From the '30s until the '50s the section of Santa Monica just south of where Wilshire Boulevard hits Pacific Coast Highway was known as Queer Alley. Today you'd never know that this primarily straight, white, and professional area was an early bastion of gay society, a land of bathhouses, cruising, and nude sunbathing. Just off the beach a huge gay bar, the Tropical Village, drew everybody from navy men to closeted celebrities to resident authors Christopher Isherwood and Stephen Spender. With encroaching gentrification and police crackdowns, the area lost much of its vogue among queers by the '60s.
Gay residents are still most definitely a presence in Santa Monica, but with nowhere near the presence they have in West Hollywood, Silver Lake, and some other parts of Los Angeles. This is still a quite welcoming, liberal community, though, and with a longstanding feminist scene, too. And with the influx in recent years of stellar restaurants and design-driven hotels, Santa Monica has steadily become a favorite gay getaway for couples, beachgoers, and those wanting a more relaxed Los Angeles vacation.
The Santa Monica Pier and the small stretch of Broadway a few blocks east are lined with arcades, gift shops, and colorful, if touristy, diversions. Despite the crowds and occasionally schlocky amusements, Santa Monica's pier and oceanfront make for a good stroll. There's an aquarium, carousel, arcade, and the Pacific Park Amusement Park, too. A fun bit of trivia: Historic Route 66 officially ends its 2,450-mile meander from Chicago right by the pier, at Lincoln and Olympic boulevards.
Near the beach, downtown Santa Monica abounds with lively dining and retail. The 3rd Street Promenade, a busy pedestrian mall south of Wilshire Boulevard, is worth checking out - it's home to the wonderful Santa Monica Farmers Market on Wednesday and Saturday mornings, as well as the swanky new Santa Monica Place shopping and retail center (anchored by Nordstrom and Bloomingdales) And along Montana Avenue, from about 7th to 20th streets, you'll find great, mostly reasonably priced boutiques, cafes, and coffeehouses.
Head south to near the Venice border, and you'll reach one of L.A's best neighborhoods for walking, Ocean Park. Along Main Street, from about Pico Boulevard south to Marine Street (at the Venice border), you'll find a quirky and inviting assortment of galleries, shops, restaurants, and coffeehouses. One highlight is architect Frank Gehry's Edgemar Center for the Arts, a stark geometric complex of cafes, shops, galleries, and courtyards.
Interior Santa Monica is mostly a bedroom suburb, worth investigating if only to visit the excellent Santa Monica Museum of Art, which presents rotating contemporary exhibits; and to check out Highways Performance Space, long associated with the outrageous Tim Miller, is one of the country's top venues for against-the-grain dance, theater, performance art, and comedy, much of it queer-produced.