Curator’s statement
As a kid, I spent many summers with my grandmother in San Francisco, so it holds a special place in my heart. As an adult, San Francisco is a great spot for its own city stop or as a gateway to wine country. From its great food to its history, San Francisco is perfect for a long weekend with your loved ones.
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Day 1: Cable cars, crooked streets

After you drop your stuff at the hotel, let's ride the iconic Cable Cars to get a feel for the city.
The boarding area at the waterfront can be busy, with lines up to an hour-long. So let's try to hack the system. You can get on a car faster by walking a few blocks over to the intersection of Taylor and North Point streets to catch the Powell-Mason line. You're going to ride this up the hill towards Union Square. Get off where it ends at the intersection of Powell and Market Streets. Union Square is home to Bloomingdales, Macys, and 170 other shops and restaurants.
After some shopping, take the Powell-Hyde Line from Union Square to the top of Lombard Street. Get off and walk down the "crooked" street. Then head to Fisherman's Wharf to visit Ghiradelli Square, Pier 39 and grab dinner and an Irish Coffee at the Buena Vista Cafe.
Day 2: Seaside sights

The best way to experience the Golden Gate Bridge is on a bike. You miss so much in a car, and it's too much to walk. This tour will take you over the bridge to the town of Sausalito. It's known for its Mediterranean-like ambiance, scenic waterfront, cute shops and stunning views of the San Francisco skyline and bay. After the tour, you can hang onto your bike or take the ferry back to SF. (Golden Gate Bridge to Sausalito Guided Bike Tour
After returning from Sausalito, walk down the waterfront or Embarcadero until you get to the Ferry Building. The Embarcadero is the city’s east-facing waterfront, with its finger piers and glistening views of San Francisco Bay. It is where San Francisco had its first growth spurt, thanks to the California gold rush of 1849. The area gets its name from the Spanish verb embarcar, which means "the place to embark." From ferries to bikes, pedicabs, skateboards and F-train street cars hailing from all over the world, you'll see every way to embark imaginable.
The Ferry Building in San Francisco is a historic landmark and bustling marketplace located along the city’s iconic waterfront, where the Embarcadero meets Market Street. It was originally constructed in 1898 as the city’s primary transportation hub for ferry services. It has been beautifully restored and transformed into a gourmet marketplace and cultural gathering spot. Finish your Seaside Sights with some shopping and dinner at the iconic Ferry Building.
Day 3: Historic haunts
Get a later start to your day! After all, you'll be worn out from all the sun yesterday. Today, get to know San Francisco through its food. A walking tour will help you learn a little more about the cultures that add to San Francisco's rich history.
There's no better way to learn about a culture than through its food. Enjoy your afternoon enjoying some dim sum and moon cakes. Then head to North Beach, San Francisco's Italian neighborhood to finish with cannoli and pizza!
Finish your day with an infamous tour of Alcatraz. I'd highly recommend doing the Alcatraz Night Tour. Going at night means smaller crowds and eerier vibes.
Day 4: Wonders in wine country

No trip to San Francisco is complete without a trip to wine country. A personalized tour gives you a little taste of everything. You'll get time in both Sonoma and Napa to explore, two wine tastings at boutique wineries and stops at iconic sights along the way.
Day 5: Cycle the city

Make the most of your last day in San Francisco with an e-bike tour. It will help you see Little Italy, the Mission District and the Castro neighborhood. The most exciting is the Painted Ladies (made famous by Full House). Don't worry, you can leave your luggage with the hotel before picking it up to head back to the airport.

Travel Advisor
Angela Tucker

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This itinerary is part of our ongoing series on travel to San Francisco. For more travel tips, check out Irving Macario’s guide, Weekend Getaway to San Francisco, California.