With that much driving I would want something like an FBody or Mustang. Torque and a nice overdrive gear is the tits when logging lots of highway miles. GTO would be nice. The seats are real comfy. The stock shifter would need to be taken out back and shot. Then put in something you would actually call a shifter instead of a pudding mixer.
I thought about it and the BMW, while an extremely smart fun option that would be enjoyable fo sho, is being pushed aside for one of the following;
Best seats ever. Tons of space. Good power. Turbo so it laughs at high elevations. Good mpjeez. Good luck.
Years ago, I read and article (I think it was in R&T) about a road trip. The author had a friend who had just purchased a pretty original 289 Cobra. They flew out, picked it up and took a leisurely drive across the country. It sounded like amazing fun.
If I was youngish (as I suspect you are) and I had the time to drive all over the country... I wouldn't do it a berklying minivan! (In fact if I ever bring home a minivan, my daughter has instructions to shoot me (but that's a separate rant)).
If you're like most people, you're probably going to an epic road trip like this exactly once in you life, right? So I would do this in a car that would be very memorable to drive. Like:
Triumph TR6
'67 Mustang Convertible
Boxster
MGB
Austin Healey 3000 (there's a v8 powered one cars . com for $10k)
Merc 450SL/500SL/560SL
240Z
Karman Ghia
Corvette
'67 - '69 Camaro
Alfa Spider
My preference changes with my mood and what I have found on the Seattle or Columbus (now leaning toward starting there and doing two complete loops) craigslist lately, but there are a few cars that I keep coming back to. They fall into two categories...
Roadsters:
Miata - A mechanically solid, slightly rough looking NA would probably be the best fun-for-the-buck answer on the sporty end of the scale (at least without running some serious reliability risks.) An MSM or early NC are stretching my budget, but would be nicer on the highway and still all kinds of fun on the Beartooth Highway (as long as it wasn't three feet deep in the snow.)
MR2 - I have owned an AW11 before and it has been both my favorite car to drive and the best value I have ever gotten out of money spent on a vehicle. Not as forgiving to drive in bad weather though. There is an extremely clean SC version in Seattle, but it is optimistically over-priced at $9.5k. I've also owned an (NA) SW20, which I didn't enjoy nearly as much. It was boring unless thrashed within an inch of its life. I've test-driven a couple of Spyders and have been highly tempted (would have bought one if I hadn't found the '86 for $1500.)
S2000, Z3/Z4, or Boxster are all appealing, but perhaps a little rich for my blood in various ways (initial coast, potential maintenance, higher strung, getting maybe a little too much attention on the highway or parked at colleges and cheap hotels.)
GT-ish:
E36 M3 - I'm shocked (shocked I tell you!) that we're into page three of this thread and this hasn't been mentioned except in the fecal sense. It has some of the same downsides as the higher-end roadsters, but at the very least I intend to take the excuse to test drive one or two.
Legacy GT - I like Subies. AWD is good in the mountains. Sporty, fast, Q-shippy wagons are fun. People also don't seem to want to sell them. (I suppose I could live with a sedan.)
V70R/850R/T5 - Sporty, Q-shippy, fast wagons... still fun. Surprisingly easier to find than Legacy GT wagons.
Late C4 or early C5 Corvette - This may be one of the smartest, most economical ways to cruise the highway in fast, fun comfort. I respect the hell out of this car, especially the newer generations, but... there is a part of me that expects Vettes to be driven by arrogant middle-aged shiny happy people and does not want to be that guy.
Others that I have considered in roughly descending order of interest:
Other BMW E30-E46 3-series - Plenty of them around in a variety of conditions, occasionally even in manual. Would be nice if I knew which all of the cornucopia of models were actually significantly more fun than a Camry.
Subaru RS 2.5/WRX/Forester XT - Ideally a wagon, not thrashed or haphazardly modded.
5-series/S-Class wagon - I have a general sense that this class of car represents more upkeep cost than I want to take on, but I might accept that for a powerful, fun wagon (I would rationalize that further, but I know GRM gets that.)
