Plan the Perfect Florida Keys Vacation

Discover a tropical paradise without ever leaving the United States: The islands of the Florida Keys are all situated within easy reach of the mainland. Home to some of the most picturesque beach towns in the world, the Keys offer a truly unique vacationing experience that rivals the Caribbean. Spanning a stretch of around 115 miles and connected by a series of impressive bridges, this vast archipelago is best explored via car over the course of several days.

After a brief period of rebuilding, the Keys are now officially up and running with all remnants of last year’s hurricane cleared away. There has never been a better time to immerse yourself in the breezy beach town mindset of these island communities. Use this guide for inspiration while you plan your visit.

First Stop: Key Largo

The most well-known of the northern Keys is Key Largo. Found just about an hour and a half outside of Miami, Key Largo is known for housing North America’s only barrier reef, which happens to be one of the largest in the world. Explore the breathtaking reef during your stay in Key Largo while snorkeling or scuba diving at the John Pennekamp Coral Reef State Park. Animal lovers will delight in the variety of marine life found in the reef.

Second Stop: Islamorada

Next on your journey down the Keys should be Islamorada. Found in the middle Keys, Islamorada offers a one-of-a-kind island experience enveloped in a distinct island vibe. From relaxing on the amazing and secluded beaches, feeding massive tarpons at Robbie’s Marina, or sampling the best local brews at the Florida Keys Brewing Co., there is something for adventure-seekers of all kinds.

With so much to do in Islamorada, you’re guaranteed to want to stay more than just one night. For a relaxing home in the Keys, Cheeca offers casually elegant accommodations and calming amenities right along the water. End the day watching an unforgettable sunset in Morada Bay, less than 10 minutes walking from Cheeca. For more information, or to book a stay at Cheeca, visit or call (866) 853-9338.


Next Up: Marathon

Continue your Florida Keys road trip, making sure to stop in Marathon Key. About an hour from Islamorada, Marathon offers its own special take on life in the Keys. One of the top attractions in Marathon is the famed Turtle Hospital, sure to be a heartwarming stop on your journey through the Keys. Marathon also offers visitors countless beaches to relax and explore, including the historic Pigeon Key.

Last Stop: Key West

After making it across the Seven Mile Bridge—the longest bridge in the Keys—you aren’t far from the farthest and final Key: Key West. Outdoor adventure, great eats, and beachside relaxation await visitors of Key West. Scuba dive 100 feet below the ocean’s surface while you explore the Vanderberg Shipwreck, the second largest in the world, or dine at a local classic, Banana Café, known for their sweet and savory crepes.

Whether you plan to visit for a couple days or want to explore the islands for a week or more, we recommend hopping in your car—or flying into MIA and picking up a rental—to uncover the best of the Keys.


The Animal Lover’s Guide to the Florida Keys

From red-shouldered hawks to six-toed cats, unique residents inhabit nearly every corner of the Florida Keys. It’s no surprise that this tropical archipelago is a favorite travel destination among animals lovers.

At Cheeca, in keeping with our commitment to eco-friendly tourism, we encourage our guests to seek out humane local organizations—such as wildlife rescues and rehabilitation centers—that allow visitors to appreciate the animals without disrupting their natural habitat. (Although, in the case of the Hemingway House cats, cuddles are encouraged.)

Learn more about our top picks for unforgettable Florida Keys animal experiences below.

The Turtle Hospital in Marathon

Located in Marathon, The Turtle Hospital first opened its doors in 1986 with a mission to “rescue, rehab, and release” injured sea turtles. This veterinary center offers guided, 90-minute educational tours that include a presentation on sea turtles, a behind-the-scenes look at the rehabilitation facilities, and an introduction to the permanent residents. Reservations are highly recommended.

Location: 2396 Overseas Highway, Marathon, Florida 33050

Florida Keys Wild Bird Rehabilitation Center

Open to the public 365 days a year, the Laura Quinn Wild Bird Sanctuary provides a humane, natural, and protected refuge to hindered birds. Permanent residents include Leopold the barred owl and Charlie the turkey vulture, among many others. Alongside the sanctuary, the Mission Wild Bird (MWB) center features three wings: administration, education, and an avian hospital.

