I think this was my fifth visit to Key West and it remains a wonderful place. It's interesting that despite being one of the great bar and sunshine capitals of the world, it doesn't get a lot of college spring break madness. I assume for two reasons: 1) It is too difficult to get to cheaply - a four hour drive from Miami or an expensive connecting flight into Key West airport. 2) It ain't cheap. Major hotels near the water are going to run you in the neighborhood of $500 a night during spring break season, even at the cheapest. The upshot is that Key West, while being party mad, is a bit more adult.
While flyng that extra leg into Key West can be appealing. There are pluses to driving the length of the Keys. The path from mainland Florida onto the first key -- Key Largo -- is a well worn stretch of US 1, but there is an alternative. You can take Card Sound Road which parallels U.S. 1 about fifteen minutes to the East. There is nothing on Card Sound Road except a toll bridge ($1) and a remarkable swamp-side dive called Alabama Jack's.
There are approximately 9,327,438 waterside fried-fish-and-cold-beer restaurants in Florida, but Alabama Jack's stands out for a few reasons: 1) It's off the beaten path yet quite crowded suggesting folks go out of their way to get there. 2) It is old -- like, my age -- with roots well back in the heart of the previous century. The rustic kitsch you see here is genuine. 3) It has a broad cross-section of clientele, from families on vacation to bikers on the road to fisherman tying their boats up to local swamp rats. At 2pm on the weekends a country band plays -- the Card Sound Machine, they've had this gig for decades -- and sweet old ladies dressed up in their homey western swing skirts twirl around the dance floor. Just a good natured place all around. Worth going the 20 minutes out of your way.
The drive along the Keys is often described as beautiful, but most of it really isn't. It's crap shops, low-end shopping centers, cheap motels, and harborside facilities, and fried-fish-dives/tiki bars in places where the waters comes in close. The first two thirds of the drive is like this and can be very frustrating -- this is not a freeway. You're talking 40-45 mph with stops all the way through Key Largo and nothing to look at except the aforementioned crap shops. When you reach the next Key, Islamorada (pronounced I'll-am-or-ah'-dah) you will slow to a crawl with no passing lanes. It's tough when you have your sights set on Key West, still two and a half hours away -- but you must chill; there's no choice. The good news is once you get through Islamorada things loosen up a bit -- you might get some nice stretches at 50 mph along with relief from the crap shops and sweet views of the Gulf on one side and the Sea on the other. About 2/3 of the way through you'll hit the famous Seven Mile Bridge which is as lovely as described, and from there you're in the home stretch to your final destination. In Key West the smart thing to do is park and not get in your car again until you leave.
There is a lot to do in the Non-Key West Keys. Fishing is huge in Islamorada and Marathon, eco-kayak-watersports tours are everywhere, and there are a couple of excellent but crowded state parks, but apart from the occasional isolated lodge where isolation is the selling point, most of the stuff on the pre-Key West Keys is single purpose. The impression I get is that it's for families driving down for a brief, inexpensive weekend, or perhaps dedicated fishing trips. If you're going to hang for any amount of time you need to go all the way to the end of the road.
Having driven US 1 to Key West many times, I have no particular interest in doing it again. The added time is too meaningful to me now. I'd prefer to fly into Key West directly and take a ten minute cab ride to my hotel. But the drive is something you should do at least once.
There is another way into Key West, and that is via a ferry from Ft. Myers or Marco Island. It's about a four hour ferry ride so it really doesn't save you any time over driving and it departs for Key West early in the morning, returning late afternoon so it doesn't really work well as a commuter since you would have to fly into Ft. Myers the evening before, get a hotel room for the evening, then a cab to the dock early the next morning. It could be an interesting as an option for a multi-point road trip, though. Visiting other parts of the Gulf coast, use the ferry to swing down to Key West for two or three nights. That could work.
In any event, Key West is worth the effort to get there. The days can be as languorous or as hectic as you want them to be. One thing I have found is that when I am in the tropics I do tend to slip into island time. I may have a whole list of activities in my head but when I get there, that umbrella drink makes the lounge chair in the sun hard to escape.
