5 Reasons to Plan a Winter Escape to the Florida Keys

The cold winter months getting you down? Cheer yourself up with a getaway to Islamorada in the Florida Keys. Explore the best nearby sights and discover the local beauty as you take in the stunning landscape. Read on to see why winter is better on Islamorada and start planning an unforgettable Florida winter vacation at Cheeca Lodge.

Escape the Cold

Kiss the snow and chilling temperatures goodbye when you set off for our tropical paradise. We keep it warm year-round here in the Keys. Whether you want to head to our white sand beaches or cruise around the crystal-clear blue water, leave your coats at home and soak up some much-needed vitamin D.

Local Experiences

The Florida Keys offer visitors completely unique experiences you can’t find anywhere else. Just a few minutes from our doors, find the Theater of the Sea. Here you can swim with dolphins, sea lions, and sharks as well as meet alligators, sea turtles, and more. Next, thrill your inner adventurer and be an explorer for a day while you discover shipwrecks hidden below the surface.

Break Up the Long Winter Months

Each year, the winter months seem to drag on and on. With few holidays and unfavorable weather, the need for a getaway feels more necessary than ever. Make your escape to our island town and soak up the warm weather. The temperatures of the Keys never dip much below the mid-70s, so visitors can enjoy all that Islamorada has to offer during the winter.

Water Activities

Stay with us in Islamorada this winter and take to the sea where you can enjoy a variety of water activities. Unlike northern beaches, the water in the Keys stays warm all year. Embark on a day full of adventure where you can snorkel, parasail, jet ski, or scuba in the clear blue water. Or enjoy the water from above on a cruise around the scenic Florida Keys landscape.

Winter Sunsets

One of our favorite parts of winter in the Keys are the stunning sunsets. Trade cold gray skies for a vibrant kaleidoscope of color in Islamorada. Each evening around 6:30pm, head to the water and watch as the sky lights up with bright oranges, pinks, purples, and yellows. Snap some pictures and your Florida winter vacation is sure to be the envy of your Instagram feed.

4 Romantic Ideas for Valentine’s Day in the Florida Keys

Set the stage for an unforgettable Valentine’s Day in the heart of the Florida Keys. An intimate and inviting oasis, Islamorada offers visitors an escape from the hustle and bustle of every day. Whether you want to spend the day on the beach, get pampered at the spa, or dine out, delight in the romantic spirit of the Keys.

Couples Massage

Kick off your day of romance with a tranquil and rejuvenating couples’ massage. Soothe your senses and unwind next to your significant other in the comfort of the Spa at Cheeca Lodge. Couples can indulge in a variety of treatments including hot stone massages, body treatments, hydrotherapy, oceanside massages and more.

Beach Picnic

Spend the day under the sun with your loved one at one of Islamorada’s most pristine local beaches. Soak up some rays and feel refreshed in the salt and sand while enjoying a scenic beachside picnic. Quiet and intimate, some of our favorite nearby beaches include Anne’s Beach, Holiday Isle Beach, and Long Key State Park.

Sunset Cruise

What better way to spend your romantic Florida Keys vacation than out on the water? Set sail just before the sun sets – champagne in hand – to see vibrant tropical colors light up the sky as the sun goes down. Toast to the many happy years to come aboard our sunset cruises.

Romantic Dinner

A classic for a reason, nothing goes better with Valentine’s Day than a romantic candlelit dinner. Get the full Florida Keys experience when you sit down for an evening of tropically inspired cuisine at our flagship restaurant, Atlantic’s Edge. Afterwards, stop by our Tiki Bar for deliciously crafted cocktails and sweeping views of shimmering Atlantic Ocean.

The perfect setting for an unforgettably romantic Florida Keys vacation, plan your stay at Cheeca Lodge using our Valentine’s Day guide.

Follow the Shipwreck Trail and Dive Through World History

The Florida Keys are home to a variety of popular tourist attractions, including everything from beaches to bars. Lesser known to those visiting, the Florida Keys also house a number of shipwrecks, preserved underwater for years. Scattered along the coral reefs and buried in the sandy shallows a few miles off shore, a trail of nine shipwrecks make up Florida Keys National Marine Sanctuary’s Shipwreck Trail.

