A man's Travel guide: San Francisco
The Iconic Man's Guide To San Francisco
Explore San Francisco’s Slightly Off the Beaten Track Top 10 Iconic Gems
San Francisco is a truly iconic city. Perhaps the most unique city in America. It enjoys a privileged geographical location with the Pacific Ocean on its west side, and San Francisco Bay to the north and east. On top of its unique location, San Francisco is crowned by the iconic beauty of the Golden Gate Bridge, forever a symbol of the mighty west.
Very few cities in the world have been blessed with such a heady combination of a gorgeous natural setting, old world charm, high tech innovation, and a wonderful mix of cultures that provides a discerning traveler with an experience that rivals (or even surpasses) many of the most iconic cities of the world.
Only in San Francisco can an Iconic Man discover a city as iconic as himself. Only in San Francisco, a traveler can start his day in a classic Italian Cafe that would not be out of place in the center of Rome (North Beach area), then enjoy a truly authentic Cantonese lunch in Chinatown, followed by a walk along the headquarters of global tech innovation in the Financial District (Uber, Lyft, LinkedIn, Twitter & many more tech companies are based here), followed by a visit to a Japanese Tea Garden (in Golden Gate Park), dinner at French Bistro (in San Francisco's little France, a.k.a. Belden Place), and close the evening in a 1930's era rooftop cocktail bar with a 360 degree view of the city and a Martini list that would have made F. Scott Fitzgerald proud (Top of The Mark).
But with so much to do and see, where should an Iconic Man start? First, let's consider that an Iconic Man is not a run of the mill tourist that wants to rush from tourist trap to tourist trap (the horror!). You have discerning tastes and, fortunately, San Francisco has iconic hidden gems in spades for a discerning traveler like you.
To help you make the most of your time in San Francisco, we've put together ten slightly off the beaten track iconic travel gems that San Francisco has to offer (because you're a traveler, not a tourist).
San Francisco's Top 10 Iconic Gems
1-Golden Gate Bridge
The Golden Gate Strait’s fame precedes the iconic bridge that spans it. The name hails from the Gold Rush era, as all boats entering San Francisco Bay from the Pacific Ocean had to enter through this narrow passage between the San Francisco Bay and the ocean. Often shrouded in fog and lined with dangerous rocky islands, the Golden Gate Strait became the resting place of many Gold Rush era schooners. When the Golden Gate Bridge opened in 1937 it was the longest and tallest suspension bridge in the world, and instantly became an iconic symbol of the mighty west and the endless possibilities it offers. The forward-looking ethos that inspired the Golden Gate Bridge lives on in the City of San Francisco as an epicenter of tech, culture, and new ideas that, sooner or later, expand beyond the city and go on to change the world.
Start your visit at the Golden Gate Bridge but avoid the crowds on the top of the span, and instead head down to Fort Point.
The Golden Gate Bridge, from Fort Point.
Fort Point is a Civil War-era fort that protected the entrance to the San Francisco Bay. The Golden Gate Bridge had to be built around it, forcing the southern tower of the bridge to be anchored further back than intended. You can reach Fort Point from a series of steps that head down from the Golden Gate Bridge's visitor center, or by strolling along Crissy Field.
Once you get to the fort, you will be rewarded with one of the most iconic views of the Golden Gate Bridge as it towers over the fort and onto the Marin Headlands on the other side of the bay. Alfred Hitchcock, that iconic man and legendary film director, recognized the power and beauty of this spot when he set a pivotal scene of his movie Vertigo here.
2-Marin Headlands
Crossing the Golden Gate Bridge not only delivers spectacular views of San Francisco Bay, the skyline of the city, and the occasional whale spouting, it also delivers the Marin Headlands.
Avoid the crowded viewing point on the Marin Side of the Golden Gate Bridge and instead head uphill on Conzelman road to perhaps the most iconic view of the Golden Gate Bridge and San Francisco. This view is indeed so iconic, that it's featured in many new car commercials. You will instantly recognize it when you get there. As a bonus, on the top of Conzelman Road, you can explore the ruins of a World War II-era gun emplacement, hastily built in 1942 after the attack on Pearl Harbor.
