Just for a get away, after school starts so not crowded. Not family, just me for a couple of days, but something nice. It's been many years since I've been there but there has to be some decent areas. Also good eateries!

For Food - skip Gaido's. It has the reputation for being the best, but has really gone down. A better bet is Rudy and Paco's downtown. Corner of Post Office (I think) and something - next to the old theater. Dinner reservations required and they have a dress code.

The Stork Club across the street is a good place for drinks and diner type food.

Any major chain hotel on the Seawall should be okay - Galvez and San Luis are high end and expensive. We've stayed at LaQuinta and it's okay. The Commodore is also okay, but nothing fancy - it's clean and fairly quiet and has a really nice pool, but is basic.

Galvez = for sure

Your post reminded me of how much I missed Hotel Galvez...so I came down for the evening & checked in. I must tell you the following:
*staff so friendly & amazing
*pool & pool bar = so relaxing
*right across the street from pleasure pier
*breakfast buffet = top notch
You are truly missing out if you don't make reservations here!
Leslie2002

Have spent a lot of time on the Island over the past few years for business. I would support that Galvez is probably the best all around for going down and enjoying a few days on the beach in a nice hotel. San Luis is fine and they are working on the rooms, but for me its more of a cluster to get in and out of.

They Hilton has supposed redone some rooms but I find it to be a rode hard hotel. Courtyard is fairly new but it already has been well abused by the beach crowds. If you want to be down by the Strand, Tremont House is a sister hotel of the Galvez with similar feel in the rooms along with good bar and breakfast.

My grandparents honeymooned at the Galvez in 1928. It's a very cool place. I'll 2nd the Tremont. It has an awesome old bar. Both, of course, are haunted