Thank you to those who’ve already read the first 2-ish months of my gap year travels. If you haven’t yet, you may want to go start there and come back.
August
This month wasn’t a very big month of traveling for me, since I had just done the 20-day road-trip in July, but I did fly back to Florida (Orlando) to do a little bit of “work.” I’m on the Board of Directors of the Florida Floodplain Managers Association, and we were having an in-person board meeting and a planning session for the upcoming national conference that we will be hosting. This was as good of an excuse as any to fly down and spend a few days in sunny rainy Florida.
I purchased my tickets on Southwest, but instead of using my accumulated Rapid Rewards points, I decided to pay mostly with some Southwest gift cards I had picked up in 2019. Hint: sometimes stores like Staples will run a sale on Southwest or Lowe’s gift cards and you can buy $100 cards for $90. I’ve done this quite a few times through the years. I also bought some Uber gifts cards on a website called Raise, where you can buy discounted gift cards that other people are trying to sell to liquidate into cash. I expected to use quite a few Ubers that week because I did not want to rent a car just to then pay to park the car at the resort. But my friend Christa ended up taking me to the airport on my return trip, so that saved me approximately $30 to get back to MCO (Orlando airport code).
The rest of the month was mostly spent at the golf course or in the pool, for those waning days of Summer in Indiana.
September
At first, a continuation of the golf and pool time, because it was just about to close the family pool. We had a family wedding over Labor Day weekend, and my parents and I took a day trip to Dayton Ohio to check out the Carillon Historical Park, which includes a lot of cool history about the industrial past in the Dayton area, as well as the Wright Brothers National Museum.
In the middle of the month, I set out towards Texas for the annual FinCon financial media conference that I’ve attended a few times and where I meet up with so many of my blogging and podcasting friends.
I started out by cutting across Indiana, down past historic New Harmony, Indiana, then across the Ohio River into Kentucky to see the waterfront areas of Paducah. I continued south to Memphis, Tennessee, where I gorged on some BBQ meats and took a loop past Beale Street before settling into my Hyatt Place (booked for free* with 5,000 World of Hyatt points). I used the asterisk there because apparently in Memphis, they still charge some taxes on award night bookings, so I had a strange $36 and change charge on my credit card. Still a pretty nice hotel stay for $36.
The next morning, I checked out of the hotel and drove past Graceland, the famous home of Elvis Presley. I crossed the southern border of Tennessee down into Mississippi (a first time in the state for me), and took a conference call while driving back north through Memphis and then west across the Mississippi River into Arkansas. The plan was to stop in Little Rock for lunch and to check out the William Jefferson Clinton Presidential Museum, but when I got there it was closed (I assume Covid). So I regrouped and drove west to Hot Springs, Arkansas to see the historic buildings of the Hot Springs National Park. That was a very worthwhile detour, and then I grabbed lunch at a cool little bar and grill on Lake Hamilton.
After lunch, I headed south to Hope, Arkansas, site of the President Clinton Birthplace Home National Historic Site, but I got there just before they closed and I didn’t get to tour the home, just the small museum galleries.
Continuing on from there, I reached Texarkana, which as the name implies, straddles the Texas and Arkansas border. I have an online friend who lives there, but he was out of town that day, so I took a selfie at the historic Post Office and Courthouse building that also straddles the state line. Grabbed some Mexican food for dinner and checked into my hotel, a Courtyard by Marriott to use up some more of my annual $300 travel credit on the Marriott Bonvoy Brilliant credit card.
I only had 2 things on my agenda the next day, check out Confections cookie shop in Lufkin (East Texas) and wind my way closer to Austin or San Antonio. I did a lot more than that, though. Starting out, I backtracked a little bit to head south into Louisiana (another first time in the state). I wanted to check out Shreveport, but before I got there, the remnants of Hurricane Nicholas beat me to it, and it was the most difficult driving I’ve ever done (even pulled off onto an Interstate off-ramp for 15-20 minutes). Since it was raining so hard, I continued west into Texas and found my way to Lufkin.
