So now I'm going to do that which I never do which is I am going to try to be a tour guide. Let me get the caveats out of the way first. This is my view of a good day in Key West and you are entirely free to disagree, or better yet add useful suggestions. There are tons of things to do in town, lots of museums and attractions and I am just going to highlight a few, so don't go all postal on me and get pissed off that I didn't mention your Aunt Muriel's favorite martini bar. I have limited myself to Key West and Stock Island because most of you stay-at-homes don't come here to drive, though frankly I'd make a beeline to Sunshine Scooters on North Roosevelt, rent a Harley and bugger off up the Keys for a look at some other islands if I were visiting. We'll let that be for a another time. I recommend renting a scooter because they are more fun than a bicycle (down people, stay down), but a bike is fine if infernal combustion is too much for your vacation. Do not rent an electric car they are too slow to be fun and are awkward to park. You may have to modify the start of your tour if you don't have a scooter, or if you rent a scooter that doesn't allow Stock Island tours, and you feel like being honest and following their rules. Here goes nothing, and someone suppress the peanut gallery for me please.
Some people like to watch the sunrise from the White Street Pier and in winter the place gets positively crowded. I would go to Dead Man's Curve near the Key Ambassador hotel. It has that informal name because before they put fencing in place a few smart people, including motorcycles ridden by the imprudent, had a tendency to kill themselves running off the road into the water. http://conchscooter.blogspot.com/2009/09/sunrise.html All that notwithstanding it makes for a good place to watch the sun come up and you will usually see a tripod or three as eager photographers gather to capture the rising of the sun.
However you are here because you got up early left your hotel on your scooter (or bicycle) and rode here to see the sunrise on your way to:
The most authentic local's place left south of Mile Marker Five, El Mocho, Stock island's most secret Cuban diner. To eat here is to be among Spanish speakers, fishermen, construction workers, body shop techs and plumbers carpenters and manual laborers. http://conchscooter.blogspot.com/2008/10/el-mocho.html You want local? Look for the little red diner on Maloney Avenue and my phone has it in its GPS so in keeping with my tradition of unhelpful bloody mindedness you can find your own way there from here...and here is the el cheapo breakfast, yours for five bucks though you might prefer grits to the fried potato bloc. Grits is good. Cheese grits is better.
After breakfast and maybe a second con leche if you are feeling expansive you will proceed down Maloney, turning right at West Marine onto 4th Avenue then turning left on Front and riding all the way to the end. This ride gives you a view of the less luxurious accommodations available to the working classes that serve Key West and keep fashionable Old Town humming.http://conchscooter.blogspot.com/2010/09/downtown-stock-island.htmlWhen you get to the end of Front Street you will see the thatched roof of the Hogfish restaurant which hipster tourists think is off the beaten track but you have beaten them out of the ball park by having breakfast at El Mocho. Go for a walk on the docks and around the back. There are real life artisans here in their workshops, quaint floating homes and a sense of waterside peace and serenity you won't find elsewhere in these busy end-of the-road islands.
You can spend some time on Stock island if you want to check out the working classes or perhaps buy an illegal fighting rooster at Bernstein Park if any of the local kids have caught a rooster on their travels and want to unload it. On your w ay back to key West check out Hurricane Hole on the south side of Highway One just on the Stock Island side of the bridge into Key West. You could come back to Hurricane Hole for a drink in the evening if you want a waterside meal away from the sunset crowds.
On your way to the cemetery if you take scenic South Roosevelt you will pass the East Martello Tower which is a fine little museum exhibiting some interesting connections to Cuba with Key West. And if that tickles your fancy head down or up Flagler to the area of 7th Street where you will see a walk in clinic which marks Government Road which heads south off Flagler to Little Hamaca Park. Government Road is in my GPS and runs behind the airport where a Cuban airliner is parked after it was hijacked to the US, confiscated and sold to a Cuban American family with a claim against the Castro government. Here it sits apparently forever:
Well that's one curiosity out of the way and if you can avoid riding to the end of government road to check out the old cold war Hawk Missile sites http://conchscooter.blogspot.com/2010/03/hawk-missiles.html you can keep on going to the cemetery in the middle of the island. I love this place and you should too. It's the best park in the city and all it requires is some peaceful contemplation from you and a modicum of respect for the dead and their families who still live in town.
