August in Maryland can be hot! The ceremony is outdoors from 5:30 - 6:00pm but it will likely still be warm. The reception will be air conditioned.
If you are flying in, we don't think you need a rental car. Downtown Annapolis is very walkable and Ubers are available as well. We will have transportation to and from the wedding and highly encourage using the shuttles as taxis and rideshare services are not typically available on Kent Island. Note that the hotels charge $25/day for parking.
While it is typically 20 minutes between Annapolis and Kent Island Resort, there will likely be Friday beach traffic and it may take up to an hour to get across the Chesapeake Bay Bridge. The provided shuttles will leave from the Graduate Hotel at 4:00 - 4:15pm to ensure on-time arrival. If you are driving yourself to the wedding, please keep traffic in mind. The venue has a waterfront bar and restaurant if you arrive early!