Location: 92080 Overseas Highway, Tavernier, Florida 33070

National Key Deer Refuge

The 8,542-acre National Key Deer Refuge is most well-known as the home of the endangered Key Deer, unique to the lower Florida Keys and a subspecies of the White-tailed deer. However, the Key Deer share this refuge with a number of other endangered species, including the Barram’s hairstreak butterfly and the Lower Keys marsh rabbit. Stop by the Visitor Center in Big Pine Key for tips on where to observe the wildlife.

Location: 179 Key Deer Boulevard, Big Pine Key, Florida 33043

Ernest Hemingway Home and Museum

Travel a bit further south to Key West and get acquainted with the many polydactyl (six-toed) cats that reside at the Ernest Hemingway Home and Museum. The 40-50 cats that live on the property grounds are believed to be the descendants of Ernest Hemingway’s cat, Snow White. Following a tradition started by Hemingway, each of the beloved felines is named after a famous person.

Location: 907 Whitehead Street, Key West, Florida 33040

Ready to explore? Book your stay at Cheeca Lodge & Spa and check out these (and other) popular Florida Keys attractions.

Plan a Last-Minute Memorial Day Getaway

The official start of summer isn’t until June 21—but we all know the season really ramps up on Memorial Day. Observed on May 28, 2018, this federal holiday first and foremost honors the sacrifice of our fallen servicemen and women. It also caps off three days packed with celebration, relaxation, and ideally, lots of sunshine. If you’ve yet to make plans, don’t worry: Cheeca Lodge & Spa is the perfect choice for a last-minute Memorial Day getaway in the Keys.

Cheeca features an abundance of on-site services and amenities that make it easy for everyone to enjoy quintessential summer fun. From snorkeling and fishing to parasailing and guided Jet Ski tours, there are plenty of aquatic activities in store at our full-service watersports facility. Group tours, private excursions, equipment rentals, and lessons are available on a daily basis. We also offer land-based sporting facilities, including six tennis courts and a renewed 9-hole, par-3 golf course.

While we love staying active at Cheeca, we also recommend taking time to unwind and soak up our beautiful island surroundings. Welcome the season while lounging alongside one of our two heated swimming pools or the saltwater lagoon; elevate your holiday experience with a cabana reservation. Our robust wellness and fitness offerings are another way to indulge your senses over the three-day weekend. Wake up with an enlightening sunrise yoga session, or treat yourself to a Detox Algae Wrap at the spa.

Of course, the best part of a Memorial Day getaway at Cheeca is our luxury accommodations. At the end of the day, you can sink into the comfort of our spacious rooms and suites, which are equipped with premium amenities and feature a soothing island-inspired atmosphere. There’s really no better way embrace the unofficial start to summer than with Cheeca—check availability and plan your escape today.

Our Favorite Spring Events in the Florida Keys

From renowned fishing competitions to local music festivals, there’s always something special happening in the Florida Keys, and the springtime is no exception. During your stay in Islamorada, in addition to enjoying the many on-site events and activities at Cheeca Lodge & Spa, you can also check out some of our favorite nearby Florida Keys events.

37th Annual Seven Mile Bridge Run
April 14, 2018

The Seven Mile Bridge Run has attracted avid runners from Marathon, FL and beyond for nearly four decades. Capped at 1,500 participants, this annual run is sponsored by the Marathon Runners Club and is held across the longest bridge in the Florida Keys.

Location: Seven Mile Bridge, Florida

Islamorada Spring Classic
April 27-29, 2018

This Gulf-side team event sees anglers targeting a wide variety of local fish (think: tarpon, trout, snapper, and more). Awards are handed out for a variety of different achievements, from most releases to heaviest fish.

Location: Islamorada, Florida

The Key Largo Original Music Festival
May 17-20, 2018

Organized by the Upper Keys Merchant Association, this four-day festival features live and original performances across multiple stages, with appearances by songwriters and bands from around the country. Genres run the gamut from pop and rock to blues and jazz.

