So... I may or may not drink my way around the World most visits. Speaking from significant expertise (sounds better than "Disney Drunk", right? jk), here's my personal take on all of the readily available options.
Recommended Places (in general order):
-California Grill. Great option in early evening. Given the food quality, I would actually suggest starting here. Your palate will be fresher, and (while fireworks are amazing) you will get the full, daylight view of both MK and Epcot in the distance. Having wine/sake and sushi at the main bar is a common outing for me.
-Trader Sam's. Depending on when you go, you will likely have a potential wait. So, going around normal dinner time is a good option here. If you can get inside directly, awesome! If not, grab a pager and start on the patio with apps out there. Nice way to kill a bulk of the time.
-Narcoossee's. This is another nice option - more for atmosphere. If you want a little romance added, this is somewhat out of the way. It typically closes a bit earlier (10pm), so you'd want to arrive before that. And, the bar is somewhat small - so there is a bit of luck there. But, for a nice, relaxing drink and bite (including dessert), this is a good option.
-Territory Lounge (and possibly Geyser Point). Territory Lounge itself is the standard Disney hotel bar. But, it gives you the chance to take the boat from MK (or Contemporary) to Wilderness Lodge at night. That feeling of distance - and the lodge's atmosphere make it a great destination. I haven't been to Geyser Point (will be this weekend - woo hoo!) - but it seems to have a little more interesting items on the menu. This is a nice place to end the evening after the monorail crawl itself.
-Barefoot Pool Bar (Poly). OK - there isn't anything special about this place or its drinks. But, it's your source for a beverage if you then want to watch Wishes from the Polynesian's beach. If you make it into Trader Sam's early - this is a good option for the next stop (assuming timing works out). Disney Iron Chef Trick - If you want something unique, stop by Pineapple Lanai first and grab a Dole Whip. Then (if you have a bartender willing to play along), ask for either a pour of rum at Barefoot (bending the rules) or one of their cocktails with pineapple juice without the pineapple juice (less bending here). Then, add Dole Whip by the spoonful (or cocktail to Dole Whip) for a unique treat to enjoy on the beach.
-Top of the World. If you happen to be DVC, this place is supposed to be great. I'm not, so I haven't made it in yet myself!
Other Options:
-Mizners (Grand Floridian) - Atmosphere is very nice upstairs. But, the drink quality has slipped a bit here from its hey day. It's now in line with all other Disney hotel bars for me.
-Citricos (Grand Floridian) - The atmosphere here is ok, but the drinks left me a bit wanting. And, the bar is along the main walkway - so it didn't have much special about it (aside from a very few tables along the window). I would hit Narcoossee's over this if I had the option.
-Tambu (Poly) - This is a fine bar, but it's the standard Disney hotel bar, again. I used to love it when there was the old lobby and no Trader Sam's. But, given the option now (outside of rain or cold), I would just go to the Trader Sam's patio (where I think the apps are better). However, one perk, you can usually can get 'Ohana bread pudding here.
-Kona Island (Poly) - This is an ok little spot and a nice place to take in the lobby. But, outside of a somewhat interesting Kona beer flight, not a ton of interesting drinks. And, the sushi is moderate - but not great. However, not a bad option to kill time or take a break that is more food heavy. Service tends to be pretty quick. And, usually, you can get 'Ohana bread pudding here, too.
-The Wave (Contemporary) - This is an ok place. For me, it's a bit generic though. Some ok beers on draft. Decent Californian wine list. But, nothing that really jumps out for me. And, it's totally interior - so the atmosphere feels the same.
-Outer Rim (Contemporary) - This is their standard Disney hotel bar. Really nothing special IMHO. The view over the pool and lake is ok - but not amazing.
- Trout Pass Bar (Wilderness Lodge) - This actually used to be my go to when it's nice outside. Like Barefoot - just to grab a beer and sit by the pool/lake and take in Wilderness Lodge. But, it is really just their pool bar. And, I have a feeling Geyser Point is going to surpass it (much like Trader Sam's did for Tambu).
-Crockett's Tavern (Ft. Wilderness) - This is a fine little place that tends to be somewhat lively, given its surroundings. But, given its location and offerings, I'd suggest Wilderness Lodge's locales first.
-Sand Bar/Cove Bar/Oasis Bar/Courtyard Bar/Beach Bar (all) - The pool bars are all pretty standard issue, especially for drinks. There are a few unique options here and there. But, I would use them only as a stop off or excuse to take in the surrounding areas.
Have a Magical Drink!!