The ultimate Los Angeles weekend – with a wine country diversion
Follow this dynamic Los Angeles weekend itinerary packed with good art, good food and even better wine.
California makes my travel list every single year. With more land than some countries (Italy, Japan, New Zealand) and more possible itineraries than would fit into a lifetime of visits, I can always find reasons to go back, and back and back again. The nexus for me is Los Angeles, a rambling, sun-soaked big city that never feels intimidating or stale. Compare its rolling, mansion-crowned hills, its ever-changing roster of food trucks and glossy new restaurants, and its cliff-edged beaches to the gray streets of my New York City home and… well… the clichés nearly write themselves.
This trip was, for me, a mix of new experiences and beloved classics. I stayed at my favorite hotel on earth, found new things to explore in a well-worn beach neighborhood, and even fit in a quick road trip to wine country. No, not that wine country, but we’ll get into that in a minute.
Here’s what I saw over a perfect California long weekend.
- When to arrive: I prefer to arrive in the morning so I have enough time to do at least one afternoon activity in Los Angeles, plus have lunch and/or dinner. Flying from the Eastern time zones creates a perceived advantage in this respect: depart early and land when it’s still early.
- How to get from the airport: I called a rideshare from Los Angeles International Airport (LAX) after I landed. It’s easy and fast.
- Getting around town: I have leveraged both rental cars and rideshares in Los Angeles. Both work well, but you’ll need to have a sense of your itinerary and do some math to understand which one makes better financial sense. (Remember that renting a car creates the added headache and cost of parking.) For this trip, I used rideshares for the Los Angeles portion of my trip and then picked up a rental car to drive up to Paso Robles. I have occasionally used Los Angeles Metro Rail to get around the city, but have still needed a car or a rideshare to get everywhere I needed to go.
- Where to stay: In my heart, nothing will ever top the Sunset Tower Hotel, a chic West Hollywood icon that feels like it still lives and breathes its Old Hollywood history. My favorite spot here is, of course, by the pool. I also enjoyed the contemporary-cool Hoxton, Downtown LA, and, farther afield, the cheeky, affordable Hotel Maya in Long Beach. In Paso Robles, the River Lodge offers an unpretentious dose of midcentury-style design. This former roadside motel has gotten a significant contemporary upgrade.
- What to pack: For summer travel, keep your clothing options light and easily packable. And just because LA is a car city, that doesn’t mean you should forgo comfortable footwear. You can and certainly should do some on-foot neighborhood exploring, and the city offers great hikes. For winter months, bring a jacket and light layers. When I visited, I regretted not packing an umbrella as I happened to be there on the city's first night of rain in months. For all seasons, sunblock is a must.
Day 1: Los Angeles
Brunch at the beach
Venice Beach is LA’s longstanding capital of quirk. Shorthand in the 60s and 70s for hippies, surfers, counterculture and psychedelics, it’s distinctly more corporate these days but retains its free-wheeling feel. After dodging rollerbladers and skateboarders on the boardwalk, and making our way past a colorful Indian chariot festival, we had a late brunch at Great White. A friend and I sat on the outdoor terrace and shared their signature warm banana bread with whipped honeycomb butter. I moved on to the crispy chicken sandwich while my friend went for the blue smoothie bowl that included blue algae, a brightly hued protein source. Be sure to make reservations on weekends.
Note that Venice Beach is relatively close to LAX along a route that avoids a lot of the city’s most complicated traffic. If your luggage isn’t too much of an impediment, it’s not a bad place to stop before you check into your hotel.
Afternoon at the sauna
After brunch, we walked back to Abbot Kinney Boulevard, Venice Beach’s main street, which tends to be busy with pedestrians on weekends. Amidst a jumble of marquee name brands and small businesses, I stopped at a greenery-hung patio. Den Mother is a wellness center that offers massages and facials in a relaxing indoor/outdoor space that feels like it’s miles away from the street scene out front. Its specialty, however, is sauna and cold plunge treatments. I did a circuit (8 minutes in the sauna, 30 seconds in the cold plunge) in a dreamy private space with a two-person sauna, a cold plunge pool and a shower. A robe, filtered water and slippers are also provided. As a cold plunge newbie, I never made it longer than ten seconds in the chilly water, but still felt deeply energized and refreshed after. 
Ice cream before bed
En route to my hotel, we stopped at Awan in West Hollywood for vegan, gluten-free Indonesian ice cream made with coconut. Flavors include quince, spiced apple oat crumble and mango chamoy swirl.
Day 2: Los Angeles
A morning walk to a Hollywood landmark
In all the times I’d been to Los Angeles, I had never done the hike up to the Hollywood sign. It’s touristy, I figured. There’s not much to see, I reasoned. And then I actually took a tour. There are multiple routes to reach the sign; I opted for an ultra-easy one with Bikes and Hikes, a company that leads daily tours to it. In 90 minutes, I learned some fun Hollywood lore, got amazing views of the city and the famous sign, and snapped some holiday-card-worthy selfies. The route I took is almost completely flat and winds through a residential neighborhood in the Hollywood Hills. I barely broke a sweat and it easily fit into my morning schedule. Bikes and Hikes also hosts longer and more difficult hikes that take visitors closer and around the back of the sign. Maybe next time.
