Updated: Apr 28
"It doesn't matter where you are going, it matters who is beside you."
Last December, my partner Matthew's sister-in-law Shirley struck upon the idea to surprise her husband, Matthew's brother Wayne, with a trip to San Francisco -- not just a trip for the two of them, but a trip that included me and Matthew. Shirley would reveal the surprise to Wayne at Christmas. Her plan roughly was to tour San Francisco, the Napa Valley and Lake Tahoe in the span of a week, and she was leaving the details up to us to work out since we'd both been through that part of the country before. She and Wayne had never been there, and both had wanted to make this trip for years. In order to make it happen, all Matthew and I had to do was arrange for our flights. Shirley took care of the car rental and all hotel reservations. The three of us agreed on a departure date of March 19. We didn't know it then, but it turned out to be one of the best vacations any of us had ever had.
In this article, I'll share some of the most memorable dining, hotel and recreational experiences from our time on the road, the good and the not-so-good, to hopefully assist you if you are planning to make a similar trip.
San Francisco - March 19, 2022 - Saturday
Matthew and I were coming from Seattle; Wayne and Shirley were coming from Jacksonville, Florida. The four of us converged at the San Francisco International Airport late that morning, brimming with excitement and anticipation for the eight fun-filled days we knew were still ahead of us. The skies were gray that day with intermittent periods of rainfall, but it did not dampen our enthusiasm in the slightest. I had been unanimously appointed chief navigator of our adventure; it was a job I was thrilled to do. One of my greatest joys is to share a travel experience with others and to see old and familiar places through the eyes of first-time visitors. Shirley had rented us a Nissan Armada -- a behemoth on wheels that was roomy and comfortable enough for four adults and their luggage, but which also made maneuvering in downtown parking lots and narrow streets a sometimes white-knuckled challenge.
A few words about San Francisco
For those of you who have been there, you already understand what makes it such a fascinating, charming and entirely unique city. If you are considering making your first-ever visit to this grand American city, be prepared to be entertained by a delightful tableau of stunning vistas, architectural wonders, grand public spaces, soaring downtown towers and residential streets lined with rows of quaint and elegant Victorian homes. What makes San Francisco far more unique than most other American cities is its geography. The city is a jumble of hills and valleys where city planners pushed streets overland, traversing steep hills, adhering to a rigid grid system, largely ignoring the challenges of topography. Some of the streets appear to climb at such precipitous angles that you fear your car will wind up sliding backward down the hill. If you are exploring on foot, your legs will get a good workout going up and down the streets. Most people know San Francisco as the "city by the bay," but few realize that it is also bordered on the west by the Pacific Ocean. In fact, the city, situated at the north end of a 7-mile-wide peninsula, is surrounded on three sides by water.
Now back to the story ...
Food and beverage were on everyone's mind leaving the airport. We headed straight for Union Square in downtown San Francisco where I knew there were lots of restaurants and pubs. We parked in a warehouse converted to a garage near the intersection of Grant and Sutter where the ramps going up were narrow and the spaces were obviously suited for much smaller vehicles than ours. Out on the street, we made our way to Union Square and got our first picture together of the trip.
[Pictured above: Me, Matthew, Shirley and Wayne.]
Finding a cocktail bar turned out to be a bit more challenging than we had anticipated. We first went to the St. Francis Hotel, picturing ourselves having drinks surrounded by elegant furnishings in one of the stately public spaces of this historic building. Nothing was open when we arrived. We then turned to our phones in search of alternatives. With the pandemic having taken its toll on so many businesses, the online maps on our phones were very much out of date -- we showed up at the door of many places that were listed as open for business on Google Maps only to find they were shuttered. We just happened to pass a pub at the corner of Sutter and Taylor where two people were emerging and just happened to remark to us that it was surprisingly wonderful. So we went into the Sutter Pub & Restaurant (700 Sutter Street) -- a small business with a half dozen tables squeezed in between the bar and the wall facing Taylor Street. Their menu features both English and American fare, and the food exceeded our expectations. The prices turned out to be, on average, much better than most other restaurants in San Francisco -- running between $13 and $18 for a lunch entrée. Beer and cocktails were similarly well priced.
