I’ve had my 883 for 3 yrs and ride 4000 mi/year. I’m 74. Last year I found I wanted to travel further. Maybe 200 mi days, more interstate, even an occasional overnight. Still mostly day trips. If you’ve been down this road, give me your thoughts. I was sure that the Sportster was my last bike, but maybe not. HD sure can keep you thinking.

 

If it's within your budget, and you're looking to go longer, definitely take a peek @ Softail line. Spring's here so many dealers will have open house/demo bike events. Sit on a few, test ride & dial-in the bike that fits.

FWIW, I'd recommend a Heritage, but I'm a bit bias.

 

I’ve got a few Sportsters, they are my favorite HD motorcycle, but I ride my Softail the most. When I wanna hot rod around, Sportster. When I want to cruise, Softail. You sit into the Softail as opposed to on top of the Sportster. Based on the riding you want to do, the Softail will fit the bill better IMO. If you haven’t already, ride one and see what you think.

 

I love Softails. You have so many options. From. stripped down plain to full on touring. Sport models too. Lots of good all day cruisers Fatboy, Heritage, Deluxe.

 

There is no "easy" answer. At the end of the day it will depend on your height, weight and what is comfortable to you.

In my case for example, I started off with an 04 Honda Shadow VLX. Nice cruiser. Excellent starter bike. My wife had to have a Harley so I needed something cheap. I am not a big guy so I didn't want to get in over my head so I went small.

After 3 or 4 years I found an 02 Wide Glide. That was basically the same bike. Only Harley and more powerful. 5 speed so better on longer trips. It is gorgeous and absolutely spoke to me with all the damn chrome LOL But what I found after about 5 years was that it is excellent for about 80 miles, but then I am squirming around. Perhaps an 18 year old seat was partly to blame? With that and having a tailbone injury last fall I test rode a bunch of bikes and finally chose a 2019 Heritage. Much more comfortable all around. The seat is nice. I have gotten used to the floor boards and I can still stretch out like I want. With the injury, I will still probably swap out the seat or have it modified. Only time and few hundred miles will tell. Fatter front tire which, I think helps smooth out the ride.

I tried a Road King which was my second choice. BEAUTIFUL bike. Not a rolling couch like the bigger Street Glides and Road Glides. Personally I couldn't relax. I felt too upright and felt like I was sitting in a chair. But that is just me. The Heritage is a little less like that. Not exactly like sitting in a recliner but definitely more relaxed than a RK.

I would suggest, checking out the local HD dealerships for their demo days. Ride a bunch. That's what they want you to do. Just remember pipes and handlebars are "cosmetic" and something you can do later. You do not have to buy new. Do some research. Find out what colors and options you might like. Be patient. Bikes come around. But the demo days is a great way to try various bikes to get started on your search.

Note: Be aware older bikes are different than newer bikes - in the same family. In my case for example, after sitting on a few older Heritages, I knew right away the 2018+ was better for me . More well balanced. Lower center of gravity. Light, not heavy. The seat was less like a rock.

Hope that helps!. Keep us posted on your progress!

 

I absolutely love my M8 Fat Boy. Very fun bike, its quick and easily gets to 120mph. Very comfy bike too with the floorboards.
If you want, one, I say go for it.
It's a very nice bike to ride.

 

I had a 1200 Sportster and loved it. I’ve had several others since and now ride a Fat boy. I’d be comfortable taking the fat boy anywhere, it handles great on the highway, and is fairly light weight. There are better bikes for long distance, but the extra weight becomes a challenge as I get older.
Good luck whatever you choose.

 

I like the look of the various Softail models, but actually prefer riding a Sportster or Dyna.

My wife is more comfortable on the back seat of my Fatboy, so that’s how we roll.

 

For me.....Low Rider for small mileage days, BMW RT for touring. If you are looking for a good all around I would look at the Heritage

 

I made that upgrade 29 years ago and never regretted it for a minute. The 883 was a fun ride but the Heritage Softail I traded it for was so much more comfortable and easier to handle despite the greater size and weight.

Just do it already.