Every year millions of tourists visit the Florida Keys but head straight to Key West, which has become quite touristy with all of the cruise traffic. They keys actually encompasses 800 keys connected by 42 bridges stretching over 180 miles. For the last 20 years we have been getting away to our favorite key which is only 80 miles south of Downtown Miami, Islamorada.
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A brief history
In the 1800s the first settlers arrived in Islamorada and were known as Conchs. The Russells, Pinders and Parkers, pioneer families built the first buildings on the island, its first church, and grew limes and pineapples. In the 1900s Henry Flagler built the Oversees Railroad and connected Islamorada to Key Largo and onto the mainland. In the early 1930s Islamorada was named “the fishing capital of the world” when The Matacumbe Club was built and people start travelling exclusively to fish
The hurricane of 1935 destroyed every building on the island and ended the railroad connecting the keys. Soon after the hotel Casa Islamorado was built and renamed by new owners Islamorada Onley Inn. The first guest was President Harry S. Truman and dignitaries and celebrities followed. In the 1960s another hurricane destroyed the Inn and Cynthia Twitchell the heir of A&P Grocery bought the property and renamed it Cheeca Lodge (her nickname was Chee and her husband was named Carl so a combination of their names is Cheeca). Over the years the television show The American Sportsman broadcast from Cheeca Lodge and referred to Islamorada as “The Sports Fishing Capital of the World”. For10 years George H.W. Bush hosted “The George Bush Cheeca Lodge Bonefish Tournament” and famous celebrities like Paul Newman, Bing Crosby and Joanne Woodward vacationed on the property.
A weekend guide
You know you have arrived in Islamorada when you see a gigantic spiny lobster on the side of the road at The Rain Barrel Artist Village (86700 Overseas Hwy). Sculptor Richard Graze created “Betsy” in 1980 and it commemorates the Lobster Mini Season that takes place every year in July. Their tacky souvenir store is the perfect introduction to the keys.
Head South ten minutes to the Bass Pro Shop that is a one stop shop for sports enthusiasts (81576 Overseas Hwy). You can buy all the gear you need to go fishing or to go the beach. Inside climb into the “Pilar” wooden ship built in 1933 which is similar to Hemingways’s famous “Pilar” ship. Both were built in the same shipyard in Brooklyn and were docked in Key West for several years.
The Bayside Marina in the back is where you can rent boats, reserve eco tours or sunset tours or schedule a fly-fishing lesson. The Islamorada Food Company next door is great for a quick bite or a drink. They have an enclosed pool where you can see sharks and tarpons. Tarpons are protected by law from killing them without a kill tag and the ones in the keys are gigantic. Anglers come from all over the world to take a picture with their prize tarpon before they release it back into the water.
In September, this Colombian restaurant Pueblito Paisa Head south one minute and arrive at the Squared Grouper Bar and Grill for lunch. Known for its great food and drinks, order their grouper sandwich or their seared tuna and enjoy sitting on the deck with the beautiful view of the marina. In the back you can find the Safe Harbor Marina where you can choose from three charter boats that have easy access to the Yellow Shark Channel and the Gulf of Mexico.
Keep going south for five minutes and find Robbie’s on the right-hand side of the road. Don’t panic, this looks like a tourist trap, and you are not here for the food. Go to the pier and buy a bucket of fish and pay the entrance fee. Walk by the dozens of pelicans that will try to steal your fish and you will arrive at an area of raised nets on the pier. Choose a fish from your bucket and stick your hand into one of the holes in the net and wait. You will not believe the size of the tarpon that will jump up and grab your fish. This is so much fun to do with the whole family. Pelicans fly around you, people scream and yell in every language as the fish jump up and down.
Next head back north and stop at Lazy Days where you can sit on the beach, have a drink and look at an amazing view. If you were lucky fishing, they will cook your catch. The menu is old school, and you can get grouper and yellowtail prepared in ten different ways.
Up the road is the Florida Keys Brewing Company where you can get a 4 or 6 flight of beer and sit in their beer garden. There is a band most nights and you can walk from here to the stores on the old highway or visit pottery and art studios off the main road.
The third Thursday of the month is the Morada Bay Art Walk where residents, artists and chefs have booths selling art, food, and drinks. The galleries open from 6pm-9pm so you can visit artists’ studios and after take a tour of the brewery.
There are so many stores, restaurants, and bars that we love in Islamorada that we recommend staying a couple of days (below find a list with our recommendations).
Our favorite view of the sunset is from Pierre’s at Morada Bay. Go at 5pm when they open and order a drink at Pierre’s Lounge that has a beautiful mahogany bar decorated with furniture from Morocco and West Africa. But you are here for the view so head outside to the beach and grab a seat on their rattan sofas. You can eat at Pierre’s, but it can be pricey. We prefer heading next door to The Beach Cafe where you can sit on the sand and enjoy fun drinks with your fish tacos or ceviche. After sunset walk three blocks north to Lorelei where they always have fun music, and you will find a local crowd.
