Your day-by-day plan
- 1
Arrive & Establish
Morning:Check-in waves; keys and parking sorted.
Breakfast & coffee:Crab Trap, Fort Walton Beach
Afternoon:Mega-provision run, room draft, fridge calendar posted.
Evening:First-night dinner in; rules, rotations, and the Venmo captain confirmed.
- 2
Full Beach Day
Morning:Reserved chair rows; sunscreen assembly line.
Breakfast & coffee:AJ's Grayton Beach
Afternoon:Games bracket, sandcastle engineering, cooler lunch.
Lunch:Barefoot BBQ
Evening:Big-table dinner at McGuire's; dollar-bill group photo.
- 3
Flotilla #1
Morning:Double-decker pontoons to Crab Island, morning slot.
On the water:Blue Crab Water Sports of Destin
Afternoon:Sandbar Olympics; back by 3.
Lunch:AJ's Oyster Shanty
Evening:Low-key night: leftovers, cards, porch.
- 4
Split Rotation #1
Morning:Golf at Kelly Plantation / offshore charter / spa unit / beach guard.
Fishing charter:Dead Fish Charters
Afternoon:Regroup at the house; catch delivered to Harbor Docks.
Drinks & nightlife:The Shrimp Shack
Evening:Harbor Docks cooks the catch for the whole table.
Drinks & nightlife:Roberto’s Pizzeria Sports Bar & Grill
Insider Tip:Two rotations mean everyone gets their pick once and nobody gets stuck on kid duty or grill duty twice.
- 5
The Rest Day
Morning:Sleep in; pancake mountain.
Breakfast & coffee:Bistrology Breakfast Brunch & Dinner
Afternoon:Pool, cards, naps; the restless bowl at Uncle Buck's Fishbowl.
Drinks & nightlife:Crush Wine Bar
Evening:Grill night; story hour on the porch becomes the trip's best memory.
Drinks & nightlife:Coyote Ugly Saloon
Insider Tip:Ten days needs two rest valleys. This is the first; Day 8 hides the second.
- 6
30A Field Trip
Morning:Caravan east; bikes in Seaside for the willing.
Drinks & nightlife:Pickle's Burger and Shake
Afternoon:Airstream-row lunch, Grayton beach hour.
Drinks & nightlife:Sammy's on the Island
Evening:Golden-hour group photo at the pavilions, then The Red Bar takes the group loud and happy.
Drinks & nightlife:Hammerhead's Bar & Grille
- 7
Split Rotation #2 (Swap Duties)
Morning:Party boat crew / shopping unit to Destin Commons / Gulfarium run with any kids in tow.
Fishing charter:Santa Rosa Charters LLC
Afternoon:Regroup; pool hour.
Shopping:Smile, Mon!
Evening:House barbecue; award ceremony for the week's fake trophies.
Drinks & nightlife:The Block
- 8
Flotilla #2 or Tiki Float
Morning:Slow start; beach hour.
Breakfast & coffee:Hardee’s
Afternoon:Second Crab Island run for the die-hards, or a group Tiki Time Destin sunset float for the mellow majority.
On the water:La Dolce Vita Watersports - Sandestin Beachside
Evening:Taco night; packing begins in theory.
Drinks & nightlife:Taco Bar
- 9
The Grand Finale
Morning:Cleanup sprint in teams, timed.
Shopping:Little Red
Afternoon:Final beach hour; showers and resort-casual assembly.
Shopping:Tillys
Evening:a sunset dinner cruise from Baytowne Marina: three decks, three courses, live band, group rates for 20 or more, and summer Tuesday/Thursday sailings end under fireworks.
On the water:Emerald Surf Water Sports
Insider Tip:The dinner cruise solves the last-big-night problem: nobody cooks, nobody drives far, everybody dances.
- 10
The Long Goodbye
Morning:Pancakes, lost-and-found sweep, staggered departures.
Breakfast & coffee:Fonville Press Market + Café
Afternoon:Last car locks up; someone always sneaks a final swim.
Family fun:Camp Watercolor
Evening:The group chat's photo dump begins its six-month editing process.
Family fun:Grayton Beach State Park
Insider Tip:Ten-day group houses justify a repeat-booking rate conversation. Ask at checkout, not next spring.
More A-List spots for this trip
Hand-picked Destin A-List businesses that fit this itinerary — tap through for hours, photos, and reviews.
Black Bear Bread Co.
George's At Alys Beach
Beach Happy Cafe
Taboo Latin Club
Bud & Alley's Waterfront Restaurant & Bar
Boss Boat Rentals 30A
Destin Party Boat Vera Marie
Island Watersports Company