Nope! It is Navy/Air Force weekend so most of the Annapolis area hotels will be booked or have increased prices. With that being said you can definitely stay elsewhere and just uber/drive to the Graduate and utilize the shuttle arrangement.
Yes! Of course you can drive yourself. There will be plenty of parking next to the club house. The front gate guard will have a guest list.
Yes! Ubering to Gibson Island is convenient. However if you don’t pre-book transportation off the island they aren’t quite the best option to leave the festivities. Because of that we will have a big ole bus to that leaves at 11 to get everyone back to the Graduate (where uber/Lyft will be more reliable)
Anything cocktail! (Lilly Pulitzer of course is encouraged for guys and gals) Fun summery dresses, LBDs, seersucker, sport coats and colored chinos are also great options. There will be grass involved so wedges, block heels or flats are recommended.