Harley Davidson California Dreamin’ Road Trip

The longest day of my life occurred during a once in a lifetime road trip with my dad and best friends on a Harley Davidson motorcycle.

Originally, I had the idea of packing a tent, a sleeping bag and some clothes to head out on a weekend adventure somewhere in the Midwest on my motorcycle. I told my friend Troy about my idea and he said he wouldn’t mind coming along for the ride. But then, I had an even bigger and better idea. Let’s do a “California Motorcycle Road Trip” I said.

The idea seemed too good to be true. What could be better than riding the beautiful coast of California on a brand new Harley Davidson? Troy and I decided that we wanted to have a bigger group because it’s always more fun riding with others. So, I asked my dad and his best friend John to come along too.

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So, my best friend, my dad and his best friend turned my long weekend motorcycle weekend into this; Taking a flight from O’hare International Airport (ORD) to Los Angeles International Airport (LAX), renting Harley Davidson’s and riding down the Pacific Coast Highway! It’s been awhile since I was last in California (2009) and I have been trying to get back ever since. I found an unheard price on airfare while using the Hopper app, $140 round-trip. I highly recommend using the Hopper app for any planned flight travels. Here is the link to their website, www.hopper.com, or just search “Hopper” on the App Store or Play Store.

Pacific Coast Highway, PCH or California State Route 1 is roughly 655miles long and has some of the best views the world has to offer. Mountains on one side and ocean on the other, what could be better?

After the flight was purchased there was no turning back and I began to map out our once in a lifetime road trip. The trip consisted of five days and six nights. We would fly from ORD to LAX the night before our road trip began and we would head out on our adventure early the next morning.

We rented our Harley Davidson motorcycles through a third party called RideFree.com and picked up the bikes from EagleRider in Hawthorne, California. RideFree.com works with EagleRider to rent out motorcycles and they were cheaper than booking directly through EagleRider.com.

Ride Free has a vast selection of bikes and as long as you book way ahead of time, you should get exactly the bike you want. RideFree.com gave us a great customer experience. The owner and our customer service agent, Wil Sakowski, was helpful in meeting all of our needs and helped answer questions about my route. He made sure the bikes were set up with hard bags and luggage racks to accommodate all of the stuff we needed to bring on the road with us.

Since we had four bikes lined up, this was quite the order and we wanted to make sure everything was right, there was no room for error. The Harley Davidson Street Glides came in at a price of $571.29 for four days. This included unlimited mileage, pickup and drop off from our hotel, cable locks, disc lock, hard bags and a luggage rack.The Harley Davidson Electra Glide w/ GPS came in at $636.54. This bike was equipped with GPS (in case our phones died or we had no service) and unlimited mileage, pickup and drop off from our hotel, cable locks, disc lock, hard bags and a storage trunk.

We decided to book overnight hotel accommodations for a couple of nights so we made sure we had a place to lay our head. The first night we booked a cheap hotel called Baymont Inn & Suites in Los Angeles for $140. One room divided by four people comes to $35 a person. Prices for the hotels we booked will vary depending on what time of your you’re going. Refer to this link here to save $25 on your first hotel booking. Our second night be booked at Yosemite Sierra Inn in Oakhurst California for $180. We weren’t sure how far we would travel each day so it was hard to book other hotels. One hang up could delay our trip by hours or even days and we didn’t want to get stuck with a hotel we paid for that we couldn’t reach in time.

If you’re keeping tabs on my trip total, I’ve spent roughly $775.29 so far on parking, airfare, bike rental and two nights at two different hotels. I will try to keep my running total as accurate as possible but I will leave out small things like meals or drinks. I will also not include gas.

On the evening of 8/30/2017, my dad, John and I arrived at O’hare Airport on our bus shuttle from Crowne Plaza hotel in Rosemont, Illinois. We didn’t park at the airport because its way too expensive. We could park at Crowne Plaza for around half the price so six days of parking for $50 was not bad at all. We split this up between three people (my dad, John and myself). We met Troy at the airport because he was getting dropped off. If you’ve never been to ORD it’s usually a madhouse but we were lucky to get from the front door to our gate in under an hour. We had time to grab a bagel for breakfast and watch the plans come in and go.

Catching our Plane from Chicago to California

To our surprise, our plane was a Boeing 787 Dreamliner. I had never been on a Boeing 787 Dreamliner, they are fairly new planes. The plane felt huge inside and the TVs on the back of every headrest were nice. The flight was pretty quick flying to the West Coast (a little over three hours) and it was so smooth. I think this had to do with the fact that the plane was massive and the newer technology newer plans are getting. Troy goes into a little 787 detail in the daily vlog video posted below, check it out.

We got into LAX earlier than expected, about an hour early actually. However, because of our early arrival, there was no space at the gate so we had to taxi, which was an experience of its own. The plane was told to stay out on the runway and we would grab a shuttle bus to the nearest gate. I had never had to do something like this before but I guess that’s what happens at one of the busiest airports in the world.

After grabbing our luggage and picking up a ride from Troy’s good friend (Maritza), we headed to the famous In N’ Out burger for a bite to eat! Food coma and all, we checked into our first hotel to get some much needed sleep before we hit the road the next day.


Wednesday Aug 30th 2017: Flight from ORD @ 6:25pm – Arrive in LA @ 8:56pm | Eat @ In-N-Out Burger. Stay the night at Baymont Inn & Suites

Miles Traveled2,026miles/5hrs

Trip Total: $775.29

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