Road King vs. Soft Tail
I'd seriously consider renting one of each at a dealer for a day and take both of them on a long Highway cruise. When your done, you'll know which one to get.
I did several extended road trips with the Heritage and never gave it a thought that it was not a "touring" bike. I toured it anyway.


In 05 I did a long road trip that had several continuous days of moderate rain. While the leather bags did not leak the rain did take a toll on the leather. It took me three days to get the leather cleaned and reconditioned.
In September of 05 I bought the Ultra. I wanted the convenience of the hard bags and the lower fairings for the long trips.
The touring family has a higher center of gravity from the Softails that takes a few minutes to get used to. The big difference I see is between engines. The balanced engine in the Softail makes for a smooth idle but at high speeds there is a bit of vibration from the balancers and chain. The Heritage "likes" to run between 65 and 70 mph. The non-balanced engine in the touring family will shake a bit at idle, but come on, how much time do you spend idling? It smooths out at higher rpms and without the balancer mechanism stealing power will give you higher speed at slightly lower rpms.
I would suggest you rent one for a weekend trip of each model and see how YOU like it.
I use the Ultra for trips over 2000 miles and the Heritage for everything else. It works for me.

Plus I have a hot spare in case of maintenance or mechanical.
The Heritage looks better, sits lower, and has a lower center of gravity. A good thing for those that are short. The Touring bikes handle better, ride better, and are smoother at highway speeds. Plus, they are better in all respects when riding two up.
As suggested earlier, I would add a windshield and bags to the Dyna and get it up to touring class before I would spend a lot of money going to a Heritage.
We have owned a Dyna, 2 Heritages, a Roadking, an FXR, and an EG Classic. I have found that if you are going to do a lot of touring, and are going to upgrade for that purpose, then get a touring bike.
Regards,
Bill
The Heritage looks better
I'm not big on the looks of a stock ULTRA, but some of the lowered stripped down baggers on this board look awesome to me.
~John
The Best of Harley-Davidson for Lifelong Riders



