La Jolla, California - This Southern California enclave may be known for its abundance of sea lions, but it played a pivotal role in the flight industry, too. Famous aviators, including Charles Lindbergh in 1930, had their first flights off the cliffs of Torrey Pines (which has great hiking views, BTW). And in the 1970s, the first hang gliders soared over the bluffs, eventually deeming it one of the most influential flying and development sites for foot-launched aviation.
Nowadays, you can try your hand at tandem paragliding or hang gliding via Torrey Pines Gliderport. Be flexible with your schedule, though: The company doesn't take reservations due to varying weather conditions, and flights are conducted on a first-come, first-serve basis. After you've soared through the sky, stay at Estancia La Jolla Hotel & Spa—it's right down the street from the Gliderport and has been around since the 1920s.