Once you get to the fort, you will be rewarded with one of the most iconic views of the Golden Gate Bridge as it towers over the fort and onto the Marin Headlands on the other side of the bay. Alfred Hitchcock, that iconic man and legendary film director, recognized the power and beauty of this spot when he set a pivotal scene of his movie Vertigo here.
2-Marin Headlands
Crossing the Golden Gate Bridge not only delivers spectacular views of San Francisco Bay, the skyline of the city, and the occasional whale spouting, it also delivers the Marin Headlands.
Avoid the crowded viewing point on the Marin Side of the Golden Gate Bridge and instead head uphill on Conzelman road to perhaps the most iconic view of the Golden Gate Bridge and San Francisco. This view is indeed so iconic, that it's featured in many new car commercials. You will instantly recognize it when you get there. As a bonus, on the top of Conzelman Road, you can explore the ruins of a World War II-era gun emplacement, hastily built in 1942 after the attack on Pearl Harbor.
San Francisco Skyline & Golden Gate Bridge from Marin
On the way back to the Golden Gate Bridge, Conzelman Road descends past a now decommissioned Nike nuclear missile launch pad (a cold war era relic open to visitors and with a couple of missiles on display). Conzelman Road also passes close to the Marine Mammal Center, where California Sea Lions and Elephant Seals get fed and treated. This is a great place to learn about the local fauna that live on California Beaches and one of the best ways to get up close and personal with these amazing animals.
The Marine Mammal Center
3-Sausalito/Tiburon
On your way out of the Marin Headlands, you will go through a single-car World War II era tunnel (built to reach the battery atop the hill). When you exit the tunnel, a right turn along Alexander Avenue will take you to the picturesque waterfront towns of Sausalito and Tiburon. Both Sausalito and Tiburon offer world-class waterfront dining, with perhaps the best view of the San Francisco skyline that you can get. The view gets even better when you're dining on a balcony above the bay, while yachts and sea birds bob along. Most of the restaurants on the water are excellent and are frequented by the many local celebrities that live there.
On your way out of the Marin Headlands, you will go through a single-car World War II era tunnel (built to reach the battery atop the hill). When you exit the tunnel, a right turn along Alexander Avenue will take you to the picturesque waterfront towns of Sausalito and Tiburon. Both Sausalito and Tiburon offer world-class waterfront dining, with perhaps the best view of the San Francisco skyline that you can get. The view gets even better when you're dining on a balcony above the bay, while yachts and sea birds bob along. Most of the restaurants on the water are excellent and are frequented by the many local celebrities that live there.
Alfresco dinning in Sausalito, overlooking San Francisco Bay
After your meal in Sausalito or Tiburon, take the Ferry back to San Francisco, with the added bonus of getting a close-up view of Alcatraz Island from the middle of the bay. This way you'll save time and money while avoiding the hordes of tourists lining up for the Alcatraz tour on Fisherman's Wharf.
4-North Beach
Once off the ferry from Sausalito, head a couple of blocks south to North Beach, San Francisco's Little Italy. North Beach's main drag, Columbus Avenue, is lined with authentic Italian cafes, bars, and restaurants. You can spend a day here just sipping a cappuccino and watching the world go by (Cafe Greco is a great place for this). America's iconic man and world-famous baseball player Joe Di Maggio was a local North Beach boy and married actress Marilyn Monroe in North Beach's Peter and Paul Church in Washington Square, just off Columbus Avenue.
City Lights Bookstore in San Francisco’s North Beach District
Finish your tour of North Beach by continuing down Columbus Avenue to the iconic City Lights bookstore and publishers. City Lights entered the modern consciousness in the 1950s as the epicenter of the "Beat Generation" when they published, among others, Alan Ginsberg, and that most iconic of men, Jack Kerouac (of “On the Road” fame).
San Francisco’s North Beach, looking towards the Financial District
Crown your North Beach tour with a drink at Vesuvio Cafe, a frequent haunt for beat poets (and Jack Kerouac's favorite North Beach watering hole) conveniently located right next door to City Lights bookstore on Jack Kerouac Alley.
