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Custom travel plans made just for you

Personalized itineraries for those who hate planning trips

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Real Times

Pacing that accounts for the actual road, so you're not driving 260 miles on the day you also hike eight.

Timed-entry slots, permit drops, and lodging that opens a year out — what to book and the day to book it.

Rain, crowds, a closed trailhead. There's a second option already in the plan.

The windows that matter
A backup for every day
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SAMPLE ITINERARY

A Real Sample Itinerary

Here is a preview of how a Wander Squirrel itinerary unfolds. Every day is detailed with realistic travel times, recommended dining, and quiet spots curated to your exact pace.

DAY 1

DAY 2

DAY 3

Arrival Details

Plans for the day

Extras

Drive day broken into realistic legs, with the overnight stop, check-in timing, and the grocery run to make before you head up the canyon.

Timed-entry window, which trailhead to hit first and when, lunch in town, and an easy afternoon option if the weather turns.

Dinner spots worth a reservation, the best sunrise pullouts, and where to be after dark for the Perseids.

What lands in your inbox

  • A day-by-day plan — activities, food, timing, and deliberate downtime

  • Maps, addresses, and drive times, so nothing needs looking up mid-trip

  • Exactly what to book and when the window opens

  • Hidden local spots, and the tourist traps worth skipping

  • Bad-weather and crowded-day backups

  • Built to read on your phone, printable for the glove box

  • Two rounds of revisions — the first draft is a starting point

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• HOW IT WORKS

Three steps, and most of the work is mine

01

STEP ONE

02

STEP TWO

03

STEP THREE

Tell me about the trip — a short form, about four minutes. "I don't know yet" is a fine answer to most of it.

We have a conversation. I send a plan and a price — within 48 hours, an outline of what I'd build and a flat quote. If I'm not the right fit, I'll say so.

You get your itinerary — usually in three to ten days depending on the trip, then two rounds of revisions to get it right.

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• Tested on the road · Where I've actually been

Trips I plan

From cozy couple escapes to family adventures to epic Friendsventures. US parks and road trips are where my notes run deepest, but I've planned and taken trips to Scotland and Costa Rica too — and the process is the same wherever you're going.

Places I've actually been: Scotland · Costa Rica · Rocky Mountain NP · Estes Park · the Black Hills · the Bahamas · Texas Hill Country · Wind Cave NP · San Antonio Riverwalk · Badlands NP · Wisconsin Dells · San Diego · Miami · Kansas City · St. Louis · Scottsdale · Minneapolis · Chicago · Lake of the Ozarks · All across Iowa

National parks · Road trips · International · Cruise port days · City weekends · Multi-family and group trips

Glenfinnan Viaduct, Scotland - Sunny June morning

Sprague Lake, Rocky Mountain NP, sunrise.

Arenal Volcano View and Lava Trails - Costa Rica

Mount Rushmore

Seaworld - San Diego

Badlands National Park - South Dakota

San Antonio River Walk - nighttime

Royal Palms South Beach - Miami

More about me
• THE PERSON BEHIND THE ITINERARY

Why me

I started Wander Squirrel because generic travel guides leave out the details that make a trip effortless — true drive times, quiet coffee stops, and realistic daily rhythms tailored to how you actually travel.

I'm one person in Iowa who plans a lot of trips — mine, my family's, and now other people's. Rocky Mountain with kids in the car, the Scottish Highlands, Costa Rica. AI is good at listing the top ten things to do somewhere. It's bad at the stuff that actually wrecks a trip: the shuttle line that's ninety minutes at 9am, the drive it calls two hours that's four with a closure, the restaurant that shut last spring. I check the things that change — and I've stood in a lot of these places myself, which is a different trip than the one the internet describes.

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Ready when you are

Tell me about your trip and I'll come back within 48 hours with a plan and a price. No obligation until you say go.