A Perfect Day in Oakland

I’m feeling an extra-dose of Oakland Pride today — I sure love living here! For the final post in my 3-part series with Uber, I’m going to take you on a little tour of Oakland, and give you a helpful itinerary for your next visit. If you are traveling to the Bay Area, consider taking a break from San Francisco and spending the day across the Bay Bridge. It’s sunny over here!

We used uberX for our entire day of exploring. It made life so easy for us. We could go door-to-door with ease, and didn’t have to deal with finding parking (which can be a big challenge in Oakland), or paying for parking (which can be very expensive in Oakland). Here’s my suggested itinerary for A Perfect Day in Oakland:

8:30 – Classic Breakfast

Start with a lazy breakfast at Sequoia Diner in the Laurel District. The menu is classic diner food, but upscaled and made with super fresh ingredients. Try the Coconut Almond Granola, or the Herb and Goat Cheese Omelet (served with a buttered slice of house made sourdough). Don’t be surprised to find a line out the door for this popular brunch spot, but it’s worth the wait.

And once you put your name down on the waiting list, you can entertain yourself at the charming gift and homewares shop, called Therapy, just two doors down.

10:00 – Redwood Forest Walk

After breakfast, it’s just a 10 min uberX ride to Robert’s Grove.

A gorgeous redwood forest that used to be a major landmark for ships coming into the Bay. It’s where we held Ralph’s Eagle Court of Honor.

As you wander through this quiet and majestic forest, you’ll notice the trees seem to be planted in circles. You can read all about that on a monument you’ll find as you explore.

If you’re with kids, you’ll be glad to hear that Robert’s Grove is part of a larger Robert’s Park that includes a pool set in the redwoods, and a”Barrier Free” wheelchair accessible children’s play ground.

11:30 – Hipster Windowshopping

When you’ve had your fill of the forest, summon another uberX to take you to the hip and hidden Temescal Alleys.

If you’re local, and you don’t know about this place, you may have driven by a dozen times and not even noticed it. Because it’s truly 2 small alleyways hidden off the main road — and lined with some of the most charming shops in town. These are small independent shops featuring local artists and artisans. You’ll find jewelry and housewares and gifts. You’ll find small batch foods and specialty items. You’ll find a barbershop.

Don’t miss Book/Shop, and if you need a snack, try a cone from Curbside Creamery ice cream.

1:00 – Lunch Downtown

For lunch, I have 2 options for you. You can walk around the block from Temescal Alley and eat at Bakesale Betty, while standing at ironing boards (so cute!). Or, grab an uberX and head to True Burger on Grand Ave.

This is an Oakland original and a Blair Family favorite. As far as I’m concerned they can do no wrong. Their burgers, their fries, their shakes — all top notch. Bonus: Pickles are self-serve and I can get extra like I prefer. : )

2:00 – Afternoon at the Lake

Half a block from True Burger, you’ll find Lake Merritt. An absolute jewel in downtown Oakland, and also America’s oldest wildlife refuge.

Fun fact: Did you ever see The Incredibles? During the big fight scene at the end — when Dash runs across the lake and Frozone uses the water to slow-up the robot? That whole thing is based on Lake Merritt and the surrounding buildings. In fact, Pixar is based nearby!

There’s a lot to do at Lake Merritt and in the surrounding park. You can rent kayaks or small sailboats. You can take a leisurely walk around the lake — the whole perimeter is about 5k. You can play on the rocks near the waters edge, or observe birds in the sanctuary

On weekends, you’ll probably hear music being performed at the bandstand. There’s a gorgeous bonsai garden, and several other gardens as well. And if you are with little ones, you’ll LOVE Children’s Fairyland. They say Walt Disney visited Fairyland, and that’s what inspired him to create Disneyland. 

4:30 – Sightseeing at Jack London Square

From Lake Merritt, take a short uberX ride to Jack London Square.

If the farmer’s market is going on, I highly recommend picking up a snack for a little lawn picnic. You can also find yummy goods at the happy shops that line the Square (try Miette for sweet treats).

At Jack London Square, you’ll find Jack London’s cabin, you’ll find a gorgeous walk along the docks, and you’ll find great views of the famous Oakland Cranes. If you like, you can rent kayaks and paddle your way through the channel. There are movie theaters and restaurants and lots of fun shopping. And there’s a famous jazz club too.

One of our favorite things to do at Jack London Square? You can catch the ferry to San Francisco. It takes you right by the cranes and under the magnificent Bay Bridge, then drops you at the Ferry Building. It’s a really lovely (and affordable way) to get some time on the water, plus you get GORGEOUS views of the city.

7:00 Dockside Dinner

After you’ve had your fill of exploring Jack London Square, grab a table at one of the waterside restaurants. There are lots of excellent options. Bocanova is one we’ve been to several times. It has indoor seating if it’s chilly, or patio seating that overlooks the boat docks.

What do you think? Does that sound like a lovely, adventurous day? Have you ever been to Oakland? Or wondered what it was like? If you’re an Oakland local, and you were planning your own Perfect Day in Oakland, what would your itinerary include? Anything you would add or subtract from the itinerary I created? And wherever you happen to live, have you ever tried to plan a tourist itinerary for your town? It’s lots of fun, I promise. I think it’s a great exercise for picturing what your city looks like from a visitors’s point of view.


Credits: Photos by Katrina Davis for Design Mom. This post was sponsored by Uber. It’s part of a 3-part series — post one is about UberPool and post two is an interview with an Uber driver.

