A Sassy Guide to Galena & the Car That Got Us There the 2020 Toyota Highlander

My family and I usually take a big trip during the summer since my sister has it off from school, but 2020 is a weird one so instead of doing a trip to say Japan we decided to do a road trip to Galena, IL. It’s about 3 and half hours west of Chicago and has tons of history. 87% of Galena’s buildings are historic buildings and can’t be torn down so it’s literally like stepping into the 1800s when this town was in its heyday. Galena is located right on the Mississippi River so it used to get a lot of steamboat traffic, but when the rivers got lower the steamboats couldn’t get through because their cargo was too heavy and the city eventually lost its luster, but it makes it such a cute getaway today!

2020 Toyota Highlander – peep that sun roof tho!

Toyota loaned us their new 2020 Highlander for the weekend and it was literally the perfect car for a family road trip. Some of our favorite features as a family included:

  • Ventilated front seats (it was so hot out this was amazing!)
  • Three-zone automatic climate control with separate second-row control panel so we each could have individualized temperature settings!
  • Wireless smartphone charging station – key for doing directions from your phone and not losing battery
  • Jim’s favorite thing – the in-dash split level shelf where he could put his mask and napkins haha
  • The Head-Up Display with speedometer and navigation assistance that appears right above the steering wheel in the glass so you don’t have to turn your head to look at directions or what music is playing!

We arrived in Galena at our B&B Felt Manor Inn on Friday evening around 5pm. I had won a gift card for a stay at the inn last year so it came in super handy when we needed a getaway that was closer to home, in-state, and had a private coach house so we didn’t need to have contact with any other guests.

Felt Manor Inn.

The coach house is completely separate from the main inn and was recently renovated and is completely modern. The rooms in the inn are more traditional to a 1800s home with no TV, etc., so I am glad we picked the coach house because we decided to have a pizza & movie night our first night in Galena. We had originally planned to eat downtown but the pizza place we wanted to try was still only doing take-out. This ended up being a blessing because downtown was PACKED to the gills with people and bachelorette parties. We felt more comfortable doing our own thing at home. We got pizza from Cannova’swhich was actually fabulous – get their speciality pizza with spinach – YUM!

We started Saturday morning early because we wanted to do some physical activity by renting bikes from Fever River Outfitters to ride along the Galena River Trail. 3 bikes for 2 hours were about $60 – a real deal to us city peeps! We went about four miles down the trail which ended at a really great view of the Misssissippi River and some really cute rainbow Adirondack chairs and then biked back.

We stopped at the Belvedere Mansion on the way back which was a real treat. This home was considered the first mansion in Galena and was owned by J. Russell Jones who owned a bunch of steamboats. The home was eventually sold after he got offered a job as a US ambassador to Belgium, but the home itself is still maintained in all its 1880s glory. A lot of the house has trinkets and treasures from all places over the US so each room has its surprises – like the original drapes from the movie Gone with the Wind are in the conservatory and there is a clock that possibly belonged to the captain of the Titanic!

Galena River Trail.

After our tour, we rode back downtown and got lunch at Dirty Gurt’s – good pub type food – and then went home to shower. I had convinced everyone that we needed to do a winery tour of Galena’s finest wineries in the area, but I failed to realize most of them closed at 5pm so we ended up only going to Galena Cellars Vineyard, but it has a gorgeous view of the hills and you can do wine flights for as low as $10. I did the rose flight and Jim did a dry wine flight.

That evening we went for dinner at a German/French hybrid restaurant called Fritz & Frites which was cute. Most of Galena’s Main Street is shut down so people can eat in the streets and it makes for a cute little view downtown.

Sunday morning we woke up relatively early again to pack up, eat our delicious breakfast from the inn (they make it fresh every morning! drool!) and went back to downtown Galena to do our own self-guided tour of the history of the downtown buildings and stopped in some of the shops like Galena Apothecary, Great American Popcorn, and Elle & Beck. On our way home we stopped at Thunderbay Falls which had these gorgeous falls and fishing (we just did the falls!), and then drove the 3 hours home.

Galena Cellars Vineyard.

COVID CONCERNS: This weekend away was literally just what the doctor ordered for me – I really needed to get out of the city. Downtown was a little crowded at times, but if you stayed at the beginning or ends of the closed off Main Street you could avoid a lot of the crowds. I would say 50% wore masks on the street and the other half didn’t so just be forewarned. All stores and restaurants require masks and a lot make you use hand sanitizer before coming in the store as well. Felt Manor Inn was completely contactless and we highly recommend it for someone looking for a hybrid Airbnb/Inn experience since you could be relatively alone but also got amazing happy hour platters, cookies, wine, and breakfast each morning left on the porch!

Drop any questions you have about our first road trip we’ve tried during the pandemic in the comments below!