Coming from the Beltway, we have always come down Connecticut Ave into the city. When I just Googled the route, it directed me down 16th Street. Considering that Connecticut Ave always seems so congested, would 16th Street be a better option. Coming in mid-day Friday.

First stop is Woodrow Wilson House. Is there parking on the street in that area?

Where on the beltway are you coming from? Usually you can find some parking somewhere in the neighborhood of the WW house.

16th Street is also quite busy. I don't see much advantage to it over Conn Ave.

Per the website, there is street parking but like most neighborhoods in DC it's going to be hit or miss. Have you considered talking the metro? It's not a bad walk from the Dupont Circle station.

Had considered the Metro, but think we'll be arriving around noon, which is too early to check into hotel first. Since we'll be coming down 95 to the Beltway, thought we may just stop there on our way in.

Would your hotel hold your luggage until check in time?
Last time DW and I went into the city we parked at the Greenbelt station (end of the Green line).
We didn't have the problem of having to find a parking spot.

Most hotels allow you to leave your bags and park your car prior to check-in time. I would certainly try to do that and then take Metro to get over to the Woodrow Wilson House (and elsewhere).

YOu can't predict which might be better, I'd say a toss up. Why are you driving into the middle of Washington, anyway? Getting from 16th over to that location is a bit of a mess, guess you'd take Columbia Rd. I'd probably just take Connecticut.

Any hotel will keep your luggage for you if that's the issue, that's what they have to do for anyone who may fly in and arrive early, it's typical.

There is some street parking around there with local restrictions (2 hr limit, which should be okay). Whether there will actually be a free space is another question, who knows. Although there probably would be some space on the street in the surrounding neighborhoods within 4-5 blocks, I imagine, if not right near it. I know there is on 24th St which isn't too far away to the west as I park on it a lot when visiting someone in the neighborhood a few blocks north of WW house.