“We want you to travel back to one of your least favorite cities,” the note read. ‘I’m used to getting a lot of weird emails, but this one I had to take a second look at. Yes, it said “least favorite city”, I wasn’t imagining it. Now you have my attention. I love things that surprise me, so when I was asked what my least favorite city was, with the opportunity to go back and have a do-over, I was intrigued.
I have a list of least favorite cities, we all do – right? They get that designation for all kinds of reasons; they are loud, polluted, poor transportation, you had a bad memory there, it’s unsafe, an ex-boyfriend lives there, or maybe you just were burned out and your frustration was taken out on that city. I started going through my list in my head; Cairo, Los Angeles, Miami, Dallas, London. I landed on Oakland, California.
Table of Contents
Why Oakland?
It was a place I visited only a couple of times when I lived in San Francisco 16 years ago. Oakland had a reputation back then, a bad one. It just seemed like a gritty, old, tired city. And why would I want to spend time in a tired city when I was living in one of the best cities in the world just across the bay?
Gritty Port of Oakland in the shadow of San Francisco
It’s been 16 years since I’ve been to Oakland, it was time to go back and give it a second chance. I had heard it had changed, but I still had a hard time seeing it as a cool destination due to my past experiences there.
The First 24 Hours of Vacation is the Most Important
According to a recent survey done by Booking.com, the first 24 hours of a holiday are crucial, the first day sets the tone for the rest of the holiday. These hours can make or break a trip. Armed with my new Booking.com research data on how to ensure a successful first 24 hours, I took off to Oakland for a do-over for 24 hours.
How to Get into the Vacation Mode
You want to get in that vacation mode as quickly as you can so that means leave your worrying behind. The research shows that the things we worry about going wrong on vacation seldom actually come true – so why worry! Instead start to do productive things that can get you in the vacation mode sooner. The first 24 hours are about relaxing and resetting. I picked out some of the ideas from the research and gave them a try.
Research in advance: I seldom do this, but I did actually try it for this trip. I searched websites and called a friend who lived there and got initial research ideas from her. It’s weird (and nice!) going to a place prepared, I seldom ever do that!
Enjoy the Journey: Like the last one, this tip was pretty obvious too – but also hard to follow at times. To enjoy the journey you should make sure you aren’t rushed and get to the airport early and have a drink or food and relax. I failed at this one. I was running late as usual and found myself grabbing a burrito quickly and running to my gate! However one thing I normally do it to take pictures of the takeoff and landing and share on my social media as it gets me excited about the journey.
Home from Home: They suggested bringing an item from home to make you feel comfortable and relaxed in your hotel room. I love this idea because I’ve been doing it for 10 years already. I travel with my little personal pillow everywhere I go – and it immediately makes me happy every night when I lay down to sleep. I often also bring a coffee travel mug and my Manduka travel yoga mat. All of these items helped me get grounded and feel happy.
Instant Calm: There’s no way better way to instant calm than applying a little self massage and pressure points according to Booking.com. This tip was new to me, but I was happy to try it. I was staying in Jack London Square right near Chinatown. In my initial pre-research I found a reflexology massage place in Chinatown and booked an appointment for when I arrived. It was absolute bliss. I walked out of Angel Feet Reflexology like a wet noodle…and oh so relaxed.
Be a Super Hero: In an effort to start your vacation fresh, they recommended to be a super hero. I figured what the hell…I went out on my giant hotel balcony, placed my hands on my hips, and stuck my chest out. They suggested I hold the pose for 90 seconds while taking three deep breaths. Done…I felt like superwoman…a really, goofy, superwoman.
Live Like a Local: This Booking.com tip wasn’t new to me, I’ve been preaching this for a while during my travels. One of my favorite things to do is try to travel as local as I can. So this recommendation was easy for me, much easier than the super hero pose! I contacted my former colleague and friend, Colleen, who has lived in Oakland for over 16 years! She was the perfect person to give me advice on what to do in the city and she’s also seen it go through gritty to pretty over the years. Thanks to Colleen, I had a plan and a local friend to travel around with.
Colleen showing me around the cemetery!
