take a day or two here as part of the trip, I might be able to help you out with a good/great rate. I can definitely set you up right in the bar/fishing entertainment world here. Those are the two choices - drinking or fishing - or both. So... that's 3 choices maybe? - (hmmm...note to self for a new hot selling T shirt). Anyway...It's a small town, I get out of the house regularly, and tend to be annoyingly outgoing, so I know lots of people - admittedly, to the detriment of most. You needn't feel obligated to become another victim, should you choose to stay here.

As for Cayo Hueso/Key Weird/Key West...I have a few tips. First, you mention driving - that is likely going to cost you. Most hotels (in the spots I would want to stay, anyway) are pretty much converted groups of houses, with a pool, that have little to no parking. Some may have limited spots, first come/first serve. You could stay at places WITH parking, like the Holiday Inns and Marriotts on the far east side of the Island as you come in, but that is 3 miles from where you likely want to be. Street parking is not happening, unless you find a meter situation (well....more on that later). But if you are OK with paying, you should easily get a spot in a city garage that time of year - can't say the rate, though, but you can pay daily or hourly.

(Before I forget - ask if the hotel has resort fees, too. They really suck - and I would not book there out of principle. Not all have them do - mine doesn't. So...parking and resort fees are key questions.

Next, October is really not a hopping month. Kids back in school, no bad winter weather anywhere...we (gloriously) have the place to ourselves right now after Labor Day (part of the reason they invented Fantasy Fest - after Halloween, I think. Had to drum up business). So when you make hotel reservations - especially a "boutique" style hotel, which I recommend, call the hotel DIRECTLY. Don't use Travelocity etc. Be nice, be friendly - but not too chatty - and say you are "thinking about" coming down, "spur of the moment", you wonder if they have any specials?, could they throw in a week long parking pass at the Key West garage?, "I'm really worried about the parking situation" (lots of hotels pay for passes and have them for just such a situation). And the clincher (or the "stick", maybe) ---> "Would I get a better deal going through Hoteltonight or booking with you RIGHT NOW?" Of course, as a savvy traveler you have already checked hoteltonight and know full well what their discounted rates are (right?...well, if not, you know the drill now). And of course, don't forget to say it may be better to call back tomorrow/discuss it with your wife/blah,blah if they don't come up with a deal (you basically threaten to spit the hook). It's the "walk out of the car dealership" move. You really can make deals easily if you are nice and get the right person on the phone. But it's also possible to get someone that really doesn't care one way or the other if you come - that's why you have to be nice and charming - they may be nice/give you a deal solely because YOU are nice. If you don't get anywhere, it may be best to ask to speak to a manager - someone with some skin in the game. They should cough up some deals pretty readily.

Wrapping up the novel now, haha...

When I go to KW, I like to stay within walking distance to the Historic Harbor. That's close to "Lower Duval" which is on the NORTH end. "Upper Duval" is the SOUTHERN end. You want to be "within walking distance", NOT right on Duval, unless you are a Zombie that requires no sleep. I like Westwinds on Eaton Street (they give me a parking pass). I also love Half Shell Raw Bar, just a few blocks away. EVERYTHING is touristy, but they at least make an effort to be a real bar - and I've managed to make Joe, a bartender there, consider me a semi-annual regular. He's got a great memory. But in this area (Eaton ST) you are also "walking close" to all of the famous bars you've heard about - Sloppy Joe's etc., and Mallory Square.

Upper Duval...the south end...the Marina district, has real beaches (with sand and everything - a Keys rarity), fishing pier, it's less wild...if that is your cup of tea? I might recommend Papa's Hideaway - but it's been years since I stayed there. But if you stay there or not, you can park free there, out in front of their gate on Louisa Street. It's a little dead end street with no "No Parking" signs that Papa's uses for guests. But it is a public street, so anyone can park there - and it has no restrictions like "need resident sticker" stuff that you see everywhere else - it's my secret spot, so hush up. It's only 2 blocks from Duval, so if you just want to take a Duval stroll some afternoon - a mile "down" and a mile back...I've done it many times. I also highly recommend, to really enhance the ambiance, getting a nice, big, brown bag beer at some market/drugstore along the way. Aaaah...so liberating. Only other place you can walk the street with a drink in the US is Vegas, that I know of, anyway. I've done it Europe and Central America, sightseeing/putzing around - don't know why I like it so much...
OK...yeah, I do...I lied...it's all about #efftheman! haha.

Anyway...enjoy! Hope that helps. Any questions, feel free.