Exploring the Overseas Highway in the Florida Keys

Mile Marker 106.6: Lake Surprise. According to the Florida Memory Blog, “[Lake Surprise] was unexpectedly encountered by the construction crews building Henry Flagler’s Florida East Coast Railway across Key Largo. The water had not appeared on preliminary surveys of the island, and it presented one of the earliest major obstacles for the project.”

Mile Marker 106.5: Buzzard’s Roost, Key Largo. A laid-back waterfront eatery, Buzzard’s Roost at Garden Cove Marina features a diverse menu, extensive wine selection, full-service bar, homemade desserts, Happy Hour specials, Sunday brunch and live entertainment most Friday and Saturday nights.

Mile Marker 106: Dagny Johnson Key Largo Hammock Botanical State Park, Key Largo. Home to 84 protected species of plants and animals, including the American crocodile, the park features one of the largest tracts of West Indian tropical hardwood hammock in the country. Wander through more than six miles of nature trails and view the native wildlife.

Mile Marker 104.1: Caribbean Club, Key Largo. First developed as a fishing club (AKA “poor man’s retreat”) by auto parts/real estate promotor Carl Graham Fisher in 1938, the Caribbean Club became famous in 1948 for purportedly being the filming site for the classic 1948 film noir Key Largo, which starred Humphrey Bogart, Lauren Bacall, Edward G. Robinson and Lionel Barrymore. (In fact, only a brief exterior shot from the movie was filmed in the Florida Keys.) In addition, the Caribbean Club has served as a filming site for the Netflix series, Bloodline. Today, the dog-friendly Caribbean Club features live music, happy hour specials and scenic waterfront sunset views. Note: the Caribbean Club is a cash-only bar with an onsite ATM.

Mile Marker 104: Jimmy Johnson’s Big Chill, Key Largo. Billed as “The Hottest Spot in the Keys to Cool Off,” Jimmy Johnson’s Big Chill is owned by the legendary former college/NFL football coach and current NFL football analyst. Enjoy spectacular sunset views from the waterfront deck at Jimmy Johnson’s Big Chill, which features live entertainment seven days a week.

Mile Marker 102.8: John Pennekamp Coral Reef State Park, Key Largo. Listed on the National Register of Historic Places, John Pennekamp Coral Reef State Park was established in 1963 as the first undersea park in the United States.

Mile Marker 101.7: Hobo’s Café, Key Largo. Enjoy award-winning burgers, chicken wings, fish sandwiches and barbecue at Hobo’s Café at this local favorite, an “authentic Keys eatery,” according to National Geographic.

Mile Marker 99.7: The African Queen, Holiday Inn Oceanside. View the iconic steamboat made famous in the classic 1951 movie, The African Queen, which was directed by John Huston and starred Humphrey Bogart and Katharine Hepburn. Docked adjacent to the Holiday Inn Key Largo, the African Queen is available for daily canal and dinner cruises.

Mile Marker 99.5: Bayside Grille & Sunset Bar, Key Largo. The home of “Keyribbean Kooking & Kocktails,” the open-air Bayside Grille features delicious seafood and pasta dishes, as well as the Bayside Sunset Bar with live entertainment Monday through Saturday. Bayside Grille boasts “the most photographed sunset in Key Largo!”

Mile Marker 99.4: Mrs. Mac’s Kitchen, Key Largo. “Eat Well, Laugh Often, Live Long.” Originally opened in 1976, the award-winning Mrs. Mac’s Kitchen is the longest running restaurant in Key Largo and offers “a classic FL Keys atmosphere.”

Mile Marker 95.2: Florida Keys National Marine Sanctuary, Key Largo. Encompassing the Florida Reef, the third-largest coral barrier reef in the world and home to more than 6,000 species of marine life, the Florida Keys National Marine Sanctuary was established in 1990.

Mile Marker 94.5: Snapper’s Restaurant, Key Largo. Opened in 1989, Snapper’s boasts a laid-back waterfront setting, fresh seafood on the menu, a bustling tiki bar, live music and tarpon feedings. What more could you possibly want from the Florida Keys?

