Aerial view of the Florida Keys.
Written By: McKenna Kelley | Art Director: Scott Tennant
From the way the ocean waves flow gently over Key Largo’s coral reefs to the way each day in Key West slowly counts down to another beautiful sunset, time just seems to move a little slower on these islands.
A trek to the Keys makes for the perfect road trip, or a great chance to put your boat through its paces, to uncover something new within state lines. In the following pages you’ll find four different approaches to seeing the Keys, all arranged by interests. No matter which way you go, you can’t go wrong.
The best-known Key is the cultural hub of the island chain. Each night, you’ll find artisans selling their goods at the Sunset Celebration at Mallory Square (400 Wall St., Key West). Follow up an assuredly gorgeous Florida sunset with a show at the 75-year-old Waterfront Playhouse (310 Wall St., Key West) or an indie film at the Tropic Cinema (416 Eaton St., Key West) down the street. During the day artists in residence display their work at The Studios of Key West (533 Eaton St., Key West), where you’ll find the colors of Key West captured on canvas during June’s “Mango Madness” exhibition.
Try an evening mixed with high-class sophistication and Key West tradition by pairing a South Florida Symphony Orchestra (Tennessee Williams Theatre, Florida Keys Community College, 5901 College Road, Key West) concert with a drink at Sloppy Joe’s (201 Duval St., Key West), one of Ernest Hemingway’s favorite haunts. Honor his memory with a rum- and grapefruit-based Papa Dobles or a Hemingway Mojito.
Summer is prime time for Key West’s cultural festivals. Through July 31, wander in the Key West Art Garden (Key West Tropical Forest & Botanical Garden, 5210 College Road, Key West), or join some of your favorite mystery writers and true crime experts at the fourth-annual Mystery Fest Key West (June 16-18, DoubleTree Resort Grand Key, 3900 S. Roosevelt Blvd., Key West), celebrating the best in “whodunit” literature.
Stay close to the cultural district at the Marquesa Hotel (600 Fleming St., Key West), a renovated “conch” house just a block from the famous Duval Street.
On your drive into the Keys, see a part of movie history on a cruise on the “African Queen” (99701 Overseas Highway, Key Largo). The boat has been restored since its use in the 1951 Humphrey Bogart-Katharine Hepburn film of the same name for in daily trips through the Port Largo Canals.
One of the Keys’ best-known art events is the Morada Way Third Thursday ArtWalk (151 Morada Way, Islamorada). In addition to selling art and jewelry, artists and musicians perform on three separate stages throughout the island’s art district on the third Thursday of each month. Stay for the weekend at The Moorings Village (123 Beach Road, Islamorada), which features 1,100 feet of private beach and 18 villas. TV fans, take note: the secluded resort’s Blue Charlotte house serves as a primary filming location for the Netflix series “Bloodline.”
Don’t pass through the first key without stopping for a slice of key lime pie from Mrs. Mac’s Kitchen (99336 Overseas Highway, Key Largo). The restaurant’s version of Florida’s official pie has garnered national attention for its ingredients, which, with the exception of the whipped cream, are completely homemade.
In Islamorada, Chef Michael’s (81761 Overseas Highway, Islamorada) lives up to its catchphrase, “peace, love and hogfish,” by serving up four preparations of the fish daily, while the rest of the menu changes depending on the day’s catches. Just up the road, Ziggie & Mad Dog’s (83000 Overseas Highway, Islamorada) is home to some of the Keys’ best steaks in a refurbished building that was once rumored to be a hot gambling spot for Al Capone’s associates.
Guests at Cheeca Lodge & Spa (81801 Overseas Highway, Islamorada) are just steps from the top-rated Atlantic’s Edge. After a round on the resort’s 9-hole golf course, stop in for a black Angus filet mignon, or bring in your fresh catch for the chef to prepare in one of three ways. Alternatively, grab a light bite and cold or hot sake at the resort’s Nikai Sushi Bar & Restaurant.
The island’s signature fruit will be feted with a key lime cocktail sip-and-stroll and pie sampling at the annual Key Lime Festival over July 4th weekend (July 1-4, Key West). After the festival, grab a meringue-topped slice at Blue Heaven (729 Thomas St., Key West), a seemingly run-down shack that has become a dining destination on the island, and break up the sugar buzz with a gloriously overstuffed lobster roll at D.J.’s Clam Shack (629 Duval St., Key West).
Plenty of Key West restaurants offer waterfront dining, but few do so as romantically as Latitudes at the Sunset Key Cottages (245 Front St., Key West). The emphasis is on fresh seafood and an extensive wine list, but resort guests can also enjoy a complimentary rum tasting each afternoon.