A leisurely bike ride is a good way to get familiar with the island. Key West has many areas with distinct personalities. Duval Street is where the madness is -- the quieter southern end terminates right near the Southernmost Point. Here masses of tourist self-organize into a line to take selfies in front of a large buoy-shaped marker. The busier north end terminates at Mallory Square where people gather along the water to watch the sunset and the street entertainers. Quick note: All along the Florida Gulf coast watching the sunset is a big deal. Folks gather on the beach, or at least the beachside tiki bars, and drink and chit-chat and enjoy the final moments of Florida sunshine.
In the north, to the west of Duval is a lovely area called the Truman Annex -- it strikes me as the closest thing to an old money neighborhood. Row houses/duplexes on well-shaded, lightly traveled side streets. I suspect most of the units are rentals so it is almost certainly not old money, although I'm sure the larger houses in the area are.
Move south next and you get to Old Town, which as I understand it was a Cuban enclave up until a few years ago. It may still be as there a hints of latin vibrancy, but over the years I've been visiting it seems to be gentrifying. Some of the ramshackle spots seem cleaned up and higher end business are sliding in, such as the most popular restaurant on Key West, the Blue Heaven. I have tried multiple time to eat there but I refuse to wait an 90 minutes for a table off-hours on a Tuesday. No restaurant is that good.
You next step south is actually public housing projects. It's probably the worst area economically on Key West and probably the place you'd go to score illicit chemicals. But to be accurate I should point out the Key West is light on crime. In fact, the last time I looked at a Key West crime map, it turned out that most violent crime occurred on the northern part of Duval and along the waterfront. This tells me that violent crime is mostly assaults either on or by drunken tourists. And even that wasn't all that common.
Moving north from "the projects," such as they are, you come to a Naval Station -- no admittance. But adjacent to the Naval Station is Fort Zachary State Park -- a real gem.
There are no great beaches on Key West. This might come as a surprise. The largest beach is Smathers Beach that runs along the southern end of the island. As a public beach, it gets a lot of activity but it's usually filled with seaweed and the facilities are not well maintained. It's also very windy and so works better for kite-boarders and such. I suppose it's fine to throw down a blanket and get some sun on the days when the seaweed stench is not too bad, but if I arranged my trip with the expectation of a lot of beach time and a was thrust on to this beach, I would be furious. There are mid-range hotels here that do just that. Beware of any properties on the southeast side of the island.
In contrast, the beach at Fort Zack ($2.50 admittance for foot or bike) is clean and well maintained and quite picturesque amid rocky outcrops. In the water the bottom is rocky, so it lacks the gentle appeal of the beaches on the Sun Coast, but it's still a terrific place for a swim or a cookout. Apart from the small, privately maintained strips of beach at some of the high-end resorts, this is the best spot on the island to enjoy the sand and sun.
There's more to Fort Zack State Park than the beach, however. There are a number of nature trails that are popular with bird watchers, and then of course, there is the fort. It is exactly what you would think an old fort would look like: An enormous trapezoidal structure of thick concrete and brick walls, with turrets and a courtyard (more correctly: parade grounds) and cannons and all that stuff out of 19th century war films. It a nice little bit of history and a pleasant little bit of exploration. The turrets themselves are accessible via old stone spiral staircases and provide sweeping views of the point where "the green of the Gulf meets the blue of the Sea" as Jimmy Buffet says.
As far as this trip goes, on a more personal level, I drank a lot. I never got drunk, but a bellini at brunch, a couple of cocktails poolside in the afternoon, wine with dinner, and nightcap or two before bed, was not unusual. I have written before about how I am generally happier person when I drink, but I don't allow myself because of expense and calories. But what the hell, I was on vacation. And so was everyone else in Key West. What lingers from a vacation at the end of road is just that: Casual slices of happiness; carefree moments of sunsets and sea breezes; al fresco cocktails and friendly fellow tourists; lizards at the pool and roosters on the road; disappointment that it has to end and gratitude for the time you had. We go back to Jimmy Buffett:
It's flashback kind of crowd
It's a cabaret sound
There's still some magic left
In this tourist town