I am planing a 1200 mile trip this month. I will be towing a 6x10 "V" nose inclosed trailer. Inside will be two dressers, a twin bed, and my M109R motorcycle. All this totals about 2500 lbs. What should I worry about before the trip? No my KK does not have a factory tow package. Any tips would be great.

Just do it ! Be smart if your in hills and Trans is hunting use the tow button. Can I have the trailer after?

i Will be towing 3800 pound on a 1600 mile trip On the summer
I am installing and extra transmission cooler just to be safe
most important is to use the tow button so transmission issues different shift points
start slow until you get to cruising speed
put 60% of the weight in the frot of the trailer and 40 on the back this wil prevent sway
I have towed 4500 pound boat 500 miles and the kk does surprisingly good, I can say better than my 5.2 zj. gas is a factor but the least you stop the better

it cruises good at around 65-68 mph or around 3400rpm in tow haul mode and is really close to the max torque of the kk that is at 4000rmp more or less.

Please use the tow haul button. It prevents the overdrive clutches from engaging. The overdrive clutches are NOT rated for towing... I know from experience. A transmission rebuild is not cheap.

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08 KK OEM skid plates, JK winch bumper w/ Hella 500s, K&N filter, JKS front discos, black out headlights w/ fogs added, blacked out & euro mod tail lights, Curt Hitch w/ oem wiring, OME Springs, JBA UCA & top plates, Cabin Filter Retro Fit, Custom Fender Mounted Light Mounts w/ Hella 500s, ATH roof bars, rear flush mount LEDs

I often tow a fully loaded camper trailer that is roughly around the 2500-2800 pounds mark. Longest single trip so far has only been around 400 miles but I didn't have any troubles. I would permanently just have the tow / haul button enabled as the KK just performs so much better. Sits around the 2800-2900 rev range on the highway (60mph / 100kph) and still has plenty of grunt to overtake if needed. I tried a couple of times to toggle it off on the flats to save economy but it just isn't worth the extra strain and constant down shifting at the first sniff of a hill. Just don't look at your fuel economy.... keep your eyes on the scenery!

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'11 Cherokee KK limited.
2" Mopar Lift.
APT Custom Rock Sliders.
Uneek4x4 Steel Bar with Runva11xp Winch.
16x8 AEV Rims Powdercoated Black. (245/75/16 Summit Mud Hogs)
Yakima Roof Basket with Side Mounted Awning.

I towed about that much or a little more from FL to WI with my KJ, a 6x12 U haul trailer. I do have the tow package though. I didn't ever switch off OD but with your KK not having the transcooler I'd do the tow haul mode. You should be ok, just watch the temp gauge, mine never budged, so I'd think you'll be fine. Powerwise these things due just fine IMO.

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05 KJ Limited 4x4 in Light Khaki: Detours USA Backbone, Warn M8000, Huskyliners, RockLizard Super Skink sliders, OME/Bilstein Lift, JBA UCA's, 245/70/17 Nitto Terra Grapplers
07 LR3 SE V8
1996 XJ Country
2015 KL Limited

KK have a Trans cooler.