JoshOvermyer.com

I have lived in Southwest Florida for over 15 years, but it wasn’t until November 2019 that I finally visited one of the most famous locations in South Florida – Key West. Due to its location at the literal end-of-the-road in the Florida Keys, Key West is approximately 6 hours away from Fort Myers by car, and that’s if you don’t run into traffic on the many bridges and narrow roads through the Keys. But I’ve had my eye on a different route, through the Gulf of Mexico and Florida Bay. The Key West Express fit that bill perfectly.

Several days a week, the Key West Express makes a daily route between Fort Myers Beach and Key West. My parents were visiting from Indiana, and since they had never been to the Keys either, I decided it would be a fun trip for us to take together over the Veterans Day weekend.

Day One

We arrived around 7am for an 8am departure, and after a little bit of a bumpy ride thanks to a passing cold front, we arrived in Key West around noon. It sure beats that 6 hours of sitting in traffic on I-75 (Alligator Alley) and the Overseas Highway (US-1). We purchased tickets for the Conch Train Tour and caught the first one after disembarking from the boat. Our tour guide/driver Doug lived most of his life in New York City, but has been visiting Key West ever since he was 5 years old, in the late 1950s, and he gave an excellent, if punny, tour. I really enjoyed it!

After the tour, we decided to head to the Harry S. Truman Little White House tour, which was so much better than we would have guessed. Truman made a huge impact on our country at the end of WWII and in the post-war years. He spent considerable time in Key West, at his doctor’s suggestion (originally), but came back another 10 times throughout the rest of his life, both before and after the end of his Presidency.

But after the early start to our day and the tours, we were getting a bit hungry. We made our way down Duval Street and stopped for sandwiches and drinks at Sloppy Joe’s Bar. Some rest was also much needed, and then we explored Duval Street some more before catching the sunset at Mallory Square.

After that, we caught an Uber to our hotel for the stay, a Hilton Garden Inn on the east side of Key West away from the busy tourist areas. We were all tired, so we watched a few episodes of “Love it or List it” on HGTV for a while before heading down to the pool bar, just 20 minutes before it was going to close. It turns out, our bartender had been to my small hometown of Winchester, Indiana (population less than 5,000) several times when he used to live in nearby Dayton, Ohio.

Day Two

The next morning, I woke up early thanks to the roosters that run around all over Key West. We took our time getting ready and checked out around 9. Then we grabbed breakfast in the hotel lobby before heading out (via Uber) to the Southernmost Point. The line was shorter than we had seen the day before, and we quickly found out why! Due to the winds and high surf, waves were crashing up against the seawall and spilling into the area around the large concrete buoy. But it took less than 10 minutes to wait our turn for our photo-op, and we moved along to the Ernest Hemingway house.

After a very interesting guided tour of the house, grounds, and cat condos, we made our way to Papa’s Pilar Rum Distillery for a free tour (included with the price of the Conch Train Tour ticket) and rum tasting. The tour guide was funny, and he shed some more insights into Hemingway’s life along with the exhibits in the distillery.

After rum, we made over to Duval Street to people-watch and grab a late lunch at Amigos (home of the square taco) which is across the street from Capt. Tony’s bar, the original location of Sloppy Joe’s Bar from 1933-37. We had curbside seats and people-watched some more while eating chips/salsa/guac. After lunch, we had to have some dessert, so we went to Key West Key Lime Pie Co., previously featured on CNBC’s show The Profit a few years ago. A famous saying in my hometown says “Try the Pie” because it’s the home of Wick’s Pies, Inc. so I tried the Key Lime pie, and it was the best I’ve ever had 😊

At this point, we were getting pretty tired, but we still had a couple hours to kill before loading back up onto the Key West Express, so we slowly made our way back to the port through some of the various shops. We stopped by a marina where many of the powerboat racing boats were showing off their vessels. One speedboat even had FIVE 400-HP motors on the back, for a total of 2,000 Horsepower! We also checked out Dante’s pool bar, if only from outside the gates to watch the beautiful people for a few minutes.

Back inside the ferry terminal, I guess we weren’t the only ones worn out from exploring Key West, because close to 200 people had already arrived and taken their seats in the boarding area of the building. Even still, we were able to load the boat 30 minutes earlier than scheduled, got seats on the mid-deck at the front of the boat and watched the Packers/Panthers game for most of the ride home. We made it back home by about 10:30PM, and I was glad to have the Monday off to recuperate from a fun weekend in Key West.

Travel Hacking

But since I never go anywhere without some travel hacking tricks, I wanted to share the two tips I used to bring down the cost of our 38-hour trip to the Keys.

First off, we booked early. Way early. The Key West Express sells vouchers during the holiday season for only $99 round-trip. This is considerably less than the typical $145-155 that a round-trip will cost during the rest of the year. The voucher is good for two years, January 1, 2020 through December 31, 2021 if purchased in the 2019 holiday season. You’ll still need to book the trip, but you apply the voucher as payment when you make the reservation.

Second, and perhaps much more boring, I used accumulated Hilton Honors points for the hotel. While a 60,000 point redemption seemed quite high, it was a deal compared to many of the cash rates available for the holiday weekend, plus the offshore powerboat racing brought a lot of extra tourists to the area for the week. The redemption came out to .5c per point, which is at the high end of the normal range for Hilton Honors points, but we also saved around $50 in taxes and fees by using points.

All in all, it was a very fun trip and we were able to keep costs relatively low by employing some travel tips. I’m not in a rush to go back anytime soon, but I’m glad we finally went down there to check it out!

