"The historic Watergate Hotel boasts perhaps one of the most recognizable rooftops in the District. Starting at 5 p.m., saddle up to the bar or rent a cabana while taking in breathtaking views of the Washington Monument, Potomac River, the Kennedy Center, and more. FYI: Reservations for Fridays and Saturdays require a minimum food and beverage spend of $75 per person." - Tierney Plumb