Virtual Cruise of the East Coast: Key West, Florida

Overwater sunsets and a cast of colorful characters are just part of the experience in this famous party place.

It’s 5:45 p.m. and the sun is going down on Mallory Square. Afro-Cuban music is coming from a makeshift group of drummers creating a suspenseful soundtrack for the guy hanging himself upside down in chains. Behind us is a live human statue painted in gold. Next to him, a man lights a ring of fire and jumps through it following his dog and cat. We’re back in Key West. We’re back to abnormal.

For the past nine months, we have been having the time of our lives, venturing from Annapolis, Maryland, up to New England for the summer and then heading south on the Intracoastal Waterway. We’ve been trying to reach the lower latitudes before we dig into our winter wardrobes, and even though we’ve arrived at the southernmost point of our one-year adventure, the December chill has us wearing jeans and fleece. But who cares? The bar stools at ­Schooner Wharf Bar are out of the wind, and folk singer Michael McCloud is alive and performing on stage.

(Mouse over the charts to see our recommendations for Key West.)


We arrive here after a 415-mile, 10-day cruise down the Florida coast from St. Augustine. Along the way we make stops in Daytona Beach, New Smyrna Beach, Melbourne, Stuart, Palm Beach, Miami and Isla­morada. From Stuart, we run outside to Miami because of good weather and the safe, well-marked inlets of Palm Beach and Miami. From Biscayne Bay, we enjoy a nonstop 70-mile run inside to Islamorada, where we unwind for a couple of days at Plantation Yacht Harbor, one of our favorite stops in all of Florida. This top-notch marina is part of Islamorada’s Founders Park, which has an Olympic-size pool, baseball diamonds, basketball and tennis courts, jogging trails, a small beach and a dog park. We especially enjoy watching the children’s Christmas shows at the outdoor theater. While here, we book a half-day fishing trip with Capt. Matt Bellinger of Bamboo Charters. Bellinger knows the backcountry waters better than just about anyone in the Keys, and we soon find ourselves with a cooler of sea trout, which we’ll grill for dinner.

After leaving Islamorada, we follow Hawk Channel on the outside to Key West, a distance of 85 miles. Since we like to be where all the action is, at least for a few days, picking up a slip at the Key West Bight Marina in the historic seaport is the best move. Our slip is close to Schooner’s. Sitting down again at this funky bar with our dog (his name is Schooner, of course) makes us feel right at home.

If you listen to McCloud’s well-worn song “Tourist Town Bar,” you’ll appreciate that Key West is made up of all kinds. To really enjoy this chunk of paradise, you need to keep an open mind. There are tourists of all stripes, many of whom are deposited on the main pier when their cruise ship lands. You can easily spot them, as they’ll be riding in the Conch Tour Train trolley cars, taking pictures and videos of everyone else. Most locals are transplanted Northerners. Again from a McCloud song, “I came down here for the weekend 25 years ago.” Many people here work in the hospitality industry, while others are diving guides or charter captains. Some are street performers, musicians or artists. And there are those who are not sure what, or even who, they are. But one thing is certain: Come sundown, everyone starts having a good time.


Indeed, Key West is known for its high number of bars and restaurants. And they range from the raunchy to the elegant. Sloppy Joe’s, Ernest Hemingway’s famous hangout, is still going strong. Yes, it’s a tourist trap, but the beers are cold, the Sloppy Joes are tasty and the band is usually pretty good, or at least loud. Another bar with a history is Capt. Tony’s Saloon, where Truman Capote and Tennessee Williams supposedly hung out. The Hog’s Breath Saloon gives new meaning to the term “raw bar,” but it’s a fun place, and you’ll likely leave wearing one of its T-shirts. “Happy hour” also means something a bit different in Key West, because it begins as early as 7 a.m. at some places.