Location: 104450 Overseas Highway, Key Largo, Florida 33037

Loop Golden Fly Invitational Tarpon Tournament
May 20-23, 2018

This prestigious invitational is one of the oldest tarpon tournaments in the world. It is limited to just 28 anglers, and eligible tarpon must measure at least 48 inches in length to earn release points, or weigh at least 70 pounds for weight points.

Location: Islamorada, Florida

Battle in the Bay Dragon Boat Competition
June 2, 2018

Held at Sombrero Beach, this beloved Florida Keys event hosts both local corporate and community teams, as well as competitive and club teams. After the race, participants and spectators alike enjoy a lively celebration with awards, music, and refreshments.

Location: Marathon, Florida

Florida Keys Guitar Festival’s Guitar Summit
June 15-17, 2018

Featuring guitarists David Feder, Mateo, and Rolando Rojas, the third annual Guitar Summit will be held at venues in Key Largo, Marathon, and Key West. This showcase of virtuoso musicians will cover several different styles of music, including blues, jazz, flamenco, and classical.

Various Locations

Visit Cheeca in the spring and check out these popular Upper Keys events. Or, if you prefer to stay at the resort, take advantage of our unparalleled on-site activities.

Miami to Islamorada: A Weekend Road Trip

The drive from Miami to Islamorada clocks in at just around 90 minutes, making Cheeca Lodge & Spa an ideal destination for a quick and easy weekend road trip. However, we do recommend taking your time: While the luxury accommodations at Cheeca are bound to be the highlight of your trip, there are plenty of unique sights to see along the way.

Coral Castle

If roadside attractions pique your interest, be sure to check out the mysterious Coral Castle. Built by Edward Leedskalnin from 1923 to 1951, this unusual structure was sculpted from more than 1,000 tons of sedimentary rock. Sure, it’s not really a castle, and it’s not really made of coral, but it’s still an impressive accomplishment by Leedskalnin.

Location: 28655 S Dixie Highway, Homestead, FL 33033

Fruit and Spice Park

This kid-friendly botanical garden and park features over 500 varieties of fruit, vegetables, herbs, and spices. Founded by Mary Heinlein and funded in part by Preston B. Bird, this park offers guided tours every day at 11am, 1:30pm, and 3pm. As a visitor, you’re welcome to taste the fallen fruit along the way—as long as you can identify it.

Location: 24801 SW 187th Ave, Homestead, FL 33031

Knaus Berry Farm

Open seasonally November through mid-April, Knaus Berry Farm is a great spot to pick up a snack during your drive. Unsurprisingly, the berries are a hot item; however, this classic farm stand and homestyle bakery also offers a tempting selection of baked goods, ice cream, and other tasty treats.

Location: 15980 SW 248th Street, Homestead, FL 33031

John Pennenkamp Coral Reef State Park

Located in Key Largo, this Florida State Park and the adjacent Florida Keys National Marine Sanctuary include approximately 178 nautical square miles of coral reefs, seagrass beds, and mangrove swamps. Guided snorkeling and scuba tours are available, or you can discover the depths while taking a ride on a high-speed, glass-bottom catamaran.

Location: 102601 Overseas Highway, Key Largo, FL 33037

Mrs. Mac’s Kitchen

This local favorite in Key Largo is the perfect place to fill up on an expansive selection of classic American and fresh seafood dishes, including cheeseburgers, fried oysters, and more. Plus, if Knaus Berry Farm wasn’t enough to satisfy your sweet tooth, Mrs. Mac’s Famous Key Lime Pie ought to do the trick.

Location: 99336 Overseas Hwy, Key Largo, FL 33037

Spiegel Grove

In 2002, the USS Spiegel Grove Thomaston-class dock landing ship was intentionally sunk to create an artificial reef, six miles off the coast of Key Largo. Divers from around the world travel to this underwater destination for a unique experience—there’s something new to see every time at this massive, 510-foot-long shipwreck.

Location: Near Key Largo, FL

Ready for your road trip? Book your stay at Cheeca and discover these and other Florida Keys attractions before you arrive.

The Legend is Back: Cheeca Lodge & Spa to Reopen on March 30, 2018

Mark your calendars: It’s almost time to Live the Legend. Cheeca Lodge & Spa is set to reopen on March 30, 2018, and we can’t wait to welcome guests back to our iconic—and completely renovated—Florida Keys resort. Months of hard work by General Manager Bob LaCasse and the entire Cheeca team have resulted in a completely reimagined experience, albeit one that delivers the same thoughtful service that generations of visitors have grown to love.

