The Best of the Bay Area in 5 Days

This day centers around hitting the main tourist spots in the city so you can focus the remaining days on diving deeper into all the city and surrounding areas have to offer. Start your day by visiting Pier 39 to view the infamous sea lions, but don't plan to spend much time there or at Fisherman's Wharf because they're both tourist traps. Take a mid-morning trip to explore Alcatraz—the views from the ferry are amazing, and the old prison is worth visiting. However, you'll want to book your tickets months in advance!

After you return, visit Cioppino's or Scoma's for lunch to try famous SF cioppino, clam chowder in a bread bowl, or other fresh seafood. After lunch, you'll want to move your body. Head to Coit tower for awesome city views. In the late afternoon, visit the Exploratorium along the Embarcadero for a fun, hands-on science museum that kids and adults will love (fun fact: I had my senior prom here!).

End your day with either a casual dinner at Gott's—the Bay's best fast-casual spot—or a nicer sit-down meal at La Mar for waterfront Peruvian food. If you still have energy after all this, visit the Tonga Room for tiki cocktails and oftentimes live music, or head to the Marina for a night out, starting at Balboa Cafe for their famous espresso martinis.

Now that the touristy stuff is (mostly) out of the way, explore the parts of SF that I loved most while living there. Head west to the Richmond and start your day with coffee at Andytown and breakfast sandwiches at Devil's Teeth (get there early to avoid a line), then go nearby to Land's End for a morning hike that takes you to the Sutro Baths and ends along Ocean Beach.

After all that walking, you'll be hungry, so enjoy a lunch of fresh poke and fish tacos at Hookfish. In the afternoon, it's time to explore Golden Gate Park! Grab a Lyft bike to explore different corners of the park, with options including having a picnic outside the Conservatory of Flowers, visiting the Academy of Sciences, or exploring the DeYoung museum.

For dinner, head south of the park for the best chicken wings in the city at San Tung, or, if a nicer dinner is appealing, head back east a bit and have dinner at the one-and-only House of Prime Rib—just make sure you book as far out as possible. If you are in the mood for after-dinner drinks and are already at House of Prime Rib, explore the bars on Polk Street or head to North Beach for a fun night out.

While much of the touristy city is far north of Market, there's so much to do on the other side! Start your day at Tartine Manufactory in the Mission for great pastries and breakfast. If you're in a shopping mood, explore the Heath Ceramics studio next door for incredible kitchenware. Then, explore the shops on Valencia Street, or, if you're feeling more adventurous, hike up Twin Peaks for great views.

Once you've built up an appetite, get burritos from La Taqueria (don't forget to ask for them "Dorado style") and bring them to Dolores Park, where you'll get a sense of the huge "park culture" in SF. Stop at Bi-Rite grocery on the way for some wine, beer, or whatever libations you choose. Enjoy the sunniest part of the city until it's time for ice cream at either Bi-Rite or Garden Creamery. Depending on how long you enjoy the park, head inside to MOMA for modern art or take some time to freshen up. Then, it's time for dinner: head to NoPa for classic American fare with a California twist, Rich Table for higher-end farm-to-table California fare, or Foreign Cinema, where a classic film is projected on the wall outside.

The Bay Area is so much more than just San Francisco, and this day is the perfect time to explore it. Rent a car to drive across the Golden Gate Bridge (or drive there and rent bikes, or walk across and back), then keep driving along to Muir Woods for beautiful redwoods. On your way back, stop at Sol Food for delicious, filling Puerto Rican eats for lunch. Then, spend the afternoon exploring the shops in beautiful Sausalito, stopping at Bar Bocce for a drink, if you feel so inclined.

On your way back to the city, head up Conzelman Road to Battery Spencer overlook for the best views and photos with the Golden Gate Bridge—if you're lucky, you might catch the sunset! After resting and recuperating at your hotel for a bit, enjoy your last dinner in the city at either Spruce or Cotogna, two of my favorite special occasion restaurants.

Spend your last day on a day trip to Napa (or, even better, spend a night or two there). Ubers can be spotty, so I recommend hiring a driver or identifying a DD for the day.

Start your day at B Cellars for a tasting where each wine is paired beautifully with a small bite. Make sure to pick up some of their rosé while there—it's only sold on site! Head a quick drive up the road to Oakville Grocery for a casual lunch of pizza, sandwiches, or salads in a lovely setting, then visit Hall for an afternoon tasting of various cabernet sauvignons. For dinner, I recommend Brix or Farmstead, or, of course, French Laundry or Auberge de Soleil if you're feeling fancy.

The next day, get Model Bakery's famous English muffins or pastries from Bouchon Bakery. Additional recommended wineries include Picayune (cool mercantile and affordable wine club that ships), Domain Chandon / Domain Carneros / Schramsberg for sparkling wine (go for Schramsberg if you can get in), Frank Family, Stag's Leap, Prisoner, Alpha Omega, Duckhorn, Nickel & Nickel, or Pineridge.