When you click on links to various merchants on this site and make a purchase, this can result in this site earning a commission. Affiliate programs and affiliations include, but are not limited to, the eBay Partner Network.
Did it, do it. The Fatboy is roomy for two up, floorboards are really comfortable, wide tires roll over anything, wind less of a problem, stability at speed is better than a Sportster. If you plan to take baggage, a Heritage is also a good choice. With a Fatboy you may need to relocate the rear turn signals for some bags. Sportster is lighter and handles better in twisties, but a Fatboy is a cruiser and built for comfort...but not as heavy as a bagger. Recommend a Memphis Shades batwing fairing to go with it.
Go for the Fat boy, I just spent 5 day's , 1,500 miles touring the north coast of England, two up with luggage, you dont need paniers, get soft luggage that goes on a rack, add a detachable back rest and rack, its cheeper than panniers.
Yep, do it. I ride two up often and it's no problem. I have mine set up with everything quick detach. I ride it stripped down with a brawler solo seat to work and around town. When it's time to take the wife for a trip. I can change the seat, put on windshield, saddlebags, backrest, and t-bag in 5 minutes.