Explore the rich history of some of the most famous shipwrecks in Florida.

The San Pedro

Found off the coast of Indian Key, find The San Pedro below the surface. This ship was a part of the 1733 Spanish treasure fleet and was caught by a hurricane in the Straits of Florida. The damage was too much and the ship sank 18 feet into the water one mile south of Indian Key.

The Bentwood

On a voyage from Tampa, Florida to Norfolk, Virginia, the Bentwood sank between the French Reef and Dixie Shoals in 1942. The Bentwood was 360 feet long and sank after colliding with another ship. It is among the most popular shipwreck dives in the Keys.

The Thunderbolt

A military ship used during World War II, the Thunderbolt was intentionally sunk in 1986 as part of a project with the Florida Keys Artificial Reef Association. The Thunderbolt now offers divers a breathtaking experience, as it lies fully intact and upright, 120 feet below the surface. Divers can find the ship about four miles south of Marathon, Florida and Key Colony Beach.

Go on your own diving adventure during your stay with us in Islamorada. Get in touch with our team plan your visit and for tips on getting to the Shipwreck Trail.

Five Unusual Sculptures You Must Visit in the Florida Keys

Diverse and eclectic, the Florida Keys offer visitors a range of unique sightseeing opportunities. Explore the local art and cultural scene and discover an array of indoor and outdoor sculptures. From a larger-than-life replica of marine life to a haunted doll, light up your social feeds with images of these Florida Keys art classics.

Christ of the Abyss

Plunge into the mesmerizing depths off the coast of Key Largo and uncover a haunting underwater sculpture. Found just below the surface, the statue – Christ of the Abyss – is a 4,000-pound, 8.6-foot bronze statue of Christ installed at the Key Largo Dry Rocks in the Florida Keys National Marine Sanctuary.

巫迪文 / WIKIMEDIA COMMONS

Betsy Lobster

Made from fiberglass, Betsy is a 30 X 40 ft. biologically correct model of a Florida Spiny Lobster. She was created in 1980 by sculptor Richard Blaze to celebrate the species, which is native to the Florida Keys. Betsy is among South Florida’s most popular roadside attractions.

JOHN SMITH / FLICKR CREATIVE COMMONS

Florida Keys Sculpture Trail

A collection of innovative and inspired works of art, the Florida Keys Sculpture Trail features one-of-a-kind pieces flown in from the Art Students League of New York. Our favorite additions to the trail include Everything Between by Sarah Thompson Moore. This experimental sculpture is made of carbon and stainless steel and resembles both a cage and a shelter. Avis Gloria & Nature Eterna by Sheila Berger is another standout from the trail. This giant bird made of forged stainless-steel stands on a pedestal in Key West.

Robert the Doll

Sometimes referred to as “the world’s most terrifying doll,” the figure – which is believed to be haunted – is part of the collection of the Martello Gallery Key West Art and Historical Museum. It was the inspiration behind the popular horror film “Child’s Play” and continues to fright and delight visitors from around the globe.

Cayobo / Flickr Creative Commons

 

 

5 Ways to Spend Thanksgiving in the Florida Keys

Swap pumpkin pie for key lime pie and spend Thanksgiving in Key West. Check out our favorite holiday events, where to catch Turkey Day football, and the best foods to add to your Thanksgiving spread. Here’s how we do Thanksgiving in the Keys.

 

Watch Thanksgiving football.

Football has long been a Thanksgiving Day tradition, and Thanksgiving in Florida is no exception. Whether you’re a Gators or Dolphins fan, you’ll be in good company this season. Here are the spots around town where you can catch some Thanksgiving football action:

 

Try local Key West specialties.

Move over creamed corn, here are some vibrant and tasty dishes from Key West that are sure to shine on Turkey Day.

