It's a while since I've been and I'm taking a buddy along to pour some margaritas down his throat and help him get over his mid-life no job crisis.
Can anyone recommend:

1. A good clean B and B that's not expensive.
2. A couple of good local, no tourist bars.
3. A couple of good, inexpensive restaurants.
4. Anything for a couple of fellers to do besides Hemingway's house ( which we intend to do as we both took a trip around his place in Cuba many years back .)
He'd probably like to go fishing as well.

Thanks in advance.

PS: What's the weather like mid-September ?

Last 2 B&B's I've stayed at were the Cypress House and Ambrosia. Not sure what your budget might be. If I had a choice of the 2 I'd take the Cypress House. Wonderful breakfast (if you don't wander out), great staff, full bar happy hour.

I love to go to Pepe's on Caroline (sit outside at the small bar), and listen to Michael McCloud @ Schooners Wharf almost every afternoon. Schooners will get more tourists than Pepe's, but no where like the Duval bars. Oh, and don't forget about the Green Parrot (especially for live entertainment at night)

What kind of food do you guys like? Pepe's has very good food, and large servings for the price (not very expensive). El Siboney (corner of Catherine and Margaret, I think) has great Cuban food. It's a little more expensive, but Blue Heaven for breakfast is a not miss if possible.

If you are moving slowly in the morning and want a neat way to see the island before you really get started, don't forget the Conch Train or Trolley. Both hit basically the same major sites, I think it's the Trolley that lets you get on and off with the pass at your leisure. I just like the train better personally. Also, check out Key West Cruise Ship Calendar to see when ships might be adding a few hundred - thousand extra bodies roaming Duval. Most cruisers seem to stay around Duval or find the closest attraction to the dock. Never gone fishing there so I don't have a recommendation about that activity.

Mid-September is mid-hurricane season. Travel insurance is a consideration, as well as checking with the B&B's weather cancellation or evacuation policies. There are some B&B's that do not give full or partial credit if you are forced to evacuate, so make sure you check on that. If there is a possibility of a big storm coming towards EYW, remember also there are limited means of evacuating. Not a large number of rentals, limited flights, etc.

Hope that helps some.

Frank

Thanks for that Frank - a couple of good ideas.
I wonder if there are any Key West-based FTers with any tips although I can understand entirely if they want to keep them to themselves.
Tourists !

Seconding a couple of drinking choices: You have to drink at The Green Parrot Bars along Caroline street are usually good. Tourists don't usually wander too far off Duval St. Schooner Wharf is also interesting.
For breakfast, although the tourists have found it and it is crowded, as stated above, you have to do Blue Heaven. Still good food and a bit of old Key West.
For the B&B, you may want to check out Simonton Court. While it is not inexpensive, it is a great B&B. Individual bungalows.

Also, are you flying in, or driving? If you are driving, there are some additional food and drinking choices.
Lorilei's in Islamarada at MM 82. Order your friend a Bushwhacker or 3. Don't drink more than 1 if you are then driving to Key West. Perhaps even stay the night in Islamorada, seeing Big Dick and the Extenders at Woody's. Stay at Holiday Isle. Great Tiki bar. Also, if you are into fishing, Islamorada is way better than Key West for fishing options.
And although touristy sometimes, Alabama Jack's on Cardsound Road is a must.

+1 for Alabama Jacks. It has been a few years since I stopped there on a drive to the Keys from Tampa. This place put us right in the mood. It must be one of those spots that Jimmy Buffet was thinking of when you wrote 'Bob Roberts Society Band' (I am now a bad Floridian since I used a Buffet reference - back the the snowy north for me).

Thanks for all the recommendations - the Green Parrot bar especially is now in my list of the best bars I've been to. Their jukebox selection alone ensures this but also it's a lesson of how easy it is to get a bar right even though it takes a lot of hard work.
The other great spot in Key West was recommended by all the locals.Alonzo's Oyster Bar right down on the harbour is doing a Happy Hour on all cocktails and appetizers from 4pm-6.30pm.Fantastic value on stuff like oysters,clams and mussels and the cocktails were the real deal too.Ideal for an early evening buzz.
Unfortunately, Holiday Isle in Islamorada was the pits. I know it was out-of-season but the place looked like a bomb site and the room was filthy.
The only poor choice in a great week down in Florida.