One of the most beautiful, classic motorcycles on the road. Everything is extremely high quality - real metal and leather everywhere. The bike looks (and is) expensive. A large part of the price you pay goes to the aesthetic qualities of the bike, and that's just fine. You'll have everyone drooling over it.
This bike is HEAVY! You will feel that weight pushing the bike during parking or if you tip it off center at all. Pushing this bike up any slight hill is nearly impossible.
In spite of the weight, low speed maneuverability is surprisingly good! It's easier to ride this bike at low speeds in tight situations than other bikes weighing half as much.
The engine (Twin Cam 88) is adequate for one rider and just slightly underpowered for a rider and passenger. It vibrates at idle, but once you are underway, it smooths out and all you feel are the power pulses. It does make wonderful Harley noises, especially at idle and under heavy throttle. Low end torque is abundant, but the max revs are low (5500rpm or so). Did I mention it sounds amazing?
Handling is focused exclusively on open road comfort, and you can cruise for hours without fatigue. Comfort on long, straight highway or in town over road imperfections is high.
Unfortunately, this bike handles very poorly when ridden aggressively and its suspension is antiquated and soft. You use half of the suspension travel just sitting on the bike!
Likewise, brakes are adequate at best, with the rear brake being good (but easy to lock up) and the front brake requiring a strong grip. Neither brake offers any real "feel", so a lockup can come without warning. The huge effort required to use the front brakes reduces the risk of this a bit, but locking the rear wheel is very easy in a panic. I'm sure the brakes are typical for a Harley, but anyone who has ridden other brands will find the brakes sub-par.
Comfort on twisty backroads is low, as the suspension cannot cope with turns at speed, and causes the bike to wander in the lane. It will wear you out if you try to keep up with Non-Harleys, and put you far behind them if you don't. It's not intended to be a canyon carver, but Harley can and should do better than this. The low cornering angles mean that there isn't as much "reserve" handling as you might expect with other bikes.
The other oddity is that the stock handlebars are too short, and cause most riders to lean farther forward than you would expect on a cruiser.
Harley stock tires are also quite hard, which increases their life span but reduces traction. I would prefer a slightly softer tire with better grip, even if I had to replace the tires a bit more often.