Ocean Beach, or OB, has the laid-back feel associated with the California hippie vibe that was once so popular many years ago. And, OB is one of the oldest beach towns in San Diego.
The OB pier, pictured here, was built in 1966 and at 1971 ft, is the longest concrete pier on the West Coast. (The longest pier on the West coast is in Santa Cruz.) There's a little cafe here where you can pick up a bite to eat. Or, hang out and watch the surfers. I've seen some incredible surfing here.
OB has the best dog beach in San Diego: http://www.oceanbeachsandiego.com/dog-beach-ob
Raglan has a great beer list, as well as food: http://www.raglanpublichouse.com/ The outdoor seating is fun for people watching.
Bo-Beau's is a fantastic restaurant with the ambiance of a cute little French farmhouse: http://www.cohnrestaurants.com/menu-restaurants/bo-beau/
The party at OB moves from the sand to the bars, so don't worry about dressing up! Pizza Port, a popular craft brewery based in Carlsbad, has opened a location here: http://www.tripadvisor.com/Restaurant_Review-g60750-d2371026-Reviews-Pizza_Port_Ocean_Beach-San_Diego_California.html