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How Should I Start When Planning a Big Trip with Rewards?

July 03, 2016
3 min read
Calendar travel planner schedule featured shutterstock 287916683
How Should I Start When Planning a Big Trip with Rewards?
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TPG reader Elliot sent me an email to ask about planning award travel:

"I have rewards from Amex, Chase, SPG and American Airlines; now I'm planning a honeymoon with my wife (maybe to Southeast Asia or South Africa), but I have no clue where to start! What's your advice?"

There seem to be two prevailing approaches to award travel. Some people simply decide where they want to go, and then set out to earn the rewards they need to get there. Others take a more opportunistic angle by collecting points and miles when they're easy to get, and then redeeming them when the moment is right (like during an award sale). Both approaches work, and you don't have to be fully devoted to one or the other.

That said, I get a lot of questions from readers like Elliot who have stockpiled rewards haphazardly and are unsure what to do with them. Don't feel bad if you fit that description; loyalty programs aren't always intuitive, and sometimes it's unclear which one you should use to maximize your travel. However, points and miles make a bad long-term investment, so it's best to have some kind of plan for them. That's why I think the first approach is easier for people who are new to the game.

The first step is to decide where you're going. Check out destinations that interest you and see which hotel brands have a presence there, keeping in mind the rewards you have available. There are plenty of great properties to choose from both at the high end and in the lower tiers. If you don't have enough points to stick with one hotel for your entire trip, you could divide your time and explore more than one area, or mix in some points + cash bookings to stretch your rewards further.

After you've narrowed your search to a few good hotel options, start looking at flights. Use Google Flights to see which airlines and alliances serve each destination, and then start checking award availability. Once you've put together an itinerary that works for you and has award space, book the hotels first, since those reservations are easier to change or cancel.

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Book your hotel first, because the reservation is more flexible. Image courtesy of The Naka Island Resort & Spa.

Planning award travel is generally easier when your schedule is flexible and you book far in advance. Setting travel goals with a realistic timeline will help ensure you have the points and miles you need, and that they don't go to waste. On the other hand, there are still opportunities when booking at the last minute, so don't give up hope if you're short on time.

For more tips on the process of booking awards, check out these posts:

If you have any other questions, please tweet me @thepointsguy, message me on Facebook or send me an email at info@thepointsguy.com.

TPG featured card

4 / 5
Go to review
Rewards rate
1XChoose to earn up to 1X points on rent and mortgage payments with no transaction fee
2XEarn 2X points + the option to earn 4% back in Bilt Cash on everyday purchases
Intro offer
Open Intro bonus
50,000 Bilt Points + Gold Status + $300 of Bilt Cash
Annual fee
$495
Regular APR
26.74 - 34.74% variable
Recommended credit
Open Credit score description
Good Credit, Excellent Credit

Pros

  • Choice to earn up to 1 Bilt Point per dollar spent on rent and mortgage payments
  • Elevated everyday earnings with both Bilt Points and the option to earn Bilt Cash
  • $400 Bilt Travel Portal hotel credit per year (up to $200 biannually)
  • $200 Bilt Cash annually
  • Priority Pass membership
  • No foreign transaction fees

Cons

  • Moderate annual fee
  • Designed primarily for members seeking a premium, all-in-one card
  • Earn points on housing with no transaction fee
  • Choose to earn 4% back in Bilt Cash on everyday spend. Use Bilt Cash to unlock point earnings on rent and mortgage payments with no transaction fee, up to 1X.
  • 2X points on everyday spend
  • $400 Bilt Travel Hotel credit. Applied twice a year, as $200 statement credits, for qualifying Bilt Travel Portal hotel bookings.
  • $200 Bilt Cash (awarded annually). At the end of each calendar year, any Bilt Cash balance over $100 will expire.
  • Welcome bonus (subject to approval): 50,000 Bilt Points + Gold Status after spending $4,000 on everyday purchases in the first 90 days + $300 of Bilt Cash.
  • Priority Pass ($469/year value). See Guide to Benefits.
  • Bilt Point redemptions include airlines, hotels, future rent and mortgage payments, Lyft rides, statement credits, student loan balances, a down payment on a home, and more.