How We Book Family Vacations Step by Step
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Our family's exact process for planning and booking trips using points and miles.
Last Updated: July 2026
How Every Trip Starts
One of the biggest misconceptions about points and miles is that every vacation starts the same way.
For us, that's definitely not true.
Sometimes a flight deal inspires the trip. Other times we've been dreaming about a destination for years and build everything around it. And occasionally, we plan a getaway simply because we want to maximize valuable travel benefits that come with our credit cards.
No matter how the trip begins, though, our booking process is usually very similar.
Here are the three ways most of our vacations start.
Option 1: A Deal Finds Us First
Some of our favorite trips started because of an incredible award flight deal.
We're subscribers to Thrifty Traveler Premium, so we receive alerts when unusually good award flights become available. If it's somewhere we've wanted to visit and the dates work, we don't spend days thinking about it—we book.
Award space can disappear quickly, so we've learned that acting fast is often the difference between getting the seats and missing out.
One of the best examples was our 40th birthday trip to Croatia.
We originally weren't planning to fly home from Switzerland, but Thrifty Traveler sent an alert for an incredible business class redemption from Zurich back to the U.S.
So we adjusted our plans, repositioned to Zurich, and flew home in business class.
That one flight deal completely changed the ending of our trip—in the best way.
Option 2: We Pick the Destination First
Not every vacation starts with a deal.
Sometimes we've already decided exactly where we want to go.
That's how we planned our trips to Thailand and Italy.
Those destinations had been on our family's bucket list, so we chose them first and then started figuring out the best way to get there using points.
Once we've chosen a destination, we begin researching:
Award flight options
Hotel availability
Which points we'll need
Transportation
Activities
How many nights we want to stay
These trips usually take a little more planning, but they're often the ones we've dreamed about the longest.
Option 3: We Build Trips Around Travel Benefits
Sometimes the destination isn't the priority.
Using travel benefits is.
Several of the travel rewards cards we carry include annual hotel credits, travel credits, or luxury hotel benefits. Rather than letting those expire, we'll look for destinations where we can maximize them.
That's exactly how we ended up booking our trip to Roatán, Honduras.
We wanted to use our Chase Travel℠ The Edit hotel credit, so we built an entire weekend around it. What started as using a credit turned into one of our favorite family beach vacations.
We also used our Fine Hotels + Resorts (FHR) benefit during our stay at the Park Hyatt Bangkok, which added valuable perks to our stay.
Sometimes those built-in benefits become the reason we take a trip we never would have planned otherwise.
👉 Read how we booked our Roatán trip using points and credits.
Step 1: Find Award Flights
Flights are almost always the first thing we book.
If we can't get there, nothing else matters.
We usually search award availability using tools like:
Airline websites
One thing we've learned is that flexibility is incredibly valuable.
Changing your departure airport, arrival airport, or even your travel dates by a single day can completely change the award availability you see.
We've even had trips where we booked the flight to our destination but hadn't found the flight home yet—or vice versa.
That probably sounds stressful, but award availability doesn't always open at the same time in both directions. Sometimes we're comfortable locking in the flights we know we want while continuing to monitor the remaining segment.
It's not for everyone, but it's a strategy that's worked well for us.
Step 2: Transfer Your Points
Once we've found the flights we want, we usually transfer flexible credit card points to the airline or hotel loyalty program before booking.
Most of our transfers come from:
Chase Ultimate Rewards®
American Express Membership Rewards®
Capital One Miles
Citi ThankYou® Points
Before you ever transfer your first point, create free loyalty accounts with the airlines and hotels you think you might use someday.
That includes programs like:
Air France/KLM Flying Blue
Virgin Atlantic Flying Club
British Airways Club
Air Canada Aeroplan
United MileagePlus
American AAdvantage
Alaska Mileage Plan
Singapore KrisFlyer
Japan Airlines (JAL)
Hyatt
Hilton
Marriott
This becomes especially important with Japan Airlines (JAL).
JAL generally requires your Mileage Bank account to be open for at least 60 days before you can redeem miles, even if you transfer the points later. We've seen people find the perfect award flight only to realize their account is too new.
Creating these free accounts ahead of time can save a lot of frustration later.
Before transferring points, we always verify that the award space is available because most transfers cannot be reversed.
Step 3: Book Direct Whenever Possible
Once the points have transferred, we usually book directly with the airline or hotel.
In our experience, booking direct makes it much easier if plans change or something goes wrong.
We do occasionally check our bank's travel portal before transferring points.
Sometimes portal pricing is actually a better value—especially for inexpensive domestic flights or hotels that don't belong to a major loyalty program.
Most of the time, though, we end up transferring points and booking directly.
Our advice is simple:
Always compare both options before you book.
Step 4: Book the Hotel
After our flights are confirmed, we start looking at hotels.
We're usually comparing:
Location
Points required
Family-friendly room options
Breakfast benefits
Parking
Resort fees
Elite status benefits
We don't automatically book the fanciest hotel.
Sometimes the best family vacation is staying somewhere simple that's within walking distance of everything we want to see.
Step 5: Transportation
Once flights and hotels are booked, we figure out how we'll get around.
Depending on the destination, that could include:
Rental cars
Ferries
Public transportation
One service we've used over and over is Welcome Pickupsfor airport transportation.
After a long international flight with kids, it's nice knowing someone is already waiting for us instead of trying to figure out transportation after we land.
Step 6: Book Activities
We don't plan every minute of every vacation.
Instead, we reserve the experiences that are most likely to sell out.
Many of our tours are booked through Viator and GetYourGuide because they're easy to compare and usually have flexible cancellation policies.
Everything else, we leave open.
Some of our favorite memories have come from simply wandering around a new city without a strict schedule.
Step 7: Stay Organized
Once everything is booked, we organize every reservation in one place.
The app we personally use is TripIt.
It keeps together our flights, hotels, trains, confirmation numbers, and travel itinerary so we're not digging through emails while standing in an airport.
Before every trip, we also double-check:
✅ Flights
✅ Hotels
✅ Seat assignments
✅ Passport expiration dates
✅ Airport transportation
✅ Tour reservations
✅ Travel insurance
Having everything organized before we leave makes travel days much less stressful.
Tips We've Learned Along the Way
Compare transfer partners and travel portals.
Most of the time we transfer points, but every once in a while the travel portal offers better value. It's worth checking both before booking.
Create loyalty accounts before you need them.
It only takes a few minutes and can prevent you from missing out on award space later.
Don't panic if every flight isn't available yet.
We've booked one direction before the other more than once while waiting for additional award space to open.
Flexibility makes all the difference.
Changing your travel by one day—or flying into or out of a different airport—can completely change what's available.
Final Thoughts
Every trip we take starts a little differently.
Sometimes it's an incredible flight deal.
Sometimes it's a destination we've been dreaming about for years.
Sometimes it's simply finding a great way to maximize travel benefits we already have.
No matter how the trip begins, the goal is always the same: find the best value, stay flexible, and make memories together as a family.
If you're just getting started with points and miles, don't feel like you have to learn everything overnight.
Start with one trip.
One redemption.
One transfer.
Before long, you'll have your own booking process—and your own family travel stories to tell.
Continue Learning
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