Key West, Florida has always seemed to march to the beat of its own drummer. About four hours’ drive south of Miami, this 7.4-square mile key (and that includes the water) is home to some amazing buildings, including Ernest Hemingway’s house and the winter home of President Harry S. Truman.
It also boasts the southernmost point of the U.S. and bustling Duval Street, where revelers often make their way from one end to the other, stopping in famous bars as they go.
Although I had stopped in Key West for a morning via cruise ship a couple of years ago, I had always been interested in taking the drive down there and spending a good few days exploring.
My dad, who had actually sailed to Key West on the Pious Puffin with Ed Bush and Captain “D” Dalson Ebanks in late 1979, was also keen to revisit the place. So at the end of May, I drove my mum, dad and best friend Lynne from Miami to Key West, following the route of the Flagler railway, with many bridges before us to cross.
Driving to Key West
There is only one road in and out of Key West. Sometimes it’s two lanes, and sometimes it narrows to one, so don’t expect to speed down there as quickly as you can. The drive is picturesque and should be made at a leisurely pace.
We left Miami and headed south, following the signs through Kendall and Homestead on US1 before coming across the “Last Chance Saloon” – a venue that wouldn’t have been out of place in a Bugs Bunny cartoon. This seemed to be a pretty good indicator that we were about to hit the official start of our journey through the Florida Keys.
Sure enough, we were now on a long stretch of road with fencing and greenery as far as the eye could see. This part wasn’t so terribly interesting, but it wasn’t long before we saw patches of water here and there, which got larger as the journey continued.
There are a few well-known stops on the way to Key West. The first we hit was Key Largo, followed by Islamorada and Marathon. It is just after Marathon that you’ll find the Seven Mile Bridge – a pretty impressive feat of construction that reveals amazing views of the water.
Although the estimated length of our trip seemed daunting when we embarked upon it, it has to be said that the time flew by. There was much to see on the way; not just wildlife, but quirky businesses, hotels, restaurants and bars. Many areas had not been affected by the heavy hand of industry and commerce.
It was clear that these places hadn’t changed much in years, which was refreshing and comforting in a lot of ways. As tourists, we were appreciating the lack of large resorts and sterile, multi-storied buildings. It was all like something out of a Jimmy Buffett song.
We saw many different birds, and even had to slow down to accommodate a deer crossing the road. There had been signs warning about the presence of deer, but we never imagined that we’d actually witness one.
As we hit the home stretch it was about 5 p.m. and the light was just right for some great photos. We got into Key West and followed the directions to our lodgings, aptly named the Key West Bed and Breakfast.
There are a number of brand hotels in the area, including the Westin Key West and the Key West Marriott Beachside Hotel, but to truly experience this unique community, I highly recommend staying at a bed-and-breakfast. The Key West Bed and Breakfast is not just an extraordinary building with comfortable rooms, art and color everywhere, and a lovely deck surrounded by greenery; the whole house has a wonderful atmosphere and the staff could not be nicer. Owner Jody Carlson has a fantastic eye for decorating, and every room is unique – filled with paintings and eclectic pieces of furniture.
We were on William Street, just a stone’s throw from the marina and a short walk from Duval Street. It was a great location.
The only thing I’ll warn any visitors about is the parking; and that applies everywhere. Luckily there was a fair bit of available street parking near our bed-and-breakfast, but the closer you get to the busy areas, the harder time you’ll have finding somewhere to slot yourself.
I had rented an SUV to accommodate the four of us and our insane amount of luggage, but I strongly suggest you rent a smaller vehicle if you can. It will greatly increase the number of parking spots you can use.
Another reason to book with somewhere like the Key West Bed and Breakfast is the personalized service you get (Liz, the house manager, was a font of information about restaurants and other points of interest) and the very competitive rates.
