A few weeks ago, reader Anu emailed with a question: can you give us tips on spending a romantic day in this beautiful city?

As relatively new Bay Area residents, she and her husband planned on celebrating their anniversary in San Francisco. Anu reported that they liked jazz and food. They wanted to do something outdoors, maybe some hiking, maybe some beach time. But then also cozy up for something romantic at night. Oh, and this would all take place on a weekday.

As is probably obvious by now, I HAD SO MANY IDEAS. Here are the four day trips I came up with (and at the end, I’ll reveal what they ended up doing. And it was totally romantic and kind of the perfect anniversary day in San Francisco.)

Cliff Hiking, Sunsets, and Yoshi’s: For the Overly Ambitious Hiker and Jazz Hound in All of Us

At least 10 hours; 7 hiking miles, 4.4 transit miles

1. Breakfast at Ella’s, on Presidio and California Streets. (It serves brunch, even on weekdays. Which is wonderful.)
2. Walk over to the fantastic markets on California Street in Laurel Heights to buy some cheeses/cured meats/chocolate, etc.
3. Walk along Sacramento Street back to Presidio Street.
4. Walk down the Lyon Street steps, gazing out over the bay and Marina and mansions.
5. Continue hiking past the Palace of Fine Arts, Crissy Field, then up and under the Golden Gate Bridge.
6. Hike on the Battery to Bluffs Trail (one of my favorite places in the city, that I haven’t had a chance to write about yet) down to Baker Beach.
7. Picnic on Baker Beach.
8. Post picnic, head up into the Sea Cliff neighborhood hood. Cross through to the Lands End Trail.
9. Hike along the Lands End trail until you get to down onto the point on Lands End.
10. Time this to coincide with sunset (mid-Nov, it’s around 5:30) just the two of you, the bluffs, the waves, and the Pacific.
11. Continue hiking to the Sutro Baths (this part of the trail is paved, so I’m not worried about it being darkish, post-sunset.)
12. Take the 38-Geary to Fillmore Street in Pacific Heights.
13. Dinner at SPQR on Fillmore.
14. Jazz show at Yoshi’s, just down the street on Fillmore. If you’d like something more casual, check out the lounge area at Yoshi’s.

This is a wildly ambitious day, but also totally awesome and memorable.

Artisan Chocolate Factories and the Parrots of Telegraph Hill: Just in Case Beach Weather Wasn’t Happening Because This is San Francisco After All

8 hours; 3 urban hiking miles

1. Brunch at the Ferry Building.
2. Walk down the Embarcadero to the Tcho Chocolate Factory on Pier 17.
3. Take in the TCHO chocolate factory tour at 2pm (they offer two free tours/day, but you need to make reservations.)
4. Post tour, hike up Filbert Street Steps and Greenwich Street Steps in Telegraph Hill (There are hidden staircases all throughout the city, forming their own off-road network. Discovering them makes for a fun day and great bay and downtown views.)
5. Check out Coit Tower.
6. Climb down, walk through North Beach (grab a latte and cannoli) to Hyde Street in Russian Hill.
7. Dinner at Seven Hills on Hyde Street in Russian Hill. (Intimate, romantic, lovely street, fresh Italian menu. When Dave and I first wrote about Seven Hills, it was a low-key Italian restaurant that was mostly empty and that certainly didn’t require reservations. But, it was just named the 4^th best restaurant by Zagat 2013. Which, it’s good people but not that good. You should still go for the neighborhood romance, but all this just means that it’s now harder to get into. Look into reservations.)
8. (If you want something more upscale, head down the hill to Perbacco/Barbacco. Or Coi, if you’re feeling extravagant.)
9. Walk through the romantic mist and fog of Russian and Nob Hill to Top of the Mark lounge, for live jazz and cocktails/wine while looking out over the city lights.

Anniversary Catamaran Cruise!: Because It’d Be Totally Cheesy Any Other Day of the Year (But You Know You Want to Do It)

7-9 hours, minimal walking

1. Lunch at the Ferry Building, take the F-line antique streetcar down to Fisherman’s Wharf (that’s where they all leave from. Just ignore the guy jumping out of the bush wearing his bush-man costume, and definitely don’t give him money).
2. Take in a day time boat tour around the bay. There are many cruise companies to choose from, but you should clearly look into this catamaran cruise, leaving at 1pm or 3pm daily. It’s a real live sail boat! The 3pm tour might be awesome this time of year, since it’ll be approaching sunset while you’re still out on the bay.
3. After the tour, get back on the F-line street car towards downtown.
4. Dinner at Boulevard. (Or Benu if you’re going extravagant. Speaking of which, how unintentionally funny and perfect is their website?)
5. I’d still recommend capping your night at Yoshi’s or Top of the Mark, depending on if you want to see an actual show or you just want tinkly jazz playing in the background. Both would require a cab ride, but it’d be easy to find a cab from the Financial District.

4. The Reverse Option 1: Eighty-Six Yoshi’s for Jazz at the Palace of Fine Arts

10 hours; 8-11 urban and cliff hiking miles (depending on whether you want to take transit)

1. If you’re driving, park somewhere in the Inner Richmond.
2. Either take the 38L-Geary bus out to Louis Diner near Sutro Baths OR walk along Geary Boulevard and Clement Street, randomly sampling yummy pastries and food from the Russian and Chinese bakeries. (Don’t miss Moscow and Tbilisi Bakery on Geary around 18th.)
3. Pack up some pastries and foods for a picnic later on.
4. Head towards Lands End/Ocean Beach (you could jump on the 38/38L Geary for a short ride)
5. Hike along Lands End through Sea Cliff, with your afternoon picnic on Baker Beach.
6. After lunch, climb through the Battery to Bluffs Trail as sunset approaches. (The golden gate bridge will be ON FIRE this time of day, making for great photo opportunities.)
7. Make your way around Crissy Field, then head into the Marina for dinner: A16.
8. After dinner, head to the Palace of Fine Arts theater for the show.
9. After the show, head up Lyon Street to the Lyon Street steps (these are also a romantic favorite, if you can’t tell…)
10. Walk over to Spruce on Sacramento Street or Swank Cocktail & Coffee Club, and cozy up for a post-show drink.
11. Figure out where you parked the car.

So, a mix of adventurous, relaxed, sight-seeing, or food-obsessed. Depending on your idea of romance, of course.

Here’s Anu’s report back, a hybrid of options 2 and 4:

1. Bring cheese and spreads for picnic supplies.
2. Hike through the Presidio to Baker Baker beach and enjoy a picnic.  They loved Baker Beach so much that they returned the following day for family photos.
3. After lunch, hike on the Battery to Bluffs trail: “The bluff’s hike was just breathtaking. Just gorgeous.”)
4. Post-hike, head to Russian Hill.
5. Explore the neighborhood.
6. Tapas at Zarzuela on Hyde Street. (“Great lamb chops and duck leg.”)

What do you guys think? Could we have done better? What would be your most romantic day in San Francisco?