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1
Puree tomatoes in processor until smooth.
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2
Strain through fine sieve, pressing on solids to release enough tomato puree to measure 2 cups.
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3
Discard any remaining puree and solids in strainer.
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4
Add 1 cup chilled Simple Syrup and pinch of coarse kosher salt to strained tomato puree; stir to blend.
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5
Transfer tomato mixture to ice cream maker and process according to manufacturer's instructions.
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6
Transfer gelato to container; cover and freeze until firm, about 3 hours.
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7
DO AHEAD: Can be made 2 days ahead.
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8
Keep frozen.
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9
Bring 1 1/2 cups Simple Syrup to simmer in small saucepan.
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10
Remove from heat; add 3 cups basil leaves to syrup and stir until wilted.
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11
Transfer basil mixture to bowl and refrigerate until cold, about 2 hours.
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12
Puree basil mixture and 6 tablespoons water in blender until smooth.
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13
Transfer basil mixture to ice cream maker and process according to manufacturer's instructions.
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14
Transfer gelato to container; cover and freeze until firm, about 3 hours.
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15
DO AHEAD: Can be made 2 days ahead.
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16
Keep frozen.
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17
Combine ricotta cheese and milk in processor; puree until smooth.
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18
Add 3/4 cup Simple Syrup and process until blended and smooth.
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19
Transfer ricotta mixture to ice cream maker and process according to manufacturer's instructions.
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20
Transfer gelato to container; cover and freeze until firm, about 3 hours.
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21
DO AHEAD: Can be made 2 days ahead.
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22
Keep frozen.
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23
Stir 1 cup sugar and 1/3 cup water in heavy small saucepan over medium heat until sugar dissolves.
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24
Increase heat and boil without stirring until color is medium amber (not deep amber), occasionally brushing down sides of pan with pastry brush dipped in water and swirling pan, about 7 minutes.
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25
Remove pan from heat.
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26
Gently drop tomatoes into hot caramel syrup, tilting pan to coat.
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27
Using fork, quickly lift out tomatoes and transfer to sheet of foil.
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28
Cool tomatoes completely.
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29
DO AHEAD: Candied cherry tomatoes can be made 5 hours ahead.
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30
Let stand at room temperature.
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31
Pour enough vegetable oil into heavy small saucepan to reach depth of 1 inch.
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32
Attach deep-fry thermometer to side of saucepan.
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33
Heat oil over medium heat to 350F.
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34
Add basil leaves and fry just until translucent, about 2 minutes.
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35
Using slotted spoon, transfer basil to paper towels to drain.
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36
DO AHEAD: Can be made 5 hours ahead.
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37
Let stand at room temperature.
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38
Using 1- to 1 1/2-inch ice cream scoop, spoon out 1 scoop of each gelato into shallow bowls or glasses.
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39
Garnish with candied cherry tomatoes and fried basil leaves and serve.