FREE STARTER KIT: YOUR FIRST FAMILY TRIP ON MILES
HEY, FRIENDS. WE’RE THE BAILEYS.

A family of five.
A little wander.
A lot of winging it.

We’re Reaghen and Jackson, and we love exploring the world with our three kids. We’re also familiar with laundry piles, forgotten snacks, and plans that need a little adjusting.

Come along for an adventure ↗
Reaghen and Jackson with their three children

This started with a love of travel.

Reaghen created We’re Just Winging It as a place to share travel, motherhood, and photography. The heart of it is simple: having children doesn’t mean your curiosity has to stay home.

Our original journal holds family trips, city days, mountain getaways, and plenty of photographs along the way. This next chapter adds practical help with points and miles, so more families can work toward the trips they want to take.

Useful advice for real family trips.

We care about the details that actually change a family’s experience: enough seats, a room that fits, a budget that includes food, and a day with space to breathe. You will find beginner-friendly guides, clearly labeled examples, and links to official sources where rules matter.

We don’t have to do every trip perfectly to make good memories. Sometimes a little planning—and a willingness to adjust—is enough to get going.

New here?

Start with a single trip and our guide to making points and miles useful for your family.

Find your starting point ↗

Read Reaghen’s original introduction or explore the travel journal.