We all need to get away from home on occasion, sometimes far away, and the Florida Keys are about as far from the Pacific Northwest as you can get and still be in one of the fifty U.S. states – Honolulu is closer to Seattle than Key West is. And the Keys make for a great winter getaway. My wife and I had a great time in Key West on our only visit and I would love to return to someday.
The following was originally posted on this site a couple of years ago. I checked all of the links, but things can change, so check the Keys News website for current information if you’re contemplating a visit in the near future.
If you are thinking about a visit to Key West, the first thing you should do is track down a copy of Jon Breakfield’s book “Key West: Tequila, a Pinch of Salt and a Quirky Slice of America.” Breakfield and his wife were living in Scotland and took a winter vacation to Key West one year. Two days into their visit they decided not to go back to Scotland. Breakfield’s book is an absolutely hilarious account of their first year in Key West. It’s also a good introduction to the Key West culture and works as a weird sort of travel guide. After reading the book, you’ll probably want to visit The Bull, a bar on Duval Street, and the Whistle Bar, which occupies the floor above. The Whistle Bar has a wrap around veranda that is one of the best people watching perches in Key West. Both figure prominently in the book. And if you’re really adventurous, you might even want to venture up one more flight to the clothing optional rooftop bar called The Garden of Eden.
Key West is a quirky place, and nothing exemplifies that better than the city’s tongue in check secession from the United States in 1982. After the Border Patrol set up a roadblock on the highway between Key Largo and Miami (to stem the flow of drugs into the country via the Keys), creating huge traffic backups and inhibiting island residents from commuting to jobs on the mainland, the mayor and city council of Key West decided that if the Border Patrol was going to treat them like they were a foreign country by setting up a de facto border crossing station, they would become one. Thus was born the Conch Republic. The move was pure political theater (the mayor “surrendered” to the commander of the naval air station at Key West the day after declaring the Conch Republic’s independence), but it resonated with the anti-establishment sentiment common among island residents, and the spirit of the Conch Republic persists to this day.
Duval Street is the main drag in Key West. It’s lined with bars and restaurants, galleries, gift shops, and much more. You can eat your way down one side of the street and drink your way back up the other, if you’re so inclined. You’ll probably meet fifty other tourists for every local, but everyone will be having a good time and you won’t care that it’s not the real Key West.
Besides Duval Street, another major tourist draw is Mallory Square and the daily Sunset Celebration. Key West is known for its sunsets and didn’t disappoint on our visit. And every evening about two hours before sunset dozens of artists, crafters, food vendors, and street performers of every stripe congregate at Mallory Square to hawk whatever it is they’re selling to the tourists gathered there to watch the sunset. It’s weird, wild, and enormously entertaining. And then there’s a beautiful sunset to cap it all off.
Key West has plenty of places of interest beyond Duval Street and Mallory Square, too. The Hemingway House is another major tourist draw. Get there early if you’re going or buy your tickets online. The line was around the block both times we thought about taking a look. The Audubon House, Key West Lighthouse Museum, Eco-Discovery Center , Fort Zachary Taylor Historic State Park , the Mel Fisher Maritime Museum, and the Key West Aquarium are all worth a visit.
If you just want to hang out at the beach, Fort Zach Park has a nice swimming beach (with an adjacent bar). South Beach at the end of Duval Street also has a beach bar and grill. Higgs Beach is four or five blocks east and has a nice beach for sunbathing and swimming. And across the street, Astro City Playground is a fun place for kids to play. To the east of Higgs Beach are C.B. Harvey Memorial Rest Beach (no bar or other amenities) and Smathers Beach. Dog Beach, a couple of blocks east of South Beach, is literally for the dogs – a dog friendly, off leash park.
Key West has dozens of fine restaurants. All of the places we dined at were excellent. We had a couple of great breakfasts at a place called Camille’s Cafe, but it appears to be closed. Blue Heaven, Cafe Sole, and a Cuban restaurant called El Siboney all had excellent food. We also lunched at a couple of Duval Street eateries (whose names I’ve forgotten) that were very good. The Lobster Shack, The Flaming Bouy, Louie’s Backyard, Sarabeth’s Kitchen, Santiago’s Bodega (tapas), Cafe Marquesa, The Cafe (vegetarian), Ambrosia (Japanese), and B.O.’s Fish Wagon (fresh and very affordable seafood) are all highly rated, also.
Nature lovers will want to check out Key West Butterfly and Nature Conservancy, Indigenous Park, Key West Nature Preserve, and Key West Wildlife Center.
If you’re interested in fishing, Trip Advisor lists more than two dozen fishing charters and tours. If scuba diving is your thing, Finz Dive Center, Captain’s Corner Dive Center, and Lost Reef Adventures all offer diving tours and are highly rated.
Tourism drives Key West’s economy and there is no shortage of available accommodations , from luxury resorts to whole house rentals to budget motels and inexpensive Airbnb rentals. We went the Airbnb route and found a reasonably affordable room in Old Town. But the closer to the historic district and Duval Street, the more expensive the accommodations become, and the longer ahead that you will need to make reservations. It’s an advantage to stay within walking distance of Old Town, as parking is limited, but if you have a car and don’t mind spending some time looking for a place to park, staying in the New Town section or on Stock Island can save you some money. Key West is bicycle friendly, has a public transit system, and taxis are readily available (some with bicycle racks), so driving into Old Town is not strictly necessary, even if you are not staying close by. Uber and Lyft are also options.
The bottom line is there are as many reasons to visit Key West as there are tourists visiting. It’s a great party town and a great place to lounge on the beach and soak up the sunshine, but it’s much more than just that. Key West is soaked in history, has a great food scene, has great fishing and diving, and is located in an incredibly beautiful natural setting.
The other Florida Keys have their own attractions, too, and the drive from Miami to Key West is an attraction on its own.
Key Largo is the closest of the keys to the mainland and many of the residents commute to the mainland, but it has many attractions that draw travelers, too. It’s the self-proclaimed “dive capital of the world” and home to the world’s largest artificial reef, among other attractions. If fishing is your thing, Islamorada bills itself as the “sport-fishing capital of the world.”
There were a number of other interesting places in the Keys that we stopped at on our way to and from Key West. One of those was the National Key Deer Refuge on Sugarloaf Key. Key deer are tiny – not much bigger than a German shepherd. Another stop we made was Bahia Honda State Park, which has a nice swimming beach and clear waters in multiple hues of blue.
The Overseas Highway through the Keys is an engineering marvel and driving it is an amazing journey, even if you don’t stop at any of the Keys along the way. The Seven Mile Bridge itself is one of the main attractions in the Keys.
If you’re contemplating a visit, flying to Key West is an option, but I’d do as we did – fly to Miami or Fort Lauderdale, rent a car, and drive the Overseas Highway. Visit the other Keys and go diving, snorkeling, fishing, or just find an uncrowded beach and soak up the sunshine away from the crowds. And, of course, take in Key West and all it has to offer. You won’t regret it. And while you’re in Florida, the Everglades are only a short drive from Miami.
Originally posted by Alan K. Lee on August 10, 2018. Updated with Covid-19 info December 14, 2020. Updated and expanded September 15, 2023.
All photos © Alan K. Lee