Chicago to Savannah: Family Road Trip Recap

My mom turned 60 the week of Thanksgiving, and so my brother, Kevin, and I decided that we would plan a family vacation — something we really hadn’t done in the better part of a decade — to celebrate. I love to give people experiences instead of stuff. This vacation was a chance to be in the moment (I barely glanced at e-mail all week), give back as adults and create some great memories with the fam. It was awesome to include Joe in a family event less emotionally fraught than wedding planning, too. Grab a mug of tea for a recap with all the details!


We chose Savannah because we were interested in going somewhere that would be warmish in late fall, that had sightseeing potential (but wasn’t super cheesy touristy) and since my mom had always talked of visiting neighboring Hilton Head and Savannah is the birthplace of Girl Scouts, it felt like the right fit. I’m so glad we made this our destination! We had just the right amount of time to explore, and the city was super easy to navigate. And Spanish moss. Everywhere.

Kevin and I wanted to cover most of the trip expenses because, let’s be real – it’s not much of a present if you’re like “Yay! We’re taking you on a vacation! Now buy your $500 plane ticket!” but we’re on a budget and so we started to look into driving the nearly 1,000 miles there. I got a pretty sweet deal on a Ford Escape by calling and pre-paying with Avis (unlimited miles) and we listed all four adults as drivers for the 14+ hour trek. Kevin is a consultant who has a ridiculous stash of Marriott points and gets government hotel rates, so he hooked us up with lodging. Of course, we downloaded Midnight in the Garden of Good and Evil audiobook and listened to part of it on the way there.

Day 1: Chicago to Asheville, NC. With a spontaneous pit stop at a fried chicken place worthy of a historical marker.

We decided to get the long drive out of the way first, stopping at a rest area for a picnic lunch and then making a spur-of-the-moment decision to visit the original KFC/Colonel Sanders Cafe in Kentucky, which was just goofy and random enough to make us feel like we were on a genuine road trip.


We stayed at the Grand Bohemian in Asheville, which was pretty luxe (thanks, Kev!) and right outside the Biltmore Estate. The hotel sent up champagne and snacks to help toast my mom, since we’d set out on her actual birthday, and we were able to get a late dinner of awesome burgers at the Village Wayside, a short walk down the street. (It was tempting to go to the fanciest McDonalds and Hardees we’d ever seen, but I’m glad we stuck to local flavor!)


We got up early and headed to the Biltmore for a tour of one of the country’s oldest and most opulent privately owned residences. I assumed it was owned by a nonprofit Foundation, a la Des Moines’ Salisbury House, but not so. Tickets are pricey, plus you could pay an extra $10-20 for an audio or guided tour. But the grounds and home are a marvel and my mom really wanted to go. We started in the gardens and then wound our way through the two-hour self-guided house tour. We scoped out downtown Asheville quickly, “fueling up” at Asheville Brewing Co. before we hit the road. Note: Planning a trip through Asheville and Savannah while pregnant and unable to partake in the alcoholic beverages is a mild form of torture.

Day 2: Asheville to Savannah, by way of Augusta (which is not the way you should go)

Joe’s bff Jimmy and his wife are currently stationed in Augusta, so we made a slight detour on a small highway to Augusta to meet up with them for dinner on our short drive. We stopped at Nacho Mama’s, which was a fun, casual restaurant downtown. I got a burrito but the nacho plates looked INSANE. Food will be a strong theme in this trip. We got into Savannah pretty late, and checked in at the Riverfront Marriott, which was a little bit dated and on the periphery of the historic district, but super cheap thanks to Kevin’s points, which also granted us access to the concierge lounge free full breakfasts and nighttime snacks. If you stay here, be sure to ask for a room that faces the river so you can see the barges go by from your balcony.

Day 3: Family portraits at Bonaventure Cemetery and the Savannah Slow Ride

As a surprise, I’d contacted a friend of a friend for a family portrait session while we were in Savannah. (Something else we hadn’t done in forever!) Jill Page, the photographer, recommended we meet up in Bonaventure Cemetery because its trees and marshy perimeter make a great backdrop. She was so right, with the bonus of not having to be self-conscious as people walk by your photo shoot because, well, it’s pretty quiet there. We had a great time exploring the cemetery afterward and it helped set the tone for how historic the city is.

After photos, we headed downtown. Since the Juliette Gordon Low House was closed on Wednesdays, we had to wait to tour the birthplace of Girl Scouts and had lunch at Soho South Cafe, which was full of art and hit the spot for a late afternoon meal.


