I am always amazed at how many fantastic, North American destinations exist, and a recent adventure to Key West, Florida, re-confirmed the fact. Visiting Key West can be accomplished by cruise ship or by car, the latter being the route I chose. A flight to Miami will get you in the right neighbourhood for your road trip south, and finding Highway 1, which winds through the many Florida Keys is easy to locate and provides an interesting and picturesque route.
The first thing you need to know is, it is a good two and a half hour drive from Key Largo at the top to Key West at the bottom (without any stops). The second tip is about the cost of fuel. Gasoline tends to be as much as fifty cents higher per gallon, than in the rest of the state. Fill up before you reach Highway 1.
Planning a fall or winter getaway to the Florida Keys, will come with higher prices and much busier tourist traffic. If you want to avoid the crowds, May or early June are nicer, albeit warmer and more humid. To me, when you're sitting on a beach feeling the warm ocean waves caress your toes, the temperature matters little, besides air-conditioning is everywhere.
Check the weather before you go. June is the start of the hurricane season, which in itself might be a unique experience, but not necessarily one you want to witness.
The first Key you come to is Key Largo. I am not sure how famous it would be if Humphrey Bogart had not chased Lauren Bacall into the Caribbean Café, in the movie named after the Key. It is a cool place to hang out and experience the culture, especially if you are into snorkelling, fishing or a multitude of ocean sports. If you are into shopping, I would bypass the Key Largo area (unless you are shopping for a margarita).
A little further along the highway is the Key of Islamorada (eye-la-mo-rada). I made the mistake of pronouncing it Islam-orada and was fully corrected... several times. The area is a bit more peaceful than Key Largo, and a great place to spend the night. The warm Atlantic waves gently lap against the white sandy shores, and the restaurants are plentiful. If you like Italian there is well-known Di Giorgio’s, famous for its seafood risotto (which is delicious, by the way). If Italian is not your thing, there are dozens of restaurants featuring seafood and meat.
Islamorada is also home to Theatre of the Sea (a smaller, scaled down version of the big Sea World attractions in Orlando and San Diego). Stopping here on your adventure south gives you a break from driving through mostly single lane traffic, which can be heavy at times. After a nice dinner and a relaxing night at one of the many hotels (book ahead), you are ready to set out and explore the trip south. There are no shortages of art galleries and souvenir shops selling kitschy stuff, as well as dozens of sandal stores and tee shirt outlets.
As you venture south, you see less of the tourist stuff and more peace and quiet. If you have the time and are so inclined, take a detour from the highway and drive through some of the subdivisions where wealthy Floridians live, or where snowbirds rent ocean side abodes. Houses tend to run anywhere from half a million for a small bungalow to 2 or 3 million for large palatial properties on the water. Rents are anywhere from $2000 a week and up, and that of course, is in US dollars.
To me the final destination was the best, and well worth the trip. The last Key, Key West, is totally different from the rest of the Keys. I would say it is very similar to New Orleans in style, albeit on a smaller scale, complete with an above ground cemetery. I have been to Florida a dozen or so times, but this was my first trek to the lower Keys and I am very glad I made it.
There are a number of quaint, boutique hotels, but I would suggest finding one as close to Duvall Street as possible. Duvall is the main drag and being able to walk there from your hotel, is a bonus. Parking in Key West is next to impossible to find, and when you eventually locate a spot you will want to leave your car for the duration of your stay.
I would say two days is probably enough for most people, and the best way to get a feel for the town is using the Hop On Hop Off service. This gives you an overview of the area, but also provides knowledgeable commentary. For the less touristy types, a walk along Duvall Street can take the better part of an afternoon, especially if you stop frequently for a cooling refreshment.
There are art stores, displaying the work of local artists and artisans, as well as clothing boutiques, which cater to the summer sunshine theme, with their brightly coloured fabrics. Also many souvenir shops where you can obtain the collection of fridge magnets or tea towel souvenirs for your loved ones back home.
Most people spend as much time in bars and restaurants, as they do in the shops. Cuban food is really big, and why not? Key West is less than 150 km from Havana. The beverage of choice is the Mojito, mainly because Ernest Hemmingway lived in Key West for a while, and Floridians have adopted him as their patron saint. A cool place to visit in town is Hemmingway's house, which is open to the public every day.
If you are a beach person head down to Himlo beach and soak up the sun. Remember to splatter yourself with sunscreen and wear a hat, because the sun will fry you within 10 minutes. Although Boca Chica is a clothing optional beach, there are many others for the more modest Canadian travellers.
Whether you fly or drive, take a cruise ship or go by bike, Key West Florida is a must on your bucket list.