My husband and I (both in our early 30's) flew into San Antonio from Madison, WI to spend a few days prior to going to Austin for a wedding over Memorial Day weekend. I was a little hesitant about going to San Antonio because I generally dislike any touristy activites and for the most point avoid chain restaurants. It was hard for me to figure out what exactly we would do with our time. We ended up having a good time, but I don't have any desire to return- we saw what we wanted to and were happy with the 2 nights we spent there.
We stayed at the Embassy Suites-Riverwalk and I would 100% recommend it. It was the nicest Embassy Suites I've ever stayed in. The place is on the Riverwalk, but away from most of the heavy traffic (only a very short walk away to most places). The rooms, breakfast and happy hour were all very impressive. The restaurant on site, Luke- also had a good happy hour and was a nice place.
Our flight arrived early afternoon and we took a taxi to our hotel. The taxi ride was pretty quick and cost ~ 30 dollars. Our room wasn't ready when we got there, so we dropped off our bags and went to take a Riverboat Tour. The tour was a nice way to orient ourselves and see what the entire riverwalk had to offer- i would recommend doing this. I think it cost ~ 9 dollars pp. After the tour, we needed to grab quick lunch, from what I read there wasn't much to offer on the Riverwalk as far as quality food goes, but I heard good things about Boudros Guacamole, so we went there. We split the Guacamole, and I had Grilled Chicken Salad. Everything was great and I was plesantly suprised with the food. Afterwards we checked into our hotel, walked to Market Square. I can't think of anything good to say about Market Square-- I seriously can not think of why this place is ever recommended on this message board. Every shop had basically the same things and the restaurants looked fine, but touristy. We sat outside and had a beer and a margarita at La Margarita. Service was beyond awful- we had to hunt the guy down whenever we wanted anything, including to pay our bill.
Later in the evening we went to Luke at the Embassy for some oysters and beer (they had a good beer selection which is hard to find on the riverwalk) during their happy hour. We then hit up the Embassy's happy hour and took a cab to the Pearl Brewery Complex. We checked out the menu at IL Sogno and were able to get a table on the patio immediately. The food was amazing- I had the black squid ink special and my husband had the Risotto. We split one of the salads as well. The focaccia bread with hummus that they start you off with was great as well. We had a bottle of Chianti along with our meal and the total came to ~ 100. Of note it did take at least an hour inbetween our salads and when our entrees were brought out- which was ridiculous. Our server didn't seem to think that was strange, which I think kinda annoyed me (he wasn't apologetic at all). But, the food was great, so I would return if I was ever in the area again.
We hit up the Embassy for breakfast and then went to catch the 1000 showing of the Alamo Imax. I thought the Imax was a nice thing to do before seeing the Alamo to remind yourself of what you learned in grade school about American History. Afterwards we checked out the mall (which wasn't very impressive as far as stores I'd like to shop at) and then walked over to the Alamo. We walked around ourselves for ~ 30 minutes and thought it was a great way to spend a morning.
Plans for the afternoon were to spend some time at the outdoor pool at the Embassy. The pool area was nice and not many people there. There are some chairs and then a total of 4 loungers (they could use more). We stayed by the pool for a few hours. Around 3 ish we got hungry for a light lunch. Again, for convenience sake we wanted to stay on the riverwalk and I remembered reading on this message board that Acenar had a happy hour that started at 3pm. So, we went to Acenar and found out HH was only inside at the bar. So, we sat outside and I got a salad (which was just ok at best) and my husband got the ceviche which was pretty bad. We each had a beer and then left- wouldn't recommend. We decided to check out the Esquire on our walk back. I really enjoyed the Esquire Tavern- first of all, they have a good beer selection and a nice quiet patio to sit on- would definately recommend this place for a chill place to get a drink. We walked back to the Embassy and then went to catch a Trolley to Southtown. I had 100% wanted to check out the Friendly Spot and it did not disappoint. I tried their Sangria, which was awesome. They also had an impressive beer selection, I got to have a Harpoon IPA, which I havn't seen at any other bar outside of Boston, so that was nice. Plans for dinner were someplace in the Soutown area as it seemed there were a lot of good places. We tossed around Bliss, Feast, The Montery, Rosarios, and El Cascabel. We decided we felt like Mexican food since we have plenty of restaurants to the quality of Bliss, Feast, and the Montery in Madison, but we don't have great Mexican food. So, since El Casabel was closed (they were only open from like 10-4 during the week?), we went to Rosarios. First impression wasn't great-- yes, they were packed on a Thursday night at 7:30 pm, but the place just seemed so big and not much "atmosphere" (yes, i know i'm picky). We had about a 20 minute wait. We had a great waiter and he recommended the fish tacos and chicken chipotle to us. Both dishes were very impressive-- we were so happy with the food. We also split the ceviche which was very good! The chips and salsa were also great. Great service and food and I would highly recommend. We took a taxi back to the riverwalk (~ 5-6 dollars) and then stopped at one of the Irish pubs for a post dinner drink. Overall, not a fan of the riverwalk at all, but would rather have just spend the weekend in Southtown or other neighborhoods.
I got up and used the fitness facility at the Embassy- it was nice, average sized fitness place. We skipped breakfast and walked to the Avis car rental place on Bohan to get our rental car (rented for the day through hotwire to drive us to Austin ~ 30 dollars with no additional fees for returning it to a different location- best deal I could find).
We got the car and then grabbed our bags at the Embassy and were off to Austin. On the way we stopped at Luling and Lockhard. Ate at City Market, Smittys and Krentz. At each place we got a sausage link (hot), 1/2 lb of ribs and 1/2 lb of brisket. City Market wins overall- best sausage and ribs, wasn't a fan of the brisket. Krentz came in a close second for ribs, but the brisket was the best here. I wasn't a huge fan of Smitty's food. It was fun stopping at each place, and we ate enough BBQ to last us for a long time. From Lockhard we drove to Austin and later that day dropped off the car off of 11th street at the Avis.
Hope this helps anyone looking to plan a trip who doesn't have kids and has a more "foodie" outlook on places to eat and drink. Overall, like I said earlier- we were happy with the trip. There are other things in the general area (Caverns and Winery regions) that you could do if you had a car the entire time. There are some great restaurants out there, but you have to make an effort to get to them (i.e. not on the riverwalk).