How to Spend Three Days in San Francisco

5 Nov
San Francisco Golden Gate Bridge and Row Houses

A Golden Gate Bridge view over classic row houses

I’ve always loved the idea of San Francisco, but never had a reason to travel there until we received a wedding invitation for Jeremy’s close post-grad friend, Damian. I quickly RSVP’d “yes” and began planning how we’d spend three days in the City by the Bay.

We took an early evening flight out of New York on a Thursday. By 1 a.m. Friday morning we had arrived in San Francisco, stopped at a local convenience store to stock up on water and snacks, and settled into our room at the Westin St. Francis on Union Square. We spent the entire long weekend exploring the city, both by ourselves and with friends, using Union Square as home base. We’ve put together how we spent three days in San Francisco. I’ve also put together a list of things I missed, which I’ll never allow Jeremy to forget.

We highly recommend taking an evening flight, especially if traveling from the East Coast. We were settled before 1 a.m. Friday morning, which allowed us six hours of sleep before we woke excited to explore.
We took an early morning flight out of San Francisco on Monday morning, which put us home mid-afternoon. We were lucky enough to be able to take both Friday and Monday off from work, but we realized that a red-eye out on Sunday evening could be possible if work was mandatory on Monday morning.

Day One

San Francisco Ferry Building view of Bay Bridge

Overlooking San Francisco's Bay Bridge from the Ferry Building

Ferry Building San Francisco with Bay Bridge

San Francisco's Ferry Building steps with a view of the Bay Bridge

Ferry Building San Francisco Historic Clock Tower

San Francisco's Historic Ferry Building Clock Tower

We started our first day in San Francisco in Union Square. We got our morning coffee and breakfast at the Starbucks on the corner of Sutter and Powell Streets, then walked our way down Market Street to The Embarcadero. We stopped at the Ferry Buildings’ Farmers Market and browsed our way through food vendors set up in the historic space. Had we known what wonders the Ferry Building held we wouldn’t have stuffed ourselves with mass market coffee and scones, and instead would have tried coffee from Blue Bottle Coffee and a classic street-food breakfast at Mijita. But our strictly visual experience was still one that gave us a peek into San Francisco’s rich history and one we’d highly recommend.

San Francisco City Lights Bookstore Jack Kerouac

Jack Kerouac Street and City Lights Book Store, San Francisco

We meandered The Embarcadero along the waterfront, passing street vendors selling San Francisco-themed artwork (I bought a watercolor of the Painted Ladies) and the piers still used for porting. At Pier 9 we turned inland, bound for City Lights Bookstore in the heart of the city’s beat poet section. City Lights had three floors of books. The top floor was dedicated entirely to poetry with a major section focused on San Francisco’s beat poets that came to prominence in the 1950s. After purchasing a book of Kerouac’s haiku we wandered the  rest of the city’s Beat section, stopped into a Beat era museum, all while repeating Mike Myers’ “Wo-Man” performance piece from So I Married an Axe Murderer: “she was a thief, you’ve got to belief, she stole my heart and my cat”.
We turned back toward the water and ventured to Fishermans Wharf. We stopped at the piers still in use for boats ferrying people back and forth to wine country and Alcatraz. We gazed at the fog-covered Golden Gate Bridge and at the harbor seals who have made their home on sun-drenched docks, and then realized we were hungry. We sat at Alioto’s restaurant in Fishermans Wharf and enjoyed a spectacular view of the Golden Gate Bridge. We wouldn’t recommend the food, it was overpriced and lacked creativity, but the view was worth every penny.

San Francisco Fishermans Wharf

Fishermans Wharf, San Francisco

After lunch we walked back to our hotel. We walked inland the entire way and this was the first time we encountered the infamous hills of San Francisco. The walk was long and most of it felt uphill. We had walked five miles around the city and a nap was in order before our night plans.


San Francisco Dubliner Bar Pre Wedding Night

Pre Wedding Celebration at the Dubliner Pub, San Francisco

We took a cab from our hotel to Dolores Street where our friends were hosting a pre-wedding bar-b-que at their home. We passed row houses and terraced houses driving through downtown, all of which were beautifully painted in shades of pastels. We walked upstairs to our friends’ second floor apartment and found a spacious living area, multiple bedrooms and bathrooms, all completely renovated. We followed the stairs to the basement, which opened to a large patio decorated with lights, a fire pit, trees and other plants. I turned to Jeremy and said, “this is where I want to live.” We enjoyed the party and late night headed to The Dubliner Bar around the corner. We stayed for hours, closing the bar. I hailed a cab for myself and my drunk husband; cabs were abundant and clearly marked.  The cab I chose was clad in Christmas lights that blinked along to the house music blasting from the speakers. My husband was dancing in the seat next to me and the cab driver was singing along. We reached the hotel, paid a surprisingly small fare and stumbled upstairs to a full nights sleep.

