The Florida Keys are a popular winter destination for RVers. Key West, in particular, has the right mix of laid back, 5-o’clock-somewhere, beach vibe and vibrant Cuban festival. There are 3 things you should book far in advance if you plan to spend any part of your winter in Key West.
We booked the RV resort 8 months ahead and still didn’t get the location we had hoped for. We waited too long to book travel from Key West over to Dry Tortugas and weren’t able to go at all. We booked a walking food tour about 6 weeks in advance. We didn’t make any other plans or reservations before we arrived and were able to see and do everything discussed below in more detail.
Geologically, this chain of small islands called the “Florida Keys” consist of exposed parts of coral reef. This string of tropical islands with white sandy beaches is 125 miles long and is nestled between the Gulf of Mexico and the Atlantic Ocean. There are actually 1,700 islands that make up the Keys but only 30 of the Keys have inhabitants.
Henry Flagler, a principal in Rockefeller, Andrews and Flagler and later a founder of Standard Oil, began building resort hotels and railroad along the east coast of Florida beginning with St. Augustine. He wanted to connect Key West to the United States to for its deep-water port and potential trade opportunities with Cuba and Latin America. Initially called Flagler’s Folly, the construction of the Overseas Railroad required many engineering innovations. $50 million dollars and 4,000 employees were needed to complete the 7 year project, but the “Eighth Wonder of the World” opened in 1912.
Sadly, the Overseas Railroad wad damaged and partially destroyed by a hurricane in 1935. Financially, the railway was unable to rebuild the destroyed sections so the roadbed and remaining bridges were sold to the state of Florida. A state road that paralleled the railroad went part way down the keys, but once they acquired the rail bed, the state retrofitted it with a new two-lane wide surface for automobile use that opened to the public in 1938.
BOOKING YOUR STAY
Key West is one of the most coveted winter vacation spots. It sits at the southernmost point in the continental US just 90 miles from Cuba at the end of the Overseas Road. We recommend booking your Key West RV accommodations up to a year in advance of travelling.
We also recommend booking your stay in Key Largo (the northernmost Key) well in advance. We stayed at a Boondockers Welcome (parent company is now Harvest Host) location in Key Largo before making the 100+ mile drive to Key West the next day.
BOOKING DRY TORTUGAS
Dry Tortugas National Park can only be reached by seaplane (Key West Seaplane Adventures linked here) or 175-passenger ferry (Yankee Freedom III link here) from Key West. No cars are allowed the island. The ferry takes 2.5hrs each way, offers a full day trip, and is the least expensive at about $200/person. The seaplane ride is 40 minutes each way, offers half day and full day trips at a cost of $371/person or $644/person respectively. Most people say the half day (2.5hrs on the island) is enough time to tour the largest brick building in the western hemisphere, Fort Jefferson, and enjoy the beach. If you plan to snorkel, you’ll need the full day (6.5hrs on the island).
TRAVEL TIP: If you plan to plan to spend the money for the seaplane, on insider shared that taking the 8am flight allows you to reach the island for 2 hours before the ferry arrives so there will be fewer people and shady spots left on the beach.
TRAVEL TIP: Don’t forget your national park pass or you’ll have to pay the park entry fee.
BOOKING A FOOD TOUR
About 6 weeks ahead of our arrival date in Key West we booked the Southernmost Food Tasting & Cultural Walk (keywestfoodtours.com). This was a great way immerse yourself in the culture, ask a local about things you may want to do in the area, get a bit of history, and find your bearings in town. Our millennial guide had only been doing the tours for a few months so there were a few times more historical information would have been helpful but the food choices more than made up for it. Everything were excellent!
TRAVEL TIP: For the reasons noted above, we did the food tour at the beginning of our visit.
NOW LET’S GO WITH THE FLOW
On the 100-mile drive from Key Largo to Key West, we drove past plenty of beachside restaurants, bars, and places claiming to have the best Key lime pie as well as several roadside attractions, like the Big Lobster on Plantation Key. We also saw some kite boarders off of Lower Matecumbe Key.
TRAVEL TIP: While we went all the way south first (and then came back up the Keys to about its midway point and stayed in Marathon), you may want to make a few stops on the way down or a few stops on the way back up so consider this when booking and book all your Florida Key stays.
Leo’s RV Park was tight pack, not inexpensive, and in a lower income residential area, but it was clean and full hook-ups worked great. Also, Doug had access to the water and used his standup paddle board (SUP) to meander through the mangroves and out into both the gulf and the ocean. The second time he went out he saw manatees.
The park’s proximity to Key West was also nice. It was only a little over 4 miles to historic downtown with easy access to the bike path.
Our initial bike ride was into historic downtown, then past Harry S. Truman Little White House, and to the marker for the Southernmost point (whose picture line was so long, it wasn’t worth it!). We worked our way back to the RV park along Smathers Beach.
