Known for its laid back atmosphere and its colorful cottages, Key West is an extremely unique tropical island city. Being able to experience a taste of Caribbean culture without having to leave the United States has guests flocking to The Keys with anticipation for the azure waters, exotic greenery and historical landmarks.
On your next visit to “Conch Republic,” roam about the island like a local and grab a drink, shop and eat on Duval Street (don’t forget to stop by Margaritaville for that Cheeseburger in Paradise!)
In addition to amazing island fare, Key West is notorious for the number of historical sites to visit: Harry S. Truman’s Little White House, The Ernest Hemingway Home and Museum and the Curry Mansion Inn, to name a few.
Make sure to take a trip to the end of US Route 1 at Mile Marker 0 while you’re exploring. US 1 is known locally as the Overseas Highway (2,369 mile interstate that connects most major cities in the U.S.) and stretches from Maine to Key West. This marker, along with the Southernmost Point in the US cement buoy, is perfect for photo ops to commemorate your visit to Key West.
The Florida Keys, that gentle arc of coral rock stretching from Biscayne Bay to the Dry Tortugas, are well known as the jumping-off point for diving and snorkeling the world's third-largest barrier reef and for providing some of the best sport fishing around. Lazing at anchor in the sultry tropical climate after some serious play rounds out most days on the water. What most boaters don't know about the Keys is their fascinating history, especially the chapter about the man who helped shape Miami and Key West --- the two cities that bookend the Keys --- by connecting them with a railroad.
The first European to see Biscayne Bay and sail through the Keys was probably Juan Ponce de Leon during his voyage of discovery in 1513. He named the Keys los Martires, or the Martyrs, because from a distance the islands looked like suffering men to him. The name we use for the archipelago today is derived from a corrupted version of the Spanish word cayo, for small island.It took another 399 years for a Gilded Age entrepreneur to link Key West with Miami via a mode of transportation other than boat. The man was Henry Morrison Flagler, and his dream, the Overseas Railway, became known as the Eighth Wonder of the World when it was finished in 1912.
The history of Florida is chocka-block with interesting characters seeking to make their marks while eveloping the Sunshine State, but no single person had more of an impact than Flagler. He was 55 years old when he first turned his attention to Florida, and by that time he and his partner, John D. Rockefeller, had monopolized the U.S. oil industry through their ownership of Standard Oil Trust.
Flagler wanted to turn the east coast of Florida into, as he put it, an American Riviera and proceeded to build hotels, bridges and a railroad to connect his resort empire, which stretched from St. Augustine to Palm Beach. When he completed a development spurt in 1894, his Florida East Coast Railway's southern terminus was in West Palm Beach. He considered the grand project finished, and he was satisfied. But Julia Tuttle was not.
Tuttle was a citrus farmer and businesswoman who in 1891 had purchased a large patch of land on Biscayne Bay. She planned to use the property to develop a new city. She quickly realized that in order for this to be feasible, the city would need reliable transportation --- and in those days, that meant the railroad. She tirelessly lobbied Flagler to extend his railroad south but to no avail. Then the freezes of 1894 and 1895 hit, wiping out the orange groves in northern and central Florida and many fortunes as well.
The story goes that Tuttle sent Flagler a basket of flowers and oranges to show him that the freezes had spared the southern part of the state. Flagler agreed to extend the Florida East Coast Railway south if Tuttle would give him some land where he could build a hotel and railway station. On February 15, 1896 construction began on the hotel, and the first train arrived at the new station on April 26. Just three months after railroad service began, the new city was incorporated. It was named Miami.
While the city of Miami was just beginning its perennial cycle of real estate boom and bust, Key West was already established as the most populous and prosperous city in Florida. By the mid-1800s the wrecking industry the salvage of ships wrecked on the key's coral reefs --- brought a tremendous amount of wealth into the city. After the Civil War, when the wrecking industry declined, Cuban cigar manufacturers began setting up flourishing businesses in Key West. By 1898, the battleship Maine had its homeport in Key West's deep-water harbor, and it was from Key West that the Maine departed for Havana, where the ship's fateful explosion would trigger the Spanish-American War.