43 thoughts on “A Perfect Day in Oakland”

  1. Check out hello flower shop behind homestead apothecary, a couple doors down for Sequoia Diner. It’s the cutest shed flower shop and Heather makes great arrangements. Peter’s kettle corn down the street…the best flavors! My dad owned a business in the Laurel for 16 years when I was growing up, so it has a very special place in my heart.

  2. When we lived in the BA, we loved to spend some time in Rockridge @college. There was a delicious coffee place there and nice stores for kids stuff.

    1. Totally. So many cute shops and great food options on College. When Maude starts school, maybe it would be fun to do a tour of the Rockridge + Claremont + Berkeley area.

  3. Off subject…PLEASE do a post on wigs! I have white hair, and it’s liberating, I love it. But, there are times when I’d love a change. Most wigs are so obvious but yours looks super. More info, please.

  4. What a fun post! I loved learning about what Oakland has to offer. I have been there only once and could have used your guide. This could be a great new Design Mom series. Let me know if you’re interested in a “Perfect Day in Albuquerque”….

    1. I would actually love that. Ben Blair and I love to think up new business ideas on dates, and one we come back to over and over again is an App that we would call A Perfect Day and it would have itineraries from locals for big and small cities alike. Lots of different options for each city depending on what you’re into.

  5. Love this and agree! I’ve been to all these spots. Oakland also has a great international food scene. I would definitely recommend Pho 84 for Vietnamese, Cafe Colucci for Ethiopian, and Cholita Linda for Tacos!

      1. Traci Barr Segal

        Pho 84 is my absolute favorite for Vietnamese food. I miss it so, now that I live in Mendocino county. So glad that you mentioned it.

  6. Sadly, Doughnut Dolly closed all of their locations! Curbside Creamery is great for a treat though (also in the alley). Their ice cream sandwiches are amazing! Cholita Linda and Burma Superstar are located right across the street and are fantastic for lunch or dinner. Cholita Linda is more casual and easy with kids. Burma Superstar gets busy, but is worth the wait!

    1. I was coming here just to plug Cholita Linda (best fish tacos EVER) and Burma- what excellent taste you have :). I just left Oakland for the East Coast and I’m having major FOMO right now.

    2. Oh no! The doors were closed at Doughnut Dolly when we shot the photos, but I just thought it was closed for the day. We ended up getting cones at Curbside Creamery. I’ll go update the post.

  7. So happy to read that Lake Merritt is now a beautiful, happy place. When I lived in Oakland 25 years ago, it was a scary do-not-go hang-out of drug dealers and thugs. We loved Fairyland back then and how sweet that it is still going. It must feel extraordinarily vintage in today’s world.

  8. LOVED the tour!! I’ve heard negative things about the dangers in Oakland. Sure felt none of that in your tour. It’s beautiful and fascinating. I am deeply impressed with how much you accomplish and record in less than a day! And it’s done so happily and with three beautiful daughters.
    Guess Maude is working on the Color Castle. Eager to have a tour of that spectacular place also.

    Thanks for the lovely, happy tour!!

    1. I’m a transplant from Europe and let me tell you – Oakland is GREAT! It gets a bad rap, and gentrification is no doubt changing the face of this city in places, but it’s just so wonderful in so many ways. The people (less snooty than SF- sorry!), more diverse, more interesting….

      Let people think it’s dangerous! It’s our secret!

  9. Love this. I’m an Oakland native and had no idea about the Temescal Alleys. Maybe they didn’t exist in their current form 20 years ago. Will have to venture back to that side of the tunnel to check it out

    1. Agreed. Start-up culture in this area can be nuts. I’m really curious to see who Uber brings on as the new CEO, and hopeful that the changes they’ve been making so far can keep improving.

  10. mandi @herbanhomestead

    Loved this! My sister lived in San Fran for years and we would visit Oakland. We loved Fairyland when my two oldest were young. Last time we were there was 8 years ago.

  11. Any qualms about supporting Uber considering their corporate culture these Days? Just curious since you have been very vocal about bullying and sexual harassment in the past.

  12. Carolyn in Utah

    I will be visiting San Francisco for your “color thing” on the 15th. I don’t know exactly what it is, but I’m excited! When I first read your post about your pop-up I called my husband and asked if I could come along on his next trip to the Bay Area (he works in high tech here in SLC). My hubby later gave me a strange look when I told him I wanted to go to a “pop-up experience”.
    Maybe I’ll go spend a day in Oakland now that you’ve shown me where to go! I’ve had the Uber app on my phone for a long time but have always felt intimidated to use it. Hey, I’m a Utah housewife!

  13. I love Oakland so much and it’s wonderful that you posted this on my birthday.

    We have really been enjoying the Oakland municipal band this summer and Sunday is their last performance of the summer at the bandstand from 1-3.

    Have you been to the Gardens of Lake Merritt? It is across from the bandstand and we treat it like our backyard as we live so close. It is so wonderful to have the lakeside park, the gardens and the lake so near. They are restful and rejuvenating since Oakland is a big city.

    Also I love Curbside Creamery because they make the best vegan ice cream, even soft serve!

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  16. This is just great!!! My husband and two kids (7,10) are planning to go to San Francisco end of March but hotels are quite expensive in North Bay around that time so we decided to stay in the East Bay. We are going to try this itinerary but probably just pick and choose. I like the Robert’s Grove (we were thinking of going to Muir Woods – but I saw another post that the redwood forest in Oakland is even better). Do we have to pay to enter the forest?

    And the Lake Merritt + Jack London Square. And hopefully we find the True Burger! We are visiting US for the 2nd time so the exploring will be quite exciting. We are not hardcore tourists – we want to relax and enjoy. Thanks a lot!

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