Your day-by-day plan
- 1
Harbor Circuit
Morning:Sleep. This itinerary respects the craft.
Breakfast & coffee:Don Cha Peruvian Food
Afternoon:Late brunch, a recovery beach hour, first oysters at Boshamps.
Breakfast & coffee:The Cone Ice Cream and Coffee
Evening:The classic crawl: live music at AJ's upstairs, gumbo-and-a-band grit at Hurricane Oyster Bar & Grill, late food and a wall of screens at Tailfins. Summer nights add fireworks over the water.
Dinner:Outcast Seafood
Insider Tip:Music on the harbor skews earlier than city hours. Bands often start at 6, so the crawl begins at sunset, not 10 pm.
- 2
Baytowne Night
Morning:Sleep in; hydrate.
Breakfast & coffee:Seacrest Sundries Market
Afternoon:Pool and nap, professional pacing before the main event.
Evening:The Village of Baytowne Wharf: dinner and a set at The Village Door (waterfront BBQ and seafood by day, an award-winning dance club after dark, running till 2 am on weekends), dueling pianos at Rum Runners (Thursday-Saturday), and dockside bands at Hammerheads on the bay. Summer Wednesdays add the free 7-9 pm concert on the Events Plaza lawn.
Dinner:Crackings. - Grayton
Insider Tip:Baytowne is inside Sandestin's gates. Stay on property or budget the rideshare, because this is not a walk-home-to-Destin night.
- 3
Grayton Send-Off
Morning:Greasy-spoon recovery breakfast at Crackings.
Breakfast & coffee:Sun Kolache Donut & Bubble Tea
Afternoon:A 30A drive, a beach hour, and a pre-show dinner in Grayton.
Shopping:For the Health of It
Evening:The Red Bar: funky room, house band, the Emerald Coast's most beloved music institution. Then home before you're tempted by a fourth night.
Drinks & nightlife:Shunk Gulley Oyster Bar
Insider Tip:October's Destin Seafood Festival and January's 30A Songwriters Festival turn this whole itinerary into a festival trip. Time it right and every venue levels up.
More A-List spots for this trip
Hand-picked Destin A-List businesses that fit this itinerary — tap through for hours, photos, and reviews.
Fokker's Pub
The Grey Taproom
The Old Beach Bar
Shrimp Basket
Bayou Bill's Crab House
G.I. Jade Tiki Bar & Bistro
Local Catch Bar & Grill
Taboo Latin Club