Day 2

We had a slow start on our second morning. Jeremy was hung-over and reluctant to get out of bed. I bribed him with the thought of a warm breakfast, and he obliged. We walked down Powell Street to the corner of O’Farrell and got a table at Lori’s Diner, a 50s-style San Francisco tradition. We sat with sunglasses on and ordered sodas, pancakes and waffles. We played Elvis songs at the personal jukebox in our booth, and soon we were feeling revived and ready to explore the city again.
This day we decided to take a ride on a San Francisco cable car. We had heard about long lines, but we waited only five minutes for the Hyde Street line, just across the street from Lori’s diner. (There are many clearly labeled stops all over San Francisco, and a great resource for understanding the cable car lines can be found here.) We took the car to the top of Lombard Street and hopped off to snap a few pictures. We looked down the winding road, watched cars make hairpin turns, and saw residents walking in and out of their front doors, starting their weekend routines.

San Francisco Lombard Street

View from the top of Lombard Street, San Francisco

Because we were at the top of the hill, we decided to walk, destination unknown. We took detours into residential areas and through parks. We used our phones’ GPS system to get us around, but mostly we were just drawn to areas that had miraculous views which spanned San Francisco proper. Our cameras were out for the entire walk, and we captured shots of what I had decided was the most beautiful city in the United States.

San Francisco top of hill view of Golden Gate Bridge

A view from the top, San Francisco

By the afternoon we found ourselves in the North Beach area of the city. We stopped for lunch at Rogue Ale’s Public House for burgers and beer. We sat outside, across from Washington Square Park, and enjoyed the crisp summer air. The food was delicious and the beer was refreshing.

We decided to wander some more on foot even though the hills were challenging, but after what we’d eaten at lunch we were happy to get the work out in. We went from North Beach, through Russian Hill, all the way to the Pacific Heights section of San Fran. In Pacific Heights we window shopped the cobble-stoned, tree-lined streets, which reminded us of New York’s Greenwich Village. Then, for our last stop of the day, we walked down Steiner Street to Alamo Square to view the Painted Ladies, made popular to me by Full House and So I Married an Axe Murder. We lounged in the park until the sun was going down. Even in the dead of August, there was a chill in the air and we were tired. “We need to go,” I said, “And not by foot.”

San Francisco Painted Ladies Alamo Square Park

Painted Ladies, Alamo Square, San Francisco

We used our phones again and found the nearest bus stop, schedule and fare sheet. Within five minutes we were on a local bus back to Union Square.

By night on our second full day we were exhausted. We had walked almost 15 miles in total, rode cable cars, buses, and taxis around the city, and partied until all hours of the night. It’s no surprise that when we returned back to the hotel to take a quick nap we ended up sleeping all night.

Day 3

San Francisco Cable Car Randall Museum Wedding

Cable Car Ride to Randall Museum Wedding Site, San Francisco

We woke up slightly peeved. How could we have wasted a night in San Francisco? We lost so many hours. But, today was our friends’ wedding, the whole reason we were in San Francisco in the first place, so we quickly brightened up. We went again to Lori’s Diner for breakfast and by the afternoon we were ready to meet a group of wedding attendees in the Westin St. Francis lobby for transportation to the ceremony site.
Our friends had reserved a private cable car for their guests, and we rode it through the city to The Randall Museum. The ceremony site was spectacular and overlooked the majority of the city.


Westin St Francis Wedding Reception San Francisco

Westin St. Francis Wedding Reception, San Francisco

The cable car brought us back to the Westin St. Francis for the reception, which was held in the top floor ballroom. The room was all windows, floor to ceiling, with one view of the Bay Bridge and another of the Golden Gate Bridge. We watched the sun set and the city lights turn bright. The reception ended and we went downstairs to our room. We packed and set our alarm for 4 a.m. to make our early Monday flight back to New York.

Things We Missed

  • Biking the Golden Gate Bridge: there are bike rental places all along Fishermans Wharf. I so desperately wanted to bike to wine country, but Jeremy was convinced I wouldn’t make it and we’d have to hire a cab driver to bring us and all our bike gear back to the rental shop.
  • Golden Gate Bridge Park: We never made it to the base of the bridge, nor did we get to explore the park. I wish that we had been able to see the bridge up close and personal.
  • Wine Country: Napa and Sausolito were high on our list of places to go, but we got so enthralled with San Francisco proper we never made it across the bay
  • The Castro & Haight-Ashbury: Two neighborhoods in San Francisco that we had wanted to explore on foot, but we would have needed another day to do so.
  • Alcatraz: We wanted to take the guided tour through Alcatraz; Jeremy is a history buff and would have enjoyed take half a day to walk through. I wanted to meet a guide named John Johnson, nickname Vicky.

    San Francisco Alcatraz

    San Francisco's Alcatraz from the top

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