Hack this trip: A Key West getaway


In this series, I plan to share practical examples of how to turn perceivably unattainable trips into affordable travel options using a little creativity and some more traditional travel hacking techniques. If you’d like to have a trip hacked, complete the online form through this link.

Goal Trip Details

A couple is looking to get away to Key West, Florida for six days in October. They’d prefer to stay at as nice a property as they can afford in a central location close to town, but also on the water.

The couple is not looking to open up any new credit cards at this time, but already has some points and miles balances from three cards they’ve opened over the past couple of years. Currently, they have about 54,000 Chase Ultimate Rewards, 52,900 Barclay miles, and 70,000 Delta SkyMiles.

FunJet offers a vacation package identical to what they’re after for $2,780.70. Although this price isn’t exorbitant, it’s understandably more than they’d like to spend for a few days away in Florida.

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With their goal price set at $1000, let’s see how we can hack this trip:




Using the couple’s stash of already accumulated Delta SkyMiles, they can easily book two round trip tickets at convenient times from Rochester to Key West for 30,000 miles each. There are low-level flights available for 25,000 apiece, but for just 5,000 more we were able to find flights at the most ideal times. In addition to the miles, they will need to pay taxes on the airfare that amount to $22.40.



The couple doesn’t want to move between hotels while they’re in Key West, so we need to find one hotel for the entire stay. They want to be at a resort with ocean views, right on the water, but also within walking distance of Duval Street and the main touristy areas of Key West. The couple has a decent stash of Chase Ultimate Rewards points that transfer to several hotel loyalty programs at at rate of 1:1. Hyatt is likely the best transfer option with their points being the most valuable. In fact, if we compare the Hyatt Key West property with the Marriott Key West, we see that a free night at Hyatt would be just 25,000 points while the free night at Marriott would cost them 45,000 points. Clearly, the Hyatt is the better deal here.

But the couple doesn’t have enough points to cover the stay completely, so we need to get a little creative. I recommend they transfer 50,000 Chase Ultimate Rewards points to Hyatt and use them to book the two weekend nights – the most expensive nights of their trip. That leaves three nights left to cover.

For the three nights they want to book, a partial ocean view king room is going for $399/night. But, they’re AAA members, so using the AAA rate can knock down the cost of the same room to $365/night with breakfast, or $1095 for the stay.

Here’s where the Barclaycard miles come in. Barclaycard miles can be used to offset travel costs at a rate of $.01 per mile. With a balance of 52,900 miles, they can offset $520 of the hotel costs, bringing their out of pocket cost down to $575.

But wait! That’s not all!

Hotel gift cards can often be purchased on eBay for less than face value. At the time of writing this, there are $200 Hyatt gift cards that can be purchased for $175. Buying two of these gift cards would save them another $50 on hotel costs. And by using the TopCashBack portal for their eBay purchase, they would get another $3.85 off (1.1% eBay cash back). This would bring their total out of pocket cost for the hotel down to $521.15 (plus taxes & fees).

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Trip summary


54,000 Ultimate Rewards from Chase Sapphire Preferred

52,900 Barclay miles from Barclaycard Arrival Plus

70,000 SkyMiles from Gold Delta SkyMiles Amex


Round trip ROC-EYW on Delta

Points used: 60,000

Cost: $22.40


Hyatt Key West

Points used: 102,900

Cost: $521.15

Total trip cost: $543.55


Consider this Key West getaway hacked.



Do you have a trip you want hacked? Fill out the “Hack This Trip” form or email me at unsettledmeliorist@gmail.com with the details.


Full disclosure: I earn a small commission for signups from the cash back links on this page. You don’t have to use my links, but I appreciate it if you do!


cover photo credit: IMG_1453 via photopin (license)


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