Your Perfect Three-Day Itinerary on The San Francisco Peninsula

Start your first day on the Peninsula exploring a couple of cities along the San Francisco Bay. Located in the heart of the Peninsula, just south of San Francisco, Burlingame is a quaint town with stunning waterfront hotels and beautiful bayside walking trails. In downtown Burlingame, you’ll find local shops and retail stores, amazing restaurants, and cafes. A must-visit store is Del’Oliva. Come ready to try different olive oils and vinegar and learn a whole lot that you never knew before.

Almost all of the local hotels sit right on the San Francisco Bay Trail that wraps 500 miles around the Bay Area. With walking and biking paths, bird and wildlife watching, and natural preserves dedicated to restoring the local wetlands, all visitors should make the Bay Trail part of their stay in Burlingame.

If you love seafood, Bayfront Park is within walking distance from New England Lobster Market & Eatery. This delicious local venue offers comfortable outdoor and indoor dining, spectacular food, and fresh seafood to-go. Do not leave Burlingame without trying a cup (or bowl) of their Lobster Corn Chowder!

When visiting the San Francisco Peninsula, make sure you carve out time to spend a day in the central tech hub, the City of San Mateo! San Mateo is a thriving community with a charming downtown area filled with amazing restaurants and the upscale, state-of-the-art Hillsdale Shopping Center.

Be sure to also save time to visit the Japanese Garden located inside Central Park in downtown San Mateo. Here you can see Koi feedings during the spring and summer months. Inside Central Park, there is a Mini Train for children that typically runs year-round on weekends from 11:00 a.m. to 3:00 p.m., and additionally on weekdays between June 15 and August 15 from 11:00 a.m. to 3:00 p.m.

Nestled between the Pacific Ocean and San Francisco Bay, Woodside is known for its beautiful preserves and biking routes. Start your morning at the historic Filoli estate. Plan to spend at least a couple of hours strolling through the gardens, touring the 54,256-square-foot historic home, walking the self-guided estate trail, dining at the Quail Café, and shopping for garden-inspired gifts in the Clock Tower Shop. 

After a morning at Filoli, head to one of several iconic restaurants in the area. Alice’s Restaurant is a local favorite and a popular spot for motorcyclists who like to drive down scenic Highway 84.

In the afternoon, head to Stanford University and wander around the beautiful campus. For art lovers, the Cantor Arts Center is a great cultural experience. The collection spans 5,000 years and features more than 38,000 works of art from around the world, including rotating exhibitions. While you’re there, we recommend stopping by Stanford’s Arizona Cactus Garden, which is especially stunning during golden hour. For a unique dining experience, check out one of several Michelin-rated restaurants in the area.

Head west toward the Pacific Ocean along Highway 92 and make your way toward Highway 1, also known as the Pacific Coast Highway. Arguably the most scenic drive in the United States, there are coastal bluffs, stunning beaches, and fresh seafood restaurants all the way along the coast. The stretch of Highway 1 down the Peninsula offers some of the best beaches and hidden gems in the Bay Area.

Make your first stop in the charming coastal city of Half Moon Bay, where you can try the seasonal catch at restaurants near Pillar Point Harbor. Shop around Main Street in downtown Half Moon Bay for unique clothing, art, gifts, and home goods. You can also purchase locally crafted spirits at one of two woman-owned distilleries, Half Moon Bay Distillery and Jettywave Distillery.

After lunch, head to Half Moon Bay State Beach and explore the Visitors Center to learn more about the history of the area. Located right off of Highway 1, this area is made up of four small beaches that form a two-mile curve of fine, white sand and relaxing coves. The waves here make for a great surfing spot!

After visiting Half Moon Bay, head up north to the city of Pacifica. Be sure to save time to explore Devil's Slide Trail for one of the most breathtaking lookout points in the area. For dinner, visit Nick’s Seafood Restaurant for a fresh meal, live music, and dancing on Fridays and Saturdays.

Or if you’d prefer, you can travel down to Pescadero State Beach and see the iconic Pigeon Point Lighthouse, which is a beautiful lighthouse that has been in operation since 1872. Spend a night under the stars at Costanoa Lodge+Camp+Resort and enjoy a unique glamping experience with several outdoor activities at your fingertips.