We are older adults, late 40's
Wine and beer drinkers, but a cocktail is a welcome diversion
We love good food and a pleasant, somewhat quiet atmosphere
Our 12 year old is often along for the ride and has a great time, too. He loves the kid's specialty drinks, especially at the Tiki Terrace.
Here's my recommendations:
Start at California Grill's Bar/Lounge early as possible. Depending on the time of year, you may get to enjoy a beautiful sunset. Have a chilled glass or two of my favorite Kim Crawford Spitfire Sauvignon Blanc with the bread basket and goat cheese ravioli app. It is the perfect way to cool-off after a warm day in the parks.
Option 1, a little off course but well worth the diversion:
Boat over to Wilderness Lodge for a very quiet drink at Territory Lounge, one of my favorite spots on property. If you are a fan of Pacific Northwest wines and/or beers and aren't fond of crowds, this is a must-do. The famous Artist Point mushroom soup is usually on the menu and I noticed that there is a wine and cheese fondue dish on the menu I'd like to try. After TL, hop on a boat to the MK and then transfer to a boat to the Poly.
Option 2: stay with monorail resorts only:
Monorail over to the Poly and get a seat outdoors at the Tiki Terrace. We much prefer this over Trader Sam's, which is too crowded and noisy for my tastes. Listen to live music, have a beautiful view or the waterfall and maybe even the Castle. Sip on a rum flight or a Dark & Stormy and eat some delicious dumplings or pork tacos. Hop on the monorail afterwards and go over to the Grand Floridian.
At the Grand Floridian, get a drink at Narcoossee's bar and take it out on the deck if it is time for MK fireworks. My favorite drink here is the Grand Martini. The splash of champagne on top makes it extra special. Another great option at the GF is getting a drink at Mizner's and listening to the band that plays in the lobby. Hop on the monorail, and go back to the Contemporary.
Depending on timing you may make it back to the Contemporary to see the MK fireworks from the viewing area, which is simply stunning. Show your receipt at the reception desk and you'll be allowed to go up as long as there's room. Stop by the bar and ask Ray (the best bartender in all of WDW) for a glass of prosecco to take outside, which is my favorite way to enjoy the fireworks.
What a LOVELY evening.