Later that evening (after a nap!) we met up with the Savannah Slow Ride folks for a haunted pedal pub tour. The company handmakes their own pedal pubs, which are a ridiculous but fun way to get around the city. Savannah is full of tour trolleys and horse-drawn carriages, but if you’re going by Slow Ride, you become one of the sights to see! Each vehicle has several no-pedal seats (being preggo, I got one) but all have cup-holders and since Savannah allows open-containers, you can get your beers to go at the various stops and enjoy them as you pedal. Joe rides regularly and his legs were pretty sore! The ride was more silly than spooky, but lots of fun. We ended our night returning to Vinnie Van Go Go’s for pizza that we brought back to the hotel, where Kev introduced us to the game Settlers of Catan while we ate.

Day 4: Thanksgiving picnic by the Tybee shore

We spent our Thanksgiving in Savannah in a super laid-back fashion. We decided to drive out to Tybee Island (it’s only about 15 miles) and although most things were closed we walked the beach, collecting shells and sharing a picnic lunch of leftovers from our driving snacks.  Tybee Island has a lovely lighthouse and marine science center that would be fun to visit on non-holiday days. We sort of crashed a fashion photo shoot on the lighthouse grounds. Whoops!


We had Thanksgiving dinner at Molly MacPherson’s, which we discovered on our slow ride the night before. It’s a Scottish pub that offers Scotch flights, so the guys drank their dinners.

Afterward, we ended the night doing a historic carriage tour around the city. There’s something magical about wrapping yourself in a scratchy blanket and seeing a city draped in Spanish moss backlit by old fashioned street lamps, to the soundtrack of clomping hooves.

Day 5: In which we ate breakfast and then get in line for lunch

Some people fast the day after Thanksgiving. We got in line at Mrs. Wilkes, an alternative (more authentic?)  to Paula Deen’s Lady & Sons. I think we got there at 10:45 a.m. and had an hour and a half to wait/digest breakfast before we were seated. Do not expect a normal restaurant experience at Mrs. Wilkes. It’s like the gastronomic equivalent of Space Mountain. You’re seated in groups of 10, with all the fixins and sweet tea already laid out on the table when you sit down. It’s a communal meal (pass the creamed corn, please!), boarding-house style.


Everyone gobbles down fried chicken (servers’ T-shirts: If the Colonel made chicken this good, he’d be a General) and biscuits and greens and pulled pork, etc. etc. Right after you’ve stuffed yourself to the brim, they bring dishes of peach cobbler or banana pudding and then you’re finished.


After lunch, we walked through the SCAD shop and mom and I finally got to do our Girl Scout pilgrimage to the Juliette Gordon Low House. Squee! It’s the 100th anniversary of Girl Scouting and I’m a lifetime Girl Scout and my mom was leader of Troop 784 until we graduated high school, so it felt like a right of passage to go and learn about how awesome Juliette Gordon Low was. What an inspiration! We were a little disappointed that the house was covered in scaffolding and that the gift shop didn’t have cooler items, but whatcha gonna do? We heard the Savannah History Museum had an exhibit up honoring 100 years of Girl Scouts, but ran out of time before we could see it.


On our last night, we finally saw Forsythe Park (in the dark) and had a last bit of local flavor for dessert – Leopold’s Ice Cream.

Day 6: Savannah to Louisville; Day 7: Louisville to Chicago

Then it was homeward bound. We veered off the interstate to take a .1 mile hike along the Appalachian Trail as a way to stretch our legs.


We spent our last night on the road in Louisville, and I’d love to go back and explore the city. We arrived a little too late to see the Louisville Slugger Museum and Factory, but we did get to snap a few photos in front of the World’s Largest Baseball Bat. And what kind of road trip would this have been had we not encountered a “World’s fill-in-the-blank” along the way! The last day we got up early and made it back home before lunch so Joe and I could continue our trek back to Iowa.

I can’t believe the next time we go on a family vacation, we’ll have a baby in tow! It was great to have one last hurrah being the kid.


P.S. My brother is the kind of person who has an app for everything and knows how to use technology to make his life way easier. He had the waze app as a GPS when we were driving and it was pretty great, then introduced us to Field Trip, too.


Filed under BS outside the Midwest

2 responses to “Chicago to Savannah: Family Road Trip Recap

  1. What a great trip! I love road trips like this and although I don’t mind flying, I think driving cross country is the BEST way to see the states.

    Savannah has been on my bucket list for awhile now and I am still kicking myself for not making it down there when I lived in South Carolina.

    I bet it is mind blowing thinking about the next vacation with babe in tow 🙂

  2. carol beamer

    The best. So glad you make it happen!

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