Kick off Day 1 with a hearty Southern breakfast at this beloved local spot. Order from their daily specials — think biscuits, grits, and classic American breakfast fare in a warm, neighbourhood atmosphere.

Step inside the stunning Florida Theatre, a beautifully preserved 1927 landmark. Explore the grand interior, check out current show listings for future evenings, and soak in the history of this iconic venue that has hosted everyone from ballet and opera to pop and jazz.

Wander Riverside Ave and browse Lady Strut Gowns — a boutique-style clothing store perfect for a bit of leisurely window shopping. The surrounding Riverside neighbourhood has charming streets to stroll and soak up Jacksonville's vibrant local scene.

Grab lunch at this laid-back sports bar and grill on Bay Street. Enjoy pub classics — burgers, chicken wings, local draft beers — in a casual, fun atmosphere complete with billiards and darts. Great for two people who want a relaxed midday meal without fuss.

Stroll over to the Jacksonville Center for the Performing Arts, a stunning modern complex housing three theaters. Browse the lobby, check out upcoming performances, and enjoy the waterfront setting on Water Street — a great way to spend a relaxed afternoon.

Head to Dorothy's Downtown for dinner, just steps from Jacksonville's core. This downtown restaurant is a great spot to unwind over a proper evening meal. Located right on E Adams St, it's perfectly positioned for a relaxed dinner before the evening ahead.

Round off the night at Jack Rabbits Live, an intimate live music venue and bar in San Marco (about 2.3 km from downtown). Catch a regional or nationally touring act in a close-up, electric atmosphere — perfect for two music lovers looking for a memorable night out. Check their schedule in advance for tonight's lineup.

Start the morning at Tulua Bistro Springfield, a top-rated brunch spot on N Main St with a stellar 4.9 rating. Grab a leisurely brunch in a relaxed setting — this highly regarded local gem is a great way to ease into Day 2.

Head out to Eartha's Farm & Market, a beloved local farm market with a 4.8 rating. Browse fresh produce, local goods, and artisan finds — perfect for travelers who love farmers markets. Note: located about 5 km from downtown Jacksonville. Open until 2:00 PM so arrive early to catch the best selection.

Swing by the San Marco Boulevard corridor and pop into Fig & Willow, a women's clothing boutique in the charming San Marco neighborhood. Browse the curated collection of clothing at a relaxed pace — great for boutique shopping lovers. Feel free to also explore the surrounding San Marco Square area on foot.

Head downtown to Indulgence Southern Bistro for a satisfying midday meal. This well-rated American restaurant on W Forsyth St is just 0.3 km from the Jacksonville city center — a great spot to rest, recharge, and enjoy some hearty Southern-inspired fare at a moderate price point.

Browse Lilly Grace Boutique, a highly rated (4.8) boutique clothing store on Hendricks Ave in the San Marco area. Perfect for boutique shopping lovers looking to pick up something unique. The store is open until 6:00 PM, giving you a comfortable window to browse without rushing.

Tonight's splurge: Cowford Chophouse, a stunning upscale steakhouse and wine bar set inside a stunning 1902 bank building on E Bay St, downtown Jacksonville. Expect high-end steakhouse fare, an impressive wine program, and a beautiful rooftop bar to kick things off — a truly special evening highlight. ⚠️ Note: This is the one planned splurge stop ($$$$), one tier above the moderate budget.

Start Day 3 at 1748 Bakehouse, a highly-rated local bakery (4.8 stars) on N Main St. Enjoy freshly baked pastries and breakfast bites in a charming neighborhood setting. A perfect, relaxed way to ease into your final day in Jacksonville.

Wind through the Historic Downtown Jacksonville district anchored near Decca Live on E Bay St. Stroll the riverfront, peek into local shops, and soak up the neighborhood vibe. A low-key buffer to rest your feet before lunch.

Settle in at The Bearded Pig for a classic Jacksonville BBQ lunch. This casual, beloved spot serves traditional smoked meats and craft tap brews, with a lively patio complete with TVs — perfect for your group to kick back, eat well, and enjoy the outdoor atmosphere.

Drive out to Pecan Park Flea & Farmers' Market (~21 km north), a massive open-air market with over 750 storefronts. Browse antiques, vintage finds, new goods, and local wares — a treasure hunt-style afternoon that's fun and unhurried. Great for boutique-style browsing on a budget.

End your Jacksonville trip on a high note at Zorbas Rooftop Bar — your one splurge stop of the day. Perched above Riverside Ave, this rooftop gastropub offers Mediterranean-inspired dishes alongside cocktails with sweeping views. The perfect send-off dinner for a final evening in the city. (Note: Price level not listed; treated as a one-tier splurge highlight.)