Two other waterfront Key West resorts are home to must-visit restaurants. One Duval at the Pier House Resort & Spa (1 Duval St., Key West) makes use of local yellowtail, crab and spiny lobster, while Hot Tin Roof at the Ocean Key Resort & Spa (0 Duval St., Key West) pours craft cocktails with names like “The Glass Menagerie” and “The Rose Tattoo,” inspired by the work of Key West resident Tennessee Williams.
John Pennekamp Coral Reef State Park (102601 Overseas Highway, Key Largo) was the first underwater state park in the U.S. and is still one of the most visited. The park is three miles wide and 25 miles long and supports a living coral reef and hundreds of marine animals. Choose from scuba diving, snorkeling or taking a glass-bottomed boat tour to experience the reef’s ecosystem.
See where workers who helped build the Old Seven-Mile Bridge – formerly a portion of Henry Flager’s railroad – once lived on Pigeon Key (Mile Marker 45, Overseas Highway). Daily historical tours guide visitors to some of the island’s remaining homes as well as the still-standing piece of the bridge.
Cross the modern Seven-Mile Bridge into Big Pine Key for a bite at the No Name Pub (102601 Overseas Highway, Big Pine Key). The building originally opened as a general store in 1931, turned into a partial brothel in the ‘40s, then became solely a pub in the ‘50s. To get a taste of a time without constant connectivity, stay at the Little Palm Island Resort (28500 Overseas Highway), located on a private island just off the nearby Little Torch Key.
Most of this key’s historic sites are centrally located in Key West’s Old Town. The Audubon House and Tropical Gardens (205 Whitehead St., Key West), built in the American Classic Revival style, is a great representation of the efforts to preserve Key West’s oldest architecture. The home was built by the wealthy Captain John Huling Geiger, and, with its lush palms and orchids, is now a popular wedding venue.
Across the street, The Custom House (281 Front St., Key West) was once used as both the customs office for the port and as a naval office but it is now a museum that preserves Key West’s maritime history. Learn more about this history at the Lighthouse Tower (938 Whitehead St., Key West).
The shadow of author Ernest Hemingway looms large in Key West, and nowhere more so than at Casa Antigua (314 Simonton St., Key West) – where he completed “A Farewell to Arms” in 1929 – and the Hemingway Home & Museum (907 Whitehead St., Key West). Each summer, Key West visitors and residents celebrate the legend with Hemingway Days (July 18-23), a festival that includes a fishing tournament, readings and a look-alike contest. Stay nearby at The Artist House (534 Eaton St., Key West) or Island City House Hotel (411 William St., Key West), two of the oldest homes-turned-hotels in the city.
You’ve found the mecca of sport fishing. Islamorada is known as the sport fishing capital of the world, and summer brings no shortage of tournaments for amateurs and professionals alike. Compete for cash and prizes in teams of three during the Islamorada Fly Dolphin Tournament (July 10-12), or take the family out to catch snapper, tuna, trout and more for the Islamorada Summer Classic (July 7-9, World Wide Sportsman, 114 Palm Ave., Islamorada).
To go at your own pace, choose from offshore fishing, backcountry fishing or flats fishing and let one of the many captains with charters at Bud n’ Mary’s Marina (79851 Overseas Highway, Islamorada) guide you on your trip. On any of the charters, the captain will provide bait, tackle, a cooler and expertise – just let your captain know if you have any special requests for locations or fish you’d like to catch at least 24 hours in advance.
Stay just down the street at the Amara Cay Resort (80001 Overseas Highway, Islamorada) and take the complimentary Mercedes shuttle to the marina or Lazy Days Oceanfront Restaurant (79867 Overseas Highway, Islamorada) to have your fresh catch prepared for dinner.
Part of Pennekamp National Park, Molasses Reef is one of the most visited dive spots in the U.S. thanks to its gorgeous, complex coral reef system and plentiful caves and ledges. Nearby you’ll find Spiegel Grove (six miles off Key Largo, advanced divers only), a wrecked Navy ship that was sunk to allow a new reef to grow.
Guests at the Key Largo Bay Marriott Beach Resort (103800 Overseas Highway, Key Largo) can pick up all their diving and snorkeling gear at the on-site dive shop. After your dive, refuel with fresh mahi-mahi prepared matecumbe-style at The Fish House (102401 Overseas Highway, Key Largo), one of Key Largo’s most popular holes-in-the-wall since it opened in 1982.
Fishing novices of all ages are eligible to enter the Key West Fishing Tournament (March through November). Anglers must simply catch a designated fish in front of a witness, have it weighed at an official weigh station and enter the fish on an entry form. The weigh station at Sunset Marina (5555 Jr. College Road, Key West) is the closest to the private beach and spacious two-bedroom, two-bathroom residences at the waterfront Hyatt Residence Club Key West Beach House (5051 Overseas Highway, Key West).