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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.

IMG Starwood SPG Phuket Naka Island banner
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.

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  • Earn 50,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $625 toward travel when you redeem through Chase Ultimate Rewards®
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  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
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  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 50,000 points are worth $625 toward travel
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