Our Recommendations:
Hotels
Cheeca Lodge & Spa
This family friendly resort has a beach, three pools (one adult), three restaurants, spa, tennis courts, a 3 par 9-hole golf course designed by Jack Nicklaus and the longest fishing pier in the keys. You can choose from beautifully tropically decorated 1- and 2-bedroom rooms with kitchens, rooms with tubs on the balcony, and individual casitas for larger groups. A private snorkeling tour or sunset tour can be arranged.
Enjoy breakfast with an ocean view at Atlantic Edge’s restaurant and drinks at sunset every night at their Tiki bar.
81801 Overseas Highway
Amara Cay Resort
This newer hotel is decorated in a modern coastal style. It has a beautiful new pool with loungers and hammocks on a beach with incredible views of the Alligator Reef Lighthouse in the distance.
Islander Resort
This resort just underwent a renovation and has great rooms that each have private outside terraces. There is a very large beach area with cabanas you can rent for the day. They also rent incredible floating cabanas equipped with center tables for your food and drinks for your party. Sandbar, sunset and snorkeling trips can be arranged.
82100 Overseas Highway
Breakfast
Bitton Bistro Café –This casual café owned by Michel Bitton has homemade French pastries, crepes and decent coffee.
Bobs Bunz– Known for its delicious cinnamon bunz and key lime cookies, this old café also has good eggs and pancakes for breakfast. The service is not great, so you are here for the greasy spoon ambience.
Café Moka – This is a small coffeshop that actually makes good coffee. Located in a cute courtyard off Village Square, this is a nice place to start your day.
Green Turtle Inn – Founded in 1947, this iconic restaurant is great at any time of the day. Guy Fieri featured their bacon wrapped Meatloaf on his show Diners, Drive-Ins and Dives. But we love their Corn Beef Hash, their Eggs Benedict with blue crab and spinach and their Bloody Marys.
Restaurants
Lazy Days- Order a table downstairs on the beach and enjoy one of the prettiest views in Islamorada. They will gladly cook anything you caught that day or order from their extensive menu. Choose from Oysters Rockefeller, Conch Ceviche or old school dishes like their Grouper St. Croix encrusted with breadcrumbs, black peppercorns and key lime butter.
Morada Bay – The Beach Café and Pierre’s Lounge
This is our favorite place in Islamorada. Get there at 5 pm when happy hour starts at Pierre’s Lounge. This beautiful bar has great drinks, but you are here for the view. Go out back where you can sit on rattan sofas on the sand and see the sunset. Later head next door to The Beach Café and enjoy the fish tacos with your favorite drink.
Kaiyo – It seems crazy to recommend a restaurant without a view, but Kaiyo Grill has fresh delicious sushi and sashimi and is loved by locals.
81701 Old Hwy
Chef Michaels – The chef’s motto is “Peace, Love and Hogfish” and Chef Michael has been cooking here for 20 years. This Florida Keys beloved restaurant also serves tilefish, triple tail, mutton snapper and even lionfish. You can choose from many sauces, but we recommend the Pontchartrain that comes with crawfish in a piquant Creole cream.
Square Grouper Bar and Grill
This fun restaurant has delicious food and excellent drinks. Ask for an outside table on the deck that overlooks a marina and order the Grouper Piccata with fried capers with key lime butter sauce or their Seared Sesame Encrusted Tuna with Asian Slaw.
80460 Overseas Hwy
Wahoo’s Bar and Grill
A great casual seafood grill with a beautiful ocean view. If you arrive by boat parking is free. Try their Firecracker Wahoo Nachos, House Smoked Fish Dip, and the Wahoo BLT Club.
Ziggie and Mad Dog’s
Once you cannot eat any more fish or seafood head here. They are known for their great steaks and pastas. You need a reservation.
Bars
Florida Keys Brewing Co.
Located in the Morada Way Arts and Cultural District, this tasting room is open to the public every day of the year. Take a tour of the brewery and then enjoy a flight of beer in the quaint beer garden.
Islamorada Brewery & Distillery
Choose from a flight of 4 or 6 beers and order some food from Spanky’s Kitchen, the food truck in the back. This fun bar is filled with locals and tourists that come for live music, rock n roll bingo or the fun trivia nights.
82229 Overseas Hwy
Lorelai
This old bar is the perfect place to see the sunset while listening to a local band. We do not recommend their food, but it is always a fun time.
82-mile marker
The Tiki Bar at Cheeca Lodge
A typical tiki bar with a gorgeous view. Perfect for a nightcap.
Shopping
Banyan Tree and Garden and Boutique
Head over to this beautiful boutique where you can buy a gift, shop for a dress, or learn how to design an orchid arrangement.
Drift- Islamorada Collective
One of the few stores that has modern, non-island apparel. They have artisanal jewelry and gifts for the home.
Ocean Gardens
This huge store is stocked with nautical gifts, coral sculptures, shells, home decor and jewelry. It is perfect to find souvenirs to take back home.
Village Square
Head to this garden setting and find two fun boutiques. Ms. Monroe Boutique has fun apparel and jewlery. Next door, Boo Kee Sue Botanics has handmade gifts and home decor: plants, macrame plant holders, baskets and rugs. Then head over to Cafe Moka and enjoy their garden setting.
MM 81.8 BaysideMM 81.8 Bayside
