Since you’re starting your trip on a Monday, you’ll miss the heavy weekend crowds, which is the absolute best way to see the Westside. Start your morning at Sidecar Doughnuts & Coffee on Wilshire. They make their doughnuts fresh every hour; if the "Huckleberry" is in season, grab it, but the "Butter & Salt" is the local cult favorite. It’s about a 15-minute walk or a 5-minute Uber down to the Santa Monica Pier from there. Get to the pier by 10:00 AM just as the gates open to beat the field trip rushes. Walk all the way to the end to watch the local fishermen, and if you're feeling nostalgic, take a spin on the solar-powered Ferris wheel for the best view of the coastline stretching toward Malibu.
Once you’ve had your fill of the Pier, head south down the Ocean Front Walk. This is a great stretch for people-watching. You’ll pass the original Muscle Beach (the rings and bars where the gymnasts play) and the South Beach Park area. Keep an eye out for the Chess Park, where you’ll see locals locked in intense matches. For lunch, you are heading to a true Santa Monica institution: Bay Cities Italian Deli & Bakery. Pro tip: don't wait in the long deli line if you just want the "Godmother" sandwich; they usually have them pre-made in the baskets by the bread. Grab a sandwich, some chips, and a San Pellegrino, and walk a few blocks back to the sand for a picnic.
After lunch, wander over to the Third Street Promenade. It’s a classic pedestrian mall, and while the shopping is great, the real draw is the street performers and the quirky Dinosaur Fountains that spray mist—perfect if the afternoon sun is getting warm. Finally, as the sun begins to dip, head to Elephante. You’ll need a reservation well in advance for this one because it's the buzziest rooftop in the city. The vibe is "Tulum meets the Mediterranean." Order the whipped eggplant and a spicy margarita, then just sit back and watch the sunset over the Pacific. It’s the quintessential "I’m in LA" moment to kick off your three-day coastal escape.
Since you’re already in the neighborhood, skip the hotel breakfast and head straight to Abbot Kinney Boulevard. Your first stop is Intelligentsia Coffee. It’s more of a "coffee laboratory" than a standard cafe; the tiered concrete seating and industrial vibe make it the ultimate spot to wake up. Order a pour-over or an oat milk latte—it’s a bit pricey at around $12 per person with a pastry, but the quality is unmatched. Once you have your caffeine fix, spend the next 90 minutes wandering Abbot Kinney Boulevard. This stretch is famous for a reason—it’s where high-end fashion meets Venice grit. Check out stores like Burro for quirky gifts or Aviator Nation for that quintessential California retro-surf look.
By late morning, escape the buzz of the shops and walk south toward the Venice Canals. This is my favorite "hidden" part of the neighborhood. Tucked between Venice Boulevard and 28th Avenue, these man-made waterways are lined with million-dollar architectural gems and charming wooden footbridges. It’s incredibly peaceful and offers a completely different perspective of Venice than what you see on TV. After a quiet loop around the water, head west for three blocks to hit the Venice Beach Boardwalk (Ocean Front Walk). This is where the energy shifts. You’ll see the legendary Venice Skate Park, the bodybuilders at Muscle Beach, and plenty of eccentric street performers. It’s loud, colorful, and a bit chaotic, but it’s the soul of the city.
For dinner, I’ve lined up a reservation at Gjelina. It’s notoriously hard to get into, so I hope you booked ahead (if not, try for a spot at the communal table). Their mushroom toast and thin-crust pizzas are legendary, but the roasted vegetable plates are the true stars here. Expect to spend about $60 per person for a shared feast. Finally, walk a few blocks back toward the sand to High Rooftop Lounge atop Hotel Erwin. It is the only rooftop bar in Venice, and on a Tuesday night, it’s the perfect place to watch the sun dip into the Pacific with a "Venice Vibe" cocktail in hand. It’ll run you about $30 for a couple of drinks, but those 360-degree views of the coastline are worth every penny.
Start your Wednesday tucked away in the lush Santa Monica Canyon at Tallula’s. This isn't your average breakfast spot; it’s a vibrant, colorful space that feels like a beach house. Order the Chilaquiles or their breakfast burrito—they use high-quality, seasonal ingredients that really set the tone for the day. Since it’s a weekday, you should be able to snag a table easily, but parking in the "Canyon" can be tight, so look for spots along Entrada Drive. From here, you’re just a five-minute drive up the Pacific Coast Highway (PCH) to one of the most stunning spots in California: The Getty Villa. Admission is free, but you must book a timed entry reservation in advance. Spend your morning wandering through the Outer Peristyle garden; the villa is a recreation of an ancient Roman house, and between the bronze statues and the view of the Pacific, you’ll forget you’re in Los Angeles.
After soaking up the antiquities, continue north for a few minutes to the Self-Realization Fellowship Lake Shrine. This is a true local secret—a ten-acre spiritual sanctuary centered around a spring-fed lake. It’s incredibly quiet, and walking the perimeter to see the Mahatma Gandhi World Peace Memorial is the perfect way to reset. Once you’ve found your zen, head up the hill into the heart of the "Palisades" to Palisades Village. This is Rick Caruso’s curated version of a town square; it’s very manicured and upscale. It’s the best spot in the area for window shopping or grabbing a quick snack at Erewhon or McConnell’s Fine Ice Creams while you people-watch—keep an eye out, as this is a major celebrity enclave.
Before the sun begins to dip, drive over to Temescal Canyon Park for a bit of movement. The Temescal Canyon Loop is a moderate hike that gets your heart rate up, but the payoff is massive. About halfway up, you’ll get a panoramic "top-of-the-world" view of the Santa Monica Bay and the coastline stretching toward Malibu. To wrap up your three-day getaway, skip the fancy white-tablecloth spots and head to The Reel Inn. It’s a legendary roadside fish shack right on the PCH. It’s walk-up counter service, totally unpretentious, and exactly what you want after a day outdoors. Grab a plate of fresh sea bass or fish tacos, find a picnic table on the patio, and toast to a perfect trip while you watch the traffic hum along the coast.