The City by the Bay: A San Francisco Vacation Guide

“Only in San Francisco.” You’ve likely heard the phrase, but its meaning doesn’t truly come alive until you experience the city yourself.

We visited the City by the Bay for the first time in early August, and it didn’t take long to see why it’s one of the most talked-about destinations in the United States.

Fog rolling over the Golden Gate Bridge, tourists riding cable cars up steep hills, packed concerts at Golden Gate Park, neighborhoods with entirely different personalities, and a lively waterfront all come together to create a uniquely San Francisco experience.

By the time we ferried across the Bay to Alcatraz and took the self-driving Waymo car around town, we understood that San Francisco isn’t just a list of attractions. Instead, it’s an experience that unfolds through its sights, sounds, and flavors.

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Historic Hotels With a San Francisco Story

We called the InterContinental Mark Hopkins home for the week, and it was fabulous. Located high on Nob Hill, this historic hotel has been an integral part of the city’s story since 1926, occupying the site of railroad magnate Mark Hopkins’ former mansion, which was destroyed during the 1906 earthquake and fire. The hotel’s architecture, grand yet welcoming, reflects the elegance of its era and the optimism of a city rebuilding itself.

For those of you who are wondering who Mark Hopkins was, he was one of the “Big Four” railroad barons who helped finance and build the Central Pacific Railroad, which later became part of the first transcontinental railroad in the United States.

Amenities include a fitness center, valet parking, two on-site restaurants (including Nob Hill Club and the famed Top of the Mark sky lounge), daily housekeeping, EV charging stations, pet-friendly accommodations, and business services.

Top of the Mark sits on the 19th floor and first opened in 1939. It became famous during World War II as a gathering spot for servicemen and their families.

Legend has it that soldiers heading off to the Pacific would share a “last drink” here before deployment, giving rise to its reputation as a place of both celebration and farewell.

Today, Top of the Mark continues that legacy with sweeping 360-degree views of the city and the Bay. The lounge offers a refined menu of cocktails and small plates, afternoon tea on weekends, and live music on select nights. My husband and I enjoyed the charcuterie plate, a birthday dessert, and incredible views of the sparkling city at night.

During our stay, I was lucky enough to tour each room type they offered, which includes standard rooms, junior suites, one-bedroom and terrace suites, as well as specialty options like the California, Nob Hill, Mark Hopkins, and Presidential suites that felt more like private residences.

Needless to say, there are options for every type of traveler and every kind of stay, whether you’re looking for a comfortable room for a weekend visit or a glamourous suite designed for entertaining and extended time in the city.

San Francisco has a way of offering experiences that feel completely its own. These aren’t just things to do. They’re the essence of what makes this city so unique.

We toured the city with San Francisco Love Tours, and it was like seeing San Francisco through the eyes of a local.

The vintage VW bus set the mood right away, giving the day a fun, nostalgic feel. Our guide, Tara, included history with humor, pointing out well-known landmarks while also sharing little-known stories.

At stoplights she blew bubbles out the window, and it was impossible not to notice how people lit up and flashed peace signs at the sight of the bus.

The small group size made the tour personal, giving us plenty of chances to ask questions without ever feeling rushed. By the end, we left with not just photos, but a deeper understanding to San Francisco’s culture.

When we visited Fisherman’s Wharf the atmosphere was lively with street performers, playful sea lions at Pier 39, plenty of shopping, family-friednly entertainment like the SkyStar obersvation wheel and a carousel, and countless places to enjoy a meal with a great view of San Francisco and the Bay.

Boudin’s famous sourdough bread bowls filled with chowder are incredibly popular here, and Trish’s Mini Donuts are always a good idea for a sweet treat.

We were craving seafood, so we stopped at Crab House at Pier 39. Walking to our table, it was clear that ordering a whole Dungeness killer crab was the thing to do.

We started with crab nachos, which came as an incredibly generous portion, before moving on to the main event: a two-pound crab cooked in their secret garlic sauce. It was perfect for sharing after such a big appetizer, and the views from our table weren’t bad either!

Visiting Alcatraz Island began with a ferry ride across the Bay, where we enjoyed views of the San Francisco skyline and the Golden Gate Bridge.

Once on the island, we were greeted by a National Park Ranger who went over our options for exploring with some great tips on parts of the island that are often overlooked. There were lots of old buildings, guard towers, and great views of San Francisco.

We started with the self-guided audio tour through the prison, which was our favorite part. Narrated by former guards and prisoners gave the experience a vivid sense of daily life inside and stories of daring escape attempts.

After the prison tour, we wandered around the island and found several spots with some of the most amazing views we’ve seen of the city.

You can buy tickets for day and night tours via Alcatraz City Cruises, but there are other options like combining Muir Woods, Sausalito, and Alcatraz during a full-day tour and even an Alcatraz night tour and bay cruise.

The Golden Gate Park weekend we experienced was electric! Dead & Company’s three-night performance at the Polo Field celebrated 60 years of the Grateful Dead, drawing close to 60,000 fans from across the country each evening.

The crowd spanned generations, with tie-dye filling the fields, special merchandise marking the milestone, and guest appearances from artists like Billy Strings, Sturgill Simpson, and Trey Anastasio.

Beyond shows like this, Golden Gate Park is also home to major annual festivals such as Outside Lands, which combines music, art, and food; Hardly Strictly Bluegrass, a beloved free event each October; and Litquake, a literary festival that brings authors and readers together in the fall.

Kayaking the San Francisco Bay with City Kayak was a memorable way to see San Francisco from a different perspective.

