The Plane Nerd Trip Report: City by the Bay Getaway – San Francisco
Airline: Delta Air Lines
Flight: DL475 BOS → SFO
Aircraft: Airbus A321neo
Seat: 3D (First Class)
Wi-Fi: Fast, Free (Delta Sync)
Flight Duration: ~6h 15m
Lodging: Marriott Fisherman’s Wharf
Highlights: Embarcadero walk, USS Hornet Museum, Coit Tower views, Golden Gate Bridge, Waymo ride, Sausalito, Muir Woods, Oracle Park, Castro, Ferry Building
Vibe: Very active trip with hiking, boat rides, breathtaking views, rich history, classic San Francisco charm, and an easygoing California coastal feel.
Rating: ⭐⭐⭐⭐☆ (Highly Recommended)
City by the Bay Getaway
Thursday
Approaching 12:45 PM, I realized I was pushing my time limit, so I threw my away message up, scrambled to grab my stuff, and summoned an Uber. I live in South Boston, so it’s usually a quick fifteen minutes to Logan, but then again sometimes it’s forty-five. Welcome to Boston. I was heading to the City by the Bay to meet my other half, who was wrapping up a weeklong work trip.
Pro Tip: If you travel for work like we do, make it work for you—take advantage of these moments when the chance arises.
Heading to the airport for a pleasure trip still gives me that little excited knot in my stomach. I always look out the car window at other motorists, almost feeling bad they aren’t going anywhere and I’m off on an adventure. The ride was about fifteen minutes, and before I knew it, I was arriving at Boston Logan’s Terminal A Uber drop-off. The cabbie union still has a stranglehold on the city, and they’re the only ones who can drop off at the terminal.
A quick elevator ride to the fourth floor brings you to an air bridge leading to the ticket counters and gates. The TSA line wasn’t bad, save the CLEAR people cutting me off—but that’s a rant for another day.
This afternoon’s flight was a 2:30 PM Delta departure on an A321neo. I used miles to upgrade to First, so I was particularly jazzed to get this party started. Delta has two Sky Clubs in Boston—one near Gate A6 and another in the Satellite Terminal (connected by underground tunnel and people movers) near Gate A18. In my humble opinion, the one near A18 is a little better but… first-world problems, I know.
I grabbed some “free” food at the club and then went to the gate. Boarding was easy, and we pushed on time. The plane was clean, the seat comfortable, and the flight attendants cheery. I particularly enjoy Delta’s Fast, Free Wi-Fi, available on more than 900 aircraft, including all Airbus A321neo jets like the one I was on, plus every A321ceo, A320, A319, A220-100/300, and Boeing 737 and 757. It’s nice to be able to transition into airplane mode and stay connected right away.
For some strange reason, I’ve never been one for in-flight entertainment systems. I’m a millennial, but I come from an airline family, so I traveled a lot as a kid. The last time I really watched an IFE was probably when I was five, on a family trip to Disney on a Delta Lockheed L-1011, eating a meal in coach and watching Die Hard on a projector. I won’t go so far as to say I want to go back to those days, but it’s a fond memory.
For those who do partake, this Delta neo had a large screen and a good selection. Wi-Fi was strong, I got a ton of work done, and the in-seat power worked perfectly.
Dinner was a delicious ravioli dish with peas and tomatoes, along with chocolate cheesecake. DO & CO caters for Delta in Boston, and they do a fantastic job. I toured their facility during my airline days—first-rate operation, on-site kitchen, and fresh ingredients. Their dedication shows in the quality of the food.
Our route took us over the Great Lakes, across Wisconsin and Minnesota, and west over the Rockies toward California. The flight was smooth, I got plenty of work done, and we touched down at SFO around 11 PM.
I was meeting my partner Mike at the hotel, and if I’m being honest, I was a little unsure what to expect. I travel a lot, but this was my first time in San Francisco. I’d heard plenty on the news—and none of it good.
The Uber pickup area was a short walk from the terminal, and I was in the car within minutes. I kept my eyes glued to the window, taking in what little I could see in the dark. The former cop in me was quietly scanning the streets, curious to see if the “Skid Row” scene everyone talks about really lived up to the hype. Hard to tell much at night, though.
I arrived at the Marriott Fisherman’s Wharf about thirty-five minutes later. We said our hellos, I dropped my bags, and we went directly to In-N-Out, which is somewhat of a tradition for us. I went with a Double-Double Animal Style and a Neapolitan shake—because when in California, you do it right.
Friday
The next morning, we woke up to sunshine and took a gorgeous walk along the Embarcadero—a scenic waterfront boulevard lined with piers, shops, and views of the Bay Bridge. Palm trees line the road and the air smells like, well, California. If you haven’t smelled it, it’s hard to describe, but as an East Coaster, I love it.
The buildings along the water are whitewashed Beaux Arts style and converge at the Ferry Building, constructed in 1898. It was once one of the world’s busiest ferry terminals until the arrival of the Golden Gate Bridge.
A Crown Princess cruise ship was boarding at the pier, happy cruisers streaming in, and the breeze off the bay made the morning perfect. Not twenty minutes into our walk, a Waymo car passed by—one of those self-driving taxis covered in sensors and contraptions. We ended up trying one later in the trip, but seeing it roll by for the first time was wild.
We took a ferry to the USS Hornet, docked at the old Alameda Naval Air Station. As a World War II enthusiast, I couldn’t wait to see her up close. The Hornet is an Essex-class aircraft carrier turned museum—and it’s not just the ship that’s historic. The pier where she’s moored is the very spot where B-25 bombers were loaded onto the original USS Hornet for the legendary Doolittle Raid—an audacious strike on Tokyo just months after Pearl Harbor.
