The Annual Anniversary Trip (Summer Highlight)
Okoboji, Iowa. A hidden gem in an otherwise boring state. AKA, my favorite place on the planet.
The Backstory
I’m going to give you all the backstory behind why we make the trip to Okoboji every year. In 2007, after we’d been dating nearly two years, I suggested we should take a trip together, somewhere we had never been. I mentioned this place called Okoboji, that I had heard of from some family friends who owned a timeshare there – Sam had never heard of it. I believe her words were, ” Oka-what now? Super cool lakes, in Iowa?” Since neither of us had been there before, we decided to give it a shot so we made reservations at the most affordable resort in town. Turns out, it is was the most affordable, with the most to offer and Okoboji is THE COOLEST place on the planet, so many things to do. Fillenwarth Beach Resort offered boat tours, waterski lessons, and, our favorite part, evening booze cruises.
We were so young
The town has boat rentals, cool bars, the whole works. Sam and I absolutely fell in love with the town, and especially Fillenwarth, and the local watering holes, so we decided to come back the next year. I had proposed in a super romantic way in between visits, so we were engaged by then and had no plans yet for a wedding. We went back, stayed at Fillenwarth again, and had the same blast that we had the first time, except this time made it a long weekend instead of just two nights. It was on this trip that, after a night of drinking ridiculously cheap beer, we decided that this was the place that we wanted to get married. The next morning we talked to the office staff about it and they were a little hesitant, but we agreed to have the wedding on a Monday when it wasn’t packed and crazy at the resort.
So I could say that the rest in history but I’ll keep going. The next year we made our reservations for our wedding trip. Same time, same place! The resort was super happy that we brought about 40 guests to visit that they were way more accommodating than they had to be. We spent the first couple days just enjoying the resort with our guests just hanging out and doing fun things. On our wedding day, after the ceremony, they put on a private booze cruise for us and our guests to celebrate! It was, in our opinion, the perfect wedding.
I do
So now its safe to say the rest is history. We have been coming back to Okoboji every year since to celebrate our anniversary in our favorite place. The only difference was, this year since we have our amazing camper, we decided to no longer stay at Fillenwarth but stay at Emerson Bay Recreational Area where we could camp and still enjoy all our favorite things for 5 nights which cost less than one night at the resort!
I had a hard time with this idea at first. We’d been going to Fillenwarth for years, why mess with a good thing? But the price was right and we did have this great camper …
Turned out, Sam was right, and camping in Okoboji was even better than I imagined. We brought our tiny home and our dogs with us and it was almost like we lived there. Don’t worry, we still managed an anniversary kiss on the dock where we got married.
If you want to travel to the Iowa Great Lakes and need a place to stay, we highly recommend Fillenwarth.
The Journey
Since this was our anniversary trip and was going to cost us far less, we booked a longer stay than our usual weekend or 3-day weekend. We only worked Monday and a half day Tuesday so we could spend a whopping 5 nights in our favorite place. After work on Monday night we loaded up the camper and got on the road around 1:00 on Tuesday for the 3 1/2 hour trek to Hawkeye country. On this trip, we also brought my parents’ boat, so Sam drove separately, towing the boat while I pulled the camper. After about an hour on the road, just north of St. Peter, MN, I got a phone call from Sam who was behind me saying that I needed to pull over immediately because the entire back bumper completely fell off the camper! So we both pulled over, picked up the bumper off the highway, put it in the back of my parents pickup that Sam was driving and continued on our way.
The reason that the bumper fell off while driving was because we had attached our bike rack to the back bumper and it was a bit too heavy. The stress from the weight of the bike rack over the time of several trips of bouncing on the road proved to be too much and it eventually gave out. It created a bit of excitement for the drive down but our heart rates quickly calmed down and the rest of the drive proved to be uneventful.
We arrived at Emerson Bay around 5:00 in the afternoon and we did our usual setup routine so we could officially begin our vacation. The sewer hose is stored in the bumper, so I had to fish it out of the bumper to hook up the sewer.
Really appreciating the gloves
Emerson Bay is a really nice campground with huge sites and full hookups and also super clean restrooms. We would highly recommend this campground. The only downside is you can only make reservations about 3 month in advance and they fill up very quickly!
