Bring a small pot of water to a boil and reduce to a simmer.
Cut an “X” on the bottom of the tomatoes to be skinned with a sharp knife. You don’t need to cut deeply, just deep enough to cut through the skin.
Using a slotted spoon, dip a tomato into the simmering water and boil for about 10 seconds. The skin should be peeling away from the tomato where you cross-hatched it.
Remove the tomato from the hot water and allow to cool enough to handle it. Peel off the rest of the skin and discard.
This method makes sense for almost any way you plan to use the tomatoes, other than roasting them, as you’ll have a whole, peeled tomato to work with. This is the best method to use if you also want to remove the seeds.
Preheat the oven to 300° F. Cut the tomatoes in half and lightly oil with olive oil. Sprinkle a little salt and pepper across the tops and place on a baking sheet, facing up.
Roast for about 3 hours. Remove from the oven and allow to cool. The peels should slip right off.
This is a method that only makes sense if you’re planning to roast the tomatoes anyway, due to the roast time!
Cut a tomato in half and grate against the largest holes on a cheese grater until you get to the skin.
This method only makes sense if you’re planning to make a tomato sauce as the tomato will be completely broken down by the grater.