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

Point Of Interest

Santa Cruz Harbor

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

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!

Hotels

Chaminade Resort & Spa

1 Chaminade Ln, Santa Cruz, CA 95065

With a stay at Chaminade Resort & Spa in Santa Cruz, you'll be by the ocean and convenient to DeLaveaga Golf Course and Mystery Spot.

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.

Beaches

Pleasure Point

E Cliff Dr, Santa Cruz, CA 95062

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.

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Scenes from Live Oak/Pleasure Point
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