Ventura is a place we love to go regularly; most especially main street. There's a lot of restaurants and thrift shopping, and if you've got enough time, you an also head to the beach to watch the sunset! Main street is also close to multiple parks and the Ventura Botanical Gardens.
An upscale, beach town along the coast. The canyons across from Malibu have many hiking opportunities and the Malibu beaches are extremely popular areas. Matt also went to school at Pepperdine, which can also be seen along the coast. There are also great restaurants along the PCH, including Nobu, Ollo, Bui Sushi, Paradise Cove, Lily's, and Country Kitchen. Popular beaches include Point Dume, Zuma Beach, and El Matador State Beach. Also in the canyon, you can visit the Calamitous Ranch cafe and the Malibu Wine Safari.
Take a drive down Topanga Canyon Road where you'll end up finding many unique shops and restaurants in the mountains, including Hidden Treasures, Topanga Homegrown, and Inn of the Seventh Ray. Driving through the canyon, you will also find an outdoor Shakespearean Theatre called Theatricum Botanicum if that's your cup of tea.
Take a walk down 3rd Street Promenade and enjoy more food and shopping. You can also go with family to the pier where Santa Monica has it's own carnival complete with games, a ferris wheel, and even a roller coaster. The Promenade also has a few clubs and bars that you can enjoy during the evening.
The heart of LA. You can do mostly anything you can think of. You can find rooftop arcades, themed sections of town, large theaters and museums, and of course, a lot of food and shopping. Some recommendations would be the Pantages Theatre, Little Tokyo, and Sawtelle Blvd.