San Luis Obispo Vacation Itinerary



Small-town charms, abundant outdoor activities, rolling wine country, and beaches galore…San Luis Obispo naturally captures the California spirit. Grab your shades and head out for a wanderlust weekend.

Bishop Peak hike San Luis Obispo

Bag Bishop

There are nine rocky morros (aka: ancient volcanic mountains) in the San Luis Obispo region, and Bishop Peak is the tallest of them all. Accessed right from town just across from Cal Poly’s campus, the hike up to Bishop is a locals’ favorite. Start the 4.5-mile round-trip trek before noon (there’s no shade) and get a double dose of heart pumping excitement: hoofing up the trail you’ll pass rock-climbers taking on more dizzying routes with names like Civilized Evil. The final push to the summit requires some scrambling up granite boulders, but the effort culminates in an eruption of magnificent scenery: views span from SLO, all the morrows, and the Coast Range down to the ocean.

CAMP: Montaña de Oro State Park is your best camping option around San Luis Obispo. Make a reservation at one of the two environmental campsites (less than a .5-mile hike in): Badger Flat (Env. #3) or Deer Flat (Env. #4). Both are perched high up on a bluff overlooking the big blue Pacific.

B&B: With its cobblestoned courtyard, ambient French accordion music and bright-flowering window boxes, the Petit Soleil feels like a little bit of Europe blew in with the sea breeze. Relax with complimentary wine tasting at night and wake up to amaretto French toast in the morning. Absolument magnifique!

Directions to Bishop Peak: From downtown San Luis Obispo, head north on Santa Rosa St. (Hwy. 1). Turn left onto Highland Dr. and drive about 1 mile to the end of the road where the trail starts. Dog-friendly!

Kayak San Luis Obispo

Positively Rockin'!

"Awesome! Nice! Whoo-hoo!" This is the most common thing you'll hear on a morning sea kayak trip with SLO Coast Kayaks. The outfitter's owner and lead guide, Vincent Shay, loves what he does—and his enthusiasm is positively contagious. He's been kayaking for more than 20 years and now runs his own show. The Fossil Point Adventure Tour is one of the best and most exciting ways to really see the Central Coast. Suitable for beginners and experienced paddlers, this excursion has it all: sea caves, hidden pocket beaches, wildlife—and Vincent! After a briefing on kayaking basics, he'll have you weaving between the pillars under Avila Pier and building your confidence with every "awesome!", "nice!", and "whoo-hoo!" Adventurous types can kayak through sea caves and dart through sea arches, while those just out to enjoy the sights can take it easy cruising with the cormorants along the rocky coast. Stop for a beach snack at Pirate's Cove, then paddle back the way you came. Nice!

TIP: SLO Coast Kayaks shares a building with Portside Coffee and the Port Harford Chandlery & Pub. Enjoy illy coffee and locally brewed Firestone Walker DBA (having the beer post-kayak, that is).

SLO Coast Kayaks (805-704-6902). The Fossil Point Adventure Tour is $70 per person. Other tours are available. Kayaks and stand-up paddleboards are available for rent without a tour.

Edna Valley wineries San Luis Obispo

Garden of Edna

Spanish missionaries saw the potential for great wine in Edna Valley, just south of San Luis Obispo, and planted the first wine grapes back in the 19th century. Today, about a dozen, mostly mom-and-pop wineries charm the valley’s country backroads. Whet your palette with the white wines of Claiborne & Churchill; their Gewurztraminer is a favorite. Explore Chamisal Vineyards, the first commercial vineyard planted in Edna Valley. Their small modern tasting room suggests Napa's influence, and their stainless Chardonnay is a crisp and refreshing summer sipper.  Located in an old schoolhouse with two bocce courts out back, Baileyana is a good place to wind down the day (the Grand Firepeak Cuvee Pinot Noir makes a great bocce partner); their wines are Old World influenced, but their thinking is New School: they have more “Sustainable in Practice” certified acreage than any winery in the state.

The City of San Luis Obispo has an excellent map of the Edna Valley wineries. There is a tasting fee of $5 to $10 at the wineries listed above.

Yosemite, Live!

Everybody has a favorite outdoor music venue: the Greek, Red Rocks—how about Yosemite? Yep, California’s iconic national park is also home to the best music festival in the Sierra: The 4-day Strawberry Music Festival at Camp Mather is an unforgettable weekend of eclectic live music, outdoor activities and pure mountain magic. Sitting at 4,500 feet and spanning more than 350 acres of pine forest and meadows, the festival lets you divide your time between 21 acts on the main stage, going hiking, taking outdoor yoga classes, or splashing around the camp’s very own Birch Lake. This Memorial Day weekend marks Strawberry Music Festival’s 30th anniversary, and plans are in the works for one of the best lineups ever: Aaron Neville, Court Yard Hounds (featuring Martie Maguire and Emily Robison of The Dixie Chicks), The Sam Bush Band, The Tim O’Brien Band and plenty more. Head to the mountains for a holiday weekend packed with two of your passions: great music and the great outdoors. It’s Yosemite, live!

BONUS: The Memorial Day weekend Strawberry Music Festival will sell out! Get your tickets now!

Strawberry Music Festivals happen May 26-30 and September 1-5. It’s kid-friendly! Get your tickets to the Memorial Day weekend festival, the Labor Day weekend festival, or both by visiting

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