Lombard Street -- "The Crookedest Street in the World"
For the next few hours, I took the crew on a guided tour of some of San Francisco's most notable landmarks. Our first stop was in the tony Russian Hill neighborhood, at the top of Lombard Street -- the narrow and twisting brick-paved drive that descends the hill for one city block in a series of tight switchbacks. A sign at the top of the drive declared all non-residential traffic to be off limits. It was clear few people were paying attention to it. We decided to be more respectful and parked our car a block away and hiked back up to the top of the drive, past multi-million-dollar homes, where we got these pictures, including the Powell/Hyde cable car.
The Palace of Fine Arts
Our next stop was The Palace of Fine Arts in the Marina District on the corner of Girard Road and Lyon Street. This is a place I highly recommend you stop to see. Slightly off the beaten path, and nearly invisible until you are right at its entrance, it is a collection of classic-looking structures that are some of the last surviving remnants of the 1915 Panama-Pacific Exposition. It was designed to resemble a fictional ruin from another time. The structures that stand there today are actually replicas of the originals, reconstructed in the 1960s. As you stroll through the entrance of the park, the grand and towering colonnades will instantly draw your eyes skyward and fix them there as you press forward along the footpaths. Take note of all of the ornamentation in the friezes and cornices when you're there and you'll see lots of interesting sculptural flourishes, including the "weeping women" atop the colonnades. The open-air rotunda is the main draw within the park and awaits you at the end of your stroll with a jaw-dropping interior of vast and awe-inspiring proportions and intricate design. The grounds are surrounded by a peaceful lagoon and dotted with a variety of trees and shrubs. A wedding party was packing up chairs and moving things out of the rotunda when we arrived.
Leaving The Palace of Fine Arts, we headed south on Divisadero Street and took a right turn onto Haight Street to swing by the corner of Haight and Ashbury, and the one-time center of the counterculture movement. The neighborhood still retains much of the vibe from its heyday in the late 1960s and the Summer of Love. That day we were passing through, the streets were packed with people, many waiting in long lines to get into businesses on Haight Street and the traffic was forbidding. Finding a place to park would have been nearly impossible, so we settled for a drive-by appreciation instead.
From the Haight-Ashbury, it's a short drive into the nation's (and perhaps the world's) most famous LGBTQ neighborhood -- The Castro. If you are traveling south on Divisadero, it turns into Castro Street which becomes the cultural axis around which the neighborhood has developed. Visitors are greeted by perhaps the largest free-flying rainbow flag in the country at Harvey Milk Plaza on the corner of Castro and Market. The businesses along Castro Street are largely clustered between Market and 19th Streets where you'll find great restaurants and shops, as well as amazing public art. Check out the rainbow-striped crosswalks as you stroll down Castro Street, and don't miss the Rainbow Walk -- a series of 30 plaques that honor the pioneers of LGBTQ rights. For me, the Castro District will always have a special place in my heart as it was a haven of acceptance during my 20s (I made lots of trips there from Seattle) and a place where I felt like I was always welcomed and part of a community.
After a quick tour of the Castro, it was time to return to Union Square and check into our hotel. For the next two nights, we stayed at the Courtyard by Marriott San Francisco Union Square, located at 761 Post Street. The hotel occupies a narrow, 1920s building that has been completely remodeled, but rooms are on the smaller side. Amenities include the usual -- in-room coffee maker with complimentary packets, refrigerator, basic toiletries, comfortable beds and pillows. Snacks and drinks are available in the lobby store, and there is a restaurant/bar on the ground floor. The hotel is very close to Union Square and within a block or two of great restaurants and a Walgreens.