You may be asking, why Lufkin? and why Confections cookie shop? Well around the time that I was gearing up to quit my job and take this gap year, Confections went viral online when a customer canceled a large (5 dozen) cookie order because the shop had made rainbow colored heart cookies for the LGBT+ club at the local high school. An outpouring of support rushed in and bought up all of those already-decorated cookies, and they grew a huge following of supportive people on Instagram and Facebook. I wanted to taste some of that magic for myself 😊
While I was there, I actually picked up an extra cookie, one decorated like a birthday cake, for my friend Brenda’s birthday. But she is in Austin and I was heading towards Houston to check out the beaches at Galveston (being the floodplain geek that I am). I stupidly planned to get her the cookie the following week when I was in Austin for FinCon, but that was going to be at least 4 days away, so I detoured to Austin to meet up with Brenda and give her the cookie. I also got to see her new BMW SUV and chat for a bit in her office before she wrapped up her day there to go to her second job at a Covid-19 vaccination clinic. She is a total badass, co-hosting a podcast and working on her PhD right now, too!
After leaving Austin, I reached out to my old coworker Luisa from 15+ years ago when we worked together in Fort Myers, Florida. She and her husband were going to get a couple drinks at a local outdoor bar, and invited me to come join them. It was great to catch up with how much had changed in the past decade and a half (I think we had seen each other once in the past 10 years, but only briefly), her whole career trajectory and the challenges of WFH and online schooling for her two teenagers (HOW ARE THOSE BABIES TEENAGERS ALREADY?) I checked into my room at the SpringHill Suites (part of Marriott) to use up some more of the $300 travel credit, and called it a night.
Saturday morning, I woke up early and went downtown San Antonio to wander around the famous River Walk. It was a very hot and humid morning, so within 2 minutes I was already drenched, but I kept walking. I stumbled upon the Alamo, which you’ll hear everyone say “is smaller than I expected it to be” and I walked around some more before heading back to my car to chug a couple Gatorades and hit the highway. I was headed to the beach!
San Antonio River Walk 
The Alamo
The purpose of this loop on the trip was to visit Port Aransas, near Corpus Christi, to stay with some friends for 3 nights at an Airbnb they were renting before the 4 days of the FinCon conference. A little rest and relaxation before the busy/loud/excitement of a conference full of money nerds. On my way to Port Aransas, I wandered south to the Padre Island National Seashore, again with free admission thanks to my National Parks pass. This was my first time ever driving directly on the beach, since that’s a big no-no everywhere in Florida except apparently still in Daytona.
After leaving the PINS, I met up with my friends at the Airbnb and we chilled out for 3 nights. There were walks to the beach, some grilling out, an adventure to a local sports bar to watch football, and another walk to the inlet to see sunset. But mostly just fun chats, a podcast interview, and some much-needed downtime.
As we left Port Aransas, I decided to take the ferry back to the mainland instead of the bridge/causeway that took me a lot further south than necessary. That was a neat experience and saved me at least 15 miles of driving. I then took all sorts of back roads to Austin, and wound up stopping at the Barton Springs Municipal Pool. This is a spring-fed, natural pool (of sorts) that is a constant 68° year-round. Perhaps a little chilly on that day, but it felt good to float and soak for a while after 4+ hours of driving.
I explored areas south of the Colorado River and had lunch at the Green Mesquite BBQ, before heading to my hotel, another Hyatt Place booked with 5,000 World of Hyatt points, by the airport. In the evening, I took a city bus downtown to meet up with conference-goers who arrived early, and I got to see several friends including JD Roth, Miranda Marquit, Jana Lynch and a whole bunch more. I took a late bus back to the airport and called it a night.
The next morning, I was going to be picking up my roommate for the conference at the airport. Jully-Alma Tavares is the founder of Investing Latina, and she would go on to win a Plutus Award for Best Personal Finance Content for Underserved Communities later in the week. We actually had not met before I picked her up at the airport, but she lives in NYC and has had 3-4 roommates for the past several years, so it didn’t phase her one bit. I was happy to have someone help cover the $900+ hotel stay for 3 nights.
After we checked into the Courtyard (by Marriott, finishing off the remaining travel credit on my credit card), I left my car with the valet so I would have access to it whenever other friends needed rides to the airport (about 15-20 minutes away). I ended up picking up my friend Jillian Johnsrud on that first day and took her back to the airport on Saturday, just as I was leaving Austin myself.
FinCon was a blast and I got to hang out in the hotel and went to meals with so many people that I interact with regularly online, but I didn’t actually buy a ticket to the conference this year and that was a mistake. I wasn’t able to go check out the presentations, Big Idea talks, and vendors, obviously, but I also wasn’t able to go to many of the social outings, and could not attend the Plutus Awards ceremony, even though I have sponsored one of the awards each of the past 3 years. My best friends in the world attend that conference, and if I ever go back to a FinCon, I’m actually buying a ticket and will be able to access everything that it entails.