Mile Marker 93.6: Florida Keys Wild Bird Center, Tavernier. The brainchild of Laura Quinn (AKA “Bird Lady”), the Florida Keys Wild Bird Center opened its doors in 1988 as a nonprofit rescue facility that nurses native and migratory birds back to health.

Mile Marker 92.6: Harry Harris Park, Tavernier. Although Harry Harris Park suffered major damage from Hurricane Irma in 2017, the park has partially reopened with access to the beach and tidal pool, playground, pavilions, BBQ grills and boat ramp.

Mile Marker 88: Marker 88 Restaurant, Islamorada. A Florida Keys tradition since 1967, Marker 88 serves fresh seafood, prime steaks and more “in an elegant Keys Casual setting on Florida Bay.”

Mile Marker 86.7: Rain Barrel Artisans’ Village, Islamorada. A series of artsy shops nestled in a tropical garden, the Rain Barrel features paintings, local sculptures, pottery and gifts. You can’t miss it – just look for the giant lobster out front!

Mile Marker 85.3: Hog Heaven Bar & Grill, Islamorada. Billed as the “Hottest Late Night Spot in the Upper Florida Keys,” this immensely popular oceanfront sports bar boasts 21 flat-screen TVs, along with indoor and outdoor dining, great barbecue and fresh seafood, live entertainment and DJ spinning tunes on weekends.

Mile Marker 85.3: Windley Key State Fossil Reef Geological Site, Windley Key. Once the site of a quarry used by Henry Flagler’s Florida East Coast Railroad to excavate fossilized coral to build the Overseas Railroad in the early 1900s, the Windley Key State Fossil Reef Geological Site features the Alison Fahrer Environmental Education Center, self-guided trails and picnic tables.

Mile Marker 84.5: Drop Anchor Resort & Marina, Islamorada. This is my favorite place to stay in the Upper Keys if I have an extra day heading down to Key West. The rooms are spacious and clean, and the outdoor pool and beach area are the perfect spots to relax and unwind.

Mile Marker 84.2: Theater of the Sea, Islamorada. Established in 1946, Theater of the Sea is one of the world’s oldest marine mammal facilities and home to dolphins, sea turtles, sea lions, sharks, stingrays, fish, birds, crocodiles and alligators. It was built on the site of a rock quarry used excavated for Henry Flagler’s Overseas Railroad in the early 1900s. Theater of the Sea offers a variety of animal interaction programs, including Swim with the Dolphin, Meet the Sea Lion, Swim with the Sharks and more.

Mile Marker 84.2: Postcard Inn Beach Resort & Marina, Islamorada. Today, the atmosphere is rather sedate, so it’s hard to believe that this is the original site of the bustling Holiday Isle Tiki Bar, home to plenty of drunken debauchery over the years. The nonstop partying era here is long gone, but guests of the Postcard Inn can enjoy a laid-back retreat, complete with a private beach.

Mile Marker 83.5: Wahoo’s Bar and Grill, Islamorada. The award-winning Wahoo’s Bar and Grill can be found “perched above the world-famous Whale Harbor Marina.” The menu at Wahoo’s features locally caught seafood such as Florida lobster, tuna, stone crabs, snapper, grouper and mahi-mahi. Enjoy scenic ocean views and happy hour specials Monday through Friday from 4 PM to 7 PM.

Mile Marker 83: Ziggie and Mad Dog’s, Islamorada. Housed in a legendary establishment originally known as Ziggie’s Conch, the restaurant was purchased in 2005 and renamed Ziggie and Mad Dog’s by late, great pro football player Jim “Mad Dog” Mandich (who played with the Miami Dolphins and was part of the “Perfect Season” in 1972). Today, Ziggie and Mad Dog’s is simply one of the finest steakhouses in South Florida.

Mile Marker 83: History of Diving Museum, Islamorada. “Immerse yourself in diving history.” First opened in 2000, the History of Diving Museum is home to “the world’s largest collection of diving helmets, hand-operated pumps, armored suits, lights and other accessory gear.” In addition, the History of Diving Museum displays photographs, memorabilia, books, film and video related to the storied tradition of diving Florida Keys and throughout the world.