Our Anniversary
After we finished our set up, we took the dogs for a nice long walk along the beautiful West Lake Okoboji then grilled burgers and had chips with Pub Cheese and Top the Tater dips for dinner then relaxed but the fire with some delicious beer. We made a quick pit stop at West O Brewery and brought back some of the best stout one can find anywhere, the Coco Stout!
Wednesday was ourseventh wedding anniversary and we had a full day of fun planned! In the morning after our usual camping breakfast we put the boat in the water and cruised across the lake and stopped so Sam could get a pair of sunglasses since she forgot hers at home.
Hey lady, want a ride?
So I dropped her off at the Central Emporium and I cruised in the boat with Toby and Buddy while we waited. With a fresh new pair of shades, Sam got back on the boat and we crossed under the highway from the West Lake to East Lake Okoboji.
We cruised along the north side of the East Lake and made a stop at the World Famous Barefoot Bar for some tropical drinks at the Tiki Bar. We go there multiple times every trip to ‘Boji. The boys enjoyed being “celebripuppies” at the Barefoot Bar; getting all the pets from strangers and buckets full of water. A couple drinks later, we jumped back on the boat and cruised back to the West Lake and boated up to Pirate Jack’s Bar in Arnold’s Park for some more of the Coco Stout from West O. After that stop, it was time to head back to the campground and get cleaned up for our romantic anniversary evening out and wait for the Rover Pet Sitter to arrive at the campground.
Once the dogs got their dinner and the sitter arrived, it was time for Sam and I to enjoy our night out to celebrate the anniversary. We got ourselves dressed up nice and climbed back into the boat and cruised back to the Central Emporium where we had booked an evening cruise on the lake. Before the cruise set sail, we stopped into The Gardens for a quick drink. It was then time to board the Siesta Cruise around the lake. It was fun to chat with some other vacationers on the boat, and the weather was absolutely perfect.
Once the cruise was done, we wandered over to Fillenwarth South Beach dock to get a picture from where we got married then climbed back into our boat and cruised across the lake for our very nice anniversary dinner at Kazarelli’s Italian Restaurant in Milford. It was a very nice and delicious dinner and we would recommend it for anyone looking to celebrate a special occasion in the Iowa Great Lakes region.
After dinner, we boarded the boat with full stomachs to cruise back to the campground and see the best dogs ever! I have to say, nighttime boating is very fun as well. Once we arrived back at the camper after racing the weather moving into the area, we sent the Rover sitter home but we were unable to have a fire that night due to some rain showers that passed through the area. That wasn’t all bad since we were pretty exhausted from all the activity during the day so we decided to turn in early and watch some TV in the camper before turning in. All in all, it was a great anniversary. Okoboji is a great place to come to celebrate special occasions!
Biking Day
The view of the trail from Sam’s bike
Thursday morning came along and the weather was perfect for a nice ride around the West Lake on the Iowa Great Lakes Trail. Unfortunately at the Emerson Bay campground, we are not allowed to leave the dogs unattended so we had to take them into town to doggie day care at Boji Bark where they would be cared for and have the opportunity to make some new friends. So after breakfast, we were off with the dogs and then back to grab our bikes and then we were on our way. After about 7 or 8 miles our first “rest” stop was at the Pub 19 at Okoboji View Golf Course. We sipped a beer, took our #biketobeer photo for social media then it was back on the trail. As we got to the north side of the lake the wind picked up and the terrain became a bit more hilly.
So the next 6 miles were a lot of work with the wind and hills so by the time we made it around to the east side of the West Lake we were STARVING! So it was back to the Central Emporium and The Gardens for lunch and another beer. We decided to eat a delicious Reuben pizza, tasty! Then after lunch it was back onto the trail after a quick stop at Smokin’ Jakes for a cheap beer. During what would have been the final leg of 7 miles, it began to rain but lucky for us, we were right near West O Brewery again so what better way to wait out the rain that to have great beer at a great brewery, so that’s just what we did. Two pints later, the rain had stopped so we decided to ride the last 3 miles to the campground. As we were just heading back into the campground, we were going down a slight hill and curve onto a wooden bridge. Sam was a few lengths in front of me and as she went onto the wet wood bridge, her tires went out from under her down she went, hard. She skidded on her side into the wall of the bridge. She hit hard enough to dent her bike helmet and it was very scary. She stood, looked at me and said “what just happened?”
