I CAME TO this city in the early months of 2003 on a whim. I was vagabonding across the country and met a woman at the Sundance Film Festival in Park City, Utah who offered me a job in Laguna Beach. After the festival was over, I drove in a general southwesterly direction until I saw the ocean.
I have lived in the town ever since (interrupted by a few long stints abroad).   
As a result, I know Laguna Beach. I know the shops, the restaurants, and the bars. I know the beaches, the trails, and the hidden surf breaks. Most of all, I know the people – kind, generous, outdoor loving, and aggravated by traffic (yet another reason to utilize the free trolley). 
I kept each of these factors in mind when designing my dream itinerary for 36-hours in town. Here it is! 
9:00am-11:00am: Arrive. Settle into your hotel and walk down to the Main Beach Boardwalk. There’s just no better way to start to feel out the town’s vibe. Join a volleyball or basketball game if you’re so inclined. See if you can spot a few of the town’s many public art installations. 
11:00am-12:00pm: Walk south to Thalia Street beach. If there are waves, you’ll see surfers at Thalia. If not, you might see some of the town’s famous skimboarders shredding along the shoreline. 
12:00pm-1:30pm: Leave the sand and head to Sapphire Laguna. The deck at this beloved restaurant looks out over PCH. More notably, the restaurant shares a corner with Michael Minutoli – the city’s “new greeter” who welcomes people to town with a wave and a few slick dance moves. While you wait for lunch to arrive, ask your server for the local only snacks that don’t appear on the menu. You’ll be glad you did. 
Sapphire Laguna 
1:30pm-4:00pm: Head further south for nine holes at Ben Brown’s Golf Course at The Ranch at Laguna Beach. What better way to introduce yourself to the secluded canyon scenery than by playing a round of golf? There’s only one way to improve upon this cruise-y experience and that’s by going “full Laguna” and playing barefoot. 
The Ranch Laguna Beach
4:00pm-6:00pm: Cross the street to the Montage Laguna Beach and take in the perfectly manicured grounds. Towards the north end of the property, go down the stairs to Treasure Island Beach Park. If you’re feeling adventurous climb over the rocks at the south end of the beach and explore the hidden spit of parched white sand there. If you’ve been holding out for your first Laguna Beach swim, take it here – where the water is calm and brilliantly cobalt. 
Treasure Island Beach Park 
6:00pm-8:30pm: In Laguna Beach, sunset viewing and dinner merge seamlessly into one another – with no shortage of restaurants that practically put “watching the day fade” on the menu. The Deck on Laguna Beach is ideal. Buy a “So-Cal Mule” or a “California Cooler” and toast the day you’ve had, then meander upstairs to Driftwood Kitchen where the fish-heavy menu is light and stylized. If you’re still in the mood for a cocktail, try the “Laguna Mule” and learn some of the rich history behind Driftwood’s bar. 
The Deck Laguna Beach 
8:30-9:45pm: In Laguna Beach dessert is most typically consumed on foot. Visit Peppertree Lane for gelato from Gelato Paradiso or walk a few blocks north to Dolce Gelato (where spectacular new flavors are invented on-site daily). Once you have a cone in hand, the most Laguna thing to do is stroll through town window shopping, listening to street musicians, and – between songs – admiring the sounds of the crashing waves across the street. 
Gelato Laguna Beach 
9:45-Late Night: Live music abounds in Laguna Beach and there’s no shortage of night spots. It’s really about defining your tastes and picking a heading. One local favorite is the dance club at Brussels Bistro, which doesn’t come alive until about this hour. The experience feels very Euro, but it’s favored by young, hip locals. The DJs spin EDM until the wee hours. When you finally spill out of Brussels it still might be warm enough for a stroll – those are the little pleasures of a city this safe. 
Brussels Bistro  
8:00am-10:00am: Forgo breakfast for a freshly roasted coffee at Laguna Coffee Co. then head to CA Surf ‘N Paddle for a standup paddle lesson. Standup paddle may be most closely associated with Hawaii, but Laguna runs a close second. There’s really no better way to understand the city’s unique, terraced geography than to take it in from the sea. Chat with your instructor about their favorite Laguna Beach secrets – perhaps you’ll score some advice worth chasing. 
Paddle boarding 
10:00am-12:00pm: Now it’s time for breakfast (sure, call it brunch) at Las Brisas overlooking Heisler Park. This is one spot that is on equal footing with tourists and locals alike – with good reason. The brunch is bountiful and the egg dishes are fun and inventive. Go ahead and tip back a mimosa too. You’ve earned it. 
las brisas 
12:00pm-1:00pm: It’s hard not to walk along the grassy bluffs of Heisler Park and just let the hours slip away. It’s just so beautiful and calming. This really may be the most tranquil place in town, it’s almost mystical how that spirit takes hold. Wander, watch the Plein Air painters, read under a tree, admire the public art (there’s LOTS of it), and ruminate on the undeniable value of a leisurely stroll. 
Plein air painters 

1:00pm-4:00pm: Now that you’re blissed out, head back downtown for some shopping. The city is peppered with unique boutiques in which the clothes on the rack feel carefully curated by the owners of each particular shop. The pervasive style could be described as Bohemian-beachy and its fun to see how each different shop spins and remixes that idea. 

4:00pm-6:30pm: Here your options diverge (like two roads in a yellow wood) – the canyon or the beach? Laguna’s famed canyons are absolutely spectacular and a hike never fails to invigorate the spirit. In the winter the canyons feel like Hawaii, in the summer they feel like Sicily. Still, this correspondent will never pass up one last swim. My choice is Crescent Bay, where the sandstone cliffs surround a stunning wedge of sand and you can see all the way to Catalina Island. Watch the sunset from the water.
Laguna Canyon 
6:30pm-9:00pm: Say goodbye to Laguna Beach in style with dinner at Broadway by Amar Santana. The chef’s plates are stylish and well balanced and the presentation is nothing short of artful – Oh no! We never made it to a Sawdust Studio Art Class at the Sawdust Art Festival! And hiking the canyons, that sounded fun! And we went 36 hours without a fish taco?
Studio Art Class, Sawdust Art 
Well, if ever there was a “Laguna Beach experience” maybe it is found in the singular moment in which you realize that there’s still more to see and you’ll just have to plan a return trip.