Mile Marker 82.2: Sunset Inn Motel, Islamorada. Looking for basic, no-frills lodging in the heart of Islamorada? Consider the Sunset Inn Motel, perhaps the cheapest motel in the Upper Keys! If you’re expectations are low, you won’t mind the rustic appeal. The premises include an outdoor pool and sun deck.

Mile Marker 82.1: Florida Keys History & Discovery Center, Islamorada. Nestled within the Islander Resort, the Florida Keys History & Discovery Center provides a fascinating glimpse of the rich history of the Upper Keys. It is also home to the Jerry Wilkinson Research Library.

Mile Marker 82: Lorelei Restaurant & Cabana Bar. We always stop at Lorelei on the way down to Key West or on our way back home. Known as “The Pulse of Islamorada,” it’s a great place to dine outside and enjoy spectacular views of Florida Bay. Open daily for breakfast, lunch and dinner, Lorelei also features live entertainment. You can’t miss it – just look for the giant mermaid!

Mile Marker 82: Cheeca Lodge & Spa, Islamorada. Encompassing 27 tropically landscaped acres, the Cheeca Lodge & Spa is a true Islamorada landmark. The Cheeca Lodge became world famous when it frequently appeared on Curt Gowdy’s long-running outdoors TV show, American Sportsman (The Curt Gowdy Lounge was dedicated here in his honor in 1999). The Cheeca Lodge has hosted many famous guests over the years such as Ted Williams, Paul Newman, Bing Crosby, Jack Nicklaus and President George Herbert Walker Bush, who cofounded the “George Bush Cheeca Lodge Bonefish Tournament.”

Mile Marker 81.9: Hooked on Books, Islamorada. Looking for a wide selection of books related to Florida Keys history, as well as fiction by Florida Keys authors and Florida Keys guidebooks? Look no further than Hooked on Books! Without exception, I stop here every time I head to Key West and pick up some reading materials related to the Keys. Hooked on Books also stocks a wide variety of fiction and nonfiction titles unrelated to the Florida Keys.

Mile Marker 81.5: Hurricane Memorial, Islamorada. First dedicated on November 14, 1937, the Hurricane Memorial honors the hundreds of victims of the devastating 1935 “Labor Day Hurricane” that hit the Florida Keys. In 1995, the Hurricane Memorial was listed on the National Register of Historic Places. A crypt within the upper level of the Hurricane Memorial contains the cremated remains of some of the victims from the hurricane. A bronze plaque reads: “Dedicated to the Memory of the Civilians and the War Veterans Whose Lives Were Lost in the Hurricane of September Second 1935.” According to some observant critics, the sculptured palm trees on the Hurricane Memorial are bent the wrong way toward the storm!

Mile Marker 81.3: Green Turtle Inn, Islamorada. The brainchild of Sid and Roxie Siderious, the legendary Green Turtle Inn was established in 1947. Yes, believe it or not, the roadside eatery once actually served sea turtles on the menu as steaks and chowders. Today, the Green Turtle Inn serves up authentic Florida Keys cooking.

Mile Marker 81: Kon Tiki Resort, Islamorada. “Kick Back and Relax in Islamorada, Florida!” If you really want to escape from the hustle and bustle of modern life, check out the Kon Tiki Resort, which features “spacious, fully equipped villa accommodations in various sizes.” Guests enjoy a heated outdoor pool, private lagoon, boat ramp and dock.

Mile Marker 79.8: Lazy Days Restaurant, Islamorada. The award-winning Lazy Days Restaurant features “relaxing oceanfront dining” where you can enjoy “feasting on exquisite Keys style dishes.” A full bar is available.

Mile Marker 79.8: Bud N’ Mary’s Marina, Islamorada. An Islamorada landmark, Bud N’ Mary’s suffered significant damage during Hurricane Irma. However, the Marina has bounced back with totally rebuilt docks, as well as reopened accommodations, dive shop, outfitters store and deli.

