We took a family mini vacation a few days before and went to DC and local area and just hung out with each other, so worth it. (Didn't get a family vacation because DS graduated and had to be at USNA in two weeks time) Coming from the west coast I also wanted DS to acclimate to time zone and weather too.Whatever feels right for you and a fun pre-PS mental break for your plebe-to-be.
Some make it a mini-vacation, do the M&M (monuments and museums) stops in DC with a few days in DC, go down to Mt. Vernon for the day, rent bicycles and do the various Potomac River bike paths, visit the National Aquarium and Ft. McHenry in Baltimore, go to a Nationals or Orioles game, head over to the Eastern Shore beaches in DE or MD (my fave: Cape Henlopen, use the “borrow a bike” program and do various park loops, https://destateparks.com/Adventures/Beaches) or the more boardwalk type experience at DE/MD beaches in Ocean City, Rehoboth, Bethany, etc. Eat beach boardwalk food! People-watch! Be far away from the Yard!
Allow a day to wander DTA (downtown Annapolis) on foot and get oriented to the historic downtown area and outlying shopping/dining/hotel clusters.
Bonus points if you find/visit:
Naval Bagels
The Amish Market (Pennsylvania Dutch cooperative market)
Chick ‘n’ Ruth’s Deli
Kilwin’s
Double-T Diner
Iron Rooster
(random cherry-picking of Annapolis favorite places, for residents, mids, families)
Triple bonus: You may need to know this sometime during your 4-year run as a parent, the tiny but well-stocked package store tucked into the back corner of the Walgreen’s on Taylor Ave, no signage out front, same strip mall as Naval Bagels, in the Navy Stadium area.
We stayed right across gate one so walking back and forth was totally doable. (Our I-day to oath was over two days).
Grandparents came PPW and that was nice.
Every family is different but whatever you think you and your family would enjoy the most because once they poof and get sucked inside the vortex.... game changes immediately!