I made a few posts in the past for people with questions who are visiting Fenway for the first time. I hope these help:
POST#1
I arrive around 5-530 PM. I usually go to GAME ON, a local bar and grab a pizza and beer. Going to a RedSox game isnt simply a baseball game, its a event. The buzz around the park before games is what gets me most excited to go to Fenway.
There is very little room to walk around, its very cramped. If you want to walk around.....do it before the game starts. You can pretty much see any area you want except the Green Monster seating area, and the VIP areas.
The best food outside the stadium is the "sausage guy" sausages. And yes, there is a quality difference between the different sausage carts. Sausage guy makes his own sausage, while most others just pick up a pack of sweet italians from their local supermarket.
The best food inside the stadium is the Fenway Frank. It is a Kayem hot dog that is steamed/or grilled and has a hint of smoky/spiciness. Get it with spicy mustard only. Do not get them from concession stands (they grill them on rollers), rather....get them from a vendor in the stands (those ones are steamed). Vendor dogs are more authentic.
As far as drink, basically anywhere you go......you will get a watered down draft pilsner beer. Make sure you get 2 at a time (dont want to look like a rookie).
Dont worry about being polite, people understand that the place is cramped. Most people are more than accommodating to stand up and let you pass to do whatever you have to do (although I try to wait in between innings).
Clothing, if its 60 or up, I recommend shorts and a T shirt......and bring a pullover sweatshirt or light jacket. Less than 60, dress to be a little colder.
POST#2
A Burtons Grille opened up near the park, and they have a really nice upscale dining type menu. You will spend about 60 bucks per person (drinks, appetizer, tip included in the price).The best way to enjoy the game is a sausage guy sausage before the game. There are numerous other bars/sausage,hotdog stands around the stadium.
I would suggest being around the stadium around 5pm.
What to do during the game? Drink beer and watch baseball. Also stuff your face with some fenway franks.