The first time I ever drove a Jeep Cherokee was not on a road. Well, I mean, I drove on a road to get to my driving course but I spent my of my time off road checking out the Trailhawk capabilities of the Jeep Cherokee. I’ll actually take the dirt and mud any day over a racetrack. But most of the time, I’m really just hitting the highway for daily errands or the occasional road trip. So my priority is more about how I feel when I driving the car and how much luxury I can cram in for an affordable price.
The 2019 Jeep Cherokee Overland is a trim that captures all the capabilities of the vehicle with all the luxury that I demand and require. Hey, just being honest here.
Let’s just start with the price so you know what page we’re on when I mentioned luxury. The base price of the Jeep Cherokee Overland 4×4 is $37,775. I’ll talk more about what features you get for that price but this particular vehicle also had some optional equipment like the Technology Group for $995 and the Full Sunroof for $1295. Add on a destination charge of $1445 and the full MSRP tops out at $41,510.
Now that we’ve gotten any sticker shock out of the way (by the way, I think it’s a reasonable price for what you get), let me show you where I took my Jeep Cherokee for the week and how I fell in love with after putting over 500 miles on it.
Good Trips Start with Great Friends
What makes a good road trip? A comfortable vehicle, an awesome destination, and great friends. You could also argue that an awesome music playlist is a must but we actually listened to podcasts and audiobooks the whole time – more to come on how the 2019 Jeep Cherokee Overland made that easy.
Stop 1 – Eldersburg, MD
The car was delivered to my home in Eldersburg which is a little northwest of Baltimore. My son and I loaded up the car and set out on a Friday morning determined to sandwich our driving in between rush hour and weekend beach traffic. We failed. But we did make it to our destination way earlier than we did when we took the same trip last year!
Stop 2 – Westhampton Beach, NY
The destination for this trip was Westhampton Beach, situated about halfway across the southern shore of Long Island. It’s our third time making this trip because that’s where we find great friends. My friend Susan is always a wonderful host for me and my son and she loves to show us the sites on the island even though we’d be more than happy to just hang out playing foosball at her gorgeous house. It was also great to drive Susan and family around so that I could get her opinion as well (spoiler: she loved it).
Even though we toured around the island, we made sure we spent time at one of our favorite spots – the actual beach in Westhampton Beach (technically, we visited a placed called Rogers Beach).
Stop 3 – Montauk
Our first stop was a trip to the far end of the island for an event in Montauk. On the way we went through Westhampton, Hampton Bays, Southampton, Bridgehampton, East Hampton (yes, I can officially say I summered in the Hamptons). We almost stopped on the way for a celebrity softball game with Alex Baldwin but settled for a picturesque view of a windmill.
Stop 4 – Oheka Castle
One thing Susan always does is ensure we have plenty to see when we visit. And I was thrilled that she was taking us someplace she had never been before. So we headed to the former country home of wealthy financier, Otto Hermann Kahn, known as Oheka Castle. We spent most of our time enjoying an incredibly elegant lunch but when we started to do a little sightseeing on the grounds, we were told that an impending wedding was going to cut our visit short.
Stop 5 – Dead Horse Bay
Before we hit the turnpike for the long drive back, we passed through Brooklyn and stopped at Dead Horse Bay, which we first visited last summer. We were hoping to capture more treasures to take home but didn’t find much more than we did the year before.
All About the 2019 Jeep Cherokee Overland 4×4
I usually spend a week in a vehicle before I write about it but I don’t usually get to put it to the test like I did with the Jeep Cherokee. We hit highway, back roads, high speeds, traffic jams, sunshine, and rain. I even drove this vehicle through the mud to put the 4×4 to the test! You can see it all in my video review of the Jeep Cherokee.
Video Review
Overall Thoughts on the 2019 Jeep Cherokee Overland
The Overland trim comes fully loaded with everything I want, need, and love. It’s full of features like heated and ventilated front seats, offers plenty of connectivity throughout the vehicle, achieves surprisingly excellent gas mileage, and dazzles the interior with its full sunroof (running almost the length of the vehicle). But the best features emerge when driving the Jeep Cherokee for the week.
Let’s start with my view from the driver’s seat because I loved driving this vehicle! And this is where all the good stuff is happening: super comfortable seats, access to my gas mileage (which averaged 26/29 for me!), and the 8.4 inch color display with Apple CarPlay.
Speaking of Apple CarPlay, this has not been an important factor for me in the past because I don’t like Apple Maps, which is the default for Apple CarPlay. I took a chance and used it on this trip and loved having access to the maps, the Podcast app, and all of my audiobooks for the trip. And Apple CarPlay is rumored to allow you to soon use Google Maps instead.
Finally, let’s talk about the drive both on the road and off. It was comfortable and powerful enough on the road that I loved taking on a long drive but maneuverable enough for short trips to the store. But no 4×4 vehicle could be adequately review without taking it a little off road. I found a deep, muddy puddle and put the Cherokee in Sand?mud mode on the SelecTerrain 4×4. I plowed through wondering if I was going to get stuck. I felt the rear wheels slip and then powered through it. That was fun!
In the past, Jeep has been known for having issues with reliability, more so with the Grand Cherokee. For this year, I’m impressed with the 2019 Jeep Cherokee Overland and although I can’t speak for any long-term driving, this has been one vehicle that I was sad to give back. And the last time that happened, I ended up buying that vehicle!
If you’re looking for a mid-sized SUV with luxury at and affordable price and gas mileage that beats most of what’s out there, take a look at the 2019 Jeep Cherokee Overland.