In 1905, President Theodore Roosevelt announced his intention to build the Panama Canal. Flagler realized that Key West would be the closest deep-water port to the canal and that the port could open up trade with ships coming in from the Pacific Coast, Latin America and Cuba. To benefit from this trade, Flagler would need a means for transporting goods from Key West to Miami. From there, the goods could continue up the East Coast. He decided that the best move would be to extend the Florida East Coast Railway. He would call it the Overseas Railroad.
Construction of the Key West Extension was an astounding feat of engineering. One hundred and 56 miles of track were laid to connect the mainland to Key West, with causeways and bridges spanning the water and marshlands across the 31 little islands along the way. The railroad was financed without government funding and remains the most ambitious engineering project ever undertaken by a private citizen. Completed in 1912 after seven years of work --- and at a cost of $50 million and the loss of hundreds of workmen's lives the Overseas Railroad was never as profitable as Flagler envisioned.
Flagler died at age 83, a year after the Key West Extension was completed, as a result of a fall down the marble stairs at his Palm Beach mansion. The Overseas Railroad met an untimely death too, in 1935. A Labor Day hurricane with a 17-foot storm surge washed away many miles of railbed, a locomotive and train and killed more than 400 people. Cruising from Miami to Key West, you'll see many of the original railway bridges now used as fishing piers and leisure walkways. And once you arrive in Key West, your inner historian will find plenty more to be delighted about. A vast number of Victorian homes have been impeccably restored, and museums and landmarks dedicated to wreckers, painters, poets and playwrights abound. Even in the city's lively contemporary scene, there are many reminders of the riches that drove Henry Flagler to build his railroad.
Sunny by day, glittering by night, Florida is irresistible. The 1,350-mile coastline is the longest of any state in the mainland United States, and its unique heritage has had countless influences, with Native American, European, Latino, and African-American cultures among them. From the graceful charm of Fernandina Beach to the casual sassiness of Key West, Florida offers miles of diversity and many facilities for large yachts. In 2016, the regional marine impact for Broward, Palm Beach and Dade counties was $11.5 billion. There are more than 8,000 vessels in the world that are 80-plus feet, and 40 percent of them call Florida's East Coast their homeport.
This quaint Victorian village is located on enchanting Amelia Island, which over the years has been inhabited by pirates, bootleggers, shrimpers and Gilded Age millionaires. As power continually changed hands, Amelia Island wound up flying the flags of eight different nations, giving today's Isle of Eight Flags Shrimp Festival (May 5-7) its name.
Notable among the 50 blocks of eclectic shops, restaurants and galleries are Books Plus, a used and new shop rich in Amelia Island stories, and Trailer Park Collectibles, which houses primitive antiques and secondhand treasures. Grab a bite at Mustard Seed Cafe & Juice Bar, or dine on French cuisine by candlelight at Le Clos, nestled in a 1906 cottage. Ever-lively Alley Cat Seafood is a beer house, wine boutique and piano bar.
Fernandina Harbor Marina, in the heart of downtown, has a 25-foot dock depth and accommodates vessels up to 250 feet.
Cobblestone streets, centuries-old buildings, hidden courtyards and alluring cafes help define this historic district of Saint Augustine -- the oldest continuously occupied town in the U.S.
Jump aboard the Old Town Trolley Tours to explore the major attractions, including a highly rated wildlife reserve. Shoppers head for the markets, both farmers and flea. The Starving Artist consignment boutique is a great place to discover the work of local artists. Foodies can choose from more than 400 eateries, including Crave Food Truck, popular for its healthy, creative offerings, and then head to Stogies Jazz Club for a night cap, some live music and, if the mood strikes, a cigar. As if all this activity weren't enough, the 43 miles of fine, golden sand beaches offer endless shelling, sunning, surfing and swimming.
Dockage is available at Camachee Cove Yacht Harbor on the ICW, which has a 7-foot dock depth and accommodates vessels up to 130 feet.