The self-guided tour was fantastic. We saw an Avenger torpedo bomber, the Apollo Block 1 command module, and an F-14 Tomcat, among other aircraft—we even squeezed into an astronaut suit. The amount of history in that one small space is pretty special.
After we disembarked, we walked back toward the ferry. The area is home to some black-site-looking buildings, and you can tell you’re on a former military installation by the markings on the road. There’s just this sense that a lot went down here. The ferry ride back was calm, the water smooth, the city hazy and beautiful.
Back at the Ferry Building, we stopped at El Porteño for some of the best empanadas I’ve ever had. From there, we walked through Levi Plaza (yes, the jeans people 😊) and started climbing Telegraph Hill. The stairs weave and bob through what seem like people’s backyards. The houses are built right into the hill—not sure how I’d feel living in one, but they’re a sight to see.
Atop Telegraph Hill sits Coit Tower, built in the 1930s with funds left by wealthy socialite Lillie Hitchcock Coit. Her will specified the money be used to add beauty to the city. The tower stands 210 feet tall, art deco in design, with interior murals painted by local artists as part of a New Deal program depicting everyday life in Depression-era San Francisco.
From the top, we had sweeping views of San Francisco, the Bay Bridge, Alcatraz, and the iconic Golden Gate. For anyone from Boston—especially Southie—Alcatraz holds a quirky bit of local history: Whitey Bulger, our infamous mobster, was briefly imprisoned there in the early 1960s. Other famous inmates included Al Capone, George “Machine Gun” Kelly,and the Birdman of Alcatraz.
The clouds lifted just enough for an incredible view of the Golden Gate Bridge. Completed in 1937, it was once the longest and tallest suspension bridge in the world, and it remains one of the most photographed.
We made our way back down toward the waterfront and stopped at Pier 39. The place was buzzing with tourists, sea lions barking on the docks, and a little yellow water taxi bobbing back and forth. We grabbed a bag of Trish’s Mini Donuts, warm and sugary, and wandered for a bit before heading back to the hotel to freshen up.
That evening, we rode one of San Francisco’s classic streetcars up the hills on the Powell & Hyde line. The operator controlled everything with a single lever—it was wild to watch. The sound of the cable underfoot, the clatter of the wheels, and the steep climb were unforgettable.
We ended the night at Oracle Park for a Giants–Padres matchup. The crisp California air, the nosebleeds, the boats idling outside the right-field wall.
Saturday
The next morning, we woke up and headed to Alamo Square, home of the famous Painted Ladies—those Victorian-style houses most people recognize from the Full House intro. The park offers a postcard view of the city skyline behind the colorful homes.
After soaking it in, it was time to try something new: the Waymo. We climbed in, closed the doors, and buckled up. It felt surprisingly safe, though a little strange seeing no driver behind the wheel. The ride was smooth and quiet—a must-try experience.
We grabbed sandwiches and made our way to Dolores Park, a favorite hangout for locals. The weather was perfect, and the views of the city were stunning. After a relaxing lunch on the grass, we called an Uber and crossed the Golden Gate Bridge to Sausalito.
Sausalito is a small waterfront town just north of the bridge—one of the prettiest places I’ve ever been. The downtown area is quaint, full of small shops, galleries, and cafés. We grabbed ice cream, watched the boats in the marina, and admired the line of vintage yachts docked nearby. The whole town feels relaxed, with a stunning view of the San Francisco skyline across the water.
To get back, we boarded a Blue & Gold Fleet ferry, one of the Bay Area’s staples. The ride was breathtaking, with clouds spilling over Sausalito like a slow-moving waterfall. From the deck, we had incredible views of the Golden Gate Bridge, Alcatraz, and the entire bay glistening in the afternoon light.
Once back in the city, we returned to the hotel and later went out for dinner at an Italian spot near Telegraph Hill. Afterward, we walked through Washington Square and made our way to Ghirardelli Square—a dream for anyone who loves chocolate. The smell alone could keep you there for hours.
Sunday
The following morning, we headed back over the Golden Gate to Muir Woods National Monument. It’s one of those places that makes you stop and appreciate how small you are. The redwoods tower hundreds of feet overhead. We did the Bridge 3 Loop, a one-mile walk along Redwood Creek through Founders Grove and Bohemian Grove. The air was cool, pine-scented, and peaceful in a way that’s hard to describe.
After the hike, we took a scenic shuttle ride down the hillside to the Larkspur Ferry Terminal before hitching another ride across the bay. From there, we rented bikes from Blazing Saddles and rode to the base of the Golden Gate Bridge. It was a great ride, but very windy—check the forecast first if you try it!
After returning the bikes, we grabbed dinner and enjoyed one last evening walk along the waterfront.
Go-Home Day
The next morning, we visited Lombard Street, the famously crooked road in San Francisco. Watching cars zigzag down the steep turns was the perfect way to wrap up the trip.
From there, we packed up, headed to the airport, and caught our Delta flight back to Boston. Everything went smoothly, and as we watched the California coast fade beneath us, we both agreed that San Francisco was absolutely worth it.
There’s no denying the city has its issues with crime and homelessness, but they’re concentrated in certain areas that can be avoided. Keep your head on straight, eyes open, and do your research. If you take a Waymo in SF, stay in safe areas—it’s still learning.
The San Francisco we experienced was vibrant, scenic, and full of charm. Flying is second nature to me, but a transcontinental long weekend isn’t for everyone. Still, I’d call it a must-see destination for anyone looking for an active, scenic long-weekend escape.
Mini Vlog Coming Soon — Stay Tuned!