Our resort has come a long way since September:

The upcoming March reopening will reveal a number of exciting property renovations, from a lobby redesign to refreshed meeting and event spaces. Guests are encouraged to check out our new bistro dining concept, Mia Cucina; renewed Jack Niklaus-designed golf course; upgraded water sports and fitness offerings; and more. In addition to our many facility enhancements, we’ll also be introducing new services and amenities that can be enjoyed throughout the resort.

Alongside these changes, and perhaps one of the more symbolic representations of our #KeysStrong spirit, our beloved 525-foot wooden fishing pier (the longest in the Florida Keys) will be completely rebuilt.

Feeling inspired? Fortunately, you can still book our limited-time reopening offer through March 7. This exclusive deal includes up to 20% off your stay in Islamorada, plus a credit to help you enjoy everything our updated resort has in store!

Whether you are a loyal guest or plan to visit Cheeca for the first time, we invite you to experience the best of the Florida Keys at our legendary resort.

The Top 5 Things to Do in Islamorada—in a Day

The tropical islands of the Florida Keys stretch for about 120 miles, offering limitless attractions and activities. And within this greater archipelago, the village of Islamorada features its fair share of things to see and do. It can all be a bit overwhelming. Fortunately, we’ve put together a suggested itinerary for enjoying some of the best things to do in Islamorada—in a single day.

Tip: Take advantage of the shuttle service provided by Cheeca Lodge & Spa, which provides transportation to attractions within a 2-mile radius.

8am – Breakfast at Atlantic’s Edge

Start your day of exploration with a fresh and satisfying breakfast spread from Cheeca’s flagship restaurant, Atlantic’s Edge. Take your pick from our Island Continental Buffet or choose from delicious hot dishes, such as buttermilk pancakes, three-egg omelets, and more.

10am – Tour the History of Diving Museum

After breakfast, you can head to the History of Diving Museum to learn about the evolution of deep sea exploration. Open daily from 10am to 5pm, this small-but-mighty museum offers a fun, hands-on educational experience, including both permanent and featured exhibitions. Don’t miss the helmet photo op in the Aquarium.

12pm – Visit Betsy the Lobster

Next, meet Betsy, a top contender for largest lobster in the world. Paying a visit to this eye-catching roadside attraction is one of the more unique things to do in Islamorada. As a representative of native wildlife, this massive spiny lobster is difficult to miss as she stands guard outside The Rain Barrel Artisan Village. Seeking souvenirs? Be sure to check out the village shops.

1pm – Lunch at Islamorada Shrimp Shack

Take a break from sightseeing and enjoy a casual lunch at Islamorada’s Shrimp Shack. This family-owned local hangout serves a menu of fried seafood staples alongside some more adventurous selections, like gator and conch.  

2pm – Feed the Tarpon at Robbie’s Marina

After lunch, drive down to Robbie’s Marina and marvel at a school of more than 100 tarpons that stop by the dock on a daily basis.These air-breathing silver giants are truly a sight to behold—plus, you can take it a step further and feed them. Admission to the dock is just $2, while a bucket of fish is $3.

4pm – Sample Beers at Florida Keys Brewing Company

Wind down the afternoon with a stop at the Florida Keys Brewing Company, known as the first Upper Keys microbrewery. Open daily, this quirky tasting room features local artwork and pours year-round and seasonal beers by the pint, flight, or growler. (Note: If you happen to be traveling with your four-legged friend, this dog-friendly brewery is a great option.)

6pm – Dinner at Nikai

At the end of the day, head back to Cheeca and enjoy dinner at Nikai, offering the freshest sushi in Islamorada right at the resort. Indulge in over 20 different rolls and sashimis, and over 35 different types of hot and cold sake to complement your meal. Plus, take in the breathtaking views of the ocean at night from the rooftop deck.

Of course, these are just a few of our favorite things to do in Islamorada. See them all, or chart your own course. Looking for more? Check out some of the resort activities offered at Cheeca, including golf and tennis.