(This post will be maintained periodically)

I thought it would be a good idea to share a list of the trips that my travel hacking [obsession] has allowed me to cover in the past few years, since really taking up the hobby in March 2016. If you are interested in finding out more the various points and miles programs I use, please browse this page (contains referral links that may benefit me, at no cost to you).

So I lied. My very first travel hacking booking actually happened before I started this hobby. I was traveling a lot for work starting in December 2014, so by August of 2015 I had a lot of Hilton Honors points. I used 80,000 for 2 nights at the Embassy Suites in downtown Indianapolis to attend my cousin’s wedding. My parents stayed in the room with me, and I slept on the pull-out couch in the “living room” portion of the suite. But the points came free from my work travel, so it didn’t cost me anything to be able to help out my parents with lodging expenses and we all stayed a couple blocks away from the wedding reception venue (the Eiteljorg Museum).

August 2016 – I used Southwest Airlines Rapid Rewards points to fly back “home” to Indiana to attend my 15-year High School Class Reunion. The reunion was co-located with a local non-profit’s wine, craft and music event at a local winery, but thunderstorms throughout the day kinda ruined the evening plans. We had 100 students in our graduating class, and 13 of us showed up for the 15 year reunion…


October 2016 – 2 nights in Downtown Orlando using Hilton Honors points. I was a Diamond member at the time, so I was able to book a special Diamond rate for 40,000 HHonors points per night, instead of the listed rate of 66,000/night.

Christmas-New Years 2016/17 – I live in Florida, but grew up in rural Indiana. I always get the mom-guilt-trip about coming home for Christmas, so I used Southwest Airlines Rapid Rewards points for my flights. I only paid $11.20 out of pocket to cover the September 11th security fee, both ways $5.60.

October 2017 – 2 nights in Orlando, across the street from Universal Studios. I used 80,000 HHonors points for a deluxe room with a view of the theme park. I could have saved (I think) 5,000 points per night by going with a standard view room, and I will actually do that going forward. It was impressive, but a little further away from the action at the park than I expected.

Christmas/New Years 2017/18 – If you haven’t noticed the theme, this is just a continuation of that same pattern. Moving along…

February 2018 – A change in my travel theme! This trip was a 2-day trip to Indianapolis, but for a very special reason. My hometown high school girls basketball team was playing at Bankers Life Fieldhouse (where the Indiana Pacers play!) in the State Championship game at the Class 2A level. I booked my flights on Southwest (again) for about 25,000 RRs. This was booked only 7 days in advance, so tickets were a little bit more expensive than I had seen only a few days earlier, but I waited until the buzzer sounded in their THRILLING OVERTIME VICTORY at the Semi-State game to book my flights. I also used 40,000 Hilton Honors points for a single night at the Homewood Suites in Downtown Indy, just 2 blocks away from Bankers Life Fieldhouse. Unfortunately the Lady Falcons did not win the State Championship, but they led at halftime and were very close the whole way, despite our two best players competing with torn ACLs. These girls are TOUGH!


April 2018 – My parents were visiting with me in Southwest Florida, but their best friends (and practically my second set of parents) were in Orlando at the Gaylord Palms Resort, so we planned to spend a day with them at their resort and in the general area of International Drive. I used 35,000 of my IHG points to book 1 night at the Holiday Inn Resort near Disney Springs. By carrying my IHG card, I automatically have Platinum Elite status, which gave us free drink coupons, free parking, and expedited check-in & check-out. We had an awesome time visiting with our friends, had margaritas with chips & salsa at Señor Frogs, and the 5 of us were able to beat an escape room in 48 minutes and change! This was an amazing trip for just burning some IHG points.

May 2018 – I’ve got a whole post on My Freedom Trip to Los Angeles, Seattle and Boston. To recap, I used Delta Skymiles (AKA SkyPesos), IHG points, Hilton Honors points, JetBlue TrueBlue Miles, and transferred a couple thousand Chase Ultimate Rewards to Hyatt for a second Hyatt redemption. JetBlue TrueBlue points (again) rounded out the trip.

