Unless you have one with the 4-cyl engine, 2000 lbs should be within
the towing capacity (3500 lb on Unlimiteds; 2000 on X, Sport, and
Rubicon; 1000 on SE).  Other than that, the weight & short wheelbase
of the Wranglers is probably the biggest limiting factor...you don't
want the boat to be driving you!

The standard TJ Wrangler with 6 cyl is rated for 2000 pound towing
capacity. The engine, brakes, axles, and frame are fine for this weight
BUT the relatively soft suspension required for good off road
performance along with the short wheelbase and high center of gravity
makes this a very poor choice of tow vehicle. It's not that you can't
accelerate or brake, it's that you can't handle emergency situations
like quick lane changes, blustery side winds, etc. The trailer just
drives the jeep where ever it feels like. You are talking about a couple
thousand miles per year on the freeways with a trailer, not just a
couple of miles to the boat landing and back.

The short wheelbase is the limiting factor in the TJ's towing rating, as
others have said. A 2,000# boat and trailer ain't so big, but for any kind
of long-distance towing like what you are looking at, you should consider at
the very least an '04-06 Unlimited, since it has a longer wheelbase than a
standard TJ. I would say at this point I could sell you my 04 Unlimited, I
even live in Michigan, but it's already sold.... :-)

hitch on the Wrangler.  This should be able to handle max 2k lbs.
Trust me, don't tow anything larger then that.

I tried to tow one of those dual-wheel Uhaul trailers down the
street.  It's scary!!!  Even unloaded at 30mph, the Jeep felt like it
would jackknife.  I returned it after driving 1 mile down the road.

If you need to tow something larger, get the Unlimited which is longer
and has more wheelbase for towing.

Nick