Peel the pineapple and cut into quarters. Cut out the stalk. Wrap a slice of bacon around each quarter. Fix the bacon with a wooden skewer.
Wash the cherry tomatoes, quarter them. Heat oil in a pan. Fry the pineapple slices on both sides for about 4 minutes until golden brown, then remove them. Arrange one slice of pineapple and 1/4 cherry tomato each on small plates and garnish with watercress and pepper berries.