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Aug 31, 2010
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Wine With . . . The Ultimate Grilled Cheese and Tomato Sandwich

by Paul Lukacs and Marguerite Thomas

It all started with a bountiful crop from our Ranch in the Sky, otherwise known as an urban rooftop garden.  Last summer the infamous tomato blight took its toll, but this year the vines kept popping out red, yellow, and purplish-green tomatoes faster than we (along with help from our neighbors) could consume them.  So all July and August we’ve been feasting on tomato salads, soups, fresh salsas, and of course tomato sandwiches.   

We’re big fans of the simple but classic tomato and mayonnaise sandwich, and have been eating plenty this summer.  But as the bounty continued to roll in from the roof garden, we began to make increasingly complex delicacies -- adding a handful of arugula here, slices of fresh mozzarella there.  Black olive tapenade and anchovies put in an appearance; so did anchovies, basil leaves, chèvre cheese and more.  By the time the season peaked a couple of weeks ago, our gastronomic experiments had culminated with what we’ve termed the Ultimate Grilled Cheese and Tomato Sandwich.  This mouthwatering extravaganza includes cheese, bacon, basil, caramelized onions, and of course ripe tomatoes. 

Not only do these toothsome sandwiches make for a great late summer supper, they also turn out to super wine partners.  While we’ve enjoyed both reds and whites with them this summer, we weren’t sure which wines really work best.  So with clear evidence that fall is approaching, we invited our friends Rick and Rebecca to help us find out, and to savor some of the last of the tomatoes clinging to our now weary vines.

Ultimate Grilled Cheese and Tomato Sandwiches  

(Serves four)   

Good quality sharp cheddar is the classic for grilled cheese sandwiches, while Gruyère makes a sandwich reminiscent of a French Croque Monsieur.  We often use a blend of both.  Grated cheese melts more evenly than sliced, and a non-stick skillet works best.  You may have to cook the sandwiches in batches and keep them warm in the oven if you don’t have enough skillets.

1 loaf good quality white bread, sliced

About 4 tablespoons butter, softened

About 4 medium  tomatoes

1 pound cheese, such as cheddar and/or gruyère

1 pound bacon

1 large or 2 medium onions, very thinly sliced

1 bunch basil

2 tablespoons olive oil

2 teaspoons sugar (optional)

1 teaspoon red or white wine vinegar

Generously butter one side of each of the slices of bread.  Slice the tomatoes and salt them lightly.  Grate the cheese.  Cook the bacon until it is fairly crisp, and spread it on paper towels to drain the grease.  To caramelize the onions, cook them slowly in the olive oil over medium-low heat, stirring frequently.  To help them brown, sprinkle on a little sugar.  Raise the heat if necessary, but do not let them burn (the whole process may take up to 20 minutes).  Stir in the vinegar. 

To assemble the sandwiches, sprinkle the cheese over the unbuttered side of half of the bread slices.  Top with the tomatoes, a spoonful of onions, the bacon, and two or three basil leaves.  Place buttered side down in a skillet and top each one with a slice of bread (buttered side up).  Cook over medium to medium-low heat until they are golden brown on the bottom side.  Press the sandwiches lightly with a spatula; then flip them carefully to cook the other side.

  t   t   t 

We found that a wide variety of wines worked well with our “ultimate” sandwiches.  The only ones that didn’t were some whites that simply proved too light and delicate.  You’ll find lots of competing favors in every bite of this supper (salty bacon, pungent cheese, zesty basil, sweet onions, etc).  As a result, the wine you choose has to have enough gumption to hold its own.  Don’t worry about tannins with reds; they won’t prove disruptive.  And unlike many dishes we try for this column, the sandwiches seem to like the smell and taste of oak.  We ever so slightly preferred the reds we tried over the whites, but some full-bodied whites worked very well.  On a hot summer or early autumn evening, they will have the added advantage of being cold so refreshing.   



Approx. Price




 Bonterra, Mendocino/ Lake Counties (California) Cabernet Sauvignon 2008






This full-bodied red in no sense overwhelmed our “ultimates,” and its dark fruit character made the sandwiches seem even more substantial than they might have otherwise.



 D’Arenberg, South Australia (Australia) Grenahce/ Shiraz/ Mourvèdre “The Stump Jump” 2008 (Imported by Old Bridge Cellars)




Very juicy and full of exuberance, this unabashed Aussie was just plain fun to drink with the sandwiches.  Much as with the Bonterra Cab, it’s dark fruit character was a real plus.



Gabbiano, Chianti Classico (Italy) 2007 (Imported by FWE Imports)







This wine offered a different sort of pleasure, as it displayed more earthy, dusty flavors (as opposed to those echoing fresh fruit).  That profile proved appealing because it so clearly complemented the bacon.



Hugel, Alsace (France) Pinot Gris “Classic” 2006 (Imported by Frederick Wildman & Sons)






Juicy and rich, with a hint of sweetness, this wine had just enough body to work with these sandwiches.  Its ripe pear character seemed to enliven the match.







Valley of the Moon, Sonoma County (California) Pinot Blanc 2009






A full-fleshed wine, showing some oak character, this Pinot Blanc was a consensus favorite.  Its autumn fruit flavors and vanilla-tinged finish made the tomatoes in the sandwich taste especially vibrant.