5-Chinatown
There are many Chinatowns in the world, but none more iconic than San Francisco's Chinatown. No cop movie set in San Francisco can miss that classic scene where the hero chases the baddies through a crowded San Francisco Chinatown where, magically, it’s always Chinese New Year and the dragons are always on parade.
Dragons on parade in San Francisco’s Chinatown
Spend some time wandering through the shops and enjoying classic Cantonese cuisine. For an even more authentic flavor of Chinatown, head to California street in the city's Richmond district, San Francisco's lesser known “second Chinatown” where locals go to get their Chinatown fix while avoiding the crowds.
6-Mission Dolores
Visiting San Francisco is like visiting many cities at once. Rome in North Beach, Hong Kong in Chinatown, Manhattan in the Financial District, and finally, old Mexico in the Mission district. This iconic neighborhood is the oldest in the city, the site of the original Spanish Mission that gave the City its name: San Francisco, after Saint Francis of Assisi.
At the heart of the Mission District, is the Mission Dolores Church. Founded in 1776, it’s the oldest surviving structure in the city. The church’s Spanish Colonial whitewashed adobe walls have seen the city grow around them. The church’s small inner courtyard cemetery (also the oldest in the city) tells the story of San Francisco's earliest settlers, including countless unmarked graves of native Ohlone Indians, the tomb of the first Mexican governor of Alta California (Captain Luis Arguello), and several Gold Rush era Irish immigrants who came west to escape the Irish potato famine, lured by the promise of countless riches beyond the Golden Gate.
San Francisco’s Mission Dolores
A couple of blocks from the mission, you will find the San Francisco Friend's School (250 Valencia St). This unassuming wooden building (built in 1905) was, for over 100 years, the original Levi’s Strauss & Company sewing factory, where the descendants of Levi Strauss (the inventor of the most iconic of American icons, the blue jean) continued his legacy from 1906 until the factory was closed in 2008. There's a mini-museum inside with photos from the factory's heyday.
Levi Strauss and the old sewing factory building represent the true legacy of the Gold Rush of 1849. A gold rush that ended up finding real gold in the streets of San Francisco not by mining the hills and rivers, but by inventing and producing an iconic item used by almost everyone in the world (Levi's blue jeans).
San Francisco’s Mission Dolores Basilica
This is the legacy of innovation that still lives on in San Francisco's tech sector, but nothing symbolizes San Francisco's iconic tech ingenuity like this old building, now home to a school with a mission to shape the young minds of San Francisco's future innovators.
7-Pelican Inn
Take a break from the hustle of the city by crossing the Golden Gate Bridge and venturing into Marin County to the Pelican Inn, a little piece of old England just a stone's throw from the North tower of the Golden Gate Bridge.
The Pelican Inn
Nestled between green wooded hills and a beautiful cove (Muir Beach), you will be greeted by the whitewashed mock Tudor walls of the Pelican Inn. This best-kept secret of hikers, travelers, and lovers of a quiet pint (or two) in a cozy British pub by the sea, has been charming those in the know for years.
8-Muir woods
The giant sequoia trees of Muir Woods have been attracting visitors from San Francisco for over 100 years, even before the Golden Gate Bridge was built. These are the largest living things on earth, towering for hundreds of feet right out of their natural habitat, the foggy valleys of Marin County. Beat the crowds by hiking to Muir Woods from the Pelican Inn (you'll thank me later). Later hike back for a well-deserved cold pint.
Giant Sequoias at Muir Woods
9-Sonoma Square/Wine Country
No visit to San Francisco would be complete without a trip to the Wine Country. California wine is famous the world over and many well-known European wineries have set up shop in the Napa and Sonoma valleys to take advantage of the excellent wine-growing soil, proximity to cooling ocean breezes, and long sunny summers that ripen vines through the fall. This wonderful combination of soil, sun, and proximity to the sea makes Napa and Sonoma one of the premium wine-growing areas on the planet.
