The Itinerary: Summer Road Trip Part 1: Pre-Trip Chaos, Cleveland Guardians, & Niagara Falls with 3 Boys

Aug 7
13 min read

I am determined to get ahead of things this time! After being four months late finishing up my Azores trip posts, I wanted to jump right in and share our summer road trip to Niagara Falls and the Finger Lakes area with the boys.

This post is Part 1 of a two-part series. Below, I’ve laid out a roadmap of our journey, followed by our honest experience at each spot—the good, the memorable, and my unfiltered thoughts on whether each stop was truly worth it.

Pre-Trip Prep & Chaos

Gearing up and getting everything ready to hit the road is always super chaotic for me—I am definitely not someone who can comfortably leave the house messy. To add to the usual scramble, I had contractors coming in to repaint our entire first floor, the two-story foyer, and the upstairs hallway. I had given up the notion that I could reasonably do this myself and I am so glad I bit the bullet for them to complete the work for me!

Prepping the house for painters, packing for myself, getting three boys packed and ready, wrapping up work deadlines, and coaching my group fitness classes felt like running a marathon before the actual trip even began. Add in the snack prep and trip fuel up ($52) and I was ready to get started. But somehow, we crossed that pre-departure finish line!

Stop 1: Rest, Catching Up, and Pampering in Columbus, Ohio (Days 1 & 2)

The first leg of the trip was an absolute lifesaver for recovery. We drove up to stay with a dear friend in her new home just outside Columbus, Ohio. It was so wonderful to see all the updates theirnew life and spend quality, uninterrupted time catching up.

After the chaotic week leading up to our departure, being able to sleep in was pure bliss. Her husband is a fantastic cook and completely pampered the boys and me with incredible meals. We enjoyed a few great drinks while getting a guided tour of his liquor cabinet—I’m pretty sure I consumed more in that single night than I have in the last two years combined! It was just sweet, grounded quality time: real talk, the boys hanging out together, and getting to see their daughter with her new baby.

Before hitting the road the next day, we took a trip down memory lane with lunch at DK Diner (DK Diner). We revisited their legendary apple fritters and fresh donuts before starting the next leg of our drive. A little cash on hand helepd avoid the 3% credit card transaction fee and totaled us $50.

Reshaping Vacation Expectations

What I wanted to accomplish with this trip was fundamentally different from our past family travels. In the past—especially when traveling internationally—I felt intense pressure to squeeze in every single sight, landmark, and tour possible. When you travel far, you never know if or when you'll ever return, so you try to do it all - or at least I aim for that.

This time, I intentionally reshaped my expectations. By shifting the focus primarily to things designed for the boys to enjoy and letting go of the need to see "everything," the pressure completely vanished. It made the entire mindset of the trip significantly easier, more relaxed, and infinitely more enjoyable for all of us.

Road Trip Lessons & Travel Systems with the Boys

As I planned this road trip, my primary goal was to include something unique, special, or personally tailored for each of my three boys. Lessons learned from our previous trip to Illinois proved that if you don't learn from your past travel mistakes, you're bound to repeat them!

To make this drive a much smoother and higher-quality bonding experience, I brought back a few of my favorite tactical road trip systems:

The Envelope System: Keeps new activities for those "I"m bored" moments super organized and tangible for the kids. I have them pull out an envelope at different intervals to keep complaining at bay. I recycled items from the last trip to IL and threw in some house favorites that haven't been seen in a while. Cost this go around = $0

An Engaging Audiobook Series: I downloaded The Incorrigible Children of Ashton Place series. We were so hooked on the story as the plot thickened that we ended up listening to the entire series over the course of the road trip! The narrator of all but the final book was fantastic!
Strict Drive-Time Caps & Less Screen Time: I intentionally mapped out our route so that our longest driving stint was no more than 4 to 5 hours a day.

Limiting screen time allowed us to actually talk, look at the landscapes around us, and pull over whenever we felt like it. We made regular stops at roadside stands and gas stations to stretch, grab snacks, have a picnic lunch, and use the restroom before getting back on the road refreshed. It drastically reduced fighting in the backseat and made the drive itself feel like part of the vacation.

