There's just something about road trips. Parts of them can suck, and parts are great, but they're usually an adventure of some sort...and moreso on a motorcycle or adventure vacation!
I once had someone I dated briefly tell me I was too 'unsettled' so we didn't continue seeing one another. Something to do with my unwillingness to say I planned on staying in this state forever...seems sort of odd, when I usually don't even know what I'll have for dinner on a given night, and I kinda like it that way.
Likewise, some people like to plan every minute of a trip...that's just not me. I do like to plan what to bring, as often buying some things en route are insanely expensive, or worse, not available (try to find a tire repair kit on a Sunday at night, on the side of the road..good luck!), and deciding on some rough route, or some particular things you'd like to do or see, is fine. But basically, 'take it as it comes’ with some general plans or highlight activity is much more 'me' than someone trying to plan every minute of the day starting at 8am (!!) or so. It's about the journey, not the destination.
I've always been up for going nearly anywhere, and trying almost anything once. Doing a search on 'adventure travel' however, opens up an entirely new dimension of vacations. From checking out Mayan ruins, riding from South America to Alaska, whitewater rafting trips..there's some truly cool stuff out there to see and do! Unfortunately, some places are quite expensive, between airfare (thank you GW Bush for these excellent gas prices; we should have free gas/oil for life with the amount of money you've funneled to your friends, err, 'spent in Iraq’ in the past.. :-/ ), lodging, transportation, attractions and if you're adding motorcycle rental (or boat, or..), it can add up quickly. Going off-season helps quite a bit, as well as avoiding the 'typical vacation weeks' (Xmas week was double the price for the same fare to Costa Rica and elsewhere compared to a week earlier or later!), and to some extent, not hitting the more 'touristy’ destinations or locales, and in general, doing your research.
While researching the Costa Rica trip, the runner up was Spain. I'd always heard Spain was a great place to visit, and it had the bonus of off-road, as well as being competitively priced. Redread was looking quite enticing, and I'd like to visit there in the future.
I still desperately want to visit Australia, but that quickly becomes a $5,000+ vacation if renting a motorcycle. I'm paid OK at work, but $5k for a week is just still kind of insane to me, no matter the destination (at least going solo). My dream trip remains to go to Europe without any plans or reservations, and basically grab a backpack and laptop, and go when and where the time seems right...for at least a month, preferably. And see Australia, somehow, sometime.
New Zealand was also looking exciting, until it got to pricing. Self-guided for 7 days at $4k was a bit too much, plus airfare, etc, at least for this time in my life. Some decent reading, however: GoTourNZ
To give some indication, car rentals for a basic car (sorry, unless it's an Elise, Tesla or similar, it's not worth paying 'extra' for a boring, large car for me!), I expect to get a weekly rate of roughly $250USD or so, or paying daily around $30-40-ish, +/- a bit, depending on location, for a basic but working vehicle with 4 wheels. Renting a motorcycle generally works out to a daily rate, with some relatively small discount on a weekly rental (but, if weekly is heavily discounted, then be prepared to adjust your trip, and go for it!), of generally between $60USD a day to $150USD per day or more. For me, I'm looking for a capable dual sport in general, leaning towards lighter (DR350, DRZ400, KTMs up to DR650) or heavier (F650GS, KTM 640), depending on the mixture of on/off road. If you want to rent a Hardley to 'look cool,' sorry, I have no idea other than 'higher and not worth it.' :-) Each destination will have different ranges of prices, depending on season in some cases, but they are ranges! Meaning, one place may quote $125/day and another $90 a day, for comparable or the same motorcycles, so do your homework! For me, $100/day or close to it, is pretty much the ideal I'm willing to pay for bike rental unless it’s really something special. If that means I change my destination to elsewhere, so be it.
