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2-Day Santa Monica Weekend Itinerary — December 19–20, 2025

Day 1 · Fri, Dec 19
Santa Monica

Explore Santa Monica Pier and Beachfront

Morning:

Start your day with a stroll along the Santa Monica Beach path, renting a bike from Wheel Fun Rentals to ride north past sunlit dunes and ocean views, then stop at Back on the Beach cafe for a hearty seaside breakfast and coffee. Afterward, head to the Annenberg Community Beach House to explore the historic Marion Davies Guest House, lounge by the pool, and try a guided tidepool walk if available — a relaxing, scenic introduction to Santa Monica before the pier crowds arrive.

Afternoon:

After a relaxed morning by the water, cross to Main Street and wander the charming shops and galleries of Santa Monica’s Third Street Promenade, popping into independent boutiques like Janie’s for coastal gifts and Kopper’s for curated home goods. Mid-afternoon, head to Tongva Park for a peaceful shaded walk and then grab a craft iced tea or small plates at Blue Daisy Café before continuing toward the Pier for evening festivities.

Evening:

As dusk falls, wander down to the Annenberg Park Lawn for a sunset picnic with provisions from The Misfit’s deli counter, then stroll along Ocean Avenue to the small but atmospheric Camera Obscura at the Ocean Park branch for an old-world view of the coastline. Finish with live music and housemade cocktails at Harvelle’s Blues Club or a relaxed wine flight at The Bungalow Santa Monica’s lounge — both cozy options to cap a seaside day.

Day 2 · Sat, Dec 20
Santa Monica

Local Culture, Shopping, and Sunset Views

Morning:

Begin with a spirited brunch at Huckleberry Bakery & Café, savoring seasonal pastries and farm-to-table plates before wandering the adjacent Montana Avenue boutiques—think Dune Jewelry for coastal mementos and Picnic for chic home finds. After shopping, take a short ride to the Broad Stage for a mid-morning arts visit (check for a matinée or gallery pop-up), then relax with a coffee at Demitasse to plan the afternoon’s cultural strolls through the neighborhood.

Afternoon:

Spend a leisurely afternoon exploring Bergamot Station’s cluster of contemporary galleries and pop-in workshops — catch a rotating exhibit at Bergamot Projects and enjoy a late-lunch small-plates board at The Hive across the street. Afterward, stroll the nearby Montana Avenue side streets for curated vintage at Playclothes or modern womenswear at GRACE — finish with a ritual stop at Fig & Olive for a light dessert and espresso before heading toward Palisades Park for the evening view.

Evening:

As golden hour approaches, head to the Palisades Bluff to watch the sun dip behind the Pacific, then stroll down to The Lobster for a classic seaside dinner with views of the pier. Afterward, explore Main Street’s evening energy with a stop at The Victorian for craft cocktails and live jazz or catch an indie film screening at Aero Theatre to round out a cultured Santa Monica night.

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