San Francisco Family Vacation – Top 10 Things to Do in The City by the Bay

My college buddy always boasted that San Francisco was better than any East Coast city. “West is best,” she’d flaunt. I’d recant that our “Right coast is better than anything left.” Our heated debates covered sunrise versus sunset, tradition over trend, colonial versus Californian.

I finally caved and visited her beloved City by the Bay last week. While I can’t say that San Fran beats Boston, San Francisco is a fascinating city, with so much to see and savor. After a week of exhausting research, here are my Eastern tips for the best of San Fran:

Top 10 San Francisco sites:

1. The Golden Gate Bridge. The best way to appreciate the impressive 1.7 mile expanse, the most photographed thing on earth, is by cycling it. Being an Easterner, you should rent bikes bright and early from Bay City Bikes. Enjoy the 10-mile trip along the city’s waterfront past Ghirardelli Chocolate Factory, along scenic Marina and Presidio Parks on your way to the bright orange. There are a handful of thigh-burner hills and the height of the bridge over the Pacific is a bit “hairy” in the designated bike lane, but then your exercise ends in sunny Sausalito with a relaxing and super scenic ferry ride back to Pier 39.

2. Take in the scene at Pier 39, the waterfront hub and home to frequent festivals, street performers, and sea lions on display. Glide on a pretty painted pony on the Pier’s centerpiece carousel – a bargain at $3 a ride. Then bite into some fresh baked sourdough bread from famous Boudin’s Bakery (making sourdough since 1849).

3. Lunch at Alioto’s on Fisherman’s Wharf, Pier 45. This 85-year old Sicilian family restaurant serves the best calamari & shrimp appetizer, a tremendous Crab Louie, and authentic Cioppino (all San Fran originals) with fantastic views of famous Fisherman’s Wharf, the Bay and the Bridge.

4. Escape to Alcatraz. Walk the waterfront Embarcadero to Pier 33 for your boat ride to prison. The Alcatraz Cruise and Tour of the Cell Blocks should frighten anyone into law obedience. The new self-guided audio tour tells harrowing tales of the infamous inmates and edgy escapes from The Rock during the prison’s primetime of 1934-1963.

5. For the finer side of San Francisco, visit the Union Squaredistrict. In the heart of the city, its like Newbury Street West with designer boutiques (Betsey Johnson, Armani), and top shelf department stores – Nordstrum, Bloomie’s, Sax. Then calm yourself over cocktails and Dungeness crab at 100-year legend John’s Grill, the historic setting of The Maltese Falcon where San Fran’s diligent detective Sam Spade dined daily at the bar. Check out the celeb photos that line the dark paneled walls while you dine in old-world style.

6. Experience Chinatown. Upon entering the Dragon’s Gate, you are immersed in Asian culture, 24 blocks of authentic restaurants, bustling markets, temples and jade jewelers. You can buy exotic potions or knock off purses, then dine on Dim Sum – no fork for you – only chopsticks in Chinatown. Tip: go one block off popular Grant Street for less touristy, real deal shops and eateries.

7. Get out of town. Take the Golden Gate Bridge and head up the scenic coastline to Muir Woods, to see our 560-acre Redwood National Park. Tip: go early ahead of the crowds, bring a jacket for the cool 2-mile walk under tremendous tree canopy. Then repast at Piatti Trattoria in nearby Mill Valley overlooking Richardson Bay.

8. For a water workout, canoe the Russian River (60-miles north of San Fran). A 10-mile paddle downstream takes you on a 3-hour tour of towering trees, past egrets and heron. Stop for a picnic and swim along your way. Nearby to Burke’s Canoe Trips is Armstrong State Forest – a beautiful forest of massive 1,400 year old redwoods that is free to visitors. Or bee-line to Korbel Winery for bubbly.

9. Within an hour of San Francisco, you can be sipping wine in Sonoma, or nipping in Napa, there are countless California wineries with tasting and tours. You’ll also encounter funky time warp towns in your travels. Northern California is amazingly pastoral and peaceful once you venture above the Bay to the land of bounteous bovines and grape vines.

10. Explore more of San Francisco’s celebrated neighborhoods, each with its own architecture, ethnicity, and culinary strength. Ride a classic Cable Car from Union Square to Nob Hill. Drive or walk down the most crooked street in the world – Lombard Street (Tip – go before traffic). Visit the hippy haven of Haight-Ashbury where peace still rules, and the city’s oldest neighborhoods “The Mission” and the Castro district where Latinos, gays and lesbians co-exist colorfully. The adopted adage of San Francisco’s Visitors Bureau is “Only in San Francisco”– well said.

Weather Note: don’t expect classic California beach weather. San Fran is cool and can be foggy, particularly in prime summer. Mark Twain is rumored to have said, “The coldest winter I ever spent was a summer in San Francisco.”

I’m not awarding a “west wins” trophy to my California colleague. San Francisco doesn’t beat Beantown, but she was “right” that her left coast City by the Bay is a top place to visit (she’ll love reading that). San Francisco ranks high as a happening, hilly, highly diverse, delicious, and delightful city. I can see why many have “left their hearts in San Francisco.”