When I left on Saturday, I drove up through Waco and Dallas, and then headed east into northeastern Arkansas for the night. I stayed in another Courtyard (by Marriott) in Jonesboro, Arkansas, so I could earn additional Marriott points to be used for future free night stays. From there, I cut across Missouri, southern Illinois and Indiana to get back to my home base in Indiana.
October
There was no overnight travel for me in October 2021, but there was one very special day-trip. I drove to Columbus Ohio to visit with my friend Amanda Page. Mandy is an educator, a freelance writer, founded a non-profit, is working on a documentary, a dog-mom and one heckuva friend. I got to meet her in Cleveland in 2019 when she drove up to spend an afternoon with me, so it was my turn to make the drive and spend the day with her, this time on her home turf. We took a walk through nature and through the adorable downtown of Worthington, had lunch at an English pub, walked some more and grabbed ice cream at Jenni’s. It was a great day of chatting, walking, laughing, and connection, and I hope we don’t have to wait 2 years to do it again.
Since I was already in Central Ohio, I drove another hour or so east to Licking Valley High School, where my friend Brent had his pizza food truck set up for the evening. This time, I was smart enough to buy two pizzas, helping him sell out by 7pm and allowing me to have leftovers for the next couple days. The first time I visited his food truck, I ate most of the pizza in the first sitting, and finished it off when I got back home that night. I wasn’t going to make that mistake again 😉
November
November was a big month of travel for me, after the light month in October. On the first, my parents and I drove down to Indianapolis to have dinner with my sister and then check into a hotel near the airport for a very early morning flight. I picked up the tab and we stayed at a Fairfield Inn & Suites (you guessed it, Marriott) so I could earn some more points for future travel. We flew out super early, connecting at Houston Hobby airport and then getting to Tucson Arizona by around 10:30am local time. My mom’s cousin Deby and her husband Jack picked us up, and we met up with my great-uncle Dudley and his wife Laura for lunch at a sports bar in Sahuarita. We were pretty tired from all the travel, so we relaxed around Uncle Dudley’s house, and walked to dinner at the clubhouse within the golf community where they live. Sharing this here because I’m not sure where else to put it: the motto of the week was “When the mountains are pink, it’s time to drink!”
On the next day, we loaded up in Jack’s SUV and drove to the Arizona-Sonora Desert Museum, but not before having a delicious lunch at Tiny’s Family Restaurant first. I had no idea the Sonoran Desert was as expansive as it is, but it was pretty cool to see some of the wildlife and of course the Saguaro cacti. We grabbed Papa Murphy’s take-and-bake pizza for a relaxed evening at home.
Lunch at Tiny’s Family Restaurant 
Afternoon at Arizona-Sonora Desert Museum
Thursday is Uncle Dudley’s golf day, and we had 13 guys play in his group (5, 4, and 4). I was using borrowed clubs that were too short for me, and old golf balls, but I still played pretty well for having never even seen the course before.
On Friday, we took a big road-trip to Bisbee and Tombstone. Bisbee was a big copper mine city, but is now bustling with hipsters. We took a tour of the Queen Mine and learned a lot about the process. Tombstone is basically a tourist trap, and unfortunately, we fell into one of those traps, visiting a comedy re-enactment of the shootout, rather than actually visit the OK Corral. But the tickets we bought included a bus tour of the city, and that was at least worth the price of admission.
Safety first! 
It was a Blast! inside the mine
Saturday was another big driving day, heading north of Tucson to the Biosphere 2 project. It was cool to see the various different biomes within one contained building, including an OCEAN in the desert! We grabbed lunch near the University of Arizona campus, which might have been a mistake since they were hosting a college football game that afternoon. Arizona ended a long losing streak that afternoon, although I’m not sure I can claim any credit for that! Haha. After lunch we headed back home to Green Valley, but not before stopping to see the Titan Missile Museum. Our tour guide was one of the men who worked inside the missile silo during the Cold War, so it was very exciting and scary to hear him run through all of the things that the 4 of them would do if they ever got the nuclear launch codes from the President or the Pentagon. And it was cool to hear that some of the missiles were refurbished and turned into some of the early rockets used by NASA.
