The Best Spots for a Drink at Sunset in the Middle Keys

Is there any better way to end a day of driving the Florida Keys than watching a dreamy sunset over the Gulf of Mexico, margarita in hand? Here’s our guide to the top bars and eateries in the Middle Keys where you can do just that.

Sunset Grille & Raw Bar

Sunset Grille & Raw Bar is a restaurant that has become a local favorite for its extensive sushi menu, its seafood dishes, its daily 3-6pm happy hour, and its weekly “Sunday Funday” DJ sets. Its signature Tiki hut sits right beside the ocean, so you get front-row views of the brilliant purple and orange sunset. 

Morada Bay Beach Café and Bar

Along with its own uninterrupted sunset views, Morada Bay Beach Café and Bar serves up Frommer’s-approved Caribbean-American cuisine, beachy surf and kiteboard-themed decor, and a breezy indoor-outdoor layout. Its setting, Morada Bay, is frequently recommended as one of the prettiest beaches for those making their way down the Keys.

Marker 88

Marker 88 is a casual and laid-back steak and seafood joint in Islamorada that draws locals for lunch, dinner, and Sunday brunch, as well as sundowners. Along with being quite historic, having opened in the late 1960s, it holds the unique claim of occupying one of the Keys’ few natural beaches.

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The Lorelei Restaurant and Cabana Bar

The Lorelei Restaurant and Cabana Bar pairs its sunsets with entertainment by local bands, like The Stone Crabs and Webb, Webb, and Davidson. Its combination of gorgeous scenery with delicious seafood and funky mermaid-inspired art has led to praise from publications like Travel + Leisure, Florida Rambler, and The Star Tribune.

The Island Fish Co. Restaurant & Tiki Bar

Hit up the Island Fish Co. Restaurant & Tiki Bar, home to the longest tiki bar in the Keys, for the last sunset of your Keys adventure. There’s a mercantile shop at this tropical-themed eatery, so you can purchase a souvenir to help remember your special evening.

Check out these spots and more on your next Florida Keys getaway. If you need a place to stay, browse the tempting offers at Cheeca Lodge & Spa.

South for the Winter: The Best Time to Visit the Florida Keys

You probably know that the Florida Keys are a classic destination for “snowbirds” escaping the icy northern winter. But how much do you know about what a winter in the Keys is actually like? Here’s an overview of all that you can expect when visiting these enchanting islands in December, January, or February.

Perfect Weather

As the rest of the country cools down, the Florida Keys warm up: The average high is a balmy 76.1 degrees Fahrenheit in December, 74.8 degrees Fahrenheit in January, and 75.4 degrees Fahrenheit in February. The rainy season of early fall has also worn off by now (along with the attendant humidity), so the months between December and March bring minimal precipitation— an average of roughly two inches per month.

A Lively Atmosphere

It’s peak season in the Keys this time of year, and many of the eateries and dive bars that close up during the summer months roar back to life. Hit up spots such as the Tiki Bar at Holiday Isle or The Lorelei Restaurant and Cabana Bar for tasty seafood, refreshing tropical cocktails, and world-famous sunset views. The scene at shopping centers from the Rain Barrel Artisans Village to the Mallory Square also picks back up; it’s a perfect time to search for that perfect Key-lime-pie mix or a lovely ocean-inspired painting.

Exciting Events

The best time to visit the Keys is December, when lit-up boats sail over the Key West Bight and Harbor, Key West Old Town holds the “Holly Jolly Holiday” trolley, and Christmas shows, Nutcracker performances, and holiday concerts takes place. Other events throughout the winter, mainly down in Key West, run from the annual car show to the New Year’s conch drop to the January Literary Seminar and Food & Wine Festival.

Ready for a winter getaway? Browse the accommodations at Cheeca Lodge & Spa and start planning your trip.

Driving the Florida Keys: Everything You Need to Know

The Florida Keys are one of America’s most famous road trip destinations. Here’s what to know before you hop in your rental convertible and take on the 113-mile Overseas Highway for yourself.

Iconic eateries

You’ll be confronted with so many seafood restaurants that you won’t even want to finish making it to Key West. Hungry Tarpon, Wooden Spoon, Lazy Days Restaurant, and Mrs. Mac’s Kitchen are just a few spots known for the region’s delicious seafood, as well as hearty desserts. Fun, kitschy decor also characterizes many of these restaurants, like dollar bills, license plates, and surfing-related gear, so feast your eyes as you savor the signature conch fritters or Key-lime pie.

