They are both great schools. I attended GDS through high school and had several close friends who attended Sidwell -- we all went to great undergrad and grad schools and are doing fine. We were able to reap the most important benefit a good education provides: choices.
FWIW, GDS has less of a campus vibe than Sidwell. It's pretty much a large building in the city with a field attached. Alumni emails tell me they're going to be expanding in the future, taking over a Safeway and a Volvo dealership in the area and moving the lower school over, so they may soon have more of a campus feel. At the high school, they allow the students to come and go whenever they want and they trust that they will be on time for class when it starts. I don't think my friends at Sidwell had that luxury. This is the reason the Obamas and the Clintons sent their kids there. My friend at Sidwell (who was a classmate of Chelsea) said the Clintons considered GDS, but that secret service security would have been pretty much impossible given its location, layout and come-and-go policy.
This translates into other areas too... there's not a lot of hand holding with coursework at GDS. You're expected to get things done by the deadline and if it's not done you're going to be held accountable. I thought the sports were stronger at Sidwell and the arts were stronger at GDS. GDS facilities seemed nicer/newer in my opinion. Overall, I had great teachers and one or two that could have been better. That's everywhere. Both schools are liberal, but that's DC.
Sometimes it's hard to keep kids grounded so I think it's important to note that I never thought I was "better" than anyone else. Might have been my parents influence too. No one told me I was attending (arguably) the best school in the area. And one more thing: I think it's important that a school offer substantial financial aid, so that's something to look for. I know GDS did, not sure about Sidwell, but it would be easy to find out. Why? Because you're going to get more diversity in the student body. Not race, but SES. I had no idea my best friend was an FA recipient (and they are lucky to call her an alumna now), but it was an eye-opening experience to spend time at her house and have exposure to how families from other economic backgrounds lived. Private school kids can miss out on that otherwise. So, while I was at a great school, I wasn't in a bubble.
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