If its getting late you could reverse the next part of the program and go to Fausto's on Fleming first or to Five Brothers a couple of blocks north of the cemetery on Grinnell for a genuine Cuban sandwich and perhaps some bollos (boy-ohs) deep fried black eyed pea balls like falafels, or perhaps a papa rellena, a ball of deep fried mashed potato with ground beef in the middle, a kind of Cuban scotch egg. Buy that and find a shady spot in the cemetery and commune with the dead. I like to think they appreciate the company of the living. There's a lot of Key West history buried here above ground. http://conchscooter.blogspot.com/2013/03/famous-dead-people.html
Fausto's Food Palace has two locations, one on White Street and one on Fleming just off Duval as though to emphasize the insularity of people who live on a four mile island but won't travel a dozen blocks to buy groceries. My wife likes to buy small containers of seaweed, antipasto, olives, octopus, and humus for instance.
Fausto's bills itself as a social gathering place but it is a supermarket on a small scale or a convenience store on a large scale.Faustos Key West | Store Departments boasts tons of yuppie foods, exotic spices, expensive labels and real butchers cutting up meat in the back, the place where you are as likely as not to see the owner doing physical labor despite his standing as a former mayor and current city commissioner.
With picnic in hand the next stop is the Art and History Museum on Front Street in the former US Customs House. http://conchscooter.blogspot.com/2012/09/key-west-art-and-history-museum.html I love this place and you will too if you want to learn about small town key west's history, its attachment to Hemingway and local Art. Do not miss the Customs House and across the street you will see the Mel Fisher museum which I also greatly enjoy.
One hopes the picnic hasn't overheated because from here you will ride down Whitehead Street to Petronia and from there you will ride west to Truman Waterfront and seek out the Fort Zachary Taylor State Park where you will rest in the shade of the pine trees (casuarinas) saved from destruction as non native trees whose shade is much appreciated by locals. There is good swimming off the beach and a concession stand that sells hot greasy food if the delicacies from the deli at Fausto's are too esoteric for your sturdy pizza enflamed taste buds.
I have my favorite picnic table at Fort Zach hidden in the shade of the sea grapes flourishing near the fence that divides the park from the Navy base at the beach. Any picnic table will serve the purpose. Walk the fort later and the nature trail, a short lesson in native flora that I forget as soon as I have walked it. If you have done a good job of whiling away the day it will be close to sunset and most people I know avoid Mallory Square unless they have out of town visitors who have never seen the fair at sunset before. Now that the Top on La Concha is slated for destruction, the bar to be replaced by a spa (!), the most votes for sunset viewing go to Truman Waterfront, unscripted, unsupervised and sparsely attended. Here's your own spot to enjoy the sunset:
Up stairs at Turtle Kraals is Shannon's favorite spot for un-obscured viewing across the water in civilized surroundings with a drink in your hand. This is the view from ground level but upstairs is really much nicer.
The other great spot is rather eccentric but that's what you are looking for right? Ride to the top floor of the city parking garage at Grinnell near Caroline (close to Finnegan's Wake coincidentally) and from there you will probably be alone, unless there is a wedding in progress, and now I shoot myself as a gentleman does, for giving away the secret local sunset viewing spot, Key West Diary: Park And Ride. Just like this feathered rat:
Santiago's is my favorite romantic dinner place at the moment, tapas, wine and impeccable service make for value for money.
I like Finnegan's Wake a no nonsense Irish pub spoiled by too many television screens but made good by Boddington's and Smithwick's on draught. And an Irish breakfast plate to die for. And strawberry shortcake and custard. I am a pig.
So, there you have it. On the subject of eating out you could have Indian food on the terrace at the Pegasus Hotel, on Southard overlooking Duval Street. Or have a proper sit down dinner at Café Sole on Southard Street. Or spend a fortune at Latitudes on Sunset Key (better to have a very reasonable lunch there if you feel like lounging). There are too many suggestions. Or go for a ride on your motorcycle.
So now if you feel like putting me straight please go back and read the first paragraph again, okay?