Personally, I would choose between Austin and San Antonio, and my choice would be San Antonio especially for a visitor from Staten Island who may be wanting to pick up on the deep Texas Southwestern thing.
A drive from Houston to San Antonio is easy. A visitor might stop off at Seguin just east of San Antonio for lunch at Los Cucos for TexMex and maybe look around town. In San Antonio, you’ll want to visit the Alamo and the River Walk.
Something I’ve never done, wanting to very much, is to drive from San Antonio to Marfa on the old and southern US 90 route hugging the Mexican border. You would drive west to Del Rio – figure about three hours – and then cross Armistad up to Alpine. Del Rio to Marfa is about four hours non stop.
Marfa to Tucson is about 7 hours and you get a freebee extra hour on the clock when you pass into Mountain Time zone.
So a guy could theoretically do what I suggest in three days and you have four or five. Is any of it to be spent in Houston, or are you planning 4 to 5 from Houston? If the latter and you want four days, I’d overnight at El Paso. Or, I could easily spend a couple nights at Marfa checking out Ft Stockton and the Davis Mountain State Park. Obviously you could spend two nights in San Antonio.
And let’s face it, many people, if choosing between Austin and San Antonio, would pick Austin. If you’re interests are in music, you might like Austin; you might like visiting UT; you might want to see the LBJ Presidential Library.Edited: 03 December 2013, 02:22
I agree about spending your time in San Antonio. There is much to see- the Alamo, Riverwalk, Missions NP, Hemisfair park, etc.
We've been twice recently during the winter and the weather was great and had a very nice visit.
If thru Luling between Houston and San Antonio at lunch them stop for BBQ there.
Us90 will be a lot nicer via Del Rio to Marfa but not fastest. from SA. Make sure to stop at the Rio Grande/Pecos River overlook and pay a visit to Judge Roy Bean visitor center and grounds in Langtry. A classic western icon Roy Bean was and I'm a long time contributor for that place so I always recommend it! Big Bend NP is not that far away and it's awesome but will take extra time. Make a short detour to White Sands NM between El Paso and Tucson. You won't be disappointed. La Mesilla near Las Cruces also makes a nice visit and with a detour in Az you can visit Bisbee and Tombstone but 4-5 days for all of this will be short.
I used to drive this at least once per year. It's a long two-day drive, as it is, so that does not leave you a tremendous amount of time for activities or side trips. I would suggest you take three days to the drive and allow a full day (two nights) along the way to visit a city. So your nights would be San Antonio; and Marfa or Alpine or El Paso.
I would definitely agree with what others have wrote in that you should choose either Austin or San Antonio. Austin is a younger, more progressive city with one of the best nightlifes in the country (live music every night at a number of venues), but San Antonio has much more to offer the casual tourist. Per food, Austin definitely has better restaurants overall, but I like the Tex-Mex that I've had in San Antonio more. Austin restaurants can be pretty pretentious as well, while San Antonio is very laid back, especially if you get out of the Downtown tourist area.
There's not a lot to do in Marfa. Marfa's attracted a number of New Yorkers who've set up art galleries in the town and hold a couple of annual art and music festivals. If you're interested in the Marfa lights, then that's just outside of town (can't remember which side of town). If you're not interested in the Marfa lights, then consider staying in Alpine. It's a cute town, and there's a great independent hotel there, the Holland.
Past Marfa, you will not miss much by driving in the dark so (I think the Prada "store" in Valentine is still there), if you have to, El Paso could be an option. Though it's only 4 hours from El Paso to Tucson, there is quite a bit to see along the way. You could visit Old Mesilla, as Tet mentioned, but there are also a couple of spots in Arizona that could be side trips, like Chiricahua National Monument and Cochise Stronghold (off US 191 south of I-10).
From Houston, you could make either San Antonio or Austin work as a stop, depending on your interests. One point to consider--in December (depending on your travel dates) the lights would be up and on along The Riverwalk, and that is lovely to see.
I second the suggestion of a small detour to White Sands NM--you won't see many other places like that.
How many drivers will you have? This is a long distance to cover with only driver and even though you will gain an hour's time along the way, night comes early. I've driven this route more than once, including some sections after dark, and I wouldn't do that again. In that part of the country, it will be darker than anything you've seen around Staten Island, which can make the driving difficult, even on the interstate. There is also the possibility of encountering wildlife on the roads--not good.
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