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With its three miles of sandy beach, dotted with palm trees on one side and lush mountains on another, the tiny city of Santa Monica – only 16 miles sq – is a quaint and chic beach town. The instantly recognizable pier marks the end of Route 66, and the spill-over from edgy Venice Beach to the south makes for a heady concoction of tourists, beach bums, and exhibitionists.

On any given day you could see tattooed scalps, monstrous muscles and retirees working on their career tans, amongst the omnipresent smell of weed. But despite pockets of eccentricity, Santa Monica is a smart and chic Los Angeles-adjacent beach town. It's here you'll find plenty of things to do, with trendy cafes for people watching, upscale boutiques for designer shopping, and some of the most expensive real estate in Los Angeles County. These are the top experiences in Santa Monica.

Head to McCabe's Guitar Shop for a night of live music

Hidden in the back of a musical instrument shop, this live venue rose to fame in the 1960s during the folk and blues revival. By day, ²Ñ³¦°ä²¹²ú±ð’s sells obscure instruments. By night, it turns into a intimate booze-free venue for 150 music aficionados. Legendary artists, from Joni Mitchell and John Lee Hooker to PJ Harvey, the Pixies, Tom Petty, and Elvis Costello, to name but a few, have performed unplugged sets here and modern greats continue to stop by.

Learn to trapeze on Santa Monica Pier

The historic pier is to Santa Monica what the Eiffel Tower is to Paris – overrun with tourists but no visit is complete without experiencing it. Built in 1909, the pier marks the last stop on Route 66. Incredibly, the 130ft high Pacific Wheel is the only one of its kind on a California pier. It's also the only solar-powered Ferris wheel in the world – take a spin for panoramic views of the city. Then, ride a rollercoaster, play carnival games, and get launched into the sky by an aerialist at an aerial workshop with the resident trapeze school .

Descend the steep Santa Monica Stairs

This not-so-secret pathway, in between multi-million-dollar houses on Adelaide Drive, plummets through the trees and lush mountains of Santa Monica Canyon via 170 steel and wooden stairs. Originally built in the 1920s, so local kids had a quicker route to school, the steps now attract fitness junkies, who come here to experience the sharp 110ft elevation change and climb the calf-pounding stairway to heart-rate heaven. Much to the dismay of the wealthy local residents, it has become a wildly popular challenge – around 1500 people workout on the narrow steel and wooden stairs every weekend.

Watch a cult movie at a vintage theater

The Aero has been showing movies since the 1940s on its single screen. Originally built by the Douglas Aircraft Company, the name being a nod to the aerospace industry, it still has many original art deco features – including the striking neon sign and single seat ticket office in the entrance hall. The movie house has featured in many films itself, including Donnie Darko (2001), Sleepwalkers (1992), and Get Shorty (1995). One of its biggest nights of the year is the annual Dusk-to-Dawn Horrorthon, which takes place around Halloween and screens back-to-back scary movies on 35mm film.

Stop for a work-out show on the real muscle beach

Although the one in Venice gets more attention, the original "muscle beach" – an outdoor gym with ropes, rings, and bars – actually opened in Santa Monica in 1934. Venice's version was named the "Weight Pen" before it adopted its "Muscle Beach Venice" moniker. Due to the busy public setting on Santa Monica Beach, with pier and ocean in the background, it's become more of a theater than a gym, with thousands of spectators stopping by each day to take pictures, as obliging resident beefcakes and gymnasts pose in between workouts.

Take a dip at the Annenberg Community Beach House

Originally a grandiose 1920s five-acre beach house built for legendary silent-era film actress Marion Davies, the Annenberg Community Beach House is now a pool and recreation center with beach views and all kinds of classes the public can sign up for. Beach volleyball, soccer and tennis, in addition, to stand-up paddle boarding and surf lessons, are all available. And, of course, don't miss taking a dip in the elaborately tiled swimming pool where Davies swam with the likes of Charlie Chaplin, Clark Gable, and Cary Grant. The adult sunset swims are a particular highlight.

Eat at Santa Monica's best retro restaurants

Near the end of America's most famous drive is – a suitably retro burger joint housed in a Googie-style building designed by prolific "modern" architects Armet and Davis. Inside is a step back in time – high chairs line the counter, patrons sip milkshakes at '60s-style leather booths and a jukebox plays timeless rock ‘n’ roll tunes. Meanwhile, two blocks from the beach, and kitsch in equal measure, is – believed to be the oldest restaurant in Santa Monica and one of the first in the state. Dressed with nautical junk, red fairy lights and props from the 1962 movie Mutiny on the Bounty, this was once a hangout spot for 1930s movie stars Carole Lombard, Charles Laughton, Errol Flynn, and Edward G Robinson. The seafood and steak are surprisingly good for such a kitschy spot.

People watch on Third Street Promenade

The tree-lined Third Street Promenade is a rare thing in Southern California – a half-mile-long pedestrian-only road. There are plenty of restaurants, bars, and stores to crawl, but the best way to soak up the atmosphere is to grab a table outside and catch one of the many live street performers, ranging from musicians and comedians to breakdancers and magicians.

Browse one man's life-long curios collection

Part museum, part curiosity shop, part prop rental company, jAdis houses one man's collection of "touches of mankind’s genius". Its doors open at certain times each week, so inquisitive folks can peruse flipbooks and plasma lights, vintage 1930s bathing suits and peculiar scientific instruments or whimsical steampunk contraptions. It also holds a replica of the robot from Fritz Lang’s 1927 film Metropolis.

Visit the Santa Monica Farmers Market

To meet the locals, head to one of the three weekly Santa Monica Farmers Markets, each attracting between 3000 and 10,000 visitors. Local producers and crafters tout their organic fruits, vegetables, flowers, baked goods, and seafood catches here. There's usually free live music to enjoy as you tuck into your bounty. Markets take place on Wednesday, Saturday and Sunday mornings.