If raunchy rock ’n’ roll and the smell of stale beer are not your cup of tea, remember that Key West is a town of extremes. As ex-New Yorkers, my wife and I can be tough restaurant critics, but we always seem to discover a new place that impresses. During this visit, it’s Sarabeth’s on Simonton Street. What’s unusual about this little, out-of-the-way gem is that it’s equally good for breakfast and dinner. Try the “goldie lox” breakfast of smoked salmon scrambled with eggs and cream cheese. We went back for dinner and were treated to fresh, flash-fried yellowtail snapper.

(Mouse over the charts to see our recommendations for Key West.)


There’s more to do in Key West than eat and drink, of course, so we start the next day with a tour of the Ernest Hemingway Home and Museum on Whitehead Street. The house, garden and pool are cozy and intimate, and I can almost feel the presence of one of America’s greatest writers as we enter his study. Next on our list is the Key West Shipwreck Museum, which takes us back to the 19th century with live re-enactments and films. A climb to the top of the 65-foot lookout tower gives us a panoramic view of the harbor and beyond. Close by is the Mel Fisher Maritime Museum and its tales of discovering sunken treasure and the ruins of slave ships from the 17th and 18th centuries. There’s a lot to learn here, so we take our time on this self-guided tour.

A couple of years ago, we took a half-day reef snorkeling trip aboard one of the Appledore schooners and had a great time. We’re happy to see that the Appledore V, which launched in 1992, is still busy taking people out for similar five-hour snorkeling trips as well as two-hour sunset sails. Sebago Key West Watersports manages the Appledore trips and also offers cruises aboard its fleet of sailing catamarans. The 7-mile sail out to the world’s third-largest barrier reef is memorable for both novices and accomplished divers.

No visit to Key West is complete without a walk along its notorious, mile-long Duval Street, an experience often referred to as the “Duval Pub Crawl.” Lined with shops, restaurants, bars, galleries, inns and all kinds of dubious tourist attractions, it often generates a carnival atmosphere, especially after sundown. Indeed, during certain events like October’s Fantasy Fest or New Year’s Eve, the freaks can easily outnumber the “normals.” This is not exactly Disney World, so you’ll want to leave the little ones at home with the grandparents during these special celebrations.


While all the interesting characters, great food, music and sightseeing activities have been fun, after a few days we are ready to go cruising. We check the weather, fill our boat’s fuel and water tanks, and head offshore for a 70-mile trip to the Dry Tortugas, which is the most remote part of the Florida Keys.

Come with us by visiting as we explore Fort Jefferson, where Dr. Samuel Mudd of the Lincoln assassination conspiracy was held. We’ll then explore part of the Everglades before deciding whether or not to cross the Gulf Stream and head over to the Bahamas.

Exploring Florida’s Keys and Beyond

We’ve finally found warm temperatures, so we’ve decided to stay in the Keys and the surrounding area for several weeks this winter. Overall, the atmosphere here is very laidback, and we find many similarities to being in the Bahamas – only without the hassles of getting there. We also appreciate being in the U.S., where we have easy access to healthcare, good food and reliable services.

**Islamorada ** 24° 50.00′ N 80° 34.00′ W
We’ve been coming to Islamorada for years mainly because of our fondness for the city’s Founder’s Park, where Plantation Yacht Harbor Marina is located. A few years ago, the marina was updated with new concrete piers, a fuel dock and boat ramp. A slip holder has access to the facilities of the public park including an Olympic sized pool, tennis and basketball courts, baseball diamonds, walking trails, a dog park and a small beach. We always enjoy having lunch outdoors at the Islamorada Fish Company just a few miles away (try their delicious beer battered whitefish) before treating ourselves to some new apparel and fishing gear at the super-sized Bass Pro Shop right next door. For dinner we’ll return to one of our favorites, the Green Turtle Inn. It may look a bit dated on the outside, but you won’t find fresher, better prepared seafood in all of Florida.