Mercedes 300D... or older SL - These are terrible (for lack of driving excitement on the one hand and risk of high costs on the other,) but fun ideas.
P71 (other panther chassis car, caprice, etc...) - Spend next to nothing, easy cruising power, never get pulled over, take a moderate hit in gas and still come out ahead in most ways. Definitely not a very sexy option, but the upsides aren't bad.
Pontiac Solstice GXP - Might need significant attention if it is in my price range. But I'd go for any of the above roadsters before getting the non-GXP version.
350Z/G35/RX-8/Genesis - When the 350Z and RX8 were first released they would have been at the top of my list. Not sure why they don't appeal so much any more, other than they seem like a compromise between the M3 and the Miata. I'd rather have one end of the scale or the other.
Audi TT - If I fit comfortably (6'1"), might go on the roadster list.
VW Jetta/Golf/Passat - GTI, TDI...? various mixes of efficient and fun. Not sure which ones in particular I should be looking for.
Saab 9-3 Mazda S/Speed sedans & wagons Acura RSX/TL/TSX
Jeep (Grand) Cherokee, Trooper, CRV, etc... - I can certainly have my pick of Jeeps in Ohio, but again, no idea what I would be looking for.
Del Sol Corolla S/Civic SI
Volvo 240 GL - Poor man's 300D? (Mercedes fans seem to hate the comparison, but it certainly makes sense to me.)
Accord/Altima
Insight/Prius - MPG, MPG, MPG, but not sure I see any reason to do this in a world with TDIs
Mustang - Like the Vette, my opinion of this car is much lower than it deserves. I'm sure there are Mustangs that would be fantastic for this trip, but I have a hard time disassociating them from a certain class of Midwest poseurs from high school and college.
Well, aside from having a hard time finding Legacy GT wagons (except for a B Spec... far out of my price range) I certainly can't complain about a lack of options!
This would certainly make the trip "memorable". 
Hah! Even if I bought something a little off the beaten path (like some of LuxInterior's suggestions) I know better than to buy a half-completed project and immediately set out on a road trip. 
In reply to pres589:
What IS that? The front end looks like a Mazda of a certain age, but...?
I agree that if you were almost considering a motorcycle, thinking of anything other than a convertible is a bit silly.
I will admit that I am a bit weird, but if I were doing this for fun with few timelines (meaning I didn't have a hard date to be done or get anywhere), I would buy the best 5k miata - no hardtop - I could find and make a rule to myself that I would do all repairs myself during the journey.
If any car is stock ride height, I think most people are surprised at the amount of off-road a car can handle.
With a miata, I guess you have a good chance of seeing and feeling the america you drive through, rather than isolating yourself from it. The miata will also be fun in the corners, be ready to hit an autox or rallyx if you have a sunday off in a city area, and will make it to the campsite without worry.
Whatever you pick, I am jealous, and I think both you and the car will have some amazing stories!
kilted_monkey wrote: Hah! Even if I bought something a little off the beaten path (like some of LuxInterior's suggestions) I know better than to buy a half-completed project and immediately set out on a road trip.
See, here's the trouble with people these days. They say: "I want to enjoy the trip itself as best I can, not just get from point A to point B."
They say they'd do it on spartan machinery (a motorcycle). So you provide a list of interesting spartan machinery (with cloth roofs and heat no less!). Then they say "I know better than to..."
An R1200GS or FJR1300A aren't "spartan" machines! Oh wait... I already told you in my first post that my choice of bike would likely have been a KLR. Guess I don't have any room to quibble with your choice of adjective then. 
Oh, don't get me wrong, I LIKED your list. But I do have far more faith that any new or well-treated KLR would take me that distance without mechanical issues than most of the cars on that list. And for me, any more than very minor wrenching on the side of the road quickly goes from 'hey, it's all part of the adventure' to just a pain in the ass.