A lot of tours/adventure/rental places, at least in Central/South America, Caribbean, etc, are done by Americans, Canadians, or other non-indigenous people, which has it's advantages and disadvantages. For some of these trips, they're basically being paid for their own vacations, or their 'retirement business,' but also, well, want to be paid like Americans or Europeans. They may or may not be flexible on pricing, but the plus side is you'll be dealing with people that have roughly the same expectations as you do in business and on some things - like you can speak English to them, and they'll let you know if a place has air conditioning or is safe to eat at or not, if you ask, versus sometimes broken English, or worse, you attempting broken Spanish/German/whatever, and believing you just booked a reasonable but clean, air conditioned place, to find it infested with bugs and 'air conditioning' means you have a window to open into the 100* outside temperatures!
'Tour companies' really range all over the place from tiny locals with barely running bikes, boats, equipment, to places that have spare parts on hand, and are well maintained. I won't say 'you get what you pay for,' because especially where it comes to vacations, everything has a range of pricing, and more is not always better. You just have to decide if the trip is about the lodging, or if someone renting out a tiny cottage in their backyard, but with running water, is right for you over Hotel Extrema or what have you, and same goes for the guides or people you're renting gear from.
An obvious way of sorting the wheat from the chaff is online - search on their website name and company name, find people that have gone with one or the other, preferably *many* accounts, as one person not concerned about money, or a particular type of trip, might say it was great, but had different expectations or desires than you. Post on a forum or two, for whatever kind of adventure you're seeking, and see what feedback comes in. I find it's almost always best to at least attempt to talk to the people you're dealing with on the phone (and use Skype if need be if you can't do free International calls).
I'm still up in the air on this one. On the one hand, I kinda like going solo. You set your own schedule, and destinations, lodging and meals included. It's freedom. It's all you, baby!
However, if you're unable to do enough research beforehand, don't speak the native language, and have no clue about the country or destination you're about to visit....I suppose I can see the appeal of a guide of some sort, or at least talking to someone that's been there, wherever there may be, before heading out entirely on your own. If you’re going with your spouse or partner - talk to them about it as well!
Again, look for people who have dealt with the guides/companies in question. This also applies to hotels/motels, etc - in some cases, 5 years ago, somewhere was great, but it's now no longer so.
So, you've narrowed down some places you might think about going to. Now what? Which one?
Here are a few things to consider, although I tend to ignore at least some of them :-)
Cost of airfare
In some cases, the airfare may cost nearly as much as the trip for lodging and activities. Unless you're rich, check pricing on all places. You may find somewhere you were considering and the lodging or rental, guides, etc are a bit more, but the airfare is less than half the price, so it works out.
Seasons
Many places have rainy or cold seasons. Use weather.com as well as wikipedia and other means to determine if your 'perfect destination' might likely be in the middle of monsoon season or heavy rains, or which time is more desirable to go there.
Politics
Some places occasionally undergo political upheaval, or have elections coming up, which may make a place less 'traveler friendly' than it used to be. Check out the US Travel Page, assuming you're a US citizen, or your equivalent Travel Warning goverment page as well as the Embassy site for your country at your possible destination. Check for travel warnings and other adverse conditions, such as outbreaks or epidemics of different flus or diseases.
Local sicknesses and related
Some locales still have outbreaks of Malaria, Avian Flu, and other badness. The government travel and embassy pages as well as wikipedia are likely to point this out, and you can/should consult with your doctor for any pre-trip inoculations you may need. Obviously, if you're traveling with children or anyone in poor health, there's an added consideration, both for pre-travel, as well as if any possible emergencies may occur while on your trip.
Medical conditions or medical availability - and insurance
If you have an existing condition, will you possibly need attention while on your trip? How far away is decent medical care? Will they even accept your insurance, or is it cash only? if you're on any medication, may sure to bring your own, with extra (you may also want to make sure it's legal to bring into the country you're visiting, in the case of being on some scary prescriptions..)
Supplies and local cost of goods
Some common items may cost a quarter at Target or CVS, but are unavailable or ten times the cost elsewhere. Sunblock, sandals, cigarettes, shampoo, razors, shaving cream, you name it. If in doubt as to bring something or are thinking, 'I'll just buy it there,' you might want to do a quick search to check the pricing, before being in for a big surprise when you're paying $30USD equivalent for a $5 bottle of sunblock!