Guide to Live Oak/Pleasure Point

Things to Do in Live Oak/Pleasure Point

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The swath of unincorporated suburbia between Santa Cruz and Capitola is known as Live Oak; near the ocean it’s called Pleasure Point; and in Santa Cruz Tribalese it’s pronounced “Eastside.”

Once scorned, formerly rural Live Oak is scrapping its way up the cool scale thanks to cute, affordable neighborhoods and a sense of self taking shape at 17th and Brommer (People’s Coffee rules).

Pleasure Point, though, will always outshine its inland sibling. A warren of wee beach bungalows peppered with mini-mansions, this neighborhood is steeped in surf culture (Jack O’Neill lives here) and claims one of the hands-down best shopping districts in the county.

At 41st Avenue and Portola is a funky district of sushi bars, coffeehouses, surf and skate shops and thrift stores with a sweet surf town vibe that does not stop.

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Restaurant Reservations

Popular Things to Do in Live Oak/Pleasure Point

American Restaurants

The Crow's Nest Restaurant

2218 E Cliff Drive, Santa Cruz, CA 95062

Perched at the mouth of the Santa Cruz Harbor, the Crow's Nest flaunts a view that dares to be outdone. Happy Hour at the Nest offers great deals on drinks and delicious appetizers. Live comedy on Sunday nights, Monday Night Football parties and live musi

Boating

Kayak Connection

413 Lake Ave., #3, Santa Cruz, CA 95062

Kayak Connection is your Sea Kayaking and Stand-Up Paddling resource for the Monterey Bay.  We have two locations in Santa Cruz and in Moss Landing at the Elkhorn Slough where we have multiple tours available for local adventures.

Entertainment

Chardonnay II

790 Mariner Park Way, Santa Cruz, CA 95062

Excursions aboard the Chardonnay II are perfect for any age group and fun for everyone from seasoned sailors to first-time adventures.

Bars

The Point Chophouse & Lounge

3326 Portola Dr, Santa Cruz, CA 95062

A Pleasure Point Tradition. Enjoy our delicious take on California comfort food, prime cuts, chops and cocktails.

Point Of Interest

Santa Cruz Harbor

American Restaurants

Shadowbrook Restaurant

1750 Wharf Rd, Capitola, CA 95010

Happy hour is short and sweet (Friday, 4-6pm) here at this decades-old Capitola institution, but it appears there's a happy crew here every night.

American Restaurants

Harbor Cafe

535 7th Ave, Santa Cruz, CA 95062

It's hard to beat a day in the sun, a delicious drink in hand and a wonderful meal. At Harbor Cafe we make sure that you have everything you need to feel right at home. Check out our doggy menu for your furry friend too!

Bars

Moe's Alley

1535 Commercial Way, Santa Cruz, CA 95063

That roadhouse you've been searching for. Blues, Reggae, Roots, Latin, Funk... a perpetual music fest for your groove. Every show at Moe's is a house party, come on home!

American Restaurants

Johnny's Harborside Restaurant

493 Lake Avenue, Santa Cruz, CA 95060

Enjoy fresh seafood in a casual atmosphere while soaking up the view of the Santa Cruz Yacht Harbor and Monterey Bay. Johnny’s Harborside specializes in fresh fish prepared just the way you like it.

Scenes from Live Oak/Pleasure Point
IMG_2523_Live Music at The ButteryFloating byHouse Wren (Troglodytes aedon)Coyote (Canis latrans)Pussy Riot at the Rio in Santa Cruzfun centertoot!santa cruz, caSanta Cruz BeachOld One: SailingOperation Surf Santa Cruz 2016House Finch (Haemorhous mexicanus)Santa Cruz sunsetBufflehead (Bucephala albeola)American Crow (Corvus brachyrhynchos)