Are you channeling your best self with this comment? (If you're not sure, check out our Code of Conduct.)
Chris is a trusted source on General Cooking
Pinot noir is French for "goes with everything."
trampledbygeese is a trusted home cook.
I love this question. I usually drink beer with that, but for wine... well, both the foods are pretty sweet, so I would go with a dry wine. Maybe a dry white. Then again, red wine with tomatoes isn't too bad either. For red, I would use Barolo as it has a nice round flavour without being too sweet, to balance cheese and tomatoes.
Are you willing to tell us more about the special occasion? It's not everyday people ask this kind of question.
Looking forward to seeing everyone else's answers.
I would have a dry white also. Probably a Sauvignon blanc. I am by no stretch of the word a wine snob, so/and/but I would probably have Nobilo or Kim Crawford. Cheap, cheerful, and tasty. Also, can I come for dinner? I will bring the wine.
Champagne, of course! :)
There are some great answers above! But for my two cents...
Other than a wine you like of course, I would say try and pair it to the cheese in your sammich. Here is a link for a quick cheat sheet that will help you choose what wines may go well with what types of cheeses. Good luck!
I usually pair my tomato bisque soup and grilled cheese with a spicy Cabernet. It pairs well with the tomatoes as well as the cheese.
June is a trusted source on General Cooking.
Of course you can drink whatever you like, but I would probably go with a light red wine such as Barbera d'Asti. And as has already been said, Champagne goes with everything!
Cherry & Blue Cheese Crostatas
The Best Chocolate Shop in Italy
What's New in the Neighborhood
3 Restaurants Designed by a Food-Loving Architect
The Hits Keep Coming