June 2018 – I had a business trip to Phoenix, with a very early morning flight scheduled out of Tampa. Since I live about 2 hours away from the Tampa airport, I didn’t want to leave my house at about 3AM to get there in time, so I drove up the night before and stayed at the Holiday Inn Westgate – Tampa airport, which allowed me to sleep in until almost 5AM and still make it with plenty of time to spare. This was a 20,000 point IHG redemption, and I stayed on a floor reserved for Platinum Elite members, with a complimentary lounge.

Thanksgiving 2018 – Fly home on Southwest Rapid Rewards points (a little over 17k) to be with family on Thanksgiving, but also to celebrate my parents 40th wedding anniversary on the Sunday after Thanksgiving.

Presidents Day Road Trip 2019 – I wrote a whole post on this trip here, but I basically just had gas expenses and food because I used 30,000 Hilton points for a night at a Hilton Garden Inn in Warner Robins GA, Chase Ultimate Rewards transferred to Hyatt for a Category 1 Hyatt Place in Sumter SC, and an Annual Free Night Certificate from Hyatt credit card for my final night at a Hyatt House in Charleston, SC.

February 2019 – Just 4 days after getting home from my roadtrip, I flew to Indianapolis for a repeat trip of the State Finals trip described above. Unfortunately it was very similar in that my HS girls basketball team led for much of the game, but eventually wound up as Runners-Up. I paid for my flights with my annual travel credit from Chase Sapphire Reserve card, crashed at my sister’s house for one night, and used 34,000 Hilton points for a night at the Home2Suites in downtown Indianapolis, about 3 blocks from Banker’s Life Fieldhouse. Aside from food, drinks and Uber rides, this was completely covered by my CSR annual credit, including parking at the airport.

May 2019 – For over a year now, I’ve been following the story of the Playing with FIRE documentary about Scott and Taylor Rieckens. I was a Kickstarter backer and watched the film 4 times at home by myself, but when I heard that tickets to the premiere in San Diego were still available less than 2 weeks before the June 1st date, I jumped at the chance to be a part of it! Flights were booked on Southwest Airlines with ~27,000 Rapid Rewards. I booked a prepaid hotel rate of $113 at the Westin in the Gas Lamp area of downtown (just a block away from the Lyceum Theatre where the film was shown), and booked my second night at the Andaz nearby with a Hyatt free night certificate that I earned by completing the first leg of the World of Hyatt brand explorer challenge (stay at 5 different Hyatt brands, earn a free night). Counting my VIP ticket, hotels, Ubers, meals, sight-seeing (USS Midway), and airport parking, this trip class me under $300 for an incredible weekend I won’t soon forget!!

September 2019 for FinCon in DC, I wound up driving, due to Hurricane Dorian threatening to hit Florida. I drove up 5 days before the conference so that I could be a tourist for a little while in Washington DC before the conference begins. I covered 1 night at a Hampton Inn in Lake Park, GA with Hilton points, paid a cash rate for Sheraton in Durham, NC, and transferred Chase Ultimate Rewards to World of Hyatt to book 1 night at the Hotel Revival Baltimore. After that, I drove back to Arlington, VA to spend 2 nights at the Courtyard by Marriott with my friends Military Dollar and Mr. Refined by Fire and went sight-seeing. FinCon itself was a cheap venture for me, which I hacked by being on staff as Volunteer Coordinator, providing a free ticket and free hotel for 5 nights. After FinCon, I needed to drive to Destin, FL for a work conference, and I used a points + cash deal for 1 night at the Tru hotel in Knoxville, TN.

October 2019 – Adventures to FI Retreat in Whitefish, Montana. I used 25,000 American Airlines miles to go from RSW-DFW-SEA-FCA then FCA-SEA-PHL-RSW. Rather than spend all night in the Sea-Tac airport, I used my IHG Free Night certificate at the Crowne Plaza across the street (I was able to walk there). And I cut costs in Whitefish by sharing a room with another attendee, Kevin from Gainesville.

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