For dinner that night, we took an Uber from the hotel to Warakubune (307 Church Street, 415-252-8383) at the corner of 15th and Church Street in the Castro District. It is a traditional sushi restaurant featuring mawarizushi -- sushi that travels around the chef's island where patrons are free to pluck enticing plates from rotation. Most mawarizushi restaurants utilize a conveyor belt system, but this restaurant uses propelled water in a canal to float mini-boats loaded with sushi and other fare past hungry customers. The food was excellent, prices were reasonable and the experience was fun, but the wait to get a spot at the island was long. I recommend getting there early in the evening to avoid a longer wait if you are traveling with a party of four or larger.
March 20, 2022
We were extremely lucky with the weather that Sunday. Warm temps and cloudless, cerulean skies followed us everywhere we went. Breakfast was take-out egg and sausage sandwiches from a nearby Starbucks. We had a long list of sights to see in and around the city that day -- or rather, I had a long list of sights to "surprise" the crew with.
Our first stop of the day was at Coit Tower in the Telegraph Hill neighborhood. It is located to the east of Columbus Avenue with the best approach by car eastward along Lombard Street. Be aware that parking at the top is limited. You can also get there by taking a scenic hike up the eastern slope via the Filbert Street stairs from Sansome Street which passes through Grace Marchant Garden, or take the stairs up from the western flank on Greenwich Street.
Completed in 1933, the tower is a slender white, fluted concrete column visible from nearly every vantage point in the eastern half of the city. It is named for Lillie Hitchcock Coit, a wealth eccentric who bequeathed substantial funds prior to her death in 1929 to build both a tower and a monument to her beloved volunteer firefighters. (Contrary to popular belief, Coit Tower was not designed to resemble a firehose nozzle.) The majestic tower rises 212 feet from the summit of the hill and has an observation deck at the top.
Views from the Coit Tower parking lot and grounds are breathtaking. On this particular day, we could see both the Bay Bridge and the Golden Gate Bridge, across the bay to Oakland and Berkeley, north to Alcatraz Island and Marin County, and west toward Russian Hill and Nob Hill. The four of us decided not to go inside the building, but instead enjoyed the views from the parking area and public stairs flanking the park. They have coin-operated telescopes mounted along the perimeter of the parking lot to help you get those eagle-eye views. There is also a café outside where you can purchase snacks and beverages. For those of you who are interested in an observation deck visit or a tour of the building, here are some of the admission fees for those activities: An elevator ride to the top will run you $10 for adults, $7 for seniors (62+) and youth (12-17), $3 for children ages 5 to 11 and free for kids until 5. Guided tours are also available -- the admission is $10/person for the full tour of the murals and $5 for a tour of the second floor only. Tours last from 30 to 40 minutes. You can get your tickets online by clicking the link above, or call 1-800-655-6751. Hours of operation are 10 a.m. to 5 p.m.
The Golden Gate Bridge and the Marin Headlands
After a pleasant visit to Coit Tower, we headed out north on US 101 across the Golden Gate Bridge and parked just on the north side at the H. Dana Bowers Rest Area & Vista Point. From there, you can get amazing views of the bridge and of the city of San Francisco.
Some of the best views of the bridge, the city and even the Pacific coast are from the Marin Headlands. To get there from the rest area and vista point, get back onto US 101 northbound and take the next exit (Alexander Avenue). Follow the signs to Marin Headlands -- you'll have to pass through a narrow, one-lane tunnel where directional traffic is regulated by a light at the entrance on both sides. The wait can sometimes be long for your turn to go through the tunnel, but on average is 10 minutes. Drive about 1,000 feet after exiting the tunnel, then take a left where the sign indicates "Coastal Route / 101." You'll climb up into the headlands and emerge on the other side where panoramic views of the ocean, the city and the bridge practically beg you to pull over to stop and gaze. There are plenty of turnouts along the winding road where you can safely park and grab some amazing photographs. Once you pass the roundabout heading east along the palisades, the road becomes a one-way route that will eventually deposit you back onto US 101, allowing you to avoid having to go back through the tunnel to return to the highway.