Selfie at Biosphere 2 
Group photo by the ocean 
Titan Missile Museum
On Sunday, we stayed closer to home, visiting the artist little town of Tubac, and a few miles south of there is the Tumacácori National Historic Park. This is where I purchased my dad’s National Parks pass that is good for the remainder of his life (as teased about in the intro to Part 1). This gave us free admission for 4 people, so we only had to pay admission for 1 more. Tumacácori was one of the Spanish missions scattered throughout the desert southwest, and it was neat to see the church building and several out-buildings that helped support life in the desert so long ago.
On Monday, Uncle Dudley and I squeezed in another round of golf, and we packed up to leave on Tuesday morning. We were able to squeeze in one more attraction when we were near the airport, which was the Pima Air & Space Museum, where we saw multiple old Air Force One planes, tons of military history, along with some commercial jets and some aviation art.
Retired Air Force Ones 
Aviation art
A few days after leaving Arizona, it was time for the second EconoMe Conference in Cincinnati. I drove down early on Friday morning because I had arranged to pick up several friends and some of the speakers at the CVG (Cincinnati-Northern Kentucky airport code) airport throughout the day. I used to be an Uber driver on the side, so this was kind of like that, except I already knew my passengers beforehand, and it would give me a bit of one-on-one time with them before the busy-ness of the 500+ person conference on Saturday and Sunday. In between airport runs, I met up with JaxBeachLife and her partner, and Emilie was able to join us for a little while, too. It was so great to finally meet Jax and spend time with Emilie again, because I hadn’t seen her since the first EconoMe Conference in March 2020.
That evening, the Stacking Benjamins podcast held an event that would be recorded as a live-taping of one of their episodes. They featured special guests Kitty and Piggy from BitchesGetRiches, which is a multiple-award-winning blog and podcast. It was a hilarious night of money nerdery, and when I got back to my hotel (this time a Hampton Inn, part of the Hilton chain), my roommate for the weekend had arrived. Darcy is also a Plutus Award-winning blogger and she would help me co-host a panel on “SlowFI” at the conference the next day with my good friend Gwen from Fiery Millennials.
I walked over to the conference center early the next morning, since I was on the volunteer squad for check-in with my friends Lynn, Flynn and Amberly. We got just about everyone checked in for the conference within an hour, and then it was time for the main stage presentations at 10. Diania welcomed us all again with a talk about the importance of Community, and then the BitchesGetRiches duo started off the talks with some hilarity that involved audience participation in writing Kitty’s resignation letter, which she will be using when she retires at the age of 35 this coming spring. Other morning speakers included Naseema McElroy (who paid off nearly 1 million dollars in debt) and Jeremy Schneider (who founded a company that he later sold for $5m but talked about leading with humility).
After a lunch break, we had 2 more rounds of breakout sessions (including the one I mentioned before), and main stage speakers for the afternoon included Paula Pant, Carl Jensen, Angel Cellucci, and Rich Jones, before a closing panel with Paula, Mr. Money Mustache (Pete Adeney), Naseema, Joe Saul-Sehy, JD Roth and Kirsten Saunders from Rich and Regular. After a dinner break, it was time for the after-party!
Sunday was the day for off-site events. The day started with an urban hike, but I was content to hang out in the hotel lobby with other stragglers. We were heading to the Fowling Warehouse, which has nothing to do with birds, but is actually kind of like bowling with footballs, but also kind of like cornhole? I took a real estate tour around Cincinnati, and then took more friends to the airport after we were done Fowling.
A couple days later, I was all packed up and ready to end my summer/fall based out of Indiana. I hit the road early (for me) around 6am, and made good time throughout the day. I got through Atlanta before 3pm, so I kept driving. I hit the Florida border not long after 6pm, so I kept driving. By the time I should have stopped, I felt like I was too close to home to spend points or $100+ on a hotel night, so I kept driving. I eventually back to my house in Florida around 11pm, which is a pretty reasonable 17 hours of driving for the 1,134 miles I covered.
The weekend before Thanksgiving, I made a trip across the state to visit the ChooseFI local group in Stuart, which is led by my friend Lisa Duke. I figured she was one of my last friends in Florida to see me back in May before the Gap Year began, so I went back to see her and give her a recap on what all I had done so far. But this time, there were a total of 5 of us who showed up, so that was fun. And I met a fellow early-retiree/semi-retiree who had just gotten back to Florida from extended travels, so that was a lot of fun, too!
I will start another post with December travels after the new year. Thanks to all who’ve read this far.
The Further Adventures of Josh, featuring Literally Everyone. I love how well-connected (and well loved) you are in this space!
I love that you were a part of both parts of these recaps! 2020 was so sad with no BGR appearances in my life!