Paddling out onto the water gave us front-row views of the Bay Bridge, the city skyline, and even passing ferries and sailboats.

The experience was both peaceful and energizing, with calm stretches near the shoreline and moments of excitement as the water opened up around us.

City Kayak made it easy, with equipment and guidance so we could simply enjoy the scenery and the adventure.

San Francisco’s Japantown is the largest in the United States and one of only three remaining in the nation.

When we visited Japantown, we were lucky to experience the Nihonmachi Street Fair, a community celebration that has been bringing people together for more than 50 years.

The streets were packed with food stalls serving everything from sushi to barbecue, along with vendors selling handmade crafts, art, and cultural goods. Stages were set up for live music and performances.

You can also explore Japantown’s other highlights, like browsing the shops inside Japan Center Malls, relaxing at the Peace Plaza with its five-tiered pagoda, or enjoying authentic ramen and sushi at the neighborhood’s many restaurants.

The Church of 8 Wheels is unlike any place we’ve skated before.

Once the Sacred Heart Catholic Church, built in 1898, it was transformed in 2013 by David G. Miles Jr., known as the “Godfather of Skate,” into San Francisco’s roller-disco haven.

Today, disco lights bounce off stained-glass windows while DJs and hype men keep the energy alive, while visitors lace up to skate beneath the old stained class windows.

Themed nights like Goth Skate or Silent Disco keep things fresh, and at its core, the mission of Church of 8 Wheels is about more than skating: it’s about community, inclusion, and the joy of movement on wheels.

San Francisco’s dining scene is packed with legendary spots, and some restaurants have become part of the city’s story just as much as its landmarks. For a taste of true classics, a night out at these long-standing favorites is an experience we loved.

Dining at the Tonga Room & Hurricane Bar is a San Francisco tradition that feels like stepping into a tropical oasis. Inside the Fairmont Hotel, this tiki-inspired restaurant and lounge has been serving guests since 1945, complete with a central lagoon (a former pool) where a band plays on a floating stage.

The atmosphere comes alive with periodic simulated rainstorms, while the menu features Polynesian-style dishes and classic mai tais.

We enjoyed the Tonga pupu platter to start, and then shared the seafood coconut curry which was an incredibly generous portion and perfect for two.

Fior D’Italia holds the title of America’s oldest Italian restaurant opening in 1886, serving the community for over 138 years! Serving hearty classics in San Francisco’s North Beach neighborhood, the menu is filled with traditional Italian favorites like house-made pastas, and rich sauces in a warm, old-world setting with live music.

We started with clams and mussels in a garlic broth which was perfect for sharing. For the main course, I tried the highly recommeneded gnocchi in a creamy tomoato sauce. The gnocchi was incredible soft and the flavor of the sauce was mouth watering. My husband decided to try the osso buco, a slow-braised veal shank, and he cleaned the entire plate!

San Francisco is an incredible destination in itself, but part of the experience of visiting lies in the easy day trips just outside the city. A short drive or ferry ride can take you to charming waterfront towns or quiet outdoor escapes, giving you a chance to experience more of Northern California without straying far from beyond the Bay.

We took a half-day small-group tour that included both Sausalito and Muir Woods, which we highly recommend if you don’t have a car.

Just across the Golden Gate Bridge or a short ferry ride across the Bay, Sausalito feels like a charming retreat from the city. I recommend taking a ferry for the views!

The waterfront town is known for its art galleries, boutique shops, and colorful houseboat communities that line the marina. Did you know Otis Redding’s Dock of the Bay was written in Sausalito? We spent time strolling the Sausalito’s cute streets and took in the views at Dunphy Park before heading to lunch.

Searching for the perfect spot with views, we chose Barrel House Tavern. Arriving early before the lunch crowds, we were lucky enough to snag seats overlooking the Bay. The setting was relaxed yet upscale, and the crab cakes and burgers are highly recommended!

A short drive from the city brings you to Muir Woods National Monument, one of the most peaceful escapes in the Bay Area. The park is home to giant redwoods that create a quiet, cathedral-like atmosphere as you walk the trails beneath them.

There are easy loops with well-maintained wooden paths, as well as longer hikes. The tallest tree in Muir Woods is over 250 feet high, and many of the redwoods are between 600 and 800 years old, with some that have been around for more than 1,000 years!

The cool air and filtered light through the towering trees made it easy to slow down and take in the park’s beauty. It’s a great way to experience the peacefulness of the outdoors away from the city.

A trip to San Francisco comes with its quirks, and knowing a few insider tips can make your visit smoother and more enjoyable. From unpredictable weather to unique ways of getting around, here are a few things to keep in mind before you go.

Layers are essential in San Francisco. The weather can shift quickly from sunny and warm in one neighborhood to cool and breezy just a few blocks away, especially near the water. A light windbreaker and sweaters are a good idea, even in summer.

The city is compact, but its famous hills make getting around an adventure. We used a mix of walking, rideshares, and public transit like Muni buses, historic streetcars, and cable cars. Ferries and even self-driving cars like Waymo are also convenient ways to explore.

Did you know San Francisco residents have a name for the fog? Yep, its Karl! On summer afternoons it often rolls over the Golden Gate Bridge and into the Bay, cooling things down in minutes. Locals embrace Karl as part of the city’s character, and you’ll even find social media accounts dedicated to his daily appearances.

San Francisco is a city that leaves a lasting impression, not because of any single attraction but because of the way it all comes together.

History, neighborhoods, food, culture, and incredible views. From ferry rides across the Bay to nights spent in historic hotels, each experience feels distinctively San Francisco and we hope you get to experience it for yourself!