©2019 by The Directionally Challenged Traveler. 


Mays Destination - San Francisco

San Francisco was always a magical place in my mind.  Numerous movies from my childhood took place there, Homeward Bound and Mrs. Doubtfire being on the top of that list.  I know, Full House was also filmed there, but I just wasn’t really a fan of that show (please don’t hate me). The city is one of the top places to see in the United States and is even sometimes called the Paris of the West.  It has a naturally romantic, laid back feel and is the perfect place for a long weekend getaway.

Day 1: The Waterfront

The first day in San Fran would be spent down by the water.  Fisherman’s Wharf is one of the most popular tourist destinations in the city, and for good reason.  While it does have a lot of souvenir shops, it does have some of the best seafood in the city. If you wanted to skip your hotel breakfast, you could grab some caffeine and crepes in the wharf and enjoy watching the city wake up around you.   Fisherman’s Wharf currently rests on land created by the rubble of buildings that were lost in the earthquake and fire of 1906. Before that, it was known as Meigg’s Wharf and was the main port of entry to San Fran for many industries. For more about the history of Fisherman’s Wharf, click here.

There are so many shops and places in the Wharf, but the one you don’t want to miss is Pier 39.  Think of it like a carnival almost every day - cotton candy, balloons, games and shops. If you’re lucky, you may be able to spot some sea lions resting in between the piers.  There is also Ghiradelli Square, and you guessed it, all of your chocolatey dreams can come true. If chocolate isn’t your thing (how dare you!), there are other places to eat and even a brewery.  


From Fisherman’s Wharf you can see both the Golden Gate Bridge and a small island.  That island is Alcatraz. Alcatraz is one of the most famous prisons in America and its most famed prisoner was Al Capone. I highly suggest taking a guided tour to learn about how the island went from a simple lighthouse to a notorious, un-escapable prison.  Since you have to take a ferry to the island and back, this will take up most of the afternoon.


Alcatraz by Out Chasing Stars

Sea lions at the Pier by Out Chasing Stars

Next, it’s up to you how active you want to be.  You can either climb the famous hills of San Francisco (and get calves of steel) or you can ride the trolly to the top of Russian Hill neighborhood. Here’s where you’ll find Lombard Street, probably the most photographed street in America.  Most people think it’s the most crooked street in San Francisco (and that is what it is known for) however, that title belongs to Vermont Street. But Lombard has better flowers, scenery, and views. You can also watch more cars struggle to get down the hill as you walk down.  There are stairs to walk down so you do not have to walk along the cars.


At the bottom of Lombard Street, you’re not too far away from Chinatown.  San Francisco’s Chinatown is the oldest in the country, being built in the 19th century.  Upon entering Chinatown, you’ll feel like you’re teleported into China. There are lanterns everywhere, the Dragon Gate, and friendly people.  For a really authentic experience, visit Stockton street. There’s better prices, fresh food stalls (including fruit and fish!)

View of San Fran from Lombard Street by The Wheel Traveler

Grab dinner in Chinatown before heading back to your hotel.  Stockton Street is where all the locals go, plenty of delicious food can be found on every corner.  


View of China Town by The Wheel Traveler

Day 2: Active City Day

This day is a bit active - wear comfortable shoes.  After breakfast, it’s time to get up close and personal with the Golden Gate Bridge.  One of the best ways to see the bridge is by bike. So rent one and enjoy the views of and from the bridge.  Visit Sausalito and the view point for some breathtaking views of the bridge and bay. Just south of the bridge is the Golden Gate Park which is a great place for a picnic lunch!

The afternoon should be spent exploring The Painted Ladies.  Well known as the houses on Full House, it is a row of elegant Victorian and Edwardian houses painted in pastels.  With the city in the background, the row really brings out the quaint charm.   Not too far away, there’s another house worth visiting. You guessed it, the Mrs. Doubtfire house!!  It’s a private residence, so you can’t go in (other than the outside shots, the movie was filmed on a set anyway), and be polite if you snap a picture.

For your last night in San Francisco, there’s no better way to see the lights of the city than Treasure Island.  There are a few wineries on the Island, including Fat Grape Winery where you can drink wine fresh from the barrel.  There’s also Sottomarino, where you can taste wines in the USS Buttercup, a submarine training vessel.

More about San Francisco

The two blogs featured in our Dream Itinerary of May have been very inspiring.  The Wheel Traveler  blogs about traveling the world while being in a wheelchair, not letting anything stop her from seeing the world!   Out Chasing Stars sees the world via sailboat, which is definitely a unique way of seeing everything. 

This post contains affiliate links which I would receive some compensation (and I am grateful for) at no extra cost to you. 

Pin this Post for Later
How to Spend Two Days in.jpg