As you may know, I have been a big proponent of travel hacking for the past several years. I started in 2016, back when I was working a job with no paid time off (no vacation, no sick, no paid holidays), so my goal was to just get started slowly, earn a few bonuses, and start socking away points that would go towards some unplanned future travel. Sure, I would take a few flights back “home” to Indiana for the holidays and such, but I didn’t really have a plan for opening, closing, or redeeming my points.

Fairly quickly, I learned that Chase offered some of the best cards in the travel hacking world. Between the Chase Sapphire Preferred, Chase Sapphire Reserve, Chase Freedom and Freedom Unlimited, and their co-branded cards with Southwest, United, Hyatt and IHG (Holiday Inn, Crown Plaza, Intercontinental), Chase cards were 6 of my first 8 cards I opened over 2.5 years. (Yes, I listed 8 different cards above – I never opened a United card and I also downgraded my Sapphire Preferred to Freedom when the first annual fee came due after 12 months).

Chase also has one of the more restrictive policies for opening cards. It’s called 5/24, which means 5 card openings in the past 24 months WITH ANY CARD ISSUER! Because I had opened a Delta Gold card by American Express, then later a JetBlue Plus card from Barclays, by the time I learned about my eligibility for business credit cards, I was well past 5/24 (somewhere around 13/24 at my highest point). So I slowed down considerably, and I waited 13 months until I dropped back down below 5 cards in the most recent 24 months, and I was finally able to get the Chase Ink (Business) Preferred card and then the Ink Unlimited a few months later.

I also started getting referrals from my friends in the blogosphere that know how much I am into the travel hacking world. In the last few months, I referred 4 other members of personal finance Twitter to different Chase cards, earning a referral bonus from Chase, and my friends got the top bonus offer on each of those cards from Chase.

And then, suddenly, I was trying to buy lunch on March 18^th and my Sapphire Reserve card got declined. No worries, they probably suspected fraud and shut down the card. So I tried to swipe my Freedom card; also declined. I almost never carry cash on me, but I had $10 that day, and I was able to pay cash for my food.

I immediately dialed the number on the back of my Sapphire Reserve card and tried to figure out what was going on. The customer service rep was nice, but clueless as to what was going on. He asked to put me on hold for a minute, and after 10 minutes he came back to say he didn’t know the reason, but they would be sending me a letter on all 6 personal credit cards and both business credit cards. They had all been closed that day.

*insert sunken feeling*

Not only was I having my favorite credit cards closed without warning and without explanation, these were some of my oldest credit cards, most of my highest limit cards, and we were on the brink of a recession amid a global pandemic. Chase was freezing out a small business owner by eliminating all lines of credit. And to top it off, they weren’t going to tell me why.

The next day, I checked my online account to see PDF versions of the letter that would arrive over a week later. “This account and/or other associated accounts have been closed at the request of the bank. Account not used as intended.” Talk about vague! I never participated in the practice of “manufactured spending” because it feels too much like money laundering to me. Every dime spent on those 8 cards in the past 4 years was for legitimate personal or business expenses, and were paid back on time and in full each month. Furthermore, I had hardly used any of the valuable Chase Ultimate Rewards points, because I was saving them for future travel that I didn’t even have planned yet. At the 2.0c per point valuation provided by The Points Guy, I was sitting on over $8,800 of future travel in my Ultimate Rewards balance. Now, I was given 30 days to redeem the points, or lose them forever.

After the initial shock wore off, I scrounged up some of my credit cards that are issued by other institutions. I fell back into a rhythm of using my Schwab Card from American Express for 1.5c per dollar spent and my JetBlue Plus card from Barclays for grocery purchases for 2x points.

I went to the local Chase branch to try and talk with a Banker, but they were booked solid for the entire day I had taken off from work. Instead, I walked up to the Teller and requested a Cashier’s Check for the full amount of my balance, and for her to close the account. I told her about what happened to my cards, and she was as shocked as I felt 2 days before.

Later that afternoon, I called the number on the back of 5 of the Chase cards. The 5 I called about each have annual fees, and it seemed to me that if the bank had closed the accounts I had paid for, they owed me at least a partial refund of the fee since I wasn’t getting those card benefits anymore. A couple of the cards had fees paid more than 6 months ago, and they refused to honor my request for even a partial refund. But I was fortunate to receive a full refund on my $450 Sapphire Reserve, $149 on Southwest Priority, and $95 on World of Hyatt cards, for a total of $694 back in my pocket within a couple weeks. It took 1-2 business days for the credit to show up on my account, and then I had to call back and request a check for the balance.

This all happened in mid-March, and I only had 30 days to redeem my Ultimate Rewards balance. I started out by redeeming 1c per point for my remaining balances, because I decided that Chase was never going to get another penny of my money ever again. That took care of about 85,000 points. Then in mid-April, I transferred 34,000 points to Southwest Airlines to top up my Rapid Rewards account along with 50,000 points to World of Hyatt for some future hotel stays. This left me with 301,000 points to either transfer or cash out, and because of the current economic climate, I cashed them out to add $3,000 to my emergency fund.

In sum, it just sucks. I would caution anyone who is interested in travel hacking to not rely so much upon one card issuer for your future travel plans. There are so many programs available besides Chase Ultimate Rewards, including American Express Membership Rewards, Citi ThankYou Points, US Bank FlexPerks, and the various hotel and airline cards. Cashback cards can also be a valuable part of your strategy.