Key West is a great place for a cigar adventure. I gotta tell you that the quality is all over the place. The real treat is going from shop to shop and meeting the rollers and puffin' as you go.
Go to cigargroup.com and look in the regional listings for Florida.
Hopefully there is still a listing of all the cigar places in the Key West. If not, stop at a tourist info place or the Chamber of Commerce and they will turn you on.
I think the last time the Mrs. and I where there we went to six different shops and loved every minute of it.
If you like cold beer and atmosphere, do not miss Captain Tony's
Bar. You can go to all the tourist places like Sloppy Joe's and the Hog's Breath, but you will find no finer bar in the USA than Captain Tony's.
Don't miss the Conch Train tour if you've never been there before.
Sure it's touristy, but you get the whole feel of the island pretty quick. It's a good way to get your bearings. Smoke a fatty down at Malory Dock at sunset and witness the spectacle of the sunset.
It's people watching at its best.
Oh, and don't miss Louie's Backyard for dinner or just drinks.
Enjoy, I'm so friggin' jealous!!