Hi Robert,
I think you’ll find things have gotten even better since your last visit. I doubt you’ll recognize the building! But lots more Burgs, and a wider range of styles, etc.
I did open a Champagne Bar in Westport called Ca Va (and yes, people call it Cava all the time). I’m not there every night, but please let me know if you’re interested. Lots of grower Champagne and other interesting Euro fizz (and some West Coast goodies as well). We have small plates, so we’re not really a dinner destination per se.
Plaza its tough for me to recommend anything right now, especially with Starker’s gone and JJ’s not yet reopened after the fire.
Lots of stuff in the Crossroads. Michael Smith/Extra Virgin has really good food and list. The former is more formal, the latter is more creative tapas. I prefer the latter experience. The Rieger Hotel has amazing cocktails, and the Chef is one of my partners in Ca Va. Howard was a Beard semi-finalist this year. Affare is another good choice - a very creative take on German cuisine, and Katrin does a great job with the list. Lots of German, Austrian and Northern Italian stuff. Grunauer is a good Austrian choice nearby. Tannin is a great wine bar. There’s another place nearby called Novel that is excellent run by a guy who worked for David Chang and has a very AFWE wine list.
Bluestem would be my dinner pick in the Westport area. Port Fonda is amazing Mexican, but a lot of people find it too hipster. I don’t.
As a disclaimer, I am friends with a lot of people who own/work at the places mentioned.
As to BBQ, Oklahoma Joe’s is pretty awesome, but in a weird way, it has become overrated at the same time. Gates is close to the same quality with a fraction of the wait (seriously, it’s like 90 minutes for takeout at Joe’s - it’s good, but it’s not two hours wait-in-line good). I would also recommend LC’s for just about anything - it’s a hike East of the Plaza, but worth the drive. It can be busy, but not two-hours-wait busy.
Let me know when you’re headed this way!