All, your feedback has been extremely helpful and we have made some modifications based on your responses. We are going to try Bistro Jeanty for dinner Thursday and keep REDD and Botega for Fri/Sat.
Regarding vineyards, I agree we may be stretching ourselves thin on Saturday, so we are going to forgo the Pride/Barnett/Spring Mountain area and instead spend our time in the St. Helena region. One couple in our group is absolutely set on Cakebread, so we are going to start there and then work our way over to O’Shaugnessy. With that in mind, any suggestions for a vineyard to visit between these two locations? We’d prefer to do something smaller, more intimate with great wine. Any additional suggestions are greatly appreciated!
Still a good hike from Cakebread to O’Shaun. Right next door to O’Shaun. is Cimarossa. A fun and intimate tour and some excellent wines. You will be right next door to your appointment. Others nearby I would recommend are Arkenstone and down on the floor, Mending Wall.
There are ton of wineries between Cakebread and O’Shaugnessy. What are you looking for? Mark is right, though, it’s a hike. Build in more than the 1/2 hour it will say on Google Maps. Deer Park Rd. isn’t a bad road, but the roads off it are small. I haven’t been to O’Shaun, but the views from Howell Mtn. are awesome. You’ll love it.
Cook in St. Helena is a good little place for lunch depending on your timing and how you’re going. You can also be passing Taylor’s if you want and that is an experience as referenced in the thread.
Seavey would be a good choice for a more intimate spot between Cakebread and O’Shaughnessy.
What experience? The experience of a shitty burger joint that every town has? I really don’t get the appeal of this place. If you’re in the culinary mecca that is Napa Valley, why go there?
Culinary Mecca might be pushing it…
Because I live near the culinary mecca that is NYC, and although it’s been a few years since I was in Napa Valley I haven’t seen a place like Taylor’s with the food/beverage/location on Broadway or 6th Avenua or anywhere else in NYC. Papaya King just doesn’t have the same vibe .
You could make the same argument about going to Cakebread. Hey, I would rather go to Cook (which I recommended), but sometimes you just need to do the tourist-y stuff. I get it. There’s lots of places we don’t go in NYC until someone comes for a visit. Sometimes it’s fun, sometimes it is to check the box.
Cakebread makes solid wine and has stuff you can’t get outside the winery, while there may be more ‘exciting’ or ‘exotic’ wineries I don’t think it’s a great comparison. Plus one of my best friends is a Cellar Lead there 
If I go there, it will be to Stag’s Leap.
Yes!!! That’s the one! THE TODD
Because you want to sit outside in glorious weather eating a delicious ahi tuna steak sandwich, washed down with a mint confetti shake. I think it’s a nice change of pace. You’re in a great culinary place, but it gets a little tiring and heavy to mash down 4 course meals twice a day for 3 days straight just because you can. Even just resting outside in the little hub of St. Helena and doing some people watching is pleasant, and if you wise up and order online before you get there you don’t have to wait in line for 40 minutes for your stuff.