Since I had set myself up for success with these tips, I was now ready to really get out and explore Oakland – in only 24 short hours!
Fun Things to do in Oakland with 24 Hours
Grand Lake/Lake Merritt
I met Colleen in the Grand Lake neighborhood and she introduced me to Lake Merritt. I love lakes in the middle of cities, especially when they have running/walking paths. Oakland has done a nice job of maintaining the paths and things to do around the lake which means that is a magnet for drawing in all types of people, making it a vibrant place for locals to gather.
Lake Merritt: You can obviously run or walk around the 3.5 mile path and see the whole lake, or simply check out the pergola built in 1913 if you are short on time like I was! It’s a lovely view of the lake, especially if there’s a nice sunset, which I wasn’t blessed with sadly. Also note the tree symbol on the ground in the Pergola, it’s the symbol of Oakland. Oakland used to be a giant oak tree forest, hence the symbol that you will find throughout the city on t-shirts, art, and basically everything!
Coffee Mill: Grab a coffee at the oldest coffee shop in Oakland!
Grand Lake Theatre: I didn’t have time to go to a movie – but if you do definitely stop here at this old institution. Check out the organ concert before the movie!
Shop: There are tons of cute shops along Grand Ave. It’s a nice mixture of new, hip stores and restaurants nestled among old bookstores, and sewing machine shops!
Piedmont Avenue
Colleen informed me to not confuse Piedmont Ave with Piedmont. Even though they are only blocks apart, Piedmont is not actually Oakland proper. And since my assignment was Oakland, I made sure to stick to Piedmont Ave. This neighborhood was another great example of local pride and old traditions.
Lo Coco’s Restaurant: Walk Piedmont Ave and you can’t miss it, there was a beautiful golden glow as patrons sat in the windows enjoying dinner, and others waited outside on the sidewalk for their table. A local neighborhood favorite if you have a craving for Italian food. They are known for their pizza’s but I ordered the hearty pasta with Bolognese sauce that had been simmering for 14 hours and topped with truffle oil – delizioso! Even on a Tuesday night this place was packed and we had to wait to get a seat – a good sign in a small neighborhood! Lo Coco Restaurant Website
Issues: A new throwback to the days of old; print magazines are not dead. This cute little store’s niche is print magazines from all over the world. You can find some of the normal names there, but what you’ll mostly find is obscure ones that are either so artsy or so niche that they only come out a few times a year. I loved this shop, I could get lost there for a while. They had some travel magazines I had never heard of before, but my favorite find was Guns and Gardens. I flipped through it and saw plenty of gardens, but wasn’t sure where the guns came in…thankfully. Issues Website
Rare Bird: Another store on Piedmont Ave that is part store, part gallery. The owner, an artist herself, wanted a forum to show her work. She came up with this community idea where she curates small, local artists’ work and sells it in the shop. You can get home goods, clothes, boom boxes, cards, prints, and jewelry in the store. It’s sort of like Etsy has come to life in brick and mortar! She also holds local art workshops in the space teaching sewing, candle making, carving, tapestry, encaustic wax, and more. She encourages locals and tourists like me to sign up to get off the computer and get in touch with your inner kid. If I only had more than 24 hours I would have loved to be a kid again! Put this on your list for unusual things to do in Oakland on your next trip! Rare Bird Website, Workshop Schedule/signup
Mountain View Cemetery: This was probably my favorite find in all of Oakland. First, I love to wander around cemeteries. However this cemetery had many other things that made it great. Cemeteries are normally private, but not this one. Mountain View Cemetery is not just a place for burying the dead, they want living people to enjoy it too. They’ve made it extremely accessible to the public and the locals seems to love it. They use it as a safe park in the community; people run, walk, and exercise here. Colleen even took her daughter here to teach her how to drive on the roads! Boy scouts come here, school groups, they have monthly tours lead by volunteer docents, and they even hold a Halloween festival for the kids with a pumpkin patch, face painting and games – INSIDE the cemetery!
