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How We Hacked Together a 4-Night, 5-Day Anniversary Trip to Miami for $640.92

I had a hard time figuring out how to categorize this blog post. While it does not quite fit into the coding category, the problem-solving, algorithmic-type approach I applied to making this work is a natural result of my computer science education. I’d like to share how I was able to utilize three different rewards cards to hack together a last minute trip to Miami this month, and only spend $640.92, which included four nights at a Marriott hotel, a five day car rental, a $138 anniversary dinner, $160 upgrades to seats with more leg room (since I am over 6′ and my wife was 8-months pregnant), a $63 Uber ride home from the airport, and a $20 cash payment to the awesome kid next door who took care of our fur child Taco. Did we skimp the rest of the time during our trip? Not exactly… Let me explain.

As many of you know, my wife and I are about to have a baby, a son to be precise. As I am writing this, we are less than four weeks out, if our son goes all the way to 40 weeks, though really, it could be any day now. We had a realization as the due date was rapidly approaching: it might be some time before we are able to take a relaxing vacation together again. Sure, we still hope to be able to live our lives after our son is here, but the fact of the matter is, we’re not sure when or how, or really, what to expect. So in late December, we hurriedly thought about getting that one last trip in. Since it has been cold and snowy, we obviously wanted a break from the weather, to go somewhere nice, relaxing, and above all, warm. At the time, I was in (or finished) the process of meeting the obligations for three different rewards cards to receive their bonuses.

I am a big fan of rewards credit cards, but really only the ones that offer large bonuses for meeting certain criteria. I pretty much only sign up for ones where the introductory year is free, but offer cash or travel based rewards (more than $300) for spending x number of dollars in y number of months. The only reason I continue to participate in such rewards programs is that I never maintain a credit card balance. I never spend money I don’t have or couldn’t pay cash for. I never have interest payments on my credit cards as I’m constantly paying them off before they’re due. Furthermore, I would never recommend anybody signing up for a credit card for emergencies or spending money they do not have. Debt is evil, and credit card programs should only be utilized for those that are disciplined with paying them off.

That said, let me talk about the three offers I utilized:

  1. Marriott Rewards Visa Signature by Chase: I love Chase. They pretty much always have the best offers out there and are always giving away free money and rewards. For our anniversary, my wife and I had utilized the Chase Sapphire preferred rewards card to get something like $500 off of our flight to Belize. Last year, they gave me $200 cash for starting a checking account with direct deposit setup, and another $200 cash for starting a saving account and maintaining a certain balance for 90 days. For this trip, I utilized their Marriott Rewards card. As of this time, they are still offering a card with $0 for the first year, and giving away 70,000 points if you spend $2000 if the first three months after the account opening. Furthermore, they automatically give you one free night at one of their category 4 or under hotels. Here’s the bad news, the category 4 hotels (and under) are usually not super close to where you want to be. Of all the various locations we looked at for our trip (eventually deciding on Miami and the Florida Keys), the hotels we looked at were a bit out of the way. This would require a car, something paid for by the next card:
  2. Barclay Arrival Plus Mastercard: this card offered 40,000 points after spending $3,000 in the first three months of the account being opened. These points can be redeemed for cash back on travel-based purchases. This would include: a car rental ($132.42), an Uber ride home from the airport (since we arrived after midnight) ($63.75), and upgrades to our seats on the flight ($160), and reimbursement for the flight taxes and fees ($52.40). Because the latter expense for the flight taxes and fees was charged in multiple different transactions, each under $25, normally, we wouldn’t have been able to get reimbursed for them (there is a minimum reimbursement amount of $25). However, I sent a message requesting cash-back and Barclay was nice enough to make a one-time exception.
  3. Frontier World Mastercard by Barclay: this card gives you enough points to book two round trip tickets to multiple destinations (though sometimes with more inconvenient flight times) if you spend $1000 in the first three months of the account opening. There is a catch though: it’s a $69 annual fee. However, I am not including that fee in the cost of our anniversary trip. Why? Because Barclay screwed up sending us the cards in the mail and we had to call customer service twice, once after not receiving the cards, and a second time, after they sent the wrong cards in the mail. After the second call, they offered to waive the $69 fee for the first year.

