I tow a 2500 lbs Pop up camper and I also have a 19ft Bayliner. Towing with it is never an issue. Its stopping with it that could be an issue. The factory tow rating on these vehicles is 1500 lbs. I have a steep driveway and I was pulling the camper up this past summer and I went to apply the brakes and it pulled her backwards. If towing anything over the recommend 1500 I would recommend trailer brakes.

 

I have a class III hitch on my 96 XJ and a factory trans oil cooler and just got done flat towing a 1995 YJ from NJ to Hobe Sound Florida. I ran at interstate speeds of 65-70 mph and at times even used the cruise. All went well, however you must be smart, pay attention and give yourself plenty of room to stop.