Out of the British cars I would have to go with the TR6 as that was my dad's one sports car in his life, a sort of consolation prize when he wasn't able to buy a 2002 (too expensive) or a 240Z (brand new and in high demand at the time). He loved its contrary Britishness (at least in hindsight) and when he first met my mom she accepted his offer of a ride home more because she was interested in the car than in him. Since then we have been a bit of a Triumph family (mom also had a Spitfire for a few years) which means I would be something of a traitor to drive an MG. I think I could be forgiven for the Austin-Healey though. 
Boxster? Given the rest of your list, don't you mean 914? 
That and the Vette are outside possibilities. I would consider the right SL, 240Z, Karman Ghia or Alfa Spider at the right price.
This will give you an idea of how scattered my search is. At the moment I am looking at:
An '86 SVO a co-worker and fox body fan linked, inviting me to 'come to the dark side.' http://seattle.craigslist.org/kit/cto/4671818296.html
Two distinctly different E30s http://columbus.craigslist.org/cto/4663225997.html http://columbus.craigslist.org/cto/4657986824.html
(I didn't know the 325E was a thing and had to do some reading. An interesting possibility at that price!)
A pretty, turn-key 350Z vert - http://columbus.craigslist.org/cto/4671908277.html
The latest of a long list of NA Miatas - http://columbus.craigslist.org/cto/4673047038.html
Aaaand... I am reading up on the Fiesta/Focus STs and trying to figure out whether the rebates available through the Military Advantage Program for cars purchased while stationed overseas is worthwhile.
(I swore off new cars. I swore off new cars. I swore off new cars.
...dammit.)
I personally would immediately scratch off the Accord, Altima, Del Sol, and Corolla S from your list. Those are all boring cars that weren't built for driving enjoyment like many of the other cars. The Civic Del sol is really small, but I haven't heard anyone refer to it as sporty.
All of the E30,E36,E46 cars are the benchmark for sport sedans for those years they were manufactured, so they are much more fun than a Camry. The ones with the sport suspension and limited slip diff would be the best ones.
For the Jetta or Golf TDI, definitely go with a 5-speed. You could do some suspension upgrades so they handle as good as the GTI.
How about a late model GTI or Focus SVT??
In reply to kilted_monkey:
That is a 1988 to 1992 Mazda 626 Turbo in hatchback format. Very rare, actually, although I have seen a couple in the wild. Very spacious, surprisingly quick, and capable of up to 40mpg in perfect conditions from the factory.
Ah, I wasn't far off! That does sound like a good mix.
Most interesting find of the day so far: Xr4ti - http://columbus.craigslist.org/cto/4658008795.html
For me, the choice is simple: E34 5-series.
Plenty of room for a big guy like me (6'2" and 220lbs). Great for long-distance highway cruising. Reliable. Quiet. Relatively fuel efficient. More than enough room to haul your stuff. It'll do fine in the snow with the right set of tires.
There's a good dealer network for a cross-country drive, plus a few specialty online retailers (Blunttech, Guten Parts, etc) that can overnight you parts if there's something you can't find locally. If you join the BMW CCA, you'll have access to members and knowledge for tech support across the continent.
It's a no-brainier for me.
http://baltimore.craigslist.org/cto/4664517914.html
Add heads, a blower, police spec steering rack, bags and maybe a set of aggressive 31" rubber
kilted_monkey wrote: This will give you an idea of how scattered my search is. At the moment I am looking at: An '86 SVO a co-worker and fox body fan linked, inviting me to 'come to the dark side.' http://seattle.craigslist.org/kit/cto/4671818296.html Two distinctly different E30s http://columbus.craigslist.org/cto/4663225997.html http://columbus.craigslist.org/cto/4657986824.html (I didn't know the 325E was a thing and had to do some reading. An interesting possibility at that price!) A pretty, turn-key 350Z vert - http://columbus.craigslist.org/cto/4671908277.html The latest of a long list of NA Miatas - http://columbus.craigslist.org/cto/4673047038.html Aaaand... I am reading up on the Fiesta/Focus STs and trying to figure out whether the rebates available through the Military Advantage Program for cars purchased while stationed overseas is worthwhile. (I swore off new cars. I swore off new cars. I swore off new cars. ...dammit.)
