In a saucepan over medium heat, combine vinegar, water, salt, and sugar. Heat until the sugar has dissolved and set aside.

Wash cherry tomatoes and remove the green tops.

Prick the tomatoes with a toothpick to make a small hole or make a small slit in each one, which allows the pickling liquid to penetrate and infuse them completely.

Clean your mason jar or airtight container.

In each jar add spices, herbs, and garlic if desired. Classic options include a clove of garlic, dill seed, mustard seeds, dill seeds, black peppercorns, and red pepper flakes. However, feel free to experiment and tailor the spices to your personal preference.

Place cherry tomatoes in each jar.

Pour the hot liquid over the tomatoes and leave about 1/2 headspace. Using a funnel can be very handy.

Remove air bubbles by tapping the jar gently on the counter or running a non-metal utensil around the sides of the jar. Add more brine if needed.

Allow the tomatoes to cool to room temperature and then move to the refrigerator.

Let the pickled cherry tomatoes refrigerate for at least 2-3 days before using. This is for the best flavor.