So… we were able to book our flight with points from the Frontier, upgrade the seats using cash-back rewards from the Barclay Arrival Plus card, rent a car using the same card, rent our hotel with points from the Marriott Rewards card, get a ride home from the airport (after we realized public transportation had stopped running) with cash-back rewards from the Barclay Arrival Plus card again,  and spend roughly all of our $640.92 on restaurants, drinks, and entertainment.

Regarding the hotels we stayed at, category 4 may not be super convenient, but they are nice hotels. 70,000 points was enough to stay at category 4 hotels for three nights (20,000 points each); plus, we had that free night at a category 4 hotel for signing up. We stayed for two nights in a suburb of Miami. This location was about a 25 minute drive to South Beach, but was walking distance to some nice restaurants. We were also able to eat some amazing Cuban food, and I had one of those Cubano sandwiches which I’ve been eager to try since watching the movie Chef. I’m happy to report that even though I universally avoid pickles and mustard, I was willing to try it on said sandwich, and the combination of flavors was actually pretty amazing (though a likely cause of my later intense heartburn).

The other two nights, we decided to stay about 30 minutes away Key Largo and a three-hour drive to Key West. We spent one of our days driving out to Key West, had an amazing early-anniversary dinner (our actual anniversary is this Tuesday) where I got the steak I was craving and she got the whole fish she was craving. We spent another day doing kayaking and a glass-bottom boat tour at John Pennenkamp Coral Reef State Park. We were a little upset that we weren’t able to go snorkeling, but there was a jellyfish alert in effect, and we were explicitly warned by our birthing doctor not to get stung while pregnant. The rest of time, we were able to relax on the beach. Our hotel was a good jumping point, and would have worked really well if we had wanted to go to Everglades National Park, or had been able to go to Biscayne National Park (there were very windy conditions in place that made some of the attractions there unavailable). Overall, we had a blast. We were able to get some relaxation in, eat some amazing food, and enjoy the warmth (it was snowing and icy the morning we left, and icy upon our return).

I would like to add a few notes about the credit card offers. Some of you may be saying to yourselves: “That’s great, but how am I able to spend $x in y months?” I offer the following suggestions:

  • I didn’t sign up for all these cards at once; I spaced them out and fulfilled the different obligations over several months. I also didn’t intend to use the rewards all at once – things just kind of came together in a “perfect storm” of sorts.
  • For a couple of months, I did the cash-envelope based system advocated by Dave Ramsey, who I learned many of my budgeting and cash management strategies from. The cash-envelope system involved putting cash for our various budgets into various labeled envelopes. Ultimately, we got tired of utilizing such a system, and now maintain a Google spreadsheet tracking our expenses and which budget they are to be paid out of. We get points, and it’s actually easier for me to keep organized, but as mentioned previously, the credit card based solution is not for everybody.
  • We donate to several charities. If a particular charity offers to ability to transfer money directly via a bank transfer (ACH Transfer), I always do this. This is because they receive a lot more of the money that I donate (maybe even all of it?) than if I donated via a credit card card payment (for which 3-6% may be deducted). I came to the conclusion that it wasn’t worth me getting points if the charity was going to receive less of what I donated. However, that being said, there are some charities that do not offer ACH transfers. One of the charities that we support only offers credit card-based donation options. My wife and I regularly support this organization, and that being the only option for donations, somewhat reluctantly reap the rewards for our donations.
  • Some apartment complexes / rental agencies offer the ability to pay rent online with credit cards. This can be a great way of satisfying credit card obligations in 2-3 months rent.
  • All of our utilities, internet, and cell phone bills are paid via rewards cards. These expenses add up quickly.
  • I try to signup when I know big expenses are coming up.

Hope you’ve enjoyed reading out our most recent life hack.

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