Gather the ripest tomatoes you can find and get ready to peel ’em.
Fill a large pot with water and bring it to a boil. Also, fill a large bowl in the sink with ice water.
Cut a small ‘X” on the bottom of each tomato with a sharp paring knife and drop them into the boiling water for 30 seconds. Transfer the tomatoes to the bowl of ice with a slotted spoon. After the tomatoes chill in the bowl for a minute or two, their skins should slide right off.
Core each tomato and roughly chop them, reserving all the juice and seeds.
Next, grab the bell pepper and cucumber. Remove the stem and seeds from the bell pepper and chop into a medium dice. Peel the cucumber and reserve 1/3 for garnish. Roughly chop up the rest of the cucumber.
Next, dump the shallots, cucumber, bell pepper, cilantro, and tomatoes into the blender, and blend until puréed. Make sure to cover the lid with a towel to reduce splashes and splatters.
While the blender is whirring away, cube and de-seed the watermelon.
Once the veggies are liquefied, add the watermelon, vinegar, olive oil, salt, and pepper.Blend until smooth and adjust seasoning if necessary.
Refrigerate the soup in the blender cup for at least 4 hours and up to 2 days.
The ingredients may separate a bit while resting in the fridge, so when you’re ready to serve, stick the soup back on the blender base and blitz it again to re-combine everything. And while you’re at it, dice up the reserved cucumber.
Ladle the gazpacho into chilled cups and top with a drizzle of olive oil, cucumber, and fresh cracked pepper.