Lands End Lookout
Next, we crossed the bridge again back into San Francisco and took the first exit to drive through the Presidio along scenic Lincoln Boulevard. The Presidio is a 1,500-acre park with hiking trails, a golf course, historic buildings, beaches and forested areas under the governance of the U.S. Park Service. There is no admission fee to enter the park and it is open 24 hours a day. Lincoln Boulevard soon turned into El Camino Del Mar as it left the park boundary, but we took a jog onto 30th Avenue south to Geary Blvd., then west onto Point Lobos Avenue. In short order, we found ourselves at the Lands End Lookout where we were treated to stunning views of the beaches below, the Pacific Ocean, and Point Lobos. Below us, at the edge of the coastline over a treeless expanse of low shrubbery, were the remains of the building that once housed the Sutro Baths. Footpaths leading out of the parking lot will conduct you down to the old Sutro Baths building, or over the wind-swept hills to the north along the Coastal Trail.
Lunch in the Outer Sunset Neighborhood
Leaving the Lands End Lookout, we continued west, then south onto the Great Highway which parallels the Pacific Ocean at the western edge of the city. From here, on a clear day like the one we were enjoying, you can get spectacular views of the coastline and the western-facing neighborhoods as they gently slope down toward the sea.
Just south of Golden Gate Park is the Outer Sunset neighborhood. With a quick search on Google, Wayne found a well-reviewed restaurant called The Sunset Cantina. Located at 3414 Judah Street (415-571-8874), the menu features several mouth-watering brunch specialties with a Mexican flair. Seating is inside the restaurant or out on the sidewalk. With the weather so fair, we elected to sit at one of the tables outside enjoying views down Judah Street leading to the ocean. Prices were fairly reasonable, ranging from $12 to $15 for brunch. I ordered the chilaquiles, a dish of tortilla chips topped with two poached eggs, avocado, chipotle and avocado crema, onions and cotija cheese and drenched in chilaquile sauce. (I took that description straight from their online menu.) See tantalizing photo below!
A short drive away from the restaurant, going up Sloat Blvd., then Portola Drive, is the second highest point in the city with panoramic views of the entire Bay Area -- a place called Twin Peaks. From up there, you have unobstructed views in every direction, with some of the city's best views of the downtown core. When you get there, however, you're not at the very top of the hill, ... yet. Take the trail up from the parking lot to reach the true summit. Finding parking when you get to the park should be easy, but it can be very windy and cold, so be sure to dress warmly. Also, be careful not to leave anything of value in your car; signs in the parking lots warn of smash-and-grabs. To get there: if you're coming from the west side of the city, heading east on Portola, just past where Woodside Avenue and O'Shaughnessy Blvd. meet, take a left turn at the next light onto Twin Peaks Blvd. If you're coming from the downtown area, follow Market Street west all the way to the top of the hill where the name changes to Portola Drive, then turn right onto Twin Peaks Blvd.
The Painted Ladies
Our final stop for the day was to see The Painted Ladies -- the iconic and highly photographed row of pastel-colored Victorians set against the backdrop of San Francisco's magnificent, vaulting skyline. Standing shoulder to shoulder on the gentle incline of Steiner Street, they face westward into Alamo Square Park where, on a clear, warm day like ours, hundreds of people lay out on the grassy slopes of the park to take in the views, meet with friends, or enjoy a picnic. The park is just four city blocks square, occupying a small hill at its center and surrounded by beautiful Victorian and Queen Anne style homes on all sides. There isn't much available street parking, so finding a spot to leave your vehicle may be challenging. We were extremely fortunate to find not only an open space next to the park, but one large enough for our enormous car. It gave us plenty of freedom to explore the park and get some great photographs.
Dinner that night was at an Italian restaurant within walking distance of our hotel. We ate at L'Ottavo Ristorante, located at 692 Sutter Street (415-922-3944). There was plenty of seating; no waiting to get a table. The food was quite good and well priced by comparison to other eateries we looked at in the area. I ordered the penne with spicy Italian sausage, pictured below.
In the Next Installment ... I'll continue the story as we journey on to the Napa Valley and then on up to Lake Tahoe and beyond, sharing more hotel and dining recommendations, as well as fun activities. Until then, dear travelers, may all your journeys be safe and rich in experience!