San Francisco, CA: An itinerary that surely won’t disappoint.

My husband and I love travelling and exploring, and simply, just being together. Every summer, we try our best to plan a trip with friends or a trip for just the two of us. This summer, we decided to plan a trip for just the two us to explore the fun, eclectic, and beautiful city of San Francisco, California. We have heard so much about the city, the bay, the attractions, and all the fun things you can do, so we decided to check it out for ourselves. Neither of us has been to California or spent much time out west, so we decided to book a flight and hotel and head west for a one week vacation/exploration to San Francisco, California.

My husband and I are planners but we like to keep our travel itineraries light with plenty of room to fill in the blanks. Now, don’t get me wrong, we always plan out the essentials: flight, hotel, and transportation. However, we leave the rest to curiosity and spontaneity. For San Francisco, we had a pretty comprehensive list of things we wanted to see and do, but as we ventured into one local place after another, we asked the locals to help us fill in the blanks.

We have since returned from our trip and had an absolute blast. My husband and I both agreed that we could not let the details of our trip go without being shared with others to also enjoy, so I’ve committed to sharing our updated itinerary with all the details and tidbits of information we learned from our trip on my blog. The goal is to build a running list of several itineraries we’ve created and experienced to share with readers, but to primarily share the raw and honest details that you don’t always get in your planning efforts.

Lombard Street

GG Bridge


The Good:

  • The weather is fabulous during the day!
  • It’s very easy to get around so there isn’t a need for a rental car. (Unless you prefer to have your own wheels! However, consider this a warning, parking is charged daily and is very expensive, so be prepared to pay a hefty price!)
  • There is so much to do and see that you could easily spend four days to a week and a half depending on what you pack into your trip. Needless to say, you will not get bored.
  • The people are wonderful and very welcoming. The residents of San Fran and nearby cities recognize and understand the city is a touristy place, but they very much appreciate the business and are happy to share details about their city and great local places to check out. You just have to ask!

The Bad:

  • The temperatures are colder in the morning and at night, so dress in layers! This can often be annoying if you plan on being out from morning through evening and don’t plan on pit-stops to your hotel or carrying a backpack. One minute you’re chilly and the next you are burning up. (See second bullet.)
  • The hills. The city of San Francisco is built on hills. What you’ve seen in the movies and on TV shows is no joke. The hills are often steeper than 45 degrees. That being said, you might be burning up walking up one of those steep hills, but once you are at the top and catch that wind you are instantly chilly.
  • San Fran is a very touristy city. There are people from all over the world that travel to the city for the same reasons we travel to the city: to see what all the talk is about. That being said, the crowds are often big, the sidewalks are busy, and depending on what you have planned there might be lines. (I’m not saying this is a terrible thing, it just requires patience and understanding.)

The Ugly:

  • San Fran is very expensive. I view San Fran as the New York City of the west coast. Like I said before, it’s a popular destination for tourists from all over the world, so prices are inflated in popular areas such as Fisherman’s Wharf, anywhere along the bay, and around Golden Gate Park. San Fran is sectioned off by districts and I recommend checking out Little Italy (North Beach) and China Town for reasonable prices on food, drinks, and souvenirs.
  • There is a lot of homelessness. I am certainly not saying homeless people are bad. However, homelessness is something that is conveniently left out of a lot of travel sites/blogs/etc. when describing certain travel destinations. Homelessness is an unfortunate reality for too many people, and I have found that homelessness populations are greater in high traffic tourist destinations and in places with more consistent weather patterns (i.e. New York City, Tampa, the Carolinas, and California.) All this being said, I think it is important to highlight that homelessness is a serious issue in San Francisco and it requires a level of awareness, understanding, and empathy when you plan to visit the city.

A few quick tips:

  • Weather (as told by the locals):

    • December-May is pretty chilly averaging around 50 degrees Fahrenheit during the day with colder temperatures in the morning and evenings.
    • June-August it starts to get a little warmer during the day averaging around 55-60 degrees Fahrenheit during the day with colder temperatures in the morning and evenings.
    • September-November is the best time to travel to San Fran because the temperatures are warmer during the day, the wind off the bay isn’t as cold, and the evening temperatures aren’t as chilly.
    • Overall, the weather in San Fran is beautiful with blue skies, mostly sunny, and very few chances of rain. Please keep in mind the Pacific Ocean is significantly colder than the Atlantic and Gulf. If you are used to the Great Lakes temperatures, then you will be perfectly fine. I just worry about the Midwesterners, Southerners, and east coast folks that are used to warmer waters. San Fran is on the bay (duh, I know!) and I say this only because the wind coming off the Pacific into the bay is cold and the wind can be ruthless. Be sure to pack layers and a wind-breaker if you have it.
  • Getting around:

    • Walking is the absolute best way to explore the city! Be sure to pack comfortable walking shoes or tennis shoes. You can certainly bring a cute pair of pumps or wedges for a nice evening out to dinner, but don’t plan on wearing those types of shoes during the day. For good foot health, I would also avoid flip flops or shoes without good arch supports. Like I said, walking is the best way to get around the city and you will do a lot of it, so you want your arches, your heels, and the balls of your feet to be supported and comfortable. Flips flops just don’t cut it.
    • Bikes are another great way to explore San Fran. There are several different bike rental companies spread out around the city with tons of different “drop off” points. My husband and I biked across the Golden Gate Bridge into Sausalito, and on a different day we biked the Golden Gate State Park to Ocean Beach, Lincoln Park, the Presidio, and dropped them off in the Marina District. We saw several people biking through the city, but I caution biking through the city because of the congestion, busy sidewalks, and smaller roads. It just becomes a little more dangerous. I recommend biking through the Golden Gate Park, along the Presidio, close to the Golden Gate Bridge (or across it), the Marina District, Fisherman’s Wharf, and along the Embarcadero.
    • The Pubic Transportation Systemà BART, MUNI, and Cable Cars. This takes a little self-direction and guidance, but it’s worth it. The BART stands for “Bay Area Rapid Transit” and takes you to limited places in the city because it primarily serves as a rapid transit for commuters into San Francisco and surrounding areas. The MUNI is the inner-city bus system that is your best bet for getting around if you aren’t into walking or biking. The MUNI will pretty much drop you off in the heart of the different districts of San Fran such as the Financial, Union, Mission, Civic, North Beach, etc. The Cable Cars, in my opinion, were hard to navigate and required standing in line because they are a popular tourist attraction. It’s worth getting on a Cable Car though just to say you rode one! Google Maps is your BEST friend when navigating the bus routes, stops, and streets you need.
    • To and from the Airport. On the way to our hotel from the airport, my husband and I took the BART to the Embarcadero Station on Market Street, which is one of the popular areas in the city. From there, we bought tickets for the “F-Line” (the street car) to Fisherman’s Wharf, which is where we stayed. From the hotel to the airport, we reserved a shuttle service with our hotel concierge that was relatively low-cost and took us directly to the airport.

Sunday, July 2

Flew from Cincinnati directly to San Francisco on Frontier. Frontier is not my favorite airline (that would be Delta for those interested in knowing, haha), but our tickets were priced well and it was a direct flight there and back. For us, Frontier worked out for this particular trip but in case you didn’t already know, Frontier charges $45 for checked bags AND carry-on bags so be prepared when they nickel and dime you.

We arrived to San Francisco, took the BART, MUNI, and F-Line (Street Car) to get to our hotel in Fisherman’s Wharf. We stayed at the Holiday Inn in Fisherman’s Wharf on Columbus Avenue because we got a good rate. I would recommend checking out Groupon, Living Social, AirBnB, and other travel booking sites for competitive rates.

After getting checked into the hotel, we spent the evening walking around Fisherman’s Wharf and indulging in an infamous clam chowder and sourdough bread bowl for dinner.

Financial District/Union Square


Monday, July 3

We wanted to grab breakfast at the Hollywood Café but the line was wrapped around the block with no end in sight so we ended up at Darren’s Café, which was very tasty and had great service!

We walked the entire city! No joke. My husband and I walked just over the equivalent of a half marathon on our first day in the city (13.66 miles). We started out in Fisherman’s Wharf and made our way to the infamous Lombard Street (“Crookedest” Street), walked through Russian Hill and then over to China Town. From there, we walked through China Town making our way towards the Financial District, Union Square, the Yerba Buena Gardens, and the Civic Center. After the Civic Center, we walked to the Mission where we stopped for dinner at El Techa (a great rooftop bar) and a few beers at Zeitgeist (see comprehensive list below.) After dinner and drinks in the Mission, we headed for a quaint little bar called “CC’s” just south of Pacific Heights or “Pac Heights.” At CC’s, we experienced the California Special which is a shot of Fernet. I strongly advise anyone and everyone to avoid this shot at all costs. The bartender and a few patrons at CC’s recommended we check out a pizza place around the corner and then head to “Buena Vista” for a famous Irish coffee, so we followed their directions! The pizza place we stopped at was okay, but not good enough to remember. However, the “Buena Vista” bar famous for their Irish coffee earned our business four of the six nights we were there. Again, see bar list below.

