If you’re looking for a fun and delicious way to spend an evening in LeFleur East, a progressive dinner at Highland Village is the perfect answer. With a mix of casual and upscale spots, Highland Village offers a walkable dining experience where you can sip, snack, and savor your way through some of Jackson’s best restaurants—all without ever getting in the car. Here’s your step-by-step guide to the ultimate Highland Village progressive dinner.

Start with Frosé in the Courtyard at Aplos

📍 Aplos – Highland Village

Kick off your evening with a refreshing frosé at Aplos, Jackson’s go-to spot for Mediterranean-inspired fare and relaxed outdoor dining. Grab a seat in the courtyard, where the string lights and bustling atmosphere set the perfect tone for the night ahead.

🍹 What to Order: Frosé—chilled, slightly sweet, and the perfect way to ease into the evening.

Craft Cocktails and Sushi at Tuk Tuk Boom

📍 Tuk Tuk Boom – Highland Village

Next, head over to Tuk Tuk Boom for a creative cocktail and some seriously good sushi. The sleek, modern vibe makes it a fun stop for drinks and a light bite before dinner.

🍣 What to Order:

• Volcano Roll – Spicy tuna and cucumber inside, topped with tuna, avocado, kabayaki sauce, and sesame seeds. A flavorful combo with just the right amount of heat.
• Craft Cocktail – The bartenders here know their stuff—ask for a recommendation based on your favorite spirit.

Wine and Small Plates at Bravo

📍 Bravo! Italian Restaurant & Bar – Highland Village

Mosey upstairs to Bravo for a glass of wine from their extensive list and a couple of shareable plates. If you’re looking for a laid-back experience, grab a seat in the lounge—Bravo’s bartenders are some of the best in Jackson, and the easygoing atmosphere makes it a great spot to linger.

🍷 What to Order:

• Antipasto Plate – A perfect mix of cured meats, cheeses, olives, and roasted vegetables.
• Grilled Portabella – Served with roasted red bell peppers, white bean hummus, and crostini—earthy, creamy, and satisfying.
• Glass of Wine – Ask for a pairing suggestion—Bravo’s wine list is one of the most thoughtfully curated in town.

End with Buttercrunch Cake on the Patio at Char

📍 Char – Highland Village

Cap off your evening with a decadent dessert at Char. The patio is the perfect spot to unwind and savor the final course of the night.

🍰 What to Order:

• Buttercrunch Cake – Layers of rich cake, crunchy toffee, and creamy frosting—there’s a reason it’s famous.
• Coffee or After-Dinner Cocktail – Keep it classic with an espresso or finish strong with a nightcap.

Make It a Night to Remember

The beauty of a progressive dinner at Highland Village is that it feels effortless. Each stop offers a new experience, from laid-back cocktails to refined small plates and indulgent desserts. Take your time, savor the flavors, and enjoy the stroll through Highland Village’s charming hallways and courtyards. This is LeFleur East at its finest.