As a tourist, the main reason to come here is to enjoy the view, the best view in Oakland. In addition the history is rich here – literally. The big Oakland and Bay Area moguls are all buried here in some incredibly architected plots. This is a must stop! Mountain View Cemetery Website
Chinatown/Uptown
An old friend of mine who lives in San Francisco took the trek under the bay to meet me for dinner in Uptown Oakland. I was telling her about all the great things I did in Oakland so far and mentioned how much I loved Chinatown. She looked at me and said – “I didn’t even know there was a Chinatown in Oakland!” Oakland’s Chinatown is actually the 4th largest in the United States. It’s not touristy, it’s real – and that’s why I loved it. It wasn’t lined with trinket stores – it was filled with restaurants, factories, and services the community actually used. I walked through the area a few times and really wanted to stop at every restaurant!
Angel Feet Relexology: There’s nothing fancy or spa like about Angel Feet, it had a definite Chinatown feel, but these are the places I love for massage. And it was cheap! I had a foot and full body massage for 75 minutes for $50. Stop here! Angel Feet Website
Sobo Ramen: There are plenty of hipster Ramen places around Oakland neighborhoods, but I preferred this old, local Chinatown favorite.
Fortune Cookie Factory: Did you know that the fortune cookie was actually invented in the Bay Area? The Fortune Cookie Factory in Oakland was a fun find I researched before I arrived in Oakland and found out they give daily tours of the factory. The storefront and inside are really simple – nothing fancy here. But this is a 3rd generation factory filled with Chinese women making tons of fortune cookies and folding them by hand. It was pretty impressive to watch. The youngest generation, Alicia, a recent college graduate is busy bringing this old tradition into the new world. She designs and makes new flavors (strawberry cheesecake, caramel, blueberry and more) that are delicious! You can special order them and even create your own fortunes if you’d like! Fortune Cookie Factory website
Oakland Museum of California: This is on the outskirts of Chinatown, but it’s the one place absolutely everyone told me to go see. The building has impressive gardens and seems to be built into a hill. They have special exhibitions here and a really cool permanent collection of California history. It’s filled with hands on exhibits. The museum lived up to all of the hype, and I’d recommend it as a stop for anyone visiting Oakland. Oakland Museum of California Website
Plum Bar and Restaurant: This was a cool spot with a heavy wood finish but some great cocktails and food to try in Uptown!
Flora and Fauna Bar: While in Uptown, we stopped in for dessert and a craft cocktail here. I loved the look of the place and the drinks were inventive!
Jack London Square
I stayed in this neighborhood at the nautical themed Waterfront Hotel. I stood out on my balcony and looked right and saw the massive cranes in the port, I looked left and saw the new restaurants, patios full of people, and live music. It was the perfect view of old port Oakland and the new Oakland. In fact trains ran right down the middle of one of the mains streets in Jack London Square. You couldn’t miss them as they’d lie on the horn as they came through on their way to the port. I loved this mix of old, gritty industrial and new.
Heinold’s First and Last Chance Saloon: This is a fun stop steeped in history. This national historic landmark built in 1880 is still running as a bar today. It was a frequent rendezvous of Jack London’s when he was a teenager. When I walked in I was surprised as it was like walking into a fun house. The bar, as well as the floor ,were slanted due to the 1906 earthquake. You had to make sure your drink didn’t slide off onto the floor! “After a couple it levels right out,” the bartender remarked to me.
There’s also a great Visit Oakland tourism store in Jack London Square that’s really helpful for planning your time in Oakland and getting an update on all of the local events happening in the area.
My 24 hours were up and I had packed an enormous amount of Oakland into those 24 hours! Hopefully you can use some of these tips, but make sure you also plan for more than 24 hours in Oakland – there’s so much to do!
My verdict on Oakland?
Oakland has changed…in a good way! But what I loved most about it was Oakland is still in this cool transition period where it’s a really great mix of old and new. Each neighborhood had its hip new stores and restaurants, but they also still had old favorites that had been there forever. This mix of old and new Oakland is what I fell in love with. Old classic restaurants next to new, hip organic restaurants. Vacuums and sewing machine stores next to art stores. In addition there was Oakland pride evident everywhere. The city seemed to keep the best parts of it old self and complimented it with new life. I had a frenzied, 24 hours in Oakland, and I’m happy to say it was a different (and great!) 24 hours.
