I’ve only been to St. Louis one other time, well over a decade ago, to see Death Cab For Cutie. I was only there for one night, so besides the music venue and the Arch, I’ve never really seen St. Louis. Until last weekend.

We were recently presented with an exciting opportunity – to go on a spontaneous road trip adventure to #ExploreStLouis! While we set our own itinerary, ExploreStLouis.com hooked us up with some awesome local businesses and at the end of this post is a chance for you to win your very own trip to explore the city!

Our Spontaneous Family Road Trip

We live a five and a half hour drive away from St. Louis. Since we were just going to be there for a long weekend, we decided to get a head start and drive a few hours after work on Thursday night. I’m glad we did because we were able to stop in Springfield, Missouri and enjoy a local dinner instead of a rushed, drive-through meal. Then on Friday, we had almost a full day in St. Louis. Arriving to town around 10:30 a.m., our first stop was the Delmar Loop. There were plenty of restaurants and little shops in the area to explore, with construction underway for a trolley line. After taking a stroll through a cute little candy shop, we were treated to lunch and drinks at Fitz’s .

Walking around The Delmar Loop
(and playing a little air guitar)

Cute little candy shop on The Loop.

Fitz’s Root Beer
Even though it’s a famous root beer company, Fitz’s is also a restaurant with a full, fun menu. We got right down to business and let Iris have dessert first (we were on vacation, after all).

While Iris opted for a MEGA root beer float, I jumped right into their adult drink menu with a Mexican Mule, made with Fitz’s ginger beer. After we got our drinks out of the way, we chowed down on burgers until we were stuffed. You can even stick around and watch them bottle the soda.

From Fitz’s we made our way over to our hotel, The Cheshire. I have to say that this boutique hotel accomplishes something most hotels do not – it’s just as wonderful for adults as it is for kids. Each guest room features a book written by the author the room is named after (we were in the A. A. Milne suite, who wrote Winnie the Pooh).

As far as the accommodations, I am a self-proclaimed hotel snob and this one passed every test. The entire hotel is unique, but being a four-diamond property the standards are also high – comfy beds, nice bath products, complimentary (and delicious) breakfast, Keurig coffee maker in the room, great pool area, and so on! And as for the front desk staff, I feel like I may have some new best friends. They were as friendly and helpful as could be.

As soon as we checked in we had to go off and explore the castle-like grounds.

For our first afternoon in St. Louis, we decided to each choose a location to explore. Iris was up first and she chose the St. Louis Zoo, which was conveniently less than a mile away from The Cheshire .

What’s the best thing about the St. Louis Zoo? It’s FREE! Because of this, we splurged the $15 for close parking, which was totally worth it. The zoo is pretty sizable, so after walking around for a couple hours we were happy to hop right into our car. This was Iris’ first zoo experience (that she could remember) and she was in HEAVEN. She really wanted to see an elephant in real life, so after a bit of searching we found ’em!

And what’s the second best thing about the St. Louis Zoo? They serve BEER!

After the zoo, we did something the whole family wanted to do – visit The Gateway Arch!

While the grounds are undergoing a massive renovation, we were still able to get our Arch on. We didn’t think we’d have enough time to go up inside, but Iris insisted. After checking at the ticket office, we found out there was no wait at all! Up we went and I’m so glad we did. It’s one of those bucket list things that just felt good to do at least once in your life.

Then it was my turn to choose our next spot! I had been dying to try the Three Sixty roof top bar, which is just a five minute walk from the Arch. Opening in the afternoons at 4 p.m., I read online that it was all-ages before 7 p.m. Located on the top of the Hilton St. Louis at the Ballpark, Three Sixty has amazing views of downtown St. Louis – from the Arch and right into Busch Stadium. We enjoyed a few appetizers and drinks, which was a lovely break after our previous adventures.

Last, but not least, it was Todd’s turn to choose a spot to explore. Being the craft beer lover that he is, of course he chose one of the many local breweries St. Louis is home to – 4 Hands. While Todd stocked up on a case of beer to bring home, we stayed for dinner, making it our last stop of the day.

Back at The Cheshire, we read a little Winnie the Pooh before ending our very full, very fun day.

Good morning from The Cheshire!

On Saturday we woke up fairly early (thanks, Iris) and, after a quick bite to eat at the hotel, went straight to the City Museum.

This place is what we were looking forward to the most. We’ve heard from so many different people that it’s a pretty spectacular experience. In fact, almost everyone who I told about our trip said, “you have to go to the City Museum.”

Well, they were right. The pictures, the stories, the bruises I have – they don’t do it justice. It’s something you have to experience to really know how awesome it is.

