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Sarasota's Upscale Tomato and Onion Sandwich

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“This is a tomato, onion and mayo sandwich, but definitely a bit upscale. It is just so good but it does require a bit more work. I wouldn't consider making this for a quick late night snack, or quick lunch. This is something you want to make for guests. Either a special lunch or light dinner party. Serve with a bowl of fresh asparagus, zucchini, or summertime soup. Key ingredients which make this so good is; a good bakery whole wheat onion roll, heirloom tomatoes, fresh herbs, arugula and good balsamic vinegar and olive oil. This really makes a fantastic sandwich.”
1hr 15mins
4 Sandwiches

Ingredients Nutrition

  • 4 whole wheat onion rolls (if you can't find onion, that is fine. But you what a hearty stone ground or whole wheat bakery styl)
  • 2 cups baby arugula (1/2 cup per sandwich)
  • Tomatoes and Onions
  • 2 large heirloom tomatoes, you want 4 thick slices of each (I used 1 purple and one yellow, 2 different tastes, but use your favorite)
  • 1 large onion, cut in 4 slices
  • 2 tablespoons balsamic vinegar (the more aged the better, but use the best you have. A store bought is fine if that is all you have )
  • 4 tablespoons olive oil (use regular olive oil vs extra virgin if possible, if not extra virgin will be fine)
  • salt
  • pepper
  • Herb Olive Aioli
  • 8 tablespoons mayonnaise (no miracle whip)
  • 14 cup olive (1/4 cup after they are chopped. I used a mix of green, black and kalamata, I usually have a jar or c)
  • 1 teaspoon fresh thyme, fine chopped
  • 1 tablespoon fresh basil, fine chopped
  • 1 teaspoon lemon zest
  • pepper


  1. Aioli -- Chop your olive, fairly fine and add to a small bowl with the mayo, lemon zest, thyme and basil. Season with a little pepper and set in the refrigerator until ready to use.
  2. Tomatoes and Onions -- In a small pan (not metal), add the olive oil and vinegar. Set the tomato and onion slices in and flip to make sure they are covered on both sides. Let marinade 30 minutes to 1 hour. Doesn't need any longer.
  3. Grill -- I really prefer these grilled, but if not, a indoor grill pan will work. I don't think a saute pan works as well but if that is all you have, it should be fine. I sprayed mine lightly with a non stick spray and brought to medium high heat.
  4. Add the onions first as they take a bit longer than the tomatoes. But we don't want them falling apart, just some nice grill marks and then begin to soften (2 minutes per side, approximately). Remove the onions off to the side and add the tomatoes and rolls. The rolls I just like to lightly toast, they take literally just 30 seconds or so. The tomatoes, about 1-2 minutes per side. You still want them firm, not soft, but lightly grilled and warmed up.
  5. Sandwich -- Spread the aioli on both sides of the bun. I add one tomato slice to the bottom roll, then the onion, then the other tomato slice, arugula and the top roll.
  6. Serve -- A nice bowl of summertime vegetable soup, favorite potato or vegetable salad, grilled potato wedges or creamy coleslaw and you have a great light dinner.
  7. ENJOY!
  8. Note: Prep time includes the marinating of the tomatoes and onions.

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