Your day-by-day plan

1
Land, Assign, Provision
Morning:Staggered arrivals; keys and parking sorted.
Breakfast & coffee:Tailfins Waterfront Grill
Afternoon:Check-in, room draft (rock-paper-scissors for the master), then a massive grocery run with a shared cart list.
Lunch:Cafe Thirty-A
Evening:First-night dinner in, plus the house rules summit (dish rotation, quiet hours, Venmo captain appointed).
Family fun:Swampy Jack's Wongo Adventure
Insider Tip:Create the shared expense thread on night one. Money weirdness is the only thing that can beat a beach week.
2
Beach Day, Fully Deployed
Morning:A reserved chair-and-umbrella row. For 10-plus people, pre-booked setups beat the 8 am towel land-grab.
Breakfast & coffee:North Beach Social
Afternoon:A beach games tournament with lunch delivered to the sand.
Lunch:Roux 30A
Evening:Big-table dinner at McGuire's (they absorb large parties well; still call ahead), then the group photo under the dollar bills.
Family fun:Camp Helen State Park
Insider Tip:Bring a pop-up canopy for the non-chair people. Shade is the currency of group beach days.
3
The Flotilla
Morning:Double-decker slide pontoon(s) to Crab Island. These boats hold up to 14, which is the entire point of them. Coolers packed, sober captains designated, waterproof speaker charged.
On the water:Wet-n-Wild Watersports
Afternoon:Sandbar Olympics: football, floats, food boats.
Lunch:The Gulf
Evening:A low-key taco night at the house; everyone's sun-drunk anyway.
Family fun:Frank Brown Park
Insider Tip:One boat per 12 people, morning slot. Afternoon double-decker rentals in July sell out a month ahead.
4
Split Squad Day
Morning:Golfers to Regatta Bay, anglers on a party boat, the spa unit to Serenity, beach loyalists holding the fort.
Fishing charter:Angler's Beachside Grill
Afternoon:Regroup; the anglers' catch goes to Harbor Docks.
Fishing charter:Reel ‘Em In Fresh Seafood and Gourmet of Seacrest located in Peddler's Pavilion on 30A
Evening:"We caught dinner" night at Harbor Docks, then the HarborWalk zip line for whoever's still vertical.
Family fun:Starcade Billiards
Insider Tip:Split-squad days are the secret to group harmony. Forced togetherness all week breaks groups.
5
30A Field Trip
Morning:Caravan east, with bikes in Seaside for the willing.
Breakfast & coffee:Sugar Land Candy, Ice Cream, & Coffee
Afternoon:Airstream-row lunch, then a Grayton beach hour.
Lunch:Stewby's Steamer & Market
Evening:A golden-hour group photo at the pavilions, then The Red Bar takes the group loud and happy, designated drivers pre-named.
Drinks & nightlife:Redds Pub 3906 Hwy 98 W Unit 1
Insider Tip:Caravans lose cars; drop a shared pin for parking and the regroup spot before leaving the house.
6
The Grand Finale
Morning:A recovery pool morning.
Breakfast & coffee:East Pass Coffee Co.
Afternoon:A house cleanup sprint so tomorrow isn't tragic, then showers and resort-casual assembly.
Lunch:Chanticleer Eatery
Evening:A group a sunset dinner cruise from Baytowne Marina: three decks, three courses, a live band, and group rates for 20-plus. Summer Tuesdays and Thursdays add fireworks off the sky deck. Alternative: a permitted beach bonfire behind the house, professionally set up and struck.
On the water:G.I. Jade Tiki Bar & Bistro
Insider Tip:The dinner-cruise-as-finale move solves the last-big-night problem. Nobody cooks, nobody drives far, everybody dances.
7
The Long Goodbye
Morning:Pancake mountain at the house, staggered departures, lost-and-found sweep.
Breakfast & coffee:Big Bad Breakfast-Inlet Beach
Afternoon:The last car locks up; someone sneaks a final swim.
Drinks & nightlife:Louis Louis
Evening:The photo-dump thread opens for business.
Dinner:South Of Philly 30A
Insider Tip:Book the same house for next year before checkout. Twelve-bedroom Gulf-front homes are the scarcest inventory on this coast.