Tuesday, July 4

We rented bikes close to Ghirardelli Square and biked the perimeter of the bay following the pathway to the Golden Gate Bridge. From there, we biked over the Golden Gate Bridge, which I highly encourage if you’re up for the challenge. It’s actually not too bad of a bike ride, but there are a few hills you have to tackle. The view from the bridge is absolutely spectacular, but you have to see it for yourself to truly appreciate its beauty. After crossing the bridge, we biked down the hills into Sausalito, which is a quaint little town along the bay with a fabulous view of the city of San Francisco. Restaurants, breweries, and shops decorated the main strip of Sausalito, so it’s safe to say we also enjoyed our time on the other side of the bridge.

We were going to take the ferry from Sausalito back to Fisherman’s Wharf, but the ferry schedule was limited and delayed due to the 4th of July holiday. We ended up grabbing a taxi back to the Wharf, due to timing, because we booked a 4th of July Bay Cruise for that evening. The Bay Cruise was a bust because the fog was really bad that evening so we couldn’t even see the fireworks. That’s okay though! It was a gamble that we took.

Wednesday, July 5

We booked a Muir Woods/Sonoma Wine Country day tour that took up the majority of our day on Wednesday. Muir Woods is a must see if you are making the trip out to California! The redwood trees are God’s work right before you. They are so beautiful and so mysterious at the same time. The only logical explanation is God’s craftsmanship.

After our trip to Muir Woods, our tour bus/guide drove our small group (12 people total) to three wineries and a short trip to the town of Sonoma. Overall, the wineries were great. I mean, it’s wine, right? How can you complain about that? However, Benjamin and I live in Bourbon Country where spirits have a rich history and deep family ties. In my opinion, the particular wineries we visited lacked the history and identity we were expecting or hoping. Our favorite winery we visited was Jacuzzi! If you are making your way through Sonoma, I would strongly encourage you stop at Jacuzzi and check it out.

Thursday, July 6

Thursday was a pretty relaxed day! We were exhausted after three longs days of adventuring and excursions. We slept in and eventually made our way to Starbucks. From there, we walked to the Golden Gate State Park from Fisherman’s Wharf, which is a pretty lengthy walk. Once we got to the park, we rented bikes and biked the monstrosity that is the Golden Gate State Park. The park is enormous with so many different attractions. We took the bikes from the far east point of the park all the way to Ocean Drive. We followed Ocean Drive up to the Cliff House and just kept going. We ended up biking all the way back to the Marina District where we returned the bikes. We staked out a quaint place to take in the gorgeous sunset over the Golden Gate Bridge.

Friday, July 7

We were completely wiped out by Friday so we spent the entire day hanging out in the Little Italy and Chinatown districts just drinking and bar hopping. There is a spunky bartender at Northstar Café in the North Beach district (“Little Italy”) that gave us a laundry list of bar recommendations for that afternoon/evening. We followed suit. Comstock was one of the bar recommendations because on Fridays they give you a free lunch with a purchase of a beer. Granted, you only get one lunch option, but it doesn’t matter given that it’s free. There isn’t much to elaborate on for Friday because the whole day was spent drinking and hanging you at different bars talking and getting to know San Franciscans.

Free Lunch at Comstock!

Saturday, July 8

On Saturday, we bought tickets for the cable car so we could closeout our San Francisco experience. Our flight left San Francisco early evening on Saturday, so the day was spent walking around Fisherman’s Wharf for the last time, eating the last of the grub, and packing up all our souvenirs.

Riding the Cable Car

What we missed:

Monterrey Bay



The “42 Must See Bars in SanFran” (copied below) became a city guide for us. We planned our day around the districts we wanted to visit and the bars in those districts we had to check out. Let me tell you, we were not disappointed. We shared this list with every bartender we talked to because we needed confirmation that these places were worth our while. The bartenders put their stamp of approval on this list and agreed this is a comprehensive and impressive list for drinking enthusiast.

42 Must See Bars in SanFran 


Diners, Drive-Ins, and Dives


The Main Attractions:

Ferry Building
Golden Gate Bridge
Pier 39
Fisherman’s Wharf
Ghirardelli Square
Golden Gate Park (deYoung Museum, California Academy of Sciences, Rose Garden, Japanese Tea Garden, AIDS Memorial Grove, Conservatory of Flowers)

Ocean Beach
Alamo Square Park & The Painted Ladies
The Mission District
Ride on the Cable Cars and Street Cars
Haight-Ashbury District

Duboce Park
Dolores Park
The Castro (Castro St from Market to 18th; birthplace of the LGBT Civil Rights Movement)
The Women’s Building
Murals in the Mission (Clarion Alley)
The Embarcadero
Muir Woods
Point Reyes
Monterrey Bay & Aquarium