Iconic bars

Piña coladas and margaritas are as much a Florida Keys staple as the aforementioned seafood snacks. In the course of planning your itinerary, or simply drifting down the highway at your comfortable pace, prepare to encounter storied dive bars from Alabama Jack’s to No Name Pub (many with their own eye-catching decor). For a local beer in lieu of the requisite margarita or piña colada, try the Florida Keys Brewing Company, hosting tours and tastings.

Unexpected attractions

Prepare to see incredible attractions unlike anything you’ve seen elsewhere, like the massive Seven Mile Bridge, the Robbie’s Restaurant tarpon pier, the giant lobster sculpture at the Rain Barrel Artisan Village, and a hospital dedicated to rehabilitating rescued turtles. The History of Diving Museum is another one-of-a-kind spot, as the world’s largest collection of diving-related artifacts, like bell helmets and cameras for underwater photography.

Beautiful scenery

One of the best parts of a Keys road trip is the amazing scenery. As you make your way south, stop at Anne’s Beach, Bahia Honda State Park, and Morada Bay for soft sands and crystal-clear waters, and John Pennekamp State Park for boat rides around snorkeling spots with lush coral reefs. And don’t miss the world-famous sunsets, either: Grab a Gulf-facing seat at the Lorelei Restaurant and Cabana Bar or embark on one of the Keys Sunset Sails.

If you need a place to rest up during your Florida Keys road trip, check out the exclusive offers at Cheeca Lodge & Spa.

An Inside Look at Our Cheeca Lodge Restaurants

Exploring Islamorada and everything it has to offer will certainly make you work up an appetite, and there are plenty of tempting dining options here to satisfy your culinary cravings. Start off by sampling the exquisite dining options at Cheeca Lodge and Spa, where our first-class restaurants provide a lovely dining experience, no matter what you’re in the mood for.

Atlantic’s Edge

Open daily from 7 a.m. to 10 p.m., Atlantic’s Edge offers a modern, tropically inspired menu that includes fresh seafood, quality steaks, and organically grown produce. Enjoy the cool ocean breeze and panoramic views of the Atlantic Ocean as you dine on the patio, or embrace a more intimate setting inside the dining room.

Mia Cucina

You’ll be transported to Naples, Italy the moment you step foot into Mia Cucina. Open daily for dinner from 5 to 10 p.m., Mia Cucina serves up authentic Neapolitan pizzas and all your favorite Italian classics in a lively, family-friendly setting. We recommend the Margherita pizza, mushroom ravioli, and heirloom grape tomato caprese. Grab a table on the patio to enjoy your meal against the backdrop of a picturesque Islamorada sunset.

Nikai Sushi Bar & Restaurant

Recently updated with a new concept and menu, Nikai Sushi Bar & Restaurant serves the finest sushi around in bold and creative ways. This oceanside establishment offers handcrafted Japanese inspired dishes that blend the fresh ingredients and flavors of the Florida Keys. You’ll also find an extensive sake list, with over 35 different hot and cold varieties to sample. The restaurant is open daily from 5:30 to 10 p.m.

If you’re spending time in the Keys, discover the exquisite dining and luxurious atmosphere of Cheeca Lodge and Spa. Explore our oceanfront accommodations and unbeatable amenities on our website, and start planning your Islamorada visit.

Family-Friendly Summer Activities in Islamorada

The summer is in full swing, and family vacation season has arrived. If swaying palm trees, warm weather, and turquoise waters sounds like your idea of paradise, look no further than the Florida Keys. Cheeca Lodge and Spa, located in Islamorada, is ready to be your guide, offering a wide range of activities, oceanfront accommodations, luxurious amenities, and more. With so many activities to choose from, you’ll have no problem filling up your itinerary. Check out our favorites below.

Discover a New World

Disappear into the clear blue waters of the Florida Keys while snorkeling off the coast of Islamorada. Cheeca Lodge offers daily snorkeling trips, allowing visitors to take in the beauty of the ocean and discover the second largest living coral reef in the world. Get face to face with Florida’s colorful marine life, such as grouper, snapper, and maybe even a lobster. Our two-hour guided tour includes snorkeling gear, wetsuits, and non-alcoholic drinks.