I spent the next few hours reading and having lunch by the pool at the hotel.
An afternoon surrounded by art
The Los Angeles County Museum of Art (LACMA) is a treasure. Even if you’ve visited before, there is always something new here. I spent a quiet afternoon wandering the galleries just a few hours before closing – a great time to lollygag in front of your favorite painting or sculpture without dodging the heads of other patrons. Don’t miss the ongoing Josiah McElheny exhibition, called Island Universe, which features enormous chandelier-like structures that explore the idea of the multiverse.
Unfussy Italian for dinner
For dinner we headed to a relatively new LA icon – the Fairfax location of Jon & Vinny’s, a contemporary take on an oldschool Italian red sauce restaurant and pizzeria. Portions are plentiful, the service and the dress code is casual and the booths and tables are often packed. Arrive early or make a reservation if you can. 
Day 3: Paso Robles
Mid-morning drive to the Central Coast
Having never explored between Los Angeles and San Francisco, I was excited to head to the Central Coast. Mid-morning, I rented a car and headed north along the Pacific Coast Highway. You can take this beautiful oceanside route or an almost equally dramatic, cacti-and-mountain-fringed inland route between Los Angeles and Paso Robles. I took one route there and the other route back. Both take about three-and-a-half hours. If you have time along the coastal route, stop for lunch in Santa Barbara or San Luis Obispo.
A high-energy dinner in town
I arrived in the early afternoon and spent some time in my lovely room at the River Lodge, a former roadside motel that’s been given a chic midcentury overhaul. (Thankfully, its enormous, fun-to-photograph neon sign remains.) Make time in your itinerary to stop by the pool, which is adults-only and guests-only and has its own cocktail bar. I, unfortunately, did not have time to do this because I spent the afternoon at a local auto mechanic dealing with a flat tire. Alas, road trips come with their risks.
After that (shoutout to the guys at Anthony’s Tire Store!) I was more than ready for dinner.
Fish Gaucho serves top-notch Mexican cuisine right in the center of Paso Robles’s compact, walkable downtown. Clearly a local favorite, the dining room was packed and alive with conversation. The specialties of the house are fresh fish and tequila, and while I skipped the tequila, the halibut tacos were a winner. 
See a wondrous after-dark light show
You can’t visit Paso Robles without going to Sensorio. More than 100,000 lights illuminate hillsides, twinkle from inside huge metal structures and bring life to human-size lanterns. This immersive art exhibit has been expanding ever since its 2019 debut. There are now six installations, including the most famous, Field of Light, which covers the rolling landscape in an endless-seeming wave of colored bulbs. Visit on Friday to Sunday nights in the winter months, and Thursday to Sunday in summer.
Day 4: Paso Robles
Spend a day at the wineries
Though they fly a bit under the radar compared to their formidable neighbors to the north – in Napa and Sonoma – the wineries of the Central Coast offer more affordable, equally excellent wines. There is also no shortage of scenery here either, with nearly 30 sq miles in the Paso Robles viticultural area dedicated to the growing of wine grapes. I stopped at two wineries; they could not have been more different in style and approach. But they illustrate the variety of wines and winery styles on offer here. I used affordable rideshares for my winery visits. Keep in mind that the spread-out nature of the area means that you might be waiting a few minutes for your car to arrive.
I started at Justin Vineyards & Winery. In addition to the sloping rows of vines and a serene tasting room and patio that overlooks them, the estate is also home to a Michelin-starred restaurant and an upscale inn. My visit lasted a few hours and I enjoyed a tasting, plus some excellent cheese and charcuterie from the restaurant. Justin is known for its Isosceles wine, a full-bodied blend of cabernet sauvignon, cabernet franc, and merlot.
For my second stop, I visited Alta Colina, a family-run winery specializing in syrah, Rhone blends and Rhone whites. Apart from its main tasting room, I also visited The Summit, a tasting platform built on a hill in the middle of the vineyard under the shade of an enormous tree. Between the views, the incredible wines (the whites were my favorites) and the hear-a-pin-drop quiet; it was such a memorable experience.
A quiet dinner before heading home
I had dinner at Parchetto, another spot downtown not far from Fish Gaucho. The bistro-style restaurant felt cozy and polished, and was the perfect way to end a day of wine tasting. Indulgent fare such as lamb shank, osso buco and steaks are the stars here, so bring your appetite. The wine list is nicely selected to go with the food and leans into French wines.
I headed home the next morning, driving my rental car from the River Lodge directly back to LAX. My parting thought was that I could have spent more time in Paso Robles. With more than 200 wineries in the area and more restaurants downtown to explore, this trip felt like a good introduction to a place that deserves repeat visits.
