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Planning a trip on rewards is the exciting precursor to taking the trip itself, and having a strategy for how to accumulate the necessary points will ensure that your trip lives up to your expectations. We’re here to show you how to plan such a strategy from start to finish.
To help you follow the process of devising a travel strategy, we’ll include an example along the way outlining how we’d plan a trip to charming San Juan, Puerto Rico based on offers available in Spring, 2017.
To get started, you’ll simply need to answer a few preliminary questions:
Where do you want to go?
When do you want to go? And are your dates flexible?
Four nights in January, no specific dates.
What airlines / hotels / other do you already have points in?
Let’s assume we have no points with any program.
With those questions answered, it’s time to identify the best way to get to your destination (ie. how many miles and on what airline?).
Check the award calendars for all the major airlines that fly to your destination, prioritizing those you have the most points on. Make sure to specify your ideal dates, as different dates might require different point totals.
Below are the NYC-to-San Juan award calendars for both American Airlines and United Airlines. The calendars show the best dates to travel in January and the total amount of points we would need for for the trip:
United’s award booking portal makes it very easy to see what the best redemption options are. After entering our search for reward flights from NYC to San Juan, we’re taken to this results page:
In the calendar at the top, we’re shown the dates for the best award rates—in United’s case, Saver Award Economy is the lowest fare and the one to plan around.
After looking at costs, the best options for the United award would cost us 35,000 miles and $11.20 in fees.
American Airlines also makes the results very easy to digest, with a calendar showing the mile costs for each date. The best rates for American are Economy MileSAAvers—those are the ones to keep an eye out for.
Fortunately, both flights are available for the lowest mileage fare. Costing just 15,000 miles each way, the whole trip would cost 30,000 miles and $11.20 in fees for a variety of date options.
Similarly, you will then do the same with where you want to stay. Limit your search to hotels that are part of large reward programs where you can redeem rewards.
What hotel options do you have in your desired destination? And how much does a free night cost in each option? Keep in mind that points are not created equal; the value of a point in one program could be wildly different from the value of a point in a different program.
Looking at the area near old San Juan, there are several great hotel options. A quick Google Maps search displays the options:
By searching for available rewards bookings, we can see what a night would cost at each hotel. We’ll limit our comparison to the Courtyard by Marriott San Juan Miramar, the Sheraton Puerto Rico Hotel & Casino, the Hyatt Place San Juan/City Center, and the Caribe Hilton for dates starting around January 20th, since the flights work around then.
Marriott's hotel search is pretty simple. When making a booking search, we simply had to select the Use Points option. Four nights at the Courtyard San Juan Miramar would cost you 100,000 points.
Sheraton is a Starwood Hotels property. Starwood has a separate site for reward bookings, so we’ll make our search on the Starwood Preferred Guest site. A night at the Sheraton Puerto Rico Hotel & Casino starts at 7,000 points, or 28,000 for a four-night stay.
The Hyatt Place San Juan/City Center comes in at 12,000 points a night, or 48,000 for a four-day stay:
Last but not least, the Caribe Hilton would run us 50,000 points a night—or 200,000 for the four-night stay.
Choose The Cards
Now that you know how many points each option requires, you can figure out if there are travel rewards opportunities to make it happen.
Check out the current card offers and sign-up bonuses—which you can see on our Top Travel Rewards Credit Cards showcase—to find the cards that will help you meet the tally for your preferred travel and hotel options. And don’t forget to include the points you’ll earn when spending to meet the minimum spend requirement.
To keep the example simple, we looked at only a few different cards. When getting started, take the extra time to become familiar with all offers and programs:
To Book Air Travel
Chase Sapphire Preferred® Card: 50,000 point sign-up bonus, $95 annual fee waived the first 12 months. Must spend $4,000 in first three months.
United MileagePlus® Explorer Card: 50,000 mile sign-up bonus, $95 annual fee. Must spend $3,000 in first three months.
Citi® / AAdvantage® Platinum Select® World Elite™ Mastercard®: 30,000 mile sign-up bonus, $95 annual fee waived the first 12 months. Must spend $1,000 in first three months.
The Chase Sapphire Preferred® is the winner here. Not only do you get 50,000 points that are transferrable to United Airlines at a 1:1 rate—leaving you with extra points for a future trip—but the annual fee is waived the first year and you get two points per dollar on both travel and dining.
To Book Hotels
Marriott Rewards® Premier Credit Card: 100,000 point sign-up bonus, $85 annual fee. Must spend $5,000 in first three months.
Starwood Preferred Guest® Credit Card from American Express: 25,000 point sign-up bonus, $95 annual fee waived the first 12 months. Must spend $3,000 in first three months.
The Hyatt Credit Card: 40,000 point sign-up bonus $75 annual fee. Must spend $3,000 in first three months.
Hilton Honors™ Card from American Express: 80,000 point sign-up bonus, no annual fee. Must spend $2,000 in first three months.
The Hilton and Hyatt cards are out as they doesn’t offer enough points to make it work. It comes down to the Marriott and Starwood cards which would both give you enough points, however not only is the Starwood card free the first year, it also let’s you redeem at a better hotel.
The offers make the choice clear, by choosing the Chase Sapphire Preferred® and the Starwood Preferred Guest® Credit Card you book a trip to San Juan from January 20th to January 24th (within the chosen time range) and only pay $11.20 in fees. That means you could book round-trip flights and four nights at a 4-star hotel in prime location for a grand total of $11.20! The same trip would cost over $1,200 if paid the “old fashioned way”.
Time To Apply
You’ve done the research, now it’s time to apply for each card. You just need to decide which one to get first.
Why one at a time? Because you have to hit spend minimums to earn sign-up bonuses, and getting both cards at once could make hitting each threshold difficult. Remember, you don’t want travel rewards to drive irresponsible spending.
To decide which to get first, consider a few factors:
Limited Time Offers: Some increased sign-up bonuses might only be available for a limited time. If one of the cards has a upcoming end date for its sign-up bonus, go with that card first.
Higher Than Average Offers: Along the same lines, if a card is offering a higher sign-up bonus than usual—even without specifying an end date—start with that card. Although there might not be an announced end date, higher offers rarely stick around for good.
Cancellation Policy: When all things are equal, check out the cancellation policy for point redemptions for each of the programs you’re considering. If one lets you cancel up to the dates of the reservation, while another is more strict, opt for the more flexible program.
Hit The Spend Bonus
Get started right away! As soon as you receive your card, start using it to pay for all your eligible expenses. And don’t forget to hook it up to your phone bills, Uber/Lyft profiles, and any other auto-pay accounts that you pay with credit card. The faster you hit your goal, the sooner you can get the bonus and move on to the next card.
And if you haven’t received your card but have a big payment to make, you can normally get your card number from your bank and pay with it online.
Book Your Trip
You’re all set! You have a set plan, you’ve earned the points you need, and all you need to do now is book your flight and hotel.
Book each part of the trip—especially if the cancellation policy is favorable—as soon as you earn the points. By booking as the points come in, you’ll minimize the chance of reward requirements going up.