In all my years coaching basketball, I had never had to use my concussion training but I did have to use it with Sam. She said she doesn’t remember crashing but she was able to pass the concussion test. We got Sam back to the camper and I told her to relax, but NOT SLEEP, while I went back to Boji Bark to get the dogs. I returned to the camper with dogs and we made up some brats for dinner and settled down around the fire for awhile before realizing how tired we were and turned in for the night ending another great, but a little scary day in ‘Boji!
National Dog Day
Friday was National Dog Day so we decided to take the best dogs ever with us all day long. Once we got up and moving, and had breakfast, we had to wait out a storm for awhile before we left the camper for the day. Post rainstorm, we loaded the boys onto the boat and set out across the lake. We again crossed from the West Lake to the East Lake and made a stop at the Barefoot Bar for one of their amazing Long Islands. We then cruised back to the Central Emporium so do some shopping.
The Bucket of Long Island at the Barefoot Bar
While I was inside looking around in the shops to get souvenirs for our nieces, Sam stayed outside with the boys and made some friends with a group of people who thought our dogs were awesome, they weren’t wrong! I finished up shopping and we went walking around Arnold’s Park and the owner of the mini-donut stand had to give the boys a whole bunch of treats and pets. They found a friend for life. After walking around Arnold’s Park, it was time to cruise back across the lake to the campground where had dinner then sat around the fire and had a couple drinks and smores. We turned in for the night after a super laid back relaxing day of vacation.
Crazy Saturday!
Saturday was our last full day in Okoboji so we had to make the most of it. After we were up and functional, we had our usual camping breakfast and took the boys for their morning walk around the campground. We then piled into the Envoy drove over to the Taco House, an Okoboji vacation must, for some super tasty Mexican food. We got our food to go and drove on over to Okoboji Brewing Company (separate of West O) for another craft beer sampling. The beers were not super great but its still worth a quick stop while vacationing. After finishing off our beers, it was back into the Envoy for the quick drive back to the campground.
We spent time in the afternoon taking it easy at the campground before making grilling up steaks for dinner. After dinner, Sam and I got ready and took Buddy (Toby was a bit too tired to make the trip) on the boat back across the lake to Arnold’s Park for the big Saturday night concert in the green space. This weekend was Casey Muessigmann, a local country singer/guitarist from Okoboji area who is on the verge of making it big. There is a story between Casey and myself from the year before on our annual Okoboji vacation but I won’t explain it here, not one of my finer moments … just know it involves a LOT of beer and a full day of puking later! If you must know, send us a comment and Sam and I will tell you the story.
Neither Sam or I are big country music fans but Casey is pretty talented and I can see how he is on the verge of making it big. During the concert Sam had yet another moment. While making a quick pit stop at the restroom, she stepped out of the restroom and the stairs were wet and she took a nasty tumble down the stairs to the ground. I was not there to witness it since I was holding our spot with Buddy but she was pretty sore when she got back. The next day, she had the biggest, nastiest bruise I have ever seen in my entire life on her leg and butt! I love my clumsy wife.
We listened to the rest of concert then loaded up the boat for the nighttime cruise back to the campground. Did I mention that nighttime boating is really cool? We got back to the campground just in time to watch the fireworks display from across the lake. We took both dogs out to the dock watch the fireworks. Buddy with all of his anxiety was startled by the loud noises and when he flinched, he fell right off the end of the dock and into the water! He immediately swam to the shore and we had to give him a bath to wash the lakewater off of him at 10:00 at night on a Saturday. He’s such a knucklehead but we love him anyway. While we waited for Buddy to dry off, we sat around the fire before turning in for the night. It was definitely a memorable Okoboji day.
The End of our Vacation
On Sunday morning, we got up and walked the dogs and ate all the breakfast leftovers from the week. We then got ready and took the boat our for one last cruise across the lake to Arnold’s Park. We ate lunch at Bob’s in Arnold’s Park, the oldest restaurant in Okoboji for some chili dogs and fries. The boys also got a few fries so they were thrilled! From there it was back to the East Lake for on last stop at the barefoot bar for one last drink at the end of our vacation. We then did our final cruise back across both lakes to the campground.
We then pulled the boat out of the water and got everything at the camper packed up for the ride home. We had to hurry our tear down because the next campers that had that site reserved were already there. Once torn down we jumped in the vehicles for the 3 1/2 hour drive home and arrived just before dark and got the camper unloaded and put away in the backyard ending our best camping trip to date! I know they will continue getting better!
