Preheat the oven to 350°F and adjust one of your oven racks to the top third of the oven.
Cut tomatoes in half and place 1 pound in a bowl, set aside.
Gently toss the other pound of tomatoes in a bowl with the olive oil, maple syrup, and salt. Arrange them in a single layer, cut side up, on a rimmed baking sheet.
Bake until the tomatoes shrink and start to caramelize around the edges, about 45 minutes. Set tomatoes aside to cool for 30 minutes.
Gently toss roasted tomatoes, fresh tomatoes, cucumber, feta cheese, onion, vinegar and basil in large bowl. Sprinkle with sea salt and ground pepper to taste.
Notes
I love feta in this salad, but you can keep it dairy-free/vegan by omitting the feta or using dairy-free feta