Earning points and miles is great, but spending them is even better! However, it can be daunting to decide how to get started when planning an itinerary booked completely on points and miles. Some people are spontaneous and will go wherever the award availability is. I prefer to choose my destination well in advance so I know I’ll have a good chance of getting the flights and hotels I want. Here’s a glimpse into my strategy for planning a vacation booked with points and miles.

Pick a destination, make a plan, and get earning

Like I mentioned, I prefer to plan way in advance to make sure the destination I want to visit is a feasible choice. Once I have an idea of where I want to go, I take a look at flights to see what points and miles I need. Making an itinerary and figuring out what points I need is one of my favorite parts of this hobby. It’s like an extremely nerdy puzzle!

scribe winery, sononma
Start by picking a destination. How about Sonoma?

If I have a lot of Chase or Amex points, I’m usually able to book as soon as the flights are available. If I need to earn more, I come up with my “ideal flight” list and make a plan for earning the necessary points through credit card sign-up bonuses, shopping deals, and surveys. For a smaller trip like Italy, I was able to make a plan, open the necessary cards, and book my flights about 10 months before departure. For a big trip like my honeymoon, I started saving points for over a year before booking anything.

If you are planning to earn miles for a specific airline rather than flexible points like Chase, Amex, or Citi, keep in mind that you will have fewer options. For example, it can be risky to make a plan that relies on Delta miles since their award chart is not public and the price for award flights can swing wildly.

Refine your points and miles vacation itinerary

Award space can be fickle. What you wanted to book when conceiving your plan may not actually be available. There’s also the possibility of award programs being devalued meaning you’ll need to earn more points to complete the redemption. I try to search periodically to see if things are looking consistent. If I notice availability is drastically lower, I usually come up with a Plan B. And some of the time, your Plan B might be a better option!

singapore suites
If I’d stuck with my original plan, I wouldn’t be flying Singapore Suites on my honeymoon!

My main reason for booking so early is that I have very little flexibility on when I can take vacation. We usually try to leave on a Friday and come back the following Sunday to maximize our time away, but of course, these are two of the busiest travel days. This makes finding award flights a lot more difficult. If you can’t be flexible on dates, try to be flexible somewhere else like your departure airport.

Start booking flights

Once the flights become available, start booking! This is the most exciting part as you start to see your plan come to life. I do some research to see exactly when I can expect the seats to be released. This will vary by airline. If I’m worried about getting the seat I want, the days leading up to the release, I’ll stalk the airline’s website to make sure I understand the release pattern. This was especially useful for booking Singapore Suites.

Start booking hotels

Once your flights are in place, your itinerary is more or less set and you can start booking hotels. You’ll have a lot more flexibility booking hotel nights than flights, but I still usually book early since it’s easy to cancel. Award availability changes frequently for hotels. If you don’t see the room you want right away, book something else in the meantime and keep checking back. You can also book a “cheaper” option and upgrade to a nicer hotel after earning more points.

Park Hyatt Milan
I originally booked a different hotel for Milan but rebooked at the Park Hyatt Milan once I earned enough points.

Fill in the blanks

I leave other travel expenses for last. This includes travel via train or car and any tours you might want to book. I don’t budget these into my plan when deciding how many points I need for the trip. If I have time to open a fixed-value travel credit card like the Capital One Venture card, I’ll use the sign-up bonus to cover out-of-pocket costs. I was able all to get three long train rides in Italy (for two people!) for free using this method. These cards are also great short flights on budget airlines when it might not make sense to use regular points or miles.

Final Thoughts

There are many strategies for planning a points and miles vacation. Due to a lack of flexibility, I try to plan far in advance. While planning can be daunting, make sure to have fun with the process. Don’t stress out if your first choice redemptions aren’t available. At the end of the day, you’ll be going an amazing vacation for next to nothing!

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