San Simeon Midweek Itinerary

Ready for a break? San Simeon is perfect for a midweek getaway to relax and decompress without the crowds. Whether it’s a solo break, a couple’s trip, or an adventure with your bestie, we’ve built out a midweek itinerary to enjoy the best of San Simeon and the surrounding area. We’ve built this for late Sunday arrival through Thursday departure but it can be adjusted earlier or later in the week to best suit your schedule.

Day 1

Arrive later in the day and check in at Cavalier Oceanfront Resort right in the heart of San Simeon. With 90 spacious oceanfront rooms, the views here are gorgeous and peaceful. Take a break after the drive by exploring the beach with access directly from the resort before heading to dinner on-site. With Hearst Ranch steaks, ocean-fresh Pacific seafood, and a curated list of Central Coast wines, Cavalier’s Coastal Kitchen provides a delectable taste of fresh with beautiful views. After dinner, relax around the firepits with some wine to feel the cares of the world wash away.

Chairs overlooking the ocean at Cavalier Oceanfront Resort

Day 2

Plan to sleep in – this is a minivacation, after all! – and grab breakfast at Cavalier’s Coastal Kitchen before hitting the road to explore. Fuel up with decadent options like Baily’s French toast or huevos rancheros, or with a classic like avocado toast or yogurt parfait. After savoring breakfast, make a point to visit an elephant seal rookery! Friends of the Elephant Seal, located just steps from Cavalier, can help best direct based on the time of year but it’s hard to miss these massive sea mammals. Heading north on Highway 1, there’s a viewing point about 10 minutes away with well-marked signs and plenty of parking. Heading further north, take a drive along the dramatic and breathtaking Highway 1 to Ragged Point when you’re ready to explore beyond elephant seals. Simply put, there are few places in the world that are as gorgeous as this. Marvel at the wonders of rugged, craggy cliffs, soaring sea birds, and exotic black sand far down below. There’s a steep trail to Ragged Point Beach that changes 400 feet in only a half mile but is well worth the efforts because the only waterfall in the area can be seen here. Be sure to bring plenty of water because heading back up is a bit more challenging! All of that hiking will definitely work up an appetite, so reward the efforts with dinner in quaint Cambria just south of San Simeon. This tiny coastal village holds a range of fabulous options, from the innovative and gorgeous Robin’s to oceanfront Moonstone Bar & Grill. Take a stroll along Moonstone Beach after dinner to enjoy one of the most peaceful places around.

Day 3

No trip to San Simeon is complete without a visit to Hearst Castle! William Randolph Hearst’s architectural marvel holds an incredible array of museum-worth art and artifacts, as well as two magnificent pools. With a variety of tours available, it’s a pleasure to be able to explore the castle midweek with fewer visitors. After touring the Castle, head across Highway 1 to Sebastian's General Store. Newly renovated and re-opened, Sebastian’s has been a staple in San Simeon for over a century. Put together a picnic lunch to bring over to Hearst Winery set right above the beach to taste through delicious Central Coast wines. And since you’re already beachfront, pick up a bottle to enjoy with your picnic on the beach or at one of the tables by San Simeon Pier.

San Simeon Hearst Ranch Winery Wine Tasting

Day 4

Before heading out of town and back to reality, visit Piedras Blancas Light Station about 15 minutes north of Cavalier. Dating back to 1875, the Light Station was once crucial to the safety of the seafarers that helped build commerce and trade along the Central Coast. Today, the Light Station is a wildlife sanctuary and historical monument. Book a tour in advance to learn all about the Light Station, the grounds, and the lives of those who once lived there. If you’re heading south to go back home, stop off in Cambria to see the Light Station’s Fresnel Lens, now safely housed in a looming glass encasement.

Piedras Blancas Light Station