Stop 2: M's Special Choice – Cleveland & The Guardians Game (Day 3)

M's special pick happened to be the very first official destination of the trip: a Cleveland Guardians baseball game in downtown Cleveland! Now, purchasing these tickets wasn't astronomical for a pro game however, this girl is used to her Smokies Package Ticket prices. Total for game and snacks = $228 (tixs) and $22 (food)

Hotel & Check-In: Hilton Garden Inn Cleveland Downtown

We stayed at the Hilton Garden Inn Cleveland Downtown. I intentionally switched our reservation to this property for three specific reasons:

Parking was included.
It was less than a 5-minute walk straight to Progressive Field (Guardians Stadium).
I could leverage my Hilton Diamond status for perks, room upgrades, and food/beverage credits.

Normally, I try to email a hotel general manager a few days in advance. Since I didn't get to it this time, I used the app's live chat feature right before checking in to say: "Hey, we are here celebrating something special for my kids! I was wondering if there is any way you could help us honor this occasion, whether that's a room upgrade or breakfast treats?"

That quick message paid off massively—they gave us four full, made-to-order breakfasts for free! Instead of paying $18 a head, the boys got to order off the menu, and I got my essential morning coffee, saving us a pretty penny right out of the gate.

When we went up to our assigned room, the boys were immediately arguing over who got to hold the keycard and open the door. The cleaning staff had to help us get in, only for us to walk inside and see someone else’s suitcase sitting on the bed! We went right back down to the front desk. The staff seemed a bit flustered with whatever else was going on that afternoon, but they made it right:

They upgraded us to a room on the top floor.
While we waited, the desk agents handed each of my boys a pack of purple Skittles, which made them super excited.
I used my Diamond member perks to grab a stash of extra snacks from the pantry shop to load into our road trip bag. The boys grabbed items tallying up to $20 which were then comped.

Budget Travel Tip: To bring down the out-of-pocket cost for this hotel, I used my Hilton Amex Business Card perk, which provides a quarterly credit. Since I hadn't stayed at a HIlton property quarterly, I redeem that credit online for a gift card. You either use it or lose it! I had about $100 saved up on gift cards from previous credits, which significantly knocked down the hotel bill, but still left it at a relatively high rate of $217.76

Game Night at Progressive Field

We walked over to the stadium about an hour before first pitch. I intentionally waited to buy our game tickets until the day of for two reasons: I wanted to make sure we didn't get rained out, and I was monitoring the air quality from the wildfires in Canada, which had been pushing heavy smoke into the region.

Thankfully, the weather turned out to be absolutely perfect!

When we got to our original section, the usher stopped to check our tickets, asking, "Oh, hey, these seats weren't purchased earlier today—did you just get them?" When I explained that we had just bought them coming into town, he smiled and said, "Well, there are open spots down in a section closer to the field. I'm happy to move you down there if it's just you and the boys!" He added, "Make sure to talk to the ball boy down there, too."

That random act of kindness gave us an unexpected $100 seat upgrade! I had looked at those lower-level seats earlier and debated whether they were worth the extra cost, so it worked out amazingly in our favor.

Our new seats were right along the first base line next to the foul pole. Back home at Smokies games, we usually sit behind home plate where foul balls rarely land. But in these seats, the very first hit was a foul ball and it came flying right toward us! It landed a bit higher up in our section, but the location was awesome. Best of all, M talked to the ball boy as advised and walked away with an official game ball that the players had just been using on the field.

The game itself was high-energy, fast-paced, and high-scoring (I think the final score was 13 to 4), featuring seven total home runs and tons of fireworks! Everyone treated themselves to stadium snacks to wrap up the night. It was an incredible, memorable way to celebrate M and his love for sports.

A Quick Note on Hotel Pricing & Value

One interesting observation from this leg of the trip: The room rate at this Cleveland hotel was almost identical to the rate we paid at our next stop in Niagara Falls—a top-tier, luxury property situated directly across the street from the falls with stunning views and brand-new renovations.

While the Cleveland hotel was totally fine and its location made walking to the stadium effortless, the room itself wasn't anything extra special. It was a good reminder of how drastically hotel pricing fluctuates based on location and convenience versus sheer luxury and amenities.

Roadside Quirks & Border Crossing to Canada (Day 4)

On our way toward Buffalo and up to Niagara, Ontario, we made a point to hunt down a kitschy roadside oddity. We chose Buffalo’s famous Shark Girl statue at Canalside. Despite navigating some tricky local construction, we found her, snapped a few funny photos with the boys, and hit the road again.