 

Key Lime Pie

Sweet and tangy key lime pie is an obvious choice. It’s basically a staple food group in Key West. While Thanksgiving is traditionally lauded as the holiday of pumpkin or apple pie, in Florida, November is key lime pie’s time to shine.

 

 

 

 

Seafood

Looking for a local alternative to traditional turkey and stuffing? Try Key West pink shrimp or spiny lobster a new take on the popular Thanksgiving dishes. While some might raise an eyebrow at the thought of ordering seafood instead of turkey, a fresh taste of the Florida Keys is sure to make for a Thanksgiving dinner that won’t soon be forgotten.

 

And of course, we can’t not mention the gorgeous weather we’re surrounded with. Where else can you spend Thanksgiving Day on the water? Here are some of our favorite day trips to work up to the big meal on Thanksgiving:

 

Hit the waves for stand up paddleboarding.

Explore the open seas by renting a paddleboard from our resort at no charge.

 

See inside Ernest Hemingway’s house.

Explore the historic Hemingway House, where the famous novelist, writer, and journalist lived in the 1930s. The designed U.S. National Historic Landmark is located just across from the Key West lighthouse at the southern end of the island.

Go kayaking at Indian Key.

One of the many islands off the coast of the Florida Keys, Indian Key is only accessible by kayak, which makes for a great workout on Thanksgiving Day!

 

It’s never too early: Plan ahead and lock in the best rate for your stay this Thanksgiving.

4 Instagram Worthy Spots in the Florida Keys

The Florida Keys are some of the most gorgeous islands in the continental United States. With stunning reefs, historic revolutionary outposts, and luscious beaches and landscapes, there’s no shortage of Insta-worthy places to snap your vacation pictures. Check out our favorite spots to kick your Instagram game up a notch.

Hemingway House

Nestled in the heart of Old town Key West is the home of lauded American author Ernest Hemingway. Refurbished as a museum (open daily), the Southern Gothic home is most famous as a dwelling space for more than 40 local cats.

Dry Tortuga

Right off Key West, Dry Tortugas National Park sits in the open water. Accessible only by boat or seaplane, Dry Tortuga is home to Fort Jefferson, the coastal military center built in 1825, from which you can take breathtaking pictures of the surrounding turquoise water.

The Southernmost Point in the Continental United States

Not many can say they’ve been to the very end of a country. Hundreds of tourists flock to the Southernmost Point to take a picture with the iconic buoy, indicating that you’re at the end of the line – just 90 miles from Cuba.

Anne’s Beach

And of course, our own backyard has some pretty beautiful vistas, too. Anne’s Beach, just a short walk from Cheeca Lodge, boasts pristine white sands and crystal-clear water.

 

3 Hidden Gems on Islamorada

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The quaint town of Islamorada is full of hidden gems worth checking out. Here are our top picks for fun activities, where to find trinkets, and the best places to explore.


Feed the Tarpon at Robbie’s Marina

The hottest restaurant in town…for fish! The Tarpon, a medium-sized fish native to the Atlantic, usually stops at Robbie’s Marina for breakfast, lunch, and dinner. Hordes of these fish linger near the marina for hours, knowing that tourists and locals alike are sure to feed them. A spectacle to behold, and well worth the $4 for a bucket of feeding fish, head here throughout the day for instant entertainment and fun.

Kayak to Indian Key

The Florida Keys are dotted with little green islands, separated from the mainland by translucent turquoise water. Most of the islands are reachable by boat, but the real adventurers hop in a kayak and paddle out to Indian Key, a historical site that’s part of the Florida State Park system. The shallow water between Islamorada and Indian Key is perfect for kayaking in an area where the island’s many hidden historical secrets and treasures allow you to explore the day away.

Morada Way Arts and Cultural District

Nestled on the small island of Islamorada is a vibrant and growing arts and culture scene. The Morada district is known for its galleries, studio spaces, boutiques, and creative restaurants, making it one of the most exciting neighborhoods in the Florida Keys. The art galleries combine lush island themes and the presence of the surrounding and engulfing Atlantic Ocean, giving way to some truly unique pieces that are adept at communicating stories of the American islands diaspora.