PIN IT FOR LATER!
Disclosure:
I was a guest of Booking.com on this trip and they sponsored my travel. However all opinions expressed here are my own!
This post contains some affiliate links. If you choose to purchase items through these links, I will earn a small commission at no extra cost to you. These commissions help reduce the costs of running this site
By Same day Taj Mahal tour by train August 24, 2017 - 6:27 am
Seems a nice place to visit, want to have all the fun that this city can able to give me. I am very delighted to read this post.
By Jérôme August 24, 2017 - 11:31 am
Great idea! There seems to be a resurgence of “second tier” cities across the continent (and the world), in my view partly because people are priced out of first tier cities, but also because the internet allows connection without living in huge cities. If you can have great food in Pittsburgh and be connected to people around the world, it’s a lot more attractive than in, say, the 1980s.
I’m trying to think of my least favourite cities… Edmonton and Phoenix come to mind, for similar reasons: way too sprawly, and terrible (opposite) weather. I’m sure they’re great in their own right if I gave them a second (or third) try.
I’m curious why you dislike London…
By Sherry August 28, 2017 - 2:08 am
I’ve just never really fell in love with London…not sure why I don’t like it. I find it sprawling, and there’s nothing really that stands out to me there. I know that sounds weird – but I didn’t find anything really unique about it.
By kristi August 24, 2017 - 11:48 am
I really liked Oakland the few times I visited. The area around the ballpark/BART stop was scary at night, but other than that, I liked it.
Their Chinatown sounds like our Asiantown in Houston (we call it that, because it’s more than just China). That’s where are all the supermarkets are located, as well as some really great asian food and services. My favorite is the Oasis Foot Spa…$25 for an hour…yay! I need to go back again.
By Overnight Jaipur tour August 29, 2017 - 7:43 am
Oakland is the place where people can spend many hours or i can say days in exploring this city, this city will never demolish the expectation of travelers.
By Jack Shuman October 10, 2017 - 10:31 pm
Oakland? I totally understand. Everything I had heard about Oakland growing up in Sacramento was negative: gangs, drugs, shootings, etc etc. And then in 2007 I started attending Cal Bears football games again like I did as a kid, 30 years prior. We would take BART to the Rockridge station in Oakland. The Cal campus is a 2 mile walk down College Avenue, and about half way you cross into Berkeley.
The Rockridge neighborhood was such a shock, it was full of life with lots of small independent stores, restaurants, and bars. A few blocks of stores and such and then a few blocks of residential, repeat. As we became regulars at a pub in the neighborhood we heard of other places in Oakland for good food and craft beer in various parts of Oaktown. Within 18 months my view of Oakland had done a total 180.
By Sherry October 11, 2017 - 1:22 am
Ahhh- a fellow convert!!!
By Izy Berry October 15, 2017 - 10:03 am
Rare bird and that Flaura and Fauna bar sound like cool places! The mix of old and new are almost always a good thing 🙂 Glad you enjoyed Oakland this time around!
By Sherry October 16, 2017 - 8:37 am
Yes – I wish I had room in my bag to do some shopping at Rare Bird! Thanks!
By Denis Mountain July 18, 2018 - 2:49 am
Lo Coco’s Restaurant is my favorite too. Their food & cafe style menu covers reminds of cafes back at home.
By Omari hudson September 15, 2018 - 9:05 pm
Everything you named in this article isn’t new. All these places have been there. The news and people who have never been to Oakland have given the city a bad rep. I was born and raised in Oakland and know of the city’s beauty. I never had any problems in Oakland. Maybe knowing more people who were born and raised there and not people who came to the city as apart of gentrification will help you to see the city of Oakland was always beautiful. It’s just now getting the recognition that it truly deserves.
By Meg June 13, 2019 - 9:06 am
Really disappointed that this blog was served to me as I prepare to visit Oakland (a place I’ve always loved). I’m disappointed because this definitely screams, “Oakland is great now that it’s been gentrified!” What a major let down.