Mile Marker 78.5: San Pedro Underwater Archaeological Preserve State Park, Islamorada. Listed on the National Register of Historic Places, the wreck of the San Pedro (part of the Spanish flotilla that sank in a hurricane in 1733) lies under 18 feet of water approximately 1.25 nautical miles south of Indian Key and is a popular site for scuba diving and snorkeling.

Mile Marker 77: Robbie’s Marina, Islamorada. Many tourists make a stop at Robbie’s Marina – home of the world-famous tarpon feeding! Robbie’s also offers watersports activities (I personally recommend renting kayaks to paddle to Indian Key), Hungry Tarpon Restaurant and local artist shops. Nursing a hangover? Just order the famous Trailer Trash Bloody Mary and you’ll be good to go!

Mile Marker 73.4: Anne’s Beach, Islamorada. Dedicated to local environmentalist Anne Eaton, Anne’s Beach is closed until further notice due to extensive damage from Hurricane Irma.

Mile Marker 70: Fiesta Key KOA & Marina, Long Key. The 28-acre, tropically landscaped Fiesta Key KOA features an onsite marina, restaurant, beach bar, pool, spa, and more.

Mile Marker 67.5: Long Key State Park, Layton. “Once Only for the Rich and Famous, Savor Natural Luxury Found Nowhere Else.” Built on the site of Henry Flagler’s Long Key Fishing Camp, Long Key State Park offers the perfect locale for swimming, kayaking, birdwatching, fishing, snorkeling, hiking and just relaxing on the beach. According to the official Long Key State Park website, all reservations are closed at Long Key State Park through December 31, 2019, due to campground reconstruction.

Mile Marker 61.1: Hawks Cay Resort, Duck Key. Billed as “the Florida Keys’ premier destination for outdoor fun,” Hawks Cay Resort offers spacious guestrooms and villas, along with recreational activities for all ages such as fishing, diving, kiteboarding, dolphin encounters and much more. The premises include a slew of restaurants, bars, marina, pools and lagoons, spa and fitness center.

Mile Marker 59: Dolphin Research Center, Grassy Key. Once the site of Santini’s Porpoise Training School (not kidding!), the Dolphin Research Center first opened in 1984 and has evolved into a world-renowned, state-of-the-art dolphin research facility. It is home to a family of bottlenose dolphins and California sea lions. Mitzi, star of the original Flipper movie in 1963, is buried here.

Mile Marker 56: Curry Hammock State Park, Marathon. “Uninhabited, Untouched and Unrivaled.” Encompassing 1,000 acres, Curry Hammock State Park is reportedly “the largest uninhabited parcel of land between Key Largo and Big Pine Key. It’s the perfect locale to launch a kayak or paddleboard and view all the wonders that make up the Florida Keys ecosystem. It also boasts a 28-site campground. Swimming, snorkeling, fishing and picnicking are other favorite activities here.

Mile Marker 53.4: The Island Fish Company Tiki Bar & Restaurant, Marathon. Don’t miss the opportunity to check out “the longest tiki bar in the Florida Keys” at The Island Fish Company, which offers fresh local seafood paired with your favorite frozen cocktails.

Mile Marker 53: Florida Keys Aquarium Encounters, Marathon. Immerse yourself in the wonders of the sea at Florida Keys Aquarium Encounters, where you can “spend the day observing the extraordinary behavior of our striking marine life.” Highlights of Florida Keys Aquarium Encounters include Coral Reef Tank, Predatory Reef Tank, Tarpon Basin, Tide Pool Touch Tank, Meet the Animals and more.

Mile Marker 51: Brutus Seafood Market & Eatery, Marathon. Seeking some of the freshest local seafood in the Florida Keys? Look no further than Brutus Seafood Market & Eatery, which features both indoor and outdoor tiki dining.

Mile Marker 50.5: Crane Point Museum & Nature Center, Marathon. The premises at the Crane Point Museum & Nature Center offer something for everyone such as wildlife viewing, Sunset Boardwalk, Hammock Loop trail, Butterfly Meadow, The Point, historic 1890’s Adderly House, The Lagoon and Orientation Hall, as well as kayak and paddleboard tours. Stop by the Crane Point Gift Shop for a souvenir of your visit.

