I've enjoyed Jimmy Buffet twice sitting on the hill at http://www.woodlandscenter.org/welcome.html which is located about 1 mile from our house. A fabulous concert and we sit on the hill of the amphitheater while enjoying some fine beverages, but we keep our tailgating down as we ride our bikes and don't want to get the dreaded BWI (biking while intoxicated).
I have seen him twice in the Washington, DC area and it it always a blast. Especially fun when tailgating with homemade sandboxes set up in the parking lot. A great island/beach atmosphere in the middle of suburbia!
Also shared an elevator with him in a Virginia Beach Marriott years ago.