FREE STARTER KIT: YOUR FIRST FAMILY TRIP ON MILES

A FAMILY OF FIVE. A WORLD OF POSSIBILITIES.

Less someday.
More let’s go.

Big adventures. Real-life budgets. A few extra snacks.
We’re making family travel feel a little more possible—with points, miles, and a willingness to wing it.

The blue Pacific Ocean meeting the green cliffs of Hawaii’s Waipiʻo Valley
FIVE OF US.
ONE BIG
WORLD.
A little aloha, a lot of possibility.
Points & miles, made simpleFamily of five, figured out togetherReal life comes along, too
NEW TO POINTS & MILES?

A little know-how. A lot more go.

All points guides ↗
Reaghen and Jackson Bailey laughing with their three children
HEY, WE’RE THE BAILEYS.

Three kids. Two parents.
Still figuring it out.

We’re Reaghen and Jackson—a family of five who loves getting out into the world together. Some days that means a new city. Some days it means getting everyone out the door.

This is our little corner for family adventures, practical points and miles, and the life that happens in between.

A little more about us ↗
FROM THE TRAVEL JOURNAL

Good places. Better memories.

Explore destinations ↗
Autumn trees in Central Park with the Manhattan skyline beyondNew York City · From our original journal

One perfect day in New York City

Bridges, bagels, park breaks, and a whole lot of exploring.

Read the story
Reaghen and Jackson outside a snowy Colorado cabinColorado · From our original journal

A little Christmas magic in Colorado

A snowy family getaway, with plenty of room for slowing down.

Read the story
Blue Pacific water and green cliffs at Waipiʻo Valley Lookout in HawaiiHawaii · From our original journal

An adventure on the Big Island

Coastlines, island days, and a place on the family travel list.

Read the story
LESS GUESSWORK, MORE ADVENTURE

Your next points trip starts here.

Browse all guides ↗
A real family points trip

Our four-night Boulder Hyatt stay: 24,000 points for the hotel

Our family used 6,000 Hyatt points per night for four nights in Boulder, Colorado. Here is the math—and how to plan your own smaller points getaway.

Family travel · 3 min read
Family travel hacking

How many points does a family need? A trip ladder from weekends to big vacations

Start with a 20,000–30,000-point hotel getaway, then plan larger family trips using actual flight, room, and transfer math.

Family travel · 3 min read
From idea to booking

How to plan a family points trip: find the destination, then the redemption

Use KAYAK Explore and Google Flights for ideas, check Hyatt and airline awards, and transfer points only after the whole family’s plan works.

Points & miles · 3 min read

A FREE LITTLE HEAD START

Your first miles trip,
one doable step at a time.

Get the 8-page starter kit for moms: simple explanations, fillable worksheets, and a plan for your family.

Get the free starter kit