Hi Katie - The best time of year is June, July and August. May and September can also be very nice, but the weather is more unpredictable. Yes, it is certainly possible to ride solo for only 2 weeks. Most people buy the horse and resell it at the end of the trip, knowing that they will take a loss. It might be possible to rent a horse, but this is a big unknown. Since the outfit that you rent from has no guarantee should the horse be lost or stolen, they will be very reluctant to enter into this kind of agreement. You are going to spend at least a week doing all your prep work - shopping and outfitting your riding horse and your pack horse. I'm not sure that it's really worth doing if you only have 2 weeks to ride. Most people give at at least a month. You can contact me with a PM and I can give you more ideas.

Thanks Kim. We are actually planning on October, because that's the soonest we can scrape up the money. Do you think it will still be worthwhile or will the weather be unbearable? Also, do you know how I can find cheap flights from America to UB because the ones I've found have been insanely expensive. Also I'm new to this forum--what's a PM?

Hi Katie- A PM is a "private message" - you click on my name to the left of my post, and you can send me a message. It's like email.
October is quite cold. Unless you are from cold climates and prepared for sub-zero nights, you might want to consider next summer instead. Take a look at the Stepperiders web site. There is a page about solo riding on that site. You need a significant amount of planning and preparation to do it right. And unless you are both experienced horsepeople, you might want to come get some training before embarking on your own.