Racine

Morning

Check out, head north

About 430 miles, ~6.5 hrs — I-64 to Louisville, then I-65 north through Indianapolis and up around Chicago.

Midday

Lunch around Indianapolis

Roughly halfway and a clean break before the Chicago-area traffic.

Late afternoon

Arrive Racine — check in

413 6th St ½, downtown Racine, a couple blocks off the Lake Michigan lakefront. Settle in.

Morning

Required Racine ritual — Kringle is the official Wisconsin state pastry. O&H Danish Bakery on Douglas Ave is the classic; go almond or cherry.

Midday

North Beach

One of the cleanest freshwater beaches in the country — 50 acres of soft sand, the Kids Cove playground, the Beachside Oasis for snacks, lifeguards on duty. Easy win for Milo.

Evening

Lakefront dinner

Reefpoint Brew House sits right on the marina — casual, lake views. Or wherever your Racine friends point you.

Morning

Six Flags Great America is ~40 min south on I-94. Gates open 10:30am — get there early for the marquee coasters before lines build.

All day

Ride plan for Milo (9)

You've got the Fast Lane Priority bundle for all 3, so you can skip the regular lines on the big rides. Most coasters are a 48" minimum (Goliath, American Eagle, Whizzer, Demon); the big three — Raging Bull, Batman, Superman — need 54", so measure him first. Hurricane Harbor water park is included if you want a cooldown.

Lunch

Food & drinks are covered

All-day dining and the souvenir drink wristbands are already on the order for all 3 — so just eat and refill whenever, no extra spend. It's their 50th-anniversary summer, so expect extra shows and bigger crowds.

Evening

Back to Racine

Easy ~40 min run back up I-94.

Morning

Slow start — Danette's sitting today out

Rain plus a headache, so Danette's resting up at the Airbnb. Keep it close and low-key today — and it's a good day to bank energy for tomorrow's long Chicago run (Field Museum + Medieval Times).

10:00 am

Dade & Savanna arrive

Got in around 10 this morning, ahead of plan — so they can join the Kringle run and the rest of the day. They're in Racine through the 26th.

12:00 pm

Lunch at Kewpee

Lunch downtown at Kewpee — one of the last original Kewpee Hamburgers anywhere, a Racine institution since the 1920s. Square burgers and the famous root beer.

~1:15 pm

Visited your old boss Kevin at Image Management's spot on Corporate Drive in Mount Pleasant, ~10 min west of downtown.

Done — good catch-up.

Afternoon

Shoe shopping for Dade

Quick stop to find shoes for Dade before the last stop of the day.

Before 5:00 pm

The required Racine ritual — Kringle's the official Wisconsin state pastry. Bendtsen's Bakery on Washington Ave is your pick (the pecan is the famous one). Grab a box for the Airbnb and one for Danette while she rests.

Bendtsen's closes at 5 sharp — swing by before it shuts, then finish at Sanctum.

Late afternoon / evening

Browse the tabletop and board-game shop on Washington Ave — board games, minis, card games, and play tables. A fun rainy-day stop and a good one for Milo.

Open latest of the day's stops — the relaxed finish after Bendtsen's.

~7:00 am

Early start — drive to Chicago, all five

General admission is timed for 9:00am, so leave Racine around 7 to give yourself a buffer for I-94 traffic. You plus Dade & Savanna head to Museum Campus; park at the Museum Campus / Soldier Field lots.

9:00 am

Timed entry confirmed (order #103668326). Open the day with the headliners — Sue the T. rex, Máximo the titanosaur, Inside Ancient Egypt, and the Hall of Gems — before the afternoon crowds.

Lunch

Museum Campus break

Eat at the museum or step out for skyline + Lake Michigan views — Shedd Aquarium and Adler Planetarium are right there for photos.

1:00 pm

Your second confirmed ticket for the day, and the one Milo will be counting down to — the Pokémon Fossil Museum special exhibit. Head over a little before 1.

6:45 pm

Booked — knights, jousting, and a hands-on (no-utensils) feast in the Schaumburg castle, with the Royalty Upgrade for all 5. Northwest of Chicago and right on the way back toward Racine. A big hit for Milo after a museum day.

Castle doors open 60 min before showtime — aim to arrive by ~5:45 pm; gratuity for your server isn't included.

Evening

Back to Racine

Drive north together; dinner in Racine with Dade & Savanna.

Daytime

Whatever you missed

More North Beach, the zoo, downtown shops — plus time with friends and with Dade & Savanna before they head out.

Evening

Grab a couple of boxed Kringles from Bendtsen's to take home — they travel well and you'll want them on the drive.

Morning

Check out, point south

The long haul starts. ~560 miles / ~8.5 hrs down through Chicago, Indianapolis, Louisville and Nashville to Murfreesboro.

Midday

Lunch near Indy or Louisville

Break it wherever you hit the wall — both are clean I-65 stops.

Evening

Overnight in Murfreesboro, TN

Just south of Nashville — your one hotel night. Book ahead; plenty of food off the I-24 exits.

Morning

Murfreesboro → home

Last leg: ~620 miles / ~9.5 hrs down I-24 to Chattanooga, then I-75 through Atlanta and into Florida.

Watch for

Atlanta + the Florida stretch

Time Atlanta to dodge the worst of it, then it’s the long familiar I-75 run home.

Evening

Home in Mulberry

Pull in, unload, eat the last of the Kringle. Trip done.