**Bahia Honda ** 24° 39.79′ N 81° 16.62′ W
After leaving Islamorada, we head outside to Hawk Channel via Snake Creek and run 45-miles to the anchorage off Bahia Honda State Park between the old Bahia Honda Bridge and the new Overseas Highway Bridge (MM37). There is a small boat basin here that accepts boats up to 50-feet, but dock space is usually hard to find and the controlling depth is only 3 ½ feet. (Call 305-872-3210 for availability.) Instead, we drop anchor in 8-feet of water just off the beautiful sandy beach. This 500-acre park is a favorite spot for campers and RV’ers, and there are even a couple of cabins that are available for rent. A concession service offers a snack bar, gift shop, kayak rentals and snorkeling trips out to Looe Key National Marine Sanctuary. We take one of the hiking trails that leads to the top of the old Bahia Honda Bridge to get a spectacular view of the anchorage, the Atlantic Ocean and the Gulf of Mexico.

**Dry Tortugas ** 24° 38.3′ N 82° 51.7′ W
After a fun week in downtown Key West (see main article), we are in the mood for a change of pace. After checking the weather forecast and preparing for an offshore passage, we head 70-miles west to the anchorage off Garden Key in the Dry Tortugas. We choose the route that passes just south of the Marquesas, which gives us an option of anchoring in the lee of one of the small keys in case of bad weather. Because the weather here can be unpredictable and there is no food or water available in the Dry Tortugas, it is important to be prepared to stay for several days. After dropping the hook off the southern end of Garden Key, we land our dinghy on the beach and take a guided tour of Fort Jefferson, which became a prison during the Civil War. It was here that Dr. Samuel Mudd, convicted of conspiracy in Lincoln’s assassination for setting the broken leg of John Wilkes Booth, was incarcerated. Across the anchorage is Bush Key, the protected refuge for the sooty tern.

**Ten Thousand Islands ** From Cape Sable to Cape Romano
Returning from the Dry Tortugas, we continue exploring the Florida Keys and then head north from Marathon, running 20-miles to East Cape and the Everglades National Park. Staying a half-mile off the shores of Cape Sable, we enter the area known as Ten Thousand Islands, which continues another 50 miles or so to Cape Romano. The white sandy beaches between East Cape and Northwest Cape are beautiful and pristine. We drop the hook for the night in the mouth of the Little Shark River, a popular stopover for those seeking shelter in bad weather. This is definitely kayak territory, and the next morning we venture a few miles through the thick mangrove habitats looking for a sampling of the 180 different species of birds that live in this 35,000-acre National Wildlife refuge. Later that day we head north and anchor off the eastern shore of Indian Key, southwest of Chokoloskee Bay. This incredibly beautiful spot has been called the “Michelle Pfeiffer” of anchorages, and as the tide goes out, a stretch of white sandy beach appears before our eyes. We kayak around the little island and discover a group of adventurous kayakers camped out.

Everglades City 25° 51.47′ N 81° 23.28′ W
Threading our way northeast five miles through Indian Key Pass, we enter the Barron River and tie up along the pier at the famous Rod & Gun Club. The list of the rich and famous who have stayed here is virtually endless, so we’ll mention just a few – from Presidents Roosevelt, Truman, Eisenhower and Nixon to actors John Wayne, Burt Reynolds, Sean Connery and Joe Pesci and from Ernest Hemingway to Mick Jagger. This anachronistic inn has quite a history, and walking through the lobby to the dining room is a trip back in time. You’ll pass under wildlife trophies, portraits of famous guests and archived newspaper clippings describing events taking place over the past century. After our appetizer of delicious gator nuggets, we enjoy our steak and blackened grouper dinner, feeling a slight sense of awe being in this hallowed room. Everglades City lies at one end of the Wilderness Waterway, the 99-mile backcountry kayak/canoe route that leads to Flamingo. Escorted eco tours are available and highly recommended. For the truly adventurous, there are suggested 9 and 5-day itineraries. Permits are required and are available at the ranger station. The town itself is a throw back to the old, unspoiled Florida, and it offers the basics most cruisers need – a grocery and hardware store, a post office and a small museum.

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