in the wings, the weekend fish fry, and their wild full moon parties.