A 47-mile stretch of beach along the coast from Jupiter to Boca Raton encompasses a number of towns called the Palm Beaches. The area, especially Palm Beach, was frequented by foreign aristocracy, prominent socialites and legendary tycoons.
Still a playground for the affluent, the area offers land and water sports for kids of all ages, with one of the largest polo clubs in the world, coral reef and wreck diving on the world's third-largest barrier reef and fabulous shopping. Then there's all the excellent food. For a taste of Old Palm Beach, the chic Ta-boo lends itself to afternoon cocktails and family dinners. Also try Buccan, a high-end bistro located near the famous Breakers Hotel.
Large yachts have three extraordinary marina choices: The Club at Admirals Cove Marina in Jupiter accommodates boats to 130 feet, has an 11-foot dock depth and is considered a natural weather refuge; the resort-style Safe Harbor Old Port Cove, in the heart of North Palm, has a full-service restaurant and dockage for yachts to 200 feet, with a 15-foot dock depth; Palm Harbor Marina, four miles south of Lake Worth Inlet, accepts yachts to 250 feet and has an 11-foot dock depth.
The site of the Fort Lauderdale International Boat Show, this beautiful city has matured from a destination for spring-breakers to a major manufacturing, maintenance and recreation center for yachts. Its hundreds of top restaurants, sophisticated streets such as Las Olas Boulevard, and 165-miles of local waterways and canals have earned it the nickname the Venice of America. The Fort Lauderdale Riverwalk promenade is thought by many to be the most beautiful mile in the state. Auto enthusiasts shouldn't miss the Fort Lauderdale Antique Car Museum, which has a Packard from every year they were manufactured.
There are countless options for great food, including Bao Bar & Asian Kitchen and S3 (Sun-Surf-Sand), which has a chic patio overlooking the beach.
The Bahia Mar Resort & Yachting Center offers 250 slips for vessels up to 300 feet and a 17-foot dock depth; Hilton Ft. Lauderdale Marina has slips for vessels up to 350 feet and a 14-foot dock depth; Hyatt Regency Pier Sixty-Six Resort & Marina accommodates vessels up to 460 feet and has a 14-foot dock depth; Marina Bay Marina Resort accommodates vessels up to 130 feet and has a 10-foot dock depth.
A collection of urban districts, charming beach villages, and unique ethnic neighborhoods, Miami Beach has an international flavor all its own.
The Design District sports more than 130 art galleries, antique dealers, high-end restaurants and one-of-a-kind shops. The stand-out Wolfsonian-FIU Museum displays 180,000 objects from the 1850s to the 1950s. The area is showcased during Art Deco weekend in January.
Often called the American Riviera, South Beach's Deco fantasyland is one of the most photographed and filmed areas in the country. Along with the stunning architecture, glamorous nightlife and shopping promenades like Lincoln Road, there actually is a spectacular beach. Nearby Collins Avenue is home to the Miami Salsa Congress, a five-day music and dance event held in July.
No one will go hungry in Miami Beach. Among the myriad amazing options are Taquiza, serving handmade torillas; Lure Fishbar, with oysters and butter-poached lobster; Otentic Fresh Food, for French fare in an intimate setting; and Sunset Harbour's gastropub, Pubbelly.
Three dockage options: Miami Beach Marina has 400 slips for vessels up to 250 feet with a 12-foot dock depth; Sunset Harbour Yacht Club on Biscayne Bay can accommodate vessels up to 210 feet and has an 8-foot dock depth; Island Gardens Deep Harbour, a new marina can accommodate yachts up to 500 feet with an 18- foot dock depth.
Just an hour south of Miami Beach lies Key Largo, the key made famous by Humphrey Bogart. Although most scenes were shot in a Hollywood studio, the background was filmed on location. Key Largo is home to John Pennecamp State Park, which has great diving opportunities. To the west is Everglades National Park and to the east is the only living coral barrier reef in the mainland U.S.
Ocean Reef Club located in Key Largo, is a sophisticated private facility dedicated to boating, birding and golfing. The member-only marina has 175 slips and can accommodate vessels up to 175 feet and up to a 9-foot dock depth.
