Sabbatical Part 1 – Florida to Wisconsin


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One of my favorite work perks is they give me a 3-month paid sabbatical every 5 years. I can take the sabbatical anytime after my 5th year anniversary and with that date in mind, I started planning for the sabbatical. I had 3 months to do whatever I wanted, and I wanted to make the most of that time in a number of ways. I wanted to return well-rested. I wanted to learn new things. I also wanted to travel, both with friends and with just my wife and me. I decided I’d split the sabbatical up into chunks to focus on those different goals. The first chunk I wanted to focus on traveling.


The Plan

I’ve visited California and Washington state briefly, but I hadn’t explored much of the US west of Wisconsin so finding an opportunity to go west was something I was very interested in. COVID was still a big issue and travel restrictions hadn’t let up everywhere just yet, so I decided to plan a trip that would likely be unaffected by COVID and also would allow me to see states I hadn’t visited yet. After much research and planning, I came up with a road trip around the US’s National Parks for my wife Claire and me. It was a large rectangle bounded by Florida, Wisconsin, Montana, and Arizona.

I wanted to maximize the amount of time we could spend on the trip, so we aimed for traveling light and keeping costs down. We decided on a, primarily camping, trip with weekly stops at hotels/cabins/airbnbs to do laundry and remember what it feels like to be indoors.

The Pass

I purchased a National Parks pass for $80 at the start of the year. That gets you into any US National Park for free. If you visit more than 3-4 parks in a year, it’s worth it to get. The pass lasts 1 year. I’m already planning to purchase one for next year.

Keeping it all Organized

I planned the trip out on Roadtrippers. I can share a link to the itinerary Claire and I created. Along with Roadtrippers, I made an old-school backup using a giant binder. The binder held all our reservations for campsites, tours, hotels, and cabins. I also kept a few extra sleeves in the binder for storing brochures and such that we picked up along the way. By the time we finished the trip, it was bursting at the seams.

Documenting The Trip

I shared daily posts on my Instagram during the trip. I’ll embed those posts below and share a bit more context where I can.

Day 1 – Heading North and Bagels

Prior to leaving on the trip, Claire and I had the car serviced to make sure it would survive the journey. The morning of our trip, we headed out to the car that we’d packed the night before and went to start the car only to find that the car wouldn’t start. Luckily it was an easy fix, the battery was dead. We had a friend give us a jump then we drove to Autozone and got the battery replaced.

From there we started driving north and arrived around lunch to visit friends in Macon that had started a successful bagel shop. We spent the afternoon with them and got to see the house they’re remodeling to eventually live in.

That evening we stayed in Chattanooga, Tennessee. We’d planned to stay there purely out of convenience but were glad we stayed. It was a cute town with a pretty incredible food scene. Claire and I had some delicious Japanese small plates and ramen. The Marriott we stayed at had a Speakeasy built into the lobby that you access from behind a bookcase that swings open. Claire and I had a nightcap there before turning in for the night.

Day 2 – Caves and Friends

Claire and I woke up early, got some coffee across the street at the Chattanooga Choochoo, then hit the road again.

Today’s stop was at Mammoth Cave. The national park offers several different tours. We opted for the Domes and Dripstones tour. The tour met up at a covered pavilion just off the national park’s parking lot. From there, we had a short introduction from a park ranger, then we all boarded buses that took us to the cave entrance. The entrance itself looks just like a small doorway in the rock that opens into a set of stairs that takes you deep into the earth. We walked at a steady pace with limited breaks and, even then, spent about 2 hours walking. The cave, as the name suggests, is massive. At one point our tour group stopped in a room of the cave that was so large they had created an amphitheater inside of it. We only got to explore a small portion of the overall cave system, and, given the chance, I’d love to return and do another tour to explore some more.

After our Mammoth Cave adventure, Claire and I continued our journey north. We stopped in Covington to visit my friends: Victor and Monica. The four of us had a late dinner in town and then settled in for the night.

Day 3 – Meet the Parents

Days 3 we met up with Claire’s family in Indianapolis for the afternoon. We drove around the city and got to see where Claire used to live and the park by her house. Then we got ramen for lunch with her parents.

Day 4 – Nature and Bonfires (unrelated)

We went on a nature walk with Claire’s mom and brother and then met up with some of Claire’s friends for a bonfire in their backyard that evening.

Day 5 – Chicago Adventures

Claire and I traveled into the city and visited the Zoo, then met up with some friends for Korean-style corndogs and giant bavarian pretzels.

Day 6 – Bikes and Babies

Claire’s dad and I did a 25-mile morning bike ride to start the day then met up with the rest of the family and headed to Claire’s brother’s baby shower. It was so unbelievably hot that day (100+) that we hopped in the swimming pool at the baby shower. We also found out later that we’d won some candy in a raffle at the event.

Day 7 – Family and Nature

Claire’s parents had arranged a small gathering with the family at a local state park called Starved Rock. We arrived at midday and did some hiking along a riverbed that ended in a small waterfall. After our hike, we had a lovely meal in the parks’ lodge with Claire’s family. They rented a cabin for Claire and me for the night.

Day 8 The North

Claire and I reached our northernmost point for the first leg of the trip on this day. We drove from Illinois up to Wisconsin stopping at the New Glarus Brewery for a pint and then continuing on up to Madison. Claire and I both lived in Madison before meeting each other, although not at the same time. This was a great opportunity to see both her and my Madison and where/what we enjoyed doing. We visited Epic, where I used to work, and visited Claire’s friends for dinner downtown that evening.


This is where I’ll wrap up the first section of our trip. I anticipate making 4 posts: 1 for each of the 4 sides of our rectangular route. The next post will be about our long trip out west from Wisconsin to Montana.

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