Mile Marker 50: Sombrero Beach, Marathon. Portions of Sombrero Beach remain closed due to damages from Hurricane Irma, although the west end of the beach is now open. Sombrero Beach is the ideal spot for swimming and picnicking. Loggerhead turtles nest here between April and October.

Mile Marker 49.5: Cracked Conch Café, Marathon. First opened in 1980, the Cracked Conch Café is known for its breakfast served every day until 4 PM. The lunch and dinner menu features burgers, wings, ribs, salads and more.

Mile Marker 49: The Stuffed Pig, Marathon. A local landmark since 1984, The Stuffed Pig is a no-frills diner serving big portions of food at reasonable prices. What more can you ask for?

Mile Marker 48.5: The Turtle Hospital, Marathon. The state-of-the-art Turtle Hospital, which opened its doors in 1986, serves as a rehab facility for injured sea turtles, conducts and assists research aiding to sea turtles and educates the public through outreach programs.

Mile Marker 48: Burdines Waterfront Chiki Tiki Bar & Grille, Marathon. A hidden gem located at the end of 15th Street in Marathon, the open-air Chiki Tiki Bar & Grille features an upstairs hut with a thatched roof and “is known for its burgers, fried fish, fried key lime pie, as well as views of the sea, boats and Boot Key’s mangroves,” according to Travel + Leisure.

Mile Marker 47.5: Porky’s Bayside BBQ, Marathon. A casual waterside eatery, Porky’s sits on the site of the former Bill Thompson’s Villas and Marina, which hosted the likes of Ernest Hemingway and Elizabeth Taylor. The barbecue is simply amazing at Porky’s, which also serves breakfast daily and hosts live entertainment nightly.

Mile Marker 47.3: Sunset Grille & Raw Bar, Marathon. The Sunset Grille is nestled at the foot of the Seven Mile Bridge underneath a thatched tiki hut and worth a stop for its laid-back vibe, delicious cuisine, large oceanfront deck and live entertainment.

Mile Marker 47: Seven Mile Bridge. An engineering masterpiece completed in 1982, the Seven Mile Bridge is part of the Overseas Highway and serves as the longest bridge in the Florida Keys. As you drive along the Seven Mile Bridge, you will view segments of the old bridge.

Mile Marker 44.8: Pigeon Key. Home to eight buildings on the National Register of Historic Places that date from work camps for the Florida East Coast Railway, five-acre Pigeon Key lies adjacent to the Seven Mile Bridge near Marathon and can only be accessed by ferry boat. Guided historical tours are offered of Pigeon Key that can be arranged at the Pigeon Key Visitor’s Center/Gift Shop (Mile Marker 47.5).

Mile Marker 36.8: Bahia Honda State Park, Big Pine Key. One of the most scenic parks in the Florida state park system, Bahia Honda (Spanish for “deep bay”) suffered much damage from Hurricane Irma. Portion of the park are still not open to the public such as Sandspur Beach and the Sandspur Campground.

Mile Marker 30.5: No Name Pub, Big Pine Key. “A nice place if you can find it.” Well off the beaten path but worth finding, the No Name Pub was first opened in 1936 (it’s previous incarnations were reportedly a bait & tackle shop and brothel!). Thousands of dollar bills line the wall and ceilings of this legendary eatery, which is known for its pizza, as well as burgers, chicken wings, nachos, conch fritters and salads. The last time we visited over the summer, we noticed a tiny Key Deer milling around across the street. To get to the No Name Pub, take North Watson Boulevard

Mile Marker 30: Bucktooth Rooster, Big Pine Key. “Food Worth Crowing About!” A great place to stop for breakfast on the way to Key West (especially if you’re nursing a hangover!), the family-style Bucktooth Rooster serves five different types of Eggs Benedict, as well as pancakes, oatmeal, French toast, breakfast burritos and quesadillas, and more. The lunch and dinner menu includes burgers, sandwiches, seafood, pasta, steaks, salads and soups. Everything is made from scratch and prices are very reasonable!