We hit some rainy weather driving into Canada, which made driving a bit treacherous, but crossing the border early Tuesday afternoon was an absolute breeze and cost $6.05 (EZ and IPass are accepted but only the physical transponders not the recent update to the windshield sticker). The line was short, the border agents asked very few questions, and we were through customs in under five minutes.

Basecamp: The Brock Niagara Falls Fallsview (Tapestry Collection by Hilton)

Our stay on the Canadian side was at The Brock Niagara Falls Fallsview (Tapestry Collection by Hilton). Parking was unfortunately not included (as if the case for pretty much all the hotels I havd looked in but it was however a cheaper rate at $45 vs the $80 at others), and our higher-floor room with a direct view of the falls was ready as soon as we arrived.

Hotel Value Strategy: Instead of paying top dollar for the massive 48-floor Hilton nearby, I booked The Brock. Not only was it significantly cheaper with a fantastic view, but we also avoided the horrific elevator wait times that plague the giant tower hotels. Plus, our rate included hot, made-to-order eggs that kept everyone full well into the afternoon! One thing of note - the taxes and parking + the mandatory fee hike up prices quite a bit. To lower costs, shoulder season allows for champagne taste on a beer budget when all the scheudles allow - all in cost was $616.62.

While resting up in the room, we leveraged one of the hotel's daily resort perks: a coupon for a free beer flight at a nearby local brewery. L really wanted a charcuterie board, so we grabbed a quick bite before heading down to the water - $31.79.

The Canadian Side: Hornblower Boat Cruise & Clifton Hill

Because of the rain, the tourist streets were completely empty, making it incredibly easy to walk around without navigating massive crowds.

Niagara City Cruises (Hornblower)

I waited to buy our boat tickets at the dock since the rain made the weather unpredictable. Once we saw there was no lightning, we bought tickets at the kiosk (you could do so online as well - $137.22 for 2 adult and 2 child passes) and walked right on. By 6:30 PM, the rain stopped, but given the mid-week timing and rainy weather, the boat was mostly empty. We had full freedom to move between the upper and lower decks to view the falls from every angle.

Pro-Tip for the Hornblower: Do not wear long pants or sneakers you plan on wearing later in the trip! Ponchos only protect your upper body. The boys got completely soaked, and their shoes were so drenched they didn't dry out until we propped them up on the car dashboard two days later - and let's just say that the car was not very welcoming when we got back to it - boy smells, ugh!
Also, if it's summertime, there is a fireworks show every evening during the Fall's light show. You can book your tour during that time and knock out all the things in one ride. The fireworks started around 10 pm, and the light show was just a bit prior to that. Or you can watch the show and fireworks from your room as we did!

Navigating Clifton Hill

Walking around Clifton Hill felt very reminiscent of the Pigeon Forge / Gatlinburg strip or Wisconsin Dells— with its tourist oddities, neon signs, and commercial attractions (Ripley's Believe It or Not, mirror mazes, high-priced ferris wheels).

Tourist Trap Warning: Unless your kids are dying to do specific arcades or you have an unlimited budget, skip the Clifton Hill attraction passes. At $15–$25 per person per activity, it quickly becomes a money pit. It is certainly fun to walk through and ,sightsee but wrangle the kiddos' expectations as it relates to your pocketbook.

Instead, we focused on classic local food highlights:

BeaverTails & Poutine: Both were huge crowd-pleasers, $13.27 for two tails, and $9.17 for a box of poutine!
Old Time Candy Shoppe: The boys loved browsing the retro sweets. We got adventurous and bought novelty "Camel Balls" sour gumballs—which were surprisingly tasty (and soft enough for my jaw to handle!) for $3.02.

Exploring the US Side & Parking Hacks (Day 5)

The next morning, we crossed back into the US to check out Niagara Falls State Park.

Canada vs. US Side Verdict: If you want luxury hotel options, high-floor views, and vibrant nightlife, the Canadian side wins hands down. The US border town immediately crossing customs feels run-down and neglected. However, the US State Park itself is green, beautiful, and very well maintained. It much better reflects the nature side and protects it wonderfully.

Parking & Trolley Strategy

We arrived at the state park around mid-day, just as the parking lots were filling up.

Park Lot 2: $10 Monday–Thursday ($15 Friday–Sunday).
Scenic Trolley: $5 per adult / $3 per child for an all-day hop-on/hop-off pass.
Free Parking Hack: If you want to skip the $10–$15 lot fee, it appeared that if you drove further down the trolley line near the Niagara Aquarium where street/lot parking is free, then just pay for the trolley pass to shuttle into the main park hubs!

