San Francisco in 4 Days: From City Streets to Wine Country

San Francisco

Sometimes, the best way to escape from your monotonous routine is to change your skyline views. That’s exactly what I did when I hopped on a flight from Boston to San Francisco for a much-needed escape. I wanted a mix of city buzz, coastal beauty, and a touch of wine country, and somehow, San Francisco delivered all that and more.

Getting There and Checking In

I flew via Alaska Airlines from Boston Logan International Airport on a 6.5 hours long direct flight and landed at San Francisco International Airport (SFO) around 12:30 PM. After grabbing my bags, I headed straight to my hotel, which I booked near Downtown, to freshen up and drop off the stuff. I always recommend booking something central; you’ll save a lot of time getting around. We stayed within reach of the main attractions, which made things super convenient.

SFO

Day 1: San Francisco City Sighting

I started my adventure with a stroll through Downtown San Francisco, passing by the hustle, the hilly roads , and the iconic cable cars crossing through intersections. My first stop was the Union Square, a lively plaza surrounded by big-name stores, hotels, and cafes. The highlight of this spot is the giant red heart sculpture right in the middle of the square.. It’s part of San Francisco’s “Hearts in SF” public art project.

Downtown San Francisco

Union Square was a happening area with tourists posing by the “Union Square” pavement marker and musicians/street artists performing making the vibe energetic.

From there, I walked up to Washington Square Park in North Beach. Locals were relaxing on the grass, some were playing with their dogs, and others were just soaking up the sun. You get a great view of Saints Peter and Paul Church, which adds a bit of charm to the skyline.

Saints Peter and Paul Church

By late afternoon, I made my way to the waterfront. Pier 43 and Pier 39 are must-visits, especially for first-timers. Pier 39 had it all, views of Alcatraz, barking sea lions, and plenty of quirky shops and snack spots. I stayed until sunset and had dinner right there by the water. I recommend grabbing a seafood dish, clam chowder in a sourdough bread bowl is the classic. You can eat it while watching the sky go golden over the Bay.

Pier 39 SFO

Day 2: Parks, Views, and Classic San Francisco Spots

This was my full exploration day. I started early at Capitol House, the architecture of which reminded me of the Harrisburg Capitol Building in Pennsylvania.

San Francisco Capitol Building

I then went down to Sue Bierman Park. It’s a small, peaceful green space near the waterfront, a perfect breather before diving back into the urban buzz. From there, I headed into the Ferry Building Marketplace, which was a heaven for foodies. Local cheese, artisan bread, oysters, fresh produce, and the smell of just-brewed coffee everywhere.

Sue Bierman Park
Sue Bierman Park
Ferry Building Marketplace
Ferry Building Marketplace

From there, I hit Rincon Park, which is within walking distance from the Ferry Building and a perfect photo spot.

Rincon Park
Rincon Park

Then came one of my favorite parts of the day, Telegraph Hill and Coit Tower. The walk up was a bit of cardio with a lot of steps, but it’s absolutely worth it. Once at the top, I went inside Coit Tower, tickets were $10 per adult (cash or card accepted).

Telegraph Hill
Coit Tower

The murals on the first floor are beautifully preserved scenes from the 1930s, painted during the Great Depression. But the real showstopper is the 360° panoramic view from the top. You can see the Golden Gate Bridge, Alcatraz, the Bay Bridge, and the downtown skyline all at once. It’s honestly one of the best views in the city.

After coming down, I strolled through Pioneer Park, which wraps around the base of the tower, and then I made my way west, stopping at the West Bluff Picnic Area. I sat there for some time soaking in the majestic views of the engineering marvel – Golden Gate Bridge, perfectly framed in the distance. It’s a wild feeling, huge, silent except for the wind, and absolutely stunning.

West Bluff Picnic Area, San Francisco

I headed back to the hotel tired, but totally satisfied with how much I managed to squeeze into one epic San Francisco day.

Summary of The Places to Visit

Here is a quick summary of places you can visit in San Francisco in chronological order:

DAY 1

  • Downtown San Francisco
  • Union Square
  • Washington Square Park
  • Pier 39

DAY 2

  • Capitol House
  • Sue Bierman Park
  • Ferry Building Marketplace
  • Rincon Park
  • Levi’s Plaza Park
  • Telegraph Hill
  • Coit Tower
  • Pioneer Park
  • West Bluff Picnic Area
  • The Presidio
  • Fort Point Viewpoint

By the time I got back to the hotel, my legs were sore and the phone was full of photos, but it was the kind of tired that feels good. San Francisco had already surprised me in the best ways, and I still had more to come.

San Francisco

Next up: A day in California’s wine country, a stop in picture-perfect Sausalito, and one last golden sendoff before flying home. Stay tuned for Part 2 of the adventure.

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