Avoid the crowds clogging Napa Valley and head instead to Sonoma. In addition to having the oldest winery in California (Buena Vista Winery), and a world class Catalan cava winery (Gloria Ferrer), Sonoma also showcases a lot of California history.
No visit to San Francisco would be complete without a trip to the Wine Country. California wine is famous the world over and many well-known European wineries have set up shop in the Napa and Sonoma valleys to take advantage of the excellent wine-growing soil, proximity to cooling ocean breezes, and long sunny summers that ripen vines through the fall. This wonderful combination of soil, sun, and proximity to the sea makes Napa and Sonoma one of the premium wine-growing areas on the planet.
Avoid the crowds clogging Napa Valley and head instead to Sonoma. In addition to having the oldest winery in California (Buena Vista Winery), and a world class Catalan cava winery (Gloria Ferrer), Sonoma also showcases a lot of California history.
Enjoy a refreshing glass of Cava at Gloria Ferrer in Sonoma
Head to Sonoma Square for a taste of Old California. The square was the stage for the Bear Flag rebellion against Mexican rule in 1846, and the birthplace of the California Republic, the forerunner of the modern state of California.
You can visit the old Mexican era barracks, the old Mission and Bear Flag monument, all right in Sonoma Square. Complete your wine country visit with a stop at the Sonoma Cheese factory for local Sonoma Jack cheese. The cheese factory is also located in Sonoma Square, near the house of the last Mexican governor of California (General Vallejo).
Enjoy an iconic day of cheese and wine sampling in Sonoma before heading back to San Francisco, just a mere 30 minutes away.
10-San Juan Bautista
San Juan Bautista is a true iconic hidden gem. Located to the south of San Francisco on the way to Monterey, this gorgeous Spanish colonial village features a beautifully preserved Spanish Mission, Mission San Juan Bautista, founded in 1797 in honor of St John the Baptist.
The Old Mission of San Juan Bautista at dusk
The tourist hordes have yet to discover this gem of the San Francisco Bay Area, in spite of it featuring prominently in Alfred Hitchcock's Vertigo.
An iconic man can easily spend the day wandering around San Juan Bautista's quaint streets, enjoying its wonderful Mexican restaurants that feature al-fresco dining in wonderfully lush gardens, browsing its many arts and craft shops with traditional Mexican art, or visiting the local craft brewery tap room set in an Old California building from the mid-1800's. Then, of course, there is the Mission itself, a jewel of Spanish Colonial baroque architecture, with an inner courtyard and a side chapel dedicated to the Virgin of Guadalupe.
The village of San Juan Bautista is truly a San Francisco Bay Area off the beaten track gem that's not to be missed.
Practical Tips:
Getting Here and Around
You can Fly into San Francisco Airport, San Jose Airport, or Oakland International Airport. By car, head north on highway 101 from Los Angeles or take interstate 5.
Getting Around
San Francisco has a very good transportation system within the city. Buy a 3-day Muni visitor passport, valid on trolleys, buses and even on San Francisco's iconic cable cars.
Take advantage of the low cost of rental cars and get a rental to explore the wine country, Muir Woods, San Juan Bautista and even the city itself. At night use Lyft and Uber to go to restaurants, bars, and nightspots.
Where to Stay
Most tourists stay in the Union Square area. An Iconic Man traveler should avoid the tourist hordes and instead book a hotel along San Francisco’s Lombard Street, some of which offer views of the Golden Gate Bridge. All hotels on Lombard street offer easy walking distance access to restaurants and bars on Chestnut Street, a lively street frequented by the beautiful people.
In Conclusion
San Francisco is an iconic city, fit for an Iconic Man to savor and explore. Use this list as a guide, but also let your sense of adventure lead you astray a bit (because that's where the fun begins for travelers, not tourists). Also, don't forget to drop us a line in the comments about your Iconic Man's San Francisco adventures, and stay tuned for more iconic adventures, fit for an Iconic Man.
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Max Milano is a novelist, filmmaker, photographer, and travel writer based in San Francisco, California. His latest novel, "Daughter of Recoleta," is available on Amazon. You can follow his travelogue at MaxMilano.com