Family-friendly Marathon Key is noted for its old Keys lifestyle and seafaring heritage, and it has many eco-attractions and education centers. The Turtle Hospital rescues, rehabs and releases turtles back into Florida waters. The Dolphin Research Center houses bottlenose dolphins and California sea lions for research and education. Seafood is obviously very fresh in Marathon. Don't miss the Keys Fisheries for their famous Lobster Reuben and the Butterfly Café at the Tranquility Resort for seafood with a Caribbean flair.
In Marathon there are two dockage options: Faro Blanco Resort & Yacht Club accommodates vessel up to 130 feet and has a 10-foot dock depth, and Marathon Marina, Boatyard & RV Resort can accommodate vessels up to 130 feet with an 10-foot dock depth.
Last stop is Key West - the footloose exuberance and spirited irreverence that characterize the Keys is amplified in the quirky collection of pastel conch houses and festive atmosphere that define Key West. The blended cultural heritage was inspired by Bahamian wreckers, commercial fishermen, spongers and Cuban cigar makers.
A variety of folks find their own particular paradise here. Begin the day savoring a cafe Cubano or cafe con leche, before visiting the Ernest Hemingway House, the Truman Little White House and the Butterfly Conservatory, or just bicycle around.
Seafood and Latin-inspired cuisine abound at Santiago's Bodega, Garbo's Grill, and El Siboney. After dinner, indulge at the dark and mysterious Better Than Sex for dessert and wine served in a chocolate- dipped glass. From midday until late at night, live music drifts out of the myriad saloons and breezy waterfront bars on Duval Street.
In Key West, Conch Harbor Marina located in the historic bight area, accepts vessels up to 185 feet with a 10-foot dock depth, plus there's a West Marine store on-site. Key West Bight handles boats up to 200-feet with a 12-foot dock depth. The largest deep-water in the keys, Stock Island Marina Village accommodates vessels up to 300 feet and has a 17-foot dock depth and high-speed fuel.
Our journey started as we pulled out of Waterford Harbor Marina in Kemah, Texas, in May aboard our sailing vessel Fidelity, a 42-foot Valiant. My husband, Kevin, Windy, our Boston terrier, and I were excited to cross the Gulf of Mexico and explore the many towns that dot the shores of Florida with hopes of finding our future homeport. Oh, the places you'll go with a 6-foot draft and 60-foot mast!
After crossing the Gulf of Mexico, our landfall was Clearwater Harbor Marina, which provides easy entry from the Gulf and plenty of deep water for a 6-foot draft (as long as you stay in the channel). The marina's floating docks are key, especially when the swift current catches. The facility is conveniently located near Cleveland Street, Clearwater's entertainment district. It's an easy trek to the beach by water taxi or a stroll over the bridge. Frenchy's Original Café is a must-do for the famous Florida grouper sandwich.
After a lovely day cruising about 40 miles offshore, we made our way to the Harborage Marina at Bayboro in St. Petersburg. We arrived after closing and were greeted by Leon, the night guard, who provided us with the ever important "keys to the gate." Windy thoroughly enjoyed her time at the marina, given the surplus of dog treats provided by the staff, which made it one of the most pet-friendly marinas we visited. It's number one on our list of possible homeports after our adventures on Fidelity wind down.
Just a short walk from Harborage is historic downtown St. Petersburg. Among other don't-miss spots, The Chattaway has great burgers and cold beers. No car is needed -- unless you want to make the trip to Mazzaro's, the best Italian market ever. Nearby, Island Nautical does great service work and repairs. We installed new dingy davits from MarTek and bought a new dinghy to hang off them.
After our stay in St. Pete, it was time to get Fidelity a little farther south. We made a quick stop at Longboat Key then continued on to the Venice Inlet to Crow's Nest Marina and finally arriving at Boca Grande Marina on Gasparilla Island. The approach into Charlotte Harbor was easy, the narrow channel and turn into the marina well marked, and the marina staff talked us into the harbor to avoid the shallows. The marina's docks were pristine, and the on-site restaurant, Miller's Dockside Bar & Grill, was the perfect place to settle into upon arrival.