Here’s just one example. You see that bus hanging off the top of that building?

Well here’s Iris in the driver’s seat.

Built in an old shoe factory, The City Museum is an art gallery and playground in one. Their “no maps” philosophy forces you to explore and see where the adventure takes you, which can often be through pitch dark mazes or down a 10-story slide. I highly recommend paying the extra $5 to go up to the roof, where you can find the bus, a ferris wheel, and other adventures.

And did I mention that there was a bar on almost level? I love this town!

Once you have your City Museum arm band, you can come and go as much as you want that day (they are open until midnight on the weekends). Even though there are plenty of spots to grab food there, we decided to walk around the corner to try out Hiro Asian Kitchen.

Boy were we glad we did. This was on of our favorite meal stops of the trip! Not only was each of our entrees delish, but the chef surprised us with a steamed bun appetizer that was AMAZING. And since Iris is definitely in a picky eating stage, I was thrilled to see that they offered a kid-friendly menu too (corn dog and tater tots for the win!). The atmosphere was fresh and modern (almost spa like), so it was a nice retreat from the hectic-ness of the museum.

While we had every intention of heading back to the City Museum, it was becoming clear that nap time was approaching quickly for Little Miss Iris. But being the awesome parents that we are, we of course had to stop off for dessert.

We found our way to The Fountain on Locust, which is an adorable, retro-style restaurant and ice cream bar. I even read on their website that it’s “the most photographed restaurant in St. Louis” which I don’t doubt at all! Iris had her heart set on a chocolate malt, while I just couldn’t choose. They are famous for their ice cream martinis, but then I spotted a champagne float. So what’s a girl to do? Order both!

Oh. My. Goodness. I had the chocolate covered almond martini and the champagne float with sherbert and raspberries. I’m going to be craving both for a very long time. I have no idea what Todd ordered because, well, I was swimming in two delicious cocktails. Have I mentioned how much I love this town?

After the short drive back to the hotel (we were amazed how easy and quick it was to get around the city), we all took a much needed nap. We woke up with time to enjoy the pool, where there were plenty of (free!) cabanas and a nice happy hour.

For our last night in St. Louis we had reservations at one of the two restaurants at the hotel, Basso at The Cheshire. We were lucky to have an extra guest at this meal! My dad, who lives in Jonesboro, Arkansas, just happened to be in town. If you follow my blog, you may have read what he’s been going through recently, so it was really special to be able to meet up with him, if only for dinner. He hadn’t been to St. Louis in a very long time, so it was kind of crazy that the stars aligned and we were there at the same time. And want to know something even crazier? After I invited my dad to dinner at Basso at The Cheshire, he told me that back in the 1970s he actually got MARRIED at that very hotel! Whoa.

Dinner was served family-style, so I took authority to order for our table. I think I may have over-ordered, but I’m glad we did. It was a lovely finale dinner for our trip and I wanted to go all out.

After dinner, we said goodbye to my dad, and took off on one last adventure: a hotel-wide scavenger hunt, which is part of The Cheshire Royal Kids Club. At check-in each kid gets a fun little packet, which includes a scavenger hunt map. If you complete it correctly and turn it into the front desk, you get a prize. Now, if you’r planning on cheating off of my map, I wouldn’t recommend it. I didn’t realize until a few in that there were actual clues that you had to find. D’oh!

After another good night’s rest, it was sadly time to hit the road… but not before one last stop on the way out of town – Strange Donuts! They had so many unique flavors that it was hard to choose, so we opted for a dozen and there were still flavors that we didn’t get to try. Maple Bacon, Campfire, Cookie Crumble, Gooey Butter Donut™, and so many more. We stuffed our faces at a park around the corner, which was truly a perfect way to end our trip: Strange, delicious, and a lot of fun.

All in all, we loved St. Louis and can’t wait to come back.

Contest is now closed. See who the winner is here!

Ready to take your own spontaneous family road trip to St. Louis?
Visit ExploreStLouis.com to start planning! Or… let me help!

Just leave a comment below about one place in St. Louis you’d like to visit for a chance to win a 2-night stay and family fun package featuring gift cards, vouchers to local attractions and more, valued at over $500. Make sure to include your real email address in the comment form, so that you can be contacted if you’re the winner. Contest ends on August 31. The email addresses will be sent to ExploreStLouis.com, who will select and notify one single collective winner during the first week of September (other websites are also collecting entries for this same contest).

Want more chances to win? Snag your own trip to STL through Explore St. Louis’ Funnest Family and Ultimate Tourist contests!

Good luck, my friends!

This is a sponsored post, but all opinions are my own.