Test Your Balance on the Water

Soak up the calming atmosphere of being out in the middle of the ocean by going on a paddleboarding excursion. Cheeca Lodge and Spa offers complimentary paddleboard rentals, making this activity even easier to enjoy. Test your balance while navigating through the warm waters off the coast, and glimpse the vibrant sea life below the surface.

Enjoy Maximum Oceanside Relaxation 

Set up camp for the day on Cheeca Lodge’s luxurious 1,100-foot private beach, where you’ll enjoy sun, sand, and warm waters. This is a great spot for the whole family, whether you’re relaxing under the palm trees, cooling off in the water, or playing games on the sand.

Discover Islamorada on Two Wheels

Explore the Keys by taking advantage of the complimentary beach cruiser rentals at Cheeca Lodge and Spa. Cruise around the town of Islamorada and see everything the area has to offer, all without spending a dime! The hotel offers bikes in a range of sizes for both children and adults.

Swim With Dolphins

Interact with friendly sea creatures, discover new worlds, enjoy personal shows, and learn about fascinating marine life at Theater of the Sea, in Islamorada. Swim with dolphins at this Florida Keys facility while learning interesting facts about these gentle creatures. Spend your morning observing the animals at the park, including dolphins, sea lions, parrots, reptiles, and various species of fish. Once you’ve finished exploring the park, relax next to the lagoon on the private beach and enjoy snorkeling, swimming, and sunbathing.

Fourth of July Beach Bash & Fireworks Extravaganza

If you’re headed to the Florida Keys to celebrate the Fourth of July, look no further than Islamorada to host your holiday plans. Located at the southern end of the Upper Keys, this stretch of five islands sums up everything the region is famous for, with colorful reefs, swaying palms, and a friendly, laid-back atmosphere. Of course, we all know that Independence Day is best celebrated with food, fireworks, friends, and family fun, and that’s exactly what you’ll find here on Fourth of July weekend.

Celebrate the cornerstone of the summer at Cheeca Lodge and Spa, located right in the middle of Upper Matacombe Key. This waterfront oasis puts on a spectacular Fourth of July party that’ll help you honor America’s birthday in style. From 6 to 9 p.m. on July 4th, the inviting property is offering all-you-can-eat food, entertainment, and a special fireworks extravaganza to close out the night. It’s a classic, all-American Fourth of July bash — on a tropical island. Tickets are available online and are open to Cheeca Lodge guests and the public.

This year, celebrate Independence Day island style, with friends, family, and gorgeous ocean views. To make the most out of your Fourth of July weekend, retreat to Cheeca Lodge and Spa to experience casual elegance in our luxury accommodations.

Vacation Wellness: Four Ways to Exercise Without Realizing It

Traveling isn’t just fun — it can be good for you, too. Getting away from it all is a great way to clear your mind and improve mental well-being. Believe it or not, travel can also be good for your physical health. Especially if you enjoy outdoor activities, you can get a great workout without even realizing it. Check out our top picks for vacation activities so fun, you won’t even realize you’re exercising.

Kayaking

If you’re coming to the Florida Keys — or any other beautiful destination with perfect weather and turquoise waters — then kayaking is an invigorating way to enjoy your surroundings. See marine life in its natural habitat, take in the sea breeze, and get a great workout while you’re at it. There’s something particularly soothing about paddling out far from shore and becoming one with the sea.

Swimming

If you enjoy being close to the water, why not just jump right in? Swimming is a great way to cool off, have fun, and stay fit. It’s also considered one of the best workouts, activating almost every muscle in your body. If you’re in Islamorada, head to Theater of the Sea, where you can swim with dolphins — how’s that for a unique workout?

Biking

Biking is known to be a great workout, but it’s also a great way to get around — making it the perfect vacation activity. Especially if you’re visiting a beautiful destination, you can take in the views as you enjoy the fresh air. You’ll also see more because you’ll be covering more ground.

Tennis

Finally, if you’re looking for a really good workout while on your travels, we recommend a round or two of tennis. Many hotels and resorts offer tennis facilities (Cheeca Lodge, for one), and it’s a great way to strengthen your heart, legs, arms, and core. And if you go somewhere tropical, you’ll get fresh air, sun, and some good exercise.

You can enjoy all these outdoor activities and more at Cheeca Lodge, in beautiful Islamorada. So what are you waiting for? Your mind and body will thank you. Visit our Wellness & Fitness page to learn more.