When I first looked at a trip to Key West I was really taken aback by some of the prices. Considering how expensive the Cayman Islands can be, I found some of the nightly rates in Key West to be truly eye-watering. After spending three nights at Jody’s place, I don’t know why anyone would want to stay anywhere else.
Drinking and dining
Key West is known for its seafood, but if shrimp, lobster and clams (oh my!) don’t float your boat, you’ll find many alternatives to please your palate. We had three places recommended to us by Liz, and all of them were fantastic.
For starters, if you go nowhere else in Key West, at least run (don’t walk) to the Eaton Street Seafood Market. We were lucky enough to have this place very nearby, but honestly I would have walked miles for one of their signature lobster rolls. It was absolutely overflowing with lobster in a toasted roll. I can’t even begin to describe the deliciousness. We also bought some shrimp and smoked fish dip, although those had to wait until later in the day, as the lobster rolls filled every crevice in our stomachs. Go there; trust me.
La Trattoria on Duval Street was another restaurant that did not disappoint. It serves great Italian food in a nice, comfortable atmosphere, and somehow manages to remove you from the bonkers bustle of everyone going up and down the pavement.
Our server was friendly, professional and efficient, and we actually tipped the water lady separately, as our glasses were never below half full. If you like Italian food, I would definitely recommend La Trattoria when you visit Key West.
The third place we tried, again, as suggested by the Key West Bed and Breakfast, was Deuce’s “Off the Hook” Grill on the corner of Simonton and Petronia St. This tiny gem is all kinds of intimate with only about six tables and a bar, and I managed to miss it completely when we first drove past its address.
We had a fantastic lunch there of fish tacos, oysters and other delectables. It’s only a block from Duval Street and absolutely worth a look. Reservations are recommended for obvious reasons.
When it comes to drinking, Key West has a plethora of pubs and bars from which to choose. Live music abounds, and you’ll only have to walk a few feet from one venue to hit the next. One of the very popular hangouts for tourists is The Bull & Whistle Bar on Duval, where The Bull is the ground floor bar, often featuring live music; the Whistle is the second floor bar with a wraparound balcony, perfect for people watching (reminiscent of New Orleans); and on the roof you’ll find the Garden of Eden – a “clothing optional” bar with age restrictions, a cover charge, and no guarantee that you’ll be able to unsee the sights you witness.
Another must-stop is Sloppy Joe’s, a Key West favorite that moved from it’s original spot but is still going strong; and Parrotheads will all be heading to Jimmy Buffett’s Margaritaville to pick up T-shirts and paraphernalia aplenty.
There are many sights to see in Key West, and one of the best ways to get the ball rolling is to take a ride on the hop-on-hop-off trolley. We took City View Trolley Tours and really enjoyed the hour-long run around Old Town.
It was a very comfortable ride and the driver gave us lots of interesting information. This is also a fantastic way to see some of the amazing old homes of Key West. Don’t be surprised if you leave there wondering how you can buy a property.
You can visit the Ernest Hemingway Home and Museum and marvel at the six-toed cats roaming the grounds; get your picture taken at the “Southernmost Point” marker; and see the exhibits in the Custom House Museum. When we were there they had a wonderful exhibit about Flagler and his railway, as well as a series of artworks from none other than Guy Harvey, depicting the story of the Old Man and the Sea.
No matter what you do, however, do not miss the “Western Union” schooner docked in the marina. Why? Because none other than Herbert Elroy Arch, Caymanian, designed her. She is a magnificent vessel with truly Caymanian ties.
At the end of a day of sightseeing, head to Mallory Square to watch the sunset, buy a beverage, and be entertained by live musicians, fire eaters, and the “Catman” himself, Dominique LeFort, who performs at the Westin Pier.
He isn’t going to be everyone’s cup of tea, but he may be the only person in the world who can actually herd cats. I would say that his show is 70 percent chatter, yelling and interpretive dance, and 30 percent actual cat tricks. The 30 percent is just about worth it.
For more information on a great place to stay and start booking your trip, see keywestbandb.com.