Golf carts are the preferred mode of transportation in these parts Windy loved riding around and eating at the Loose Caboose, where she ordered from the doggie menu. The landscape's many banyan trees are remarkable, and the pastel-colored "old Florida"-style homes are atmospheric and beautiful. It was a great spot to slow down and enjoy the quieter side of things.
Before we got too settled in this lovely place, we decided to move on. We awoke to a thick layer of fog that lifted by mid-morning, when we were already well underway to our next stop, Pink Shell Beach Resort & Marina in Fort Myers Beach. On approach, the busy port was full of commercial and recreational boats but provided a good depth for Fidelity and was extremely easy to navigate.
Dave, the marina's harbormaster, was incredibly hospitable, but unfortunately we were forced to leave early due to an approaching storm front. We set sail for Marco Island Marina, which would be our home for the next couple of months. As we approached Capri Pass, we were thrilled by the sight of boats sailing in the waters of Marco Island.
Marco Island is a great port with easy access to Gulf sailing, deep water and plenty of dining and entertainment options. The channel into the marina is well marked and the fairways are wide enough for an easy docking experience. Some of our favorite spots for a bite to eat during our time there were the Island Gypsy Cafe´ (a dinghy ride away from the marina), the Italian Deli (excellent New York-style pizza) and the Esplanade.
After several months on Marco Island, Fidelity was ready to head to Key West. By now, Chris Parker, the weather guy, had become Fidelity's most important satellite crew member. There was a small window between storm fronts so we took it and sailed to Stock Island Marina Village in Key West. We had a fun stay, and the marina shuttle was more than sufficient for exploring downtown Key West.
Marathon Marina and RV Resort was our next stop. The marina has new, concrete floating docks, and the on-site Lazy Days South was the perfect spot for happy hour and dinner.
Then it was on to Miami. We cruised past Key Biscayne and downtown Miami to Miami Beach Marina. Giovanni, the dockhand, was a pro with the lines, which came in handy because a strong current surges through the marina but the prime location makes the effort worth it. We enjoyed South Beach's Art Deco architecture, not to mention the bars, restaurants and beach, and then decided it was time for our next destination, Fort Lauderdale.
Bucking the current through Government Cut, Fidelity had her first sail in the Atlantic. Our timing was near perfect with the 17th Street Bridge opening, and a quick turn put us into the Hyatt Regency Pier Sixty-Six Marina. The on-site restaurants, Grille 66 and Pelican Landing, were both great dinner spots. A little bit farther aheld, Louie Bossi's Ristorante Bar Pizzeria, 15th Street Fisheries, and South Port Raw Bar rounded out our top picks for food, atmosphere and price in Fort Lauderdale.
Soon enough, it was time to get underway to Jacksonville and up the coast before hurricane season. A few quick stops we made during this leg of the trip deserve mention. Lake Park Harbor Marina, just north of Riviera Beach, is a great stopover, with floating docks and a low-key atmosphere. Fort Pierce City Marina in Fort Pierce is another wonderful destination the floating docks were in excellent condition and the staff knowledgeable. At Cocoa Village Marina in Cocoa Beach, the dockmaster and crew greeted us personally and made us feel right at home. And Hammock Beach Resort in Palm Coast was a true luxury with swimming pools, restaurants, and doggie treats for Windy.
After the 20-plus-nautical-mile, winding ride past Matanzas Pass, we pulled into the St. Augustine Municipal Marina, and the masterful docking crew handled everything like a finely tuned machine. St. Augustine was a particularly lovely stop and is number two on our list of top ports of call, offering everything from history to dining to shopping. Windy loved her morning walk through the historic part of town, and almost every restaurant we visited welcomed her with a bowl of ice water.
But hurricane season was approaching. It was time to move Fidelity to her summer home. We sailed offshore and then motored up the St. Johns River to Jacksonville's Marina at Ortega Landing. And then we immediately began to look at locations where we might put her in the winter, and to make plans to explore the East Coast in the spring. With so many great ports to chose from, we have some homework to do.