"It was late summer and the weather was getting colder, the days shorter. We had all been cooped up inside all summer and decided it was time to get out. We got on the boat and saw nobody around. We went swimming for a while then headed to one of the many dockside restaurants and had a great meal and drinks. After tanning nude on the boat, we all jumped in and enjoyed the cooling waters of the bay on our skin. We saw only one other boat that day and they seemed more interested on what they were doing than the skinny dipping happening not far away. It was a great day!" - Bradford Mamalas
Go : Get on a boat just over the far side of the Chesapeake Bay Bridge on Kent Island in Maryland. It's only about 20 minutes east of Annapolis. Head south down the coast and in 10 minutes you'll find yourself alone in the beautiful clear waters of the Chesapeake Bay. Enjoy the day in your own private paradise.
Stay : Annapolis has plenty of places to stay from quaint B&Bs to more luxurious accommodations such as the Annapolis Waterfront Hotel or the Academy Bed and Breakfast. On Kent Island there are more "mom & pop" vacation rental homes which are suited for large groups of 8-10 people rather than chain locations, although you will also find B&B options near by your local Hilton or Holiday Inn.
Eat : I'd recommend down town Annapolis for some quality night life after spending all day Skinny Dipping on the bay. Plenty of local flavors. Try the Oyster Shooters at O'Brien's.
Drink : Annapolis has great drinking options to choose from such as the prohibition chic lounge and restaurant Dry 85, or the Metropolitan Kitchen and Lounge – an American eatery with local cuisine. If you stay around the bay for the evening and have the opportunity to cruise by boat, be sure to try one of the infamous themed dock bars such as the Tiki Barge or watch the sunset at Hemmingway’s restaurant on Kent Island.