Well don't test drive either of the ST hatches because they will make you want a new car. They are that much fun and comfortable! It's near the end of the year I bet you could get an awesome deal! Ford has been marking them down quite a bit over this past year..
In reply to clutchsmoke:
and with the RS on the horizon I'd expect the offers to get even sweeter
So, I said I was surprised no one had mentioned the E36 M3. It is still on my shortlist (ideally in manual/convertible form) and I am curious if there are any particular reasons that it isn't your choice for a road trip? Is it the fact that it is first and foremost a track weapon, or...?
Mazda 5. Should have plenty of room for cargo or in case you need to sleep in it. It would also handle well if you tinker with the suspension a little bit also. close to 30 mpg also.
As others have said, you want a Legacy GT wagon.
Second choice (far down) would be a Volvo V70 XC, but it's nowhere near as fun to drive (more comfortable, though)
I am back in Ohio and the proper, hands-on search has begun. Driving my mom's (formerly my) Honda Fit around and I am reminded that it is actually a pleasant car to drive with two caveats: when you want power, it takes a moment to think before delivering (and doesn't deliver much) and the seat just doesn't go far enough back to be comfortable on the long haul.
Here are the cars I have driven so far, as determined by who from craigslist was available soonest and what I happened to drive by en route:
Crown Vic Police Interceptor - Twice the price of most P71s, but just about as close to mint as a 120k mile Interceptor is ever likely to be, with amusingly immaculate records. If I could convince myself that it would be remotely fun to drive, this would be the panther chassis to buy. However, I think something a little more visceral is going to beat it out. (Oh, that was 80mph? Ho hum.) https://columbus.craigslist.org/cto/4675001861.html
MR2 Spyder - Reconfirmed that I love the slot-car feeling of lightweight mid-engine cars. Also reconfirmed that yes, that gap above the 'spare tire' is really all the storage you get. No... seriously, we're not kidding. The engine is easier to get to than it is in the AW11, but is that really worth giving up on a trunk entirely? Did Toyota think this was an Elise?
Boxster - Stopped at a lot full of interesting cars on my way to Columbus to see the next car, this was the only one in my price range. I sat in it, but declined to drive it as it was an automatic. On my way home, immediately after driving the MR-S, I decided I might as well see how it compared. Conclusion: I definitely want to drive a manual. Even missing a third pedal, it was far more comfortable and potent than the MR2. The tiptronic shifting wasn't as engaging as doing it yourself, but it was certainly far more fun and distinctive than the basically-just-for-show paddles in the Fit! Plus, only about 1000x more storage room than the MR2, more than enough for a road trip.
S52-swapped E30 - I shouldn't post this here or someone on this board may sneak this out from under me. This is the top candidate so far, despite being a little over my self-imposed limit. This car appears to have been done absolutely right. No rust. (CA chassis.) Only minor flaw is that the driver's seat doesn't look so great (still comfy.) Not sure it is worth what he is asking, but I don't have a good point of comparison other than the fact that other clean, lightly modded (but not swapped) E30s can be had for half as much. https://columbus.craigslist.org/cto/4632203626.html
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Ｆｕｒｔｈｅｒ ｅｄｉｔ：whoa... what's up with that font?
kilted_monkey wrote: MR2 Spyder - Reconfirmed that I love the slot-car feeling of lightweight mid-engine cars. Also reconfirmed that yes, that gap above the 'spare tire' is really all the storage you get. No... seriously, we're not kidding. The engine is easier to get to than it is in the AW11, but is that really worth giving up on a trunk entirely? Did Toyota think this was an Elise?
You have found the really only thing about this car that makes it impossible to have as a primary vehicle. Otherwise, it is probably my favorite car I have ever owned and I may own another, if I can grab one that someone did a clean 2zz install and it comes with a hardtop.
On the MR2 Spyder, you seem to be overlooking the storage comparment behind the seats.
There is even custom luggage available.
Here is a fun thread of bike racks on Spyders:
http://forums.mtbr.com/car-biker/mr2-spyder-bike-rack-578072.html
I was thinking this is what you meant for custom luggage:
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