Since the boys were still recovering from getting drenched on the Hornblower, we passed on doing the "Cave of the Winds" or "Journey Behind the Falls." The boat cruise gave us all the power, sound, and scale of the falls we needed.

Road Trip Fueling & Tailgate Picnic System

Before hitting the hiking trails, we pulled off for an organized tailgate lunch using my organized chaos of a trunk and the 3-Drawer Road Trip System:

Drawer 1 (Activity Envelopes): Daily budget, games, and surprise activity cards.
Drawer 2 (Meal Prep & Staples): Oatmeal packets, cereal, tuna, bread, peanut butter, bagels, plates, and utensils.
Drawer 3 (Road Trip Snacks): Fun treats, candy, and chips to prevent expensive gas station impulse buys.
Cooler: Protein shakes, Alani energy drinks, Gatorade/BodyArmor, and soda treats chosen by the boys.

We put together classic peanut butter sandwiches paired with Harvest Snaps and protein chips, finishing off lunch with fruit gummies before heading out.

Gorge Hikes & Side Quests: Whirlpool, Devil's Hole, & Beyond

Whirlpool State Park & Devil’s Hole

We drove north along the gorge to hit two scenic, low-crowd nature stops, both of which were free:

Whirlpool State Park: Amazing natural viewpoints overlooking where the violent river currents swirl into a massive natural whirlpool.
Devil’s Hole State Park: After several wrong turns on the drive (freaking NY) , we found the trail and tackled the 422-step descent down the gorge wall (dubbed by the boys as the path to "Satan's Butthole"). M loved counting every single step. It was a great, active challenge that burned off built-up car energy!
A third stop was tacked on to see the remains of the old power station and the column that still stands after another station collapsed.

Niagara-on-the-Lake & The Screaming Tunnel

We crossed back into Canada for the late afternoon and spent time exploring Niagara-on-the-Lake. Crossing back into Canada cost another $6.05.

Unlike Clifton Hill, Niagara-on-the-Lake has a charming, upscale, romantic vineyard aesthetic. We parked for $3.74 for two hours and stopped at local shops for a maple syrup tasting experience (learning about the different grades and harvest times) and browsed cute boutiques and ice cream parlors. We grabbed a few maple syrup souvenirs ($8.24) from a local farm and then some candy from us and family ($31.55).

Before heading back toward our hotel, we stopped by the famous Screaming Tunnel—a haunting limestone railroad tunnel featured in classic local lore and movies that the boys thought was super cool to see in person.

A&W Canada & Hotel Pool Wind-Down

We grabbed a quick dinner around 4:30 PM at an A&W Canada ($21.36). Hilariously, we walked right into senior hour—every other customer in the restaurant was over 65!

We rounded out the evening back at The Brock, burning off the last bit of the boys' energy in the hotel's uniquely renovated indoor pool area. Tucked away on an interior floor, it featured cozy lounge chairs, cabanas, a sauna, and enforced family vs. adult-only swim hours. It was the perfect, relaxing finish to our Niagara adventure.

A Surprise Grandparent Gift & Farewell to Niagara (Day 6)

Our final morning in Niagara started with an amazing stroke of luck. While we were enjoying our made-to-order breakfast at the hotel, a sweet grandparent sitting at the neighboring table struck up a conversation and handed us five free passes to the Skylon Tower—saving us $75 on the spot!

We took a pleasant 20-minute morning walk along the parkway to reach the tower by 10:00 AM, beating the afternoon rush. We rode up to the observation deck for panoramic 360-degree views of both the American and Horseshoe Falls. Since the passes were free, we splurged on one of those cheesy green-screen souvenir photos of us going over the falls in a barrel—a hilariously cute keepsake from the trip at $34.83.

After taking photos at Table Rock and the Visitor Center, we headed back to the hotel. Thanks to my Hilton Diamond status, we enjoyed a late checkout, letting us pack up smoothly without rushing.

We exited Canada and made our way into New York, stopping at a rest stop for some of the more expensive fast food I've purchased and to refuel the car - food tallying (32.52 for three meals and gas at $53.75). To hear about the rest of our vacation adventure and see the beauty of New York, tune in for Part Two....

Feel free to pepper me with questions or for any details I may have missed!