Welcome to the site!

This is a difficult question but with your daughters challenge, is she aware enough to keep her hands from flailing about? The challenge I see (in this circumstance) with a sidecar is that it's got a wheel awfully close to the passenger compartment. If she flails about it's possible that her hand could get frightfully close to that wheel.

 

You will need training but, a basic MSF course won't cut it. Sidecars are totally different to operate than 2 wheeled motorcycles. The controls are the same but that's about it. Check the MSF website for info. Also, go to sidecar.com for more info.
As far as a bike, look for a used Ultra or Electraglide Classic, there's nothing wrong with a Road King either as someone here has already suggested but with three people you will need the extra luggage on a trip.
You had said that you would put the wife on the back and your daughter in the sidecar, That's OK, I've done it but remember that if the motorcycle passenger is heavier than the sidecar passenger it's like removing gravity from the sidecar and it WILL come up on the right hand turns. It's manageable but you will need to use caution.
Take a course, even if it's reading a training manual and PRACTICE PRACTICE PRACTICE. Once you learn, you will find out that sidecars are a ball, everyone seems to like them and they seem to be more visible in traffic that a regular motorcycle.
Keep in touch, let us know how it works out for you.

 

Before you sink $30k plus into a Harley and sidecar, you should buy something less expensive and ride for a season. You are going to be responsible for your wife and daughter. Plus anyone of you might not like riding once they have been out for awhile. Be smart, get some experience on bike before you head out on 1000 lbs of Harley and sidecar.
Ride safe

 

See If Woody Stevens would be willing to let go of his from Wild Hogs! Dudley may not appreciate it.

My suggestion would be to def. take the course. It will teach you a lot of stuff. You will learn more as you ride. I dont know much about sidecars, so cant help you there. But Im sure the internet is full of information.

Good luck. Your daughter will have a blast.

 

This is the best answer in my twisted mind. You buy an FLH fully dressed touring bike for you & your daughter & your Wife gets her own Soft tail so you can all ride together & not worry about a side car!
Lots of ladies here ride their own iron & they are still ladies!
Stuff to chat about over coffee!!
Hatch.

 

I totally agree with this one. depending on your wife's taste, maybe a sportster or dyna as well. Cant go wrong with any model.. all just depends on personal taste and comfort.

 

I think you have totally unrealistic expectations. Riding a motorcycle is physically and mentally demanding. The bigger the motorcycle, the more physically demanding. Riding 2 up is more demanding. Riding 2 up with a sidecar is even more demanding, I would imagine.
Take the MSF course. Personally I am glad I had 20k miles of experience on a Vulcan 750 before I bought my Ultra this year. I didn't ride 2up before I had 1k miles solo. I have 6k on my bike, and am just becoming one with my bike.
Many others will say start out with the bike you want.
Take it easy and good luck.

 

The fact is that most of us on here have no experience riding with a sidecar so take our opinions with a grain of salt as they say. Now having said that I think for the three of you an Ultra Classic fully loaded with the sidecar added is the way to go. Definitely more comfort for your wife riding behind you and plenty of secure storage as well as the heavy weight will be beneficial in handling a sidecar.

Many suggest taking a safety course like the MSF one and that is good but if you don't plan on riding a two wheel bike I think you would be better off finding a course or experienced individual to teach you how to ride and handle a sidecar. They do handle differently in turns from a motorcycle.

My respects to you for wanting to spend this kind of time and experience with your daughter and wife. This could turn out to be a beautiful thing. Good luck.

 

If you're just wanting to take your daughter out for a tour about town.
check out the Russian made Ural's.
http://www.imz-ural.com/

They are 1/3 the cost and great for just running around town.
The 800cc motor limits your cross country ( IMO ).

Several models come with two wheel drive in the rear ( both wheels pull ).

Just a thought ( $10k rather then $30+ for a Harley with sidecar )

 

Sounds like a plan to me...and am glad you want to spend time with you family like this.

It IS doable, but I do agree with taking it easy and learning before going on any planned runs. Riding in residential neighborhoods at 25 MPH for a long while, and parking lot practice is ESSENTIAL in my opninion.

Alot of the opinions on here are coming from guys who genuinely don't want to see you get hurt.

The ural might be a good idea, but it will be totally inadequate for pulling 3 people plus gear on any long distance trip.

IMHO, for long distance touring, the Harley Ultra Classic is the one to get, and a matching sidecar is easy enough to find. Do a Google search.

Good point on the daughter throwing her arms around with the wheel right there, so a full fender over the wheel, etc. is a must.

Oh, and helmets for all 3 of you should be considered a necessity.

The ultra also has a CB setup, where you can talk to each other if need be as you are riding.

Good luck, keep us posted. I am interested in hearing how this goes.

~Joe