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.

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.

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.

Our Favorite Islamorada Watersports & Aquatic Activities

Islamorada is surrounded by bright, warm, inviting waters, so it’s no surprise that any stay here revolves around the sea. Of course, we recommend that you try all the inviting aquatic activities and exciting watersports on offer. Read on to learn about the most popular ways to enjoy those beautiful Gulf waters.

Scuba Diving

The Florida Reef is one of the largest in the world, averaging four miles across and stretching over 150 miles from end to end. As the only living coral barrier reef in the US, it’s definitely worth exploring, and a scuba-diving session is the best way to do it. Get face to face with colorful marine life and explore enchanting shipwrecks up close.

Snorkeling

If you don’t want to bother with all the scuba gear, snorkeling is a great alternative. Keep things light, with just a mask and fins, and enjoy a glimpse into the vibrant underwater world. You’ll still be able to explore the reef and many of its most popular sites.

Hobie Cat Sailing

Hobie Cats are small sailboats that are easy to learn and operate. The design features two plastic hulls with a trampoline-style deck stretched between them, making the boat unsinkable. Unlike a traditional sailboat, there’s no boom, meaning Hobie Cats are also safer for beginners.

Parasailing

Parasailing is an exhilarating — yet perfectly safe — way to take in your scenic surroundings. Enjoy spectacular views from about 500 feet above the water as a boat tows you around the island. You might even catch a glimpse of dolphins playing in the surf!

Sunset Cruise

If that sounds like a bit too much adrenaline for you, opt for a soothing sunset cruise. Islamorada is known for its gorgeous sunsets, and trust us — they look even better from the deck of a sailboat. Enjoy being one with the water and not having to worry about a thing, and toast a glass of wine as the sun dips behind the waves.

Jet Skiing

If you prefer to be in the driving seat, then rent a jet ski and cruise the waves on your own or with a tour group. Feel the sea breeze and the wind in your hair as you race across the water, and get an up-close look at Florida’s wildlife in its natural habitat.

So which exciting water sport or soothing aquatic activity suits your style? If you’re planning a visit to Islamorada, book a stay at Cheeca Lodge, which offers all the above on property. Check out the resort’s activity page for pricing and availability.

Four Must-Try Summer Activities in Key West

Summertime in the Florida Keys is perfect for a relaxing getaway, with beaches to lounge on and marine life to discover. However, there’s a lot more to Key West than just scuba diving and suntanning. From the island’s fascinating history to its quirky culture, no trip would be complete without experiencing everything this picturesque destination has to offer. Read on to learn about four of our favorite activities in Key West.

Fort Zachary Taylor

Built in 1898, Fort Zachary Taylor is one of Key West’s most impressive historical sites. And thanks to its location, next to one of the island’s most beautiful beaches, you’ll probably find yourself in the area during your stay. Tour the fort to learn about its role in the US Civil War and to see the country’s largest collection of Civil War cannons.

Ernest Hemingway Home and Museum

One look at the tropical paradise of Key West, and it’s easy to see how Ernest Hemingway fell in love with the island. One of America’s most celebrated authors, Hemingway lived here with his wife for over ten years. Tour his exquisite colonial-style home, built in 1851, and admire the spectacular collection of furniture, art, and antiques, all carefully restored and preserved.

Duval Street and Mallory Square

When you’ve had enough history, it’s time to experience Key West’s vibrant contemporary culture. All the action is centered around Duval Street, where you’ll find lively bars, fun souvenir shops, and lovely restaurants. Enjoy an afternoon stroll along the thoroughfare, and time your walk to reach Mallory Square by sunset. Each night brings the Key West Sunset Celebration, with performers, artists, and food vendors creating a festive, party atmosphere.

Key West Butterfly and Nature Conservatory

For animal lovers, there’s more to see here than just the marine life. Key West Butterfly and Nature Conservatory is a glass-enclosed sanctuary that houses over 50 butterfly species and over 20 exotic bird species. Admire these colorful creatures and find out more about them in the learning center.

If the sun, sand, and sea weren’t enough to tempt you, these can’t-miss activities might just convince you to choose Key West for your summer getaway. If you do, a stay at Cheeca Lodge will put you in prime position to enjoy the best of the island. Browse our latest offers and discover Key West for yourself.

Blooming Islamorada Fruit Trees at Cheeca Lodge

Retreat to our seaside haven in the Florida Keys and enjoy all the benefits our lush tropical climate has to offer. If you walk along the grounds of Cheeca Lodge, you’ll notice a number of flowering trees in bloom, with an abundance of fresh fruit on their branches. Our fruit-bearing plants are scattered around the property and produce a variety of fruits at different times of the year. These fruits are highlighted in our restaurant menus and cocktails, and are there for our guests to enjoy.

Our Cheeca Lodge Staff encourages you to enjoy the fresh fruit and pick a few pieces to take with you to eat. We’re happy to answer any questions you may have about the various varieties of fruit.

Our lush, colorful property features the following fruit-bearing plants:

  • Four varieties of mango
  • Loquat
  • Jackfruit 
  • Lychee 
  • Carambola (star fruit) 
  • Guava
  • Six-plus varieties of banana
  • Barbados cherries 
  • Mulberry
  • Red papaya
  • Two varieties of fig
  • Pineapple

Enjoy a fruit-filled getaway to Islamorada when you reserve your stay at Cheeca Lodge today.


Insider’s Guide to Islamorada

Nestled toward the top of the Florida Keys lies Islamorada, a sport-fishing hotspot with a lot to offer in and out of the water. Named “purple isle” by its first inhabitants, Islamorada is undeniably captivating. A narrow spit of land surrounded by turquoise waters teeming with marine life, this key embraces the harmony between man & nature. Let us be your guide to properly embrace the island lifestyle that Islamorada has to offer.

Where to Stay

Setting the standard for luxury amongst Islamorada hotels, Cheeca Lodge offers endless relaxation and embraces the laid-back lifestyle of the surrounding area. With 27 lush tropical acres, Tahitian-style lagoon and waterfall, private 1,100-foot palm-fringed beach, 525-foot classic wooden fishing pier, beachfront Tiki bar, two pools, a 9-hole golf course, and a full line of land-based and watersports, Cheeca Lodge and Spa is the dream destination for your Islamorada vacation.

What to Do

Located in the Sportfishing Capital of the World, Cheeca Lodge is a premier destination for serious anglers. Charter a boat and find over 500 species of fish within minutes from shore. A host of other activities can be found at our Islamorada luxury resort, including snorkeling, sea kayaking, bicycling, and scuba diving.

Where to Eat Known for its upscale dining in a laid-back island setting, Chef Michael’s is a hit among the locals of Islamorada. Try Chef Michael’s delectable hogfish or the signature catch of the day. Looking for a beachfront setting to enjoy your meal? The Morada Beach Café offers light Mediterranean fare featuring an island-inspired menu of seafood and craft cocktails. Or opt for the best sushi and Japanese cuisine that Islamorada has to offer at Nikai Sushi Bar & Restaurant.