Trusted Guide to Highway 101

If you haven’t crossed a cruise up (or down) Highway 101 off your bucket list it’s a must. Good news, we’ve got you covered on all the must sees in San Diego, San Francisco, and everywhere in between. Lucky for you, it’s nearly impossible to make a bad stop along the way!

>San Diego 

Even though just one sunset viewing might suffice, San Diego has so much more to offer. One day in this surfer bustling, fish taco lovin’ town might not be enough to cover it all. Leave it to our Trusted Guide to San Diego to help you plan your itinerary from start to finish. 

San Diego > Encinitas (35 minutes)

Haven’t had enough of the beach scene or wanting some healthy grub? Make a pit stop in Encinitas and visit the numerous beaches, the Self-Realization Meditation Gardens, grab a smoothie at Eve Encinitas, or stop at Goodonya Organic on Mainstreet for a killer turkey sandwich or avocado toast.

Encinitas > Venice Beach (2 hours)

You’ll drive right through Huntington Beach on your way to LA. Don’t let the infamous LA traffic deter you from making a stop in Venice Beach, the neighboring hood to Santa Monica. Take a stroll down the ever-so Intsagramable Abbott Kinney Street and then make your way to the Santa Monica Pier for a ride on the ferris wheel. Last but not least, hike the Hollywood Sign!

Venice Beach > Malibu (40 minutes)

Park along the road to watch the surfers or enjoy a farm-to-table lunch on the water at Malibu Farms.  Needing a refreshment? Pack your cheese and crackers and picnic at Malibu Wines or schedule a safari tour through the vineyard lined hills of Malibu. For more LA recs you can check out our Trusted Guide to Los Angeles.

Malibu > Santa Barbara (1 hr, 20 minutes)

SB, where the beaches are b-e-a-utiful and the food and wine scene is hard to beat. Be sure to take a stroll down the shop-lined State Street to Stearn’s Wharf. There are lively restaurants and bars on every corner and you can’t go wrong. Some faves? For good pizza (and coffee) check out Lucky Penny or Test Pilot for funky vibes and tiki cocktails.

Santa Barbara > San Luis Obispo (1 hr, 45 minutes)

For one last coastal stop before you head inland stop in Pismo Beach to walk the pier or grab a bite with a view at The Cliffs Hotel. Rumor has it San Luis Obispo, or SLO as they call it, is the happiest town in America. Home to Cal Poly, this University town is bustling with cute shops, restaurants and smiling locals. Oh, and while you’re there, see if you can find Bubblegum Alley!

San Luis Obispo > Big Sur (3 hours)

Big Sur is one of the most iconic parts of the West Coast. And for road trip purposes, the most self explanatory- just drive! It’s hard not to pull over at every viewpoint to take in the incredible views (*selfie sticks are encouraged). If you’re looking for a restaurant stop at Nepenthe to grab a bite alongside some breathtaking views.

Big Sur > Carmel-by-the-Sea/Monterey (1 hour)
There is a whole lot to do between Big Sur and Monterey, including the notorious 17 mile drive. For aneasy hike you can check out Point Lobos Natural Reserve Park as you leave Big Sur and head towards Carmel. Take walk down Ocean Ave in Carmel until you hit the grandiose white beach. Warning, dolphin sitings are more common than not. Take the (well worth it) 17 mile route from Pebble Beach towards Monterey, another quant sea-side town. Visit the Monterey Bay Aquarium or rent bikes and ride along the bay!

Monterey > San Francisco (2 hr, 30 minutes)

The last leg, and the beauty ain’t over yet! Stop in Half Moon Bay for a hike along the coast, horseback riding or a beer at the Half Moon Bay Brewing Company. Once you hit SF you have a whole new world of exploring to do! Leave it to the Trusted Guide to San Francisco to help you there 😉

Tip for accommodations:

  • VRBO or Airbnb are often the easiest and most affordable option. Be sure to ask the owner for a list of their favorite locals spots and activities
  • Bed and Breakfasts
  • Hotel Tonight is an app for cheaper rates when same-day booking

Chelsea Rolfes
Chelsea, an Ohio native, is a Medical-Surgical nurse who began her nursing career in Chicago and soon after became a travel nurse. Chelsea’s zest for life and adventure has brought her to Seattle, Denver, San Diego, San Francisco and Austin. She has developed a true passion for health and wellness and aims to be an inspiration for those around her. She uses her Instagram account, @healthy_withchelsea, as a platform to showcase her recipes, food photography, and her active, healthy lifestyle from city to city. She can’t wait to see where her enthusiasm for living a happy, healthy life will take her in the future!