Mile Marker 28.5: Kiki’s Sandbar Bar & Grille, Little Torch Key. A laid-back beachfront eatery, Kiki’s offers “pub grub & seafood favorites,” an outside patio, live music, nice selection of craft beers and wine, and boat dock.

Mile Marker 27.3: Looe Key Reef Resort, Dive Center & Tiki Bar, Ramrod Key. Enjoy access to the Looe Key National Marine Sanctuary at Looe Key Reef Resort, which offers a dive center, tiki bar and 24 guestrooms.

Mile Marker 27.5: Boondocks Grille & Drafthouse, Ramrod Key. Billed as the “Largest Tiki Bar in the Keys,” Boondocks Grille features “Southern Cooking Keys Style,” as well as an 18-hole mini golf course, pet-friendly outside patio and live entertainment.

Mile Marker 22.5: Square Grouper Bar & Grill, Cudjoe Key. “My Favorite Joint.” Open seasonally, the Square Grouper Bar & Grill features fresh local seafood, as well as steaks, pork, lamb shanks, duck breasts and more.

Mile Marker 20: Mangrove Mama’s, Sugarloaf Key. A legendary “tropical-themed seafood shack,” Mangrove Mama’s was destroyed by Hurricane Irma, but has since been rebuilt and reopened. It’s the perfect place to spot for a bite to eat and ice-cold beer as you head to or out from Key West. Save room for the award-winning Key Lime Pie.

Mile Marker 17.7: Sugarloaf Lodge & Tiki Bar, Sugarloaf Key. The family owned Sugarloaf Lodge is a Lower Keys landmark and features comfortable accommodations, an outdoor pool, a full-service marina, bait shop, fishing charters and kayak rentals. Stop by the Tiki Bar – the “best waterfront Tiki Bar in the Lower Keys” – for your favorite cocktail and enjoy live entertainment nightly along with scenic views.

Mile Marker 10: Geiger Key Marina, Geiger Key. “An old Florida fish camp … the way the Keys used to be.” Do you want a glimpse of the “authentic” Florida Keys where you can “hang with the locals”? Stop by the Geiger Key Marina and enjoy fresh seafood, an ice-cold beer and live music. There’s a popular RV campground here, too. It’s a great place to stop on your way into or out of Key West.

Mile Marker 5.1: Boyd’s Key West Campground, Stock Island. For “southernmost hospitality,” nothing beats a visit to Boyd’s Key West Campground! Years ago, we visited Boyd’s, pitched two adjacent tents and promptly headed to Duval Street to party during a torrential downpour with some serious winds. When we returned hours later, only one tent remained (the other had totally blow away!). So, we piled into one tent and endured a night of hell with a nonstop lightning storm. Great times! Seriously, if you plan to camp near Key West, Boyd’s, which first opened in 1963, is the perfect spot! The campground features a pool and tiki hut, boat ramp, picnic pavilion and laundry facilities.

Mile Marker 5.1: Hogfish Bar & Grill, Stock Island. Billed as “A Great Place if You Can Find It,” the Hogfish Bar & Grill is located on the shrimp docks (AKA Safe Harbor Marina) in Stock Island and known for its “One & Only World Famous ‘Killer’ Hogfish Sandwich.” It’s a true locals spot that offers delicious fresh seafood, a full bar, outdoor dining with scenic waterfront views and live music on weekends.

Mile Marker 4.6: Hurricane Hole Restaurant & Marina, Stock Island. Known to locals as simply “The Hole,” this laid-back eatery and bar offers “Relaxed Florida Keys Dining like you Remember.” Enjoy fresh seafood and scenic dockside views at Hurricane Hole, which features daily Happy Hour specials between 4 PM and 7 PM.

Mile Marker 0: Corner of Fleming & Whitehead Streets, Key West. Congratulations, you’ve reached the end of the road! Don’t miss the opportunity to by a total tourist and have your picture taken in front of the U.S. 1 Mile Marker Zero sign. Get there early or you’ll have to wait in line for your turn! Then drop by the nearby Green Parrot Bar and enjoy an ice-cold beer or your favorite cocktail. By the way, U.S. 1 stretches 2,369 miles from Key West to Fort Kent, Maine.

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