Back in mid-July, Olivia and I made a semi-spur of the moment decision to head down I-95 to visit her family in Boca Raton, Florida, with a few scheduled stops along the way. Check out the video recap of part 1 of our trip below:
We have been looking to get on the road in some capacity for awhile now and the opportunity presented itself with Olivia having nearly a full week off of work. We had originally planned to make a trip down to Savannah GA the last weekend of June but had postponed due to COVID spikes. This time around we included it as our “mid-point” destination on the drive south.

I’ve visited Savannah twice before and each time left me excited to return. Such a beautiful city that is chock full off history and culture; it is a treat to visit. You know you’re in an special place when all you need to do is walk around to take in the sights. Every block is adorned with 100+ year old buildings, towering live oak trees, and countless historic events to learn about. It is definitely one of my favorite places to visit in the south.
Half the reason for the long drive (as opposed to getting on the plane) was to be able to bring our little golden Eleanor along for the adventure. Because of this, I booked the Residence Inn nestled within the heart of the historic downtown. The hotel turned out to be the perfect choice, as it was within walking distance of everything we wanted to do. Even more so during the age of COVID, the hotel seemed extremely clean and we felt very safe staying with all the extra safety measures they had in place.
We arrived in Savannah around 2pm on a Saturday afternoon and immediately got on our walking shoes to head down to the City Market area, just a short 10 minute stroll from the hotel. Of course, the first stop in the 90+ degree heat was a visit to Wet Willie’s to get a frozen adult beverage–just what we needed to cool off in the heat. Upon entering the main area of City Market, we immediately noticed a few differences in how others were treating the presence of COVID. The mask wearers were somewhat few and far between (except for inside bars/restaurants where the city had just mandated mask-wearing), and it just seemed super lax and casual considering the current state of things. It was a little unnerving but we did the best we could. At Wet Willie’s (our only stop) they were doing a fantastic job of mask enforcement, social distancing, and even a temperature check upon entry. Nice work Willie!

From there, we decided to continue down to the beautiful riverfront area, chock full of beautiful old buildings, cobblestone streets, and just an all-around old-school feel. Definitely one of my favorite places to people watch as well. After nearly sweating out everything we had in our bodies, I opted for one more frozen drink (necessary) and we took off for the hotel. We did, however, stop for a delicious slice of pizza on the way back at Vinnie A Go-Go’s. Amazing thin crust pizza that was just the snack we needed to get us to dinner.
After a quick nap at the hotel, we ventured out again to find something to eat for dinner. Most of the places we initially checked out were either closing early or did not have any availability. We were told a similar story at our 3rd stop at Ruth Chris Steakhouse, but Olivia somehow managed to snag a last minute reservation online. Score! We had 30 minutes to kill–just enough time to grab drinks (across the street) at one of my favorite spots in Savannah: Rocks on the Roof.

Rocks on the Roof is an awesome rooftop bar right on the Savannah river on top of the Hotel Bohemian. The bar has some downright beautiful views, and it was a great place to take in the sights and get us warmed up for steak.
Ruth Chris did not disappoint, as my filet was cooked perfectly and the service was absolutely excellent. We had one of the last reservations of the night, so between the spread out tables and lack of people nearby, we felt like we had the place to ourselves! Of course, we had to do dessert, and the cheesecake that I ordered was delicious. A great was to end our one night stay in Savannah.
The next morning, we were up early to find some breakfast and get on the road. We landed on a local favorite that happened to be close-by the hotel called J. Christopher’s. I had my signature chicken and waffles that turned out to be pretty good. Definitely not the best chicken I’ve had but the waffle was superb. After devouring our food and heading back to the hotel, we packed our things and grabbed the dog to hit the road for Florida.

We were able to get to South Florida with no issues whatsoever, also managing to pick-up Olivia’s older brother Austin from the Palm Beach airport on the way. We enjoyed a great meal that evening, spending time with Olivia’s father, step-mom, and grandmother. Upon catching-up on everything going on in our lives and scarfing down our dinners (takeout from SmashBurger, mhhmm), the group decided to make the short walk to the local frozen yogurt store. Nothing better.
The next day started early with a breakfast at one of our favorite french bakeries called Saquella Cafe. This place is super legit and everything I’ve eaten there has been amazing. This time around I kept it simple with a bagel and cream cheese, a side of fruit, and, of course, a nice helping of bacon. It was plenty for me and a great way to get our morning started.

After a few hours at the hotel catching up on work and sending emails, we decided to grab an afternoon drink at a local German spot called the Bierhaus. About thirty minutes into our drinks, Olivia randomly received an email stating that she had been accepted to a master’s of Nursing program at UNC Chapel Hill. This is something she had been looking forward to after being placed on the waitlist a few months prior. It was so incredibly perfect for her to get this news when we were there with her family. She has worked so hard for this and I am so incredibly proud of her. I know she is gonna kill it!
After another fantastic dinner with Olivia’s family at her favorite restaurant (Season’s 52), we decided to call it an early night back at the hotel. Tomorrow, we would hit the road once more to head to one of our favorite places in the world, Universal’s Studios Orlando.

One last tasty breakfast with the fam on Tuesday morning and we were saying our goodbyes. It’s always tough leaving because we always have such a great time together. We will certainly be back to visit soon. Until the next time, stay tuned for part 2 of our epic road trip: Orlando!
– Walker
Check out a few more photos from the first part of our trip below:




