The food tour started at a popular local eatery and then worked its way down to Deval Street. We ate at El Siboney known for their traditional Cuban food and sangria, rum at The Speakeasy Inn a & Rum Bar, Mahi-Mahi at Mangos, conch fritters at Kaya Island Eats, and Cortadito (1/2 cane sugar with ½ Cuban Espresso) and Key lime pie at Cuban Coffee Queen!
Immediately following the food tour, we’d discovered that the key for our bike lock was missing from his pants pocket. He had remembered hearing something drop at the first restaurant, but when I asked if they’d found it, they hadn’t. Doug went in to the restaurant and insisted they take another look and they found it. We were able to unlock the bikes and ride back to the RV without calling an Uber.
Between the food tour and our bike ride to historic downtown, we got a real sense for the layout and how we wanted to spend our other days.
Key West Butterfly and Nature Conservatory is a family-friendly way to spend a few hours. You almost can’t help but leave the site stress-free. Colorful butterflies flit by, a pair of flamingos dance in the water, and birds sing as guest stroll the very short path around the conservatory. Your only stress might be the jam packed gift shop decorated in pinks, purples, and baby blues on the way out.
We made our way back to Deval Street afterwards to stroll through some art galleries, window shop, and have a larger meal at the Mangos restaurant from our prior food tour.
We were in Key West for my birthday (39 again!) so headed straight for Blue Heaven for brunch. This iconic restaurant serves up Floridain-Carribean cuisine in a tropical setting. Although the wait can take a while, they have it dialed in with a small bar associated with the restaurant just across the street where you can grab your mimosa or Bloody Mary while you wait. Live music is typical at the restaurant, and we had a few unusual dining companions – chickens and roosters that wander amongst the guests.
Most people visit Hemingway House while in Key West, but we were both more interested in the Mel Fisher Maritime Museum. Mel Fisher was scuba pioneer in southern California who got the treasure hunting bug and dedicated his life to finding to the sunken ship of Atocha, a Spanish Ship laden with New World treasure and on its way back to Spain when a hurricane hit and it sunk off of the coast of Florida. Mel and his wife began diving to try and find the wrecked ship in 1969. By the mid-70s, they’d found several objects, but not the bulk of the cargo and in 1975, his son, daughter-in-law, and a member of Mel’s crew died after their salvage boat capsized in rough seas. This didn’t deter the team who’s leader Mel would say daily “Today’s the Day”. They eventually discovered the Atocha’s mother lode cargo off the coast of Florida. It contained over 30 tons of silver bullion, objects of pure gold, silver dishes and coins, and jewels. He and his team salvaged $400 million from the wreck and had to wage a legal battle against the state of Florida that went all the way to the Supreme Court to hold onto his treasure.
In addition to the story of the Atocha and Mel Fisher story, this museum had information on the history of pirates in the Key West area and a really interesting display on the effort it takes to recover and then stabilize any items found from old wrecks to prevent them from simply disintegrating in an air environment.
I’m not saying you shouldn’t see Hemingway House, but we highly recommend visiting this museum.
There are plenty of water sport opportunities in Key West or you can just sit on the soft, white sandy beaches and watch the turquoise waves somersault forward. This is a great way to relax and it just doesn’t seem right to leave Key West without some beach time!
There’s a bike path that follows the Overseas Highway. Doug rode it north to Sugarloaf Key and the National Key Deer Rescue, but he didn’t see any of the pint sized Key deer.
We did, however, enjoy the bike ride over to a dinner of grilled hogfish with a nice sunset near the marina at Stock Island.
Key West has a vibrant LGBTQ+ community. Additionally, they have more than one drag show in town, but we happened to be here for New Years and Key West has a unique New Year’s Eve tradition – instead of dropping a ball at the stroke of midnight, Key West lowers a drag queen named “Sushi” who sits inside a huge ruby red high heeled slipper. In our over 20 years together, we have never gone out on New Year’s Eve, but we couldn’t pass up this tradition. I mean…when would we ever see a drag queen shoe drop?! Despite some pushy crowds and the lady I called rude, it was a great way to ring in the New Year!
We heard some rumblings that “Sushi” had been doing the New Year’s drop for over 20 years and that 2022 was her last one. I can’t imagine that they would retire the tradition, so who knows what 2023 will bring!
Not only is the journey to the Southernmost point in the US entertaining, but you can enjoy various watersports, beautiful beaches, old town architecture, interesting museums, serene settings, historical sites, literary giants, random roosters, delicious food, bouncing bars, a lively nightlife, rum and Key lime pie with the off-kilter locals.
The key to a great subtropical Key West visit is to book your stay, the trip to Dry Tortugas, and a food tour early. Then just enjoy the many activities that present themselves when you arrive.
