Highland Village makes a progressive dinner almost too easy. Casual spots and upscale ones sit close enough together that you can sip, snack, and work your way through some of Jackson’s best restaurants on foot, no parking lot required twice. Here’s how to do it right.

START WITH FROSÉ IN THE COURTYARD AT APLOS

Aplos – Highland Village

Start at Aplos, Jackson’s spot for Mediterranean inspired food and an outdoor courtyard that knows what it’s doing. Grab a seat outside under the string lights and let the evening get rolling.

What to order: Frosé. Cold, a little sweet, and a solid way to ease into a long evening.

CRAFT COCKTAILS AND SUSHI AT TUK TUK BOOM

Tuk Tuk Boom – Highland Village

From there, walk over to Tuk Tuk Boom for a cocktail and genuinely good sushi. It’s a clean, modern space, the kind of stop that works whether you’re easing into dinner or just stopping for a drink.

What to order:

• Volcano Roll: spicy tuna and cucumber inside, topped with tuna, avocado, kabayaki sauce, and sesame seeds. Enough heat to notice, not enough to ruin the rest of the night.
• A craft cocktail: the bartenders know their craft. Tell them your usual spirit and let them take it from there.

WINE AND SMALL PLATES AT BRAVO

Bravo! Italian Restaurant & Bar – Highland Village

Head upstairs to Bravo for a glass of wine and a couple of shareable plates. The lounge is the move if you want to settle in for a while. The bartenders are among the best in Jackson, and nobody’s rushing you out.

What to order:

• Antipasto Plate: cured meats, cheeses, olives, and roasted vegetables. The kind of plate built for sharing and slow conversation.
• Grilled Portabella: served with roasted red bell peppers, white bean hummus, and crostini. Earthy, creamy, satisfying.
• A glass of wine: ask for a pairing. Bravo’s list is one of the most thoughtfully built in town.

END WITH BUTTERCRUNCH CAKE ON THE PATIO AT CHAR

Char – Highland Village

Finish at Char, where the patio is built for exactly this kind of ending.

What to order:

• Buttercrunch Cake: layers of cake, toffee crunch, and creamy frosting. It’s famous around here for good reason.
• Coffee or an after dinner cocktail: an espresso to keep it simple, or a nightcap to finish the night the way it deserves.

A NIGHT WORTH REPEATING

A progressive dinner through Highland Village works because it doesn’t try too hard. Each stop hands you something different: easy cocktails, thoughtful small plates, a dessert worth the walk to get there. Take your time. Let the courtyards and the evening do the rest. This is LeFleur East doing what it does best.