Oakland: What to Do, Where to Eat and Sleep

Oakland Gondola 5Is Oakland the new Brooklyn? Many tourism industry experts think so since the city and its businesses have been making some major investments into the area, including a brand spanking new, $6 billion  which now takes people to and from another world class city: San Francisco.

When I got invited to Oakland to do my weekly , which I co-host with Chris McGinnis, I decided to make a long weekend out of it. When I told a few friends who live in the San Francisco area my plans, they told me I was crazy! They said that Oakland is dangerous and that it’s always—and still—featured in one of the lead stories on the local news for murders.

I regretted my decision—until I arrived. Sure, Oakland has some rough spots, but what U.S. city doesn’t? I invited some of those weary San Francisco friends who hadn’t been to this part of the Bay Area in ages to join me and they discovered, like I did, that Oakland actually may indeed be the Brooklyn of the west coast.

So why would you want to go? Obviously, Oakland can’t compare with its big sister San Francisco just as Brooklyn can’t with Manhattan (in certain ways at least). But one of the main reasons you’d want to go there, besides the weather being nicer, is that it’s much cheaper. Especially hotels. In fact, with San Francisco’s rising hotel costs, many travelers, pursuing both business and leisure, are actually booking their hotels outside the city everyone leaves their heart in.

Getting to and from Oakland from San Francisco is easy. Just hop on the BART (Bay Area Rapid Transit) and you’ll be in the heart of San Francisco in less than twenty minutes and for under $4. Not too shabby, eh? But if you do go, don’t just commute to and from Oakland. Be sure to spend some quality time at a few of Oakland’s attractions and restaurants. Some of them are world class. Here’s what to do, what to see and where to eat and sleep in Oakland.


Oakland Urban Winery Bike Tour 2Urban Winery Bike Tour
One of the most unusual things I did was go on an urban winery bike tour. Apparently many winery owners decided that up in the winelands, they were missing the urban life. They realized that they can do everything they can up in Sonoma or Napa that they can in Oakland, except grow the grapes. So now they just purchase grapes from different vineyards and ship them down (it’s an hour’s drive). This gives them the freedom not only to live the city life again but to make different blends since they aren’t just confined to one vineyard.

offers the urban bike tour I did and it costs $90, a price that includes visits to three of Oakland’s 20 wineries. It takes five hours and includes a gourmet picnic lunch. I didn’t have a lot of free time so I only visited two of the wineries and skipped the lunch, and I still loved it. FYI: The wineries I visited were and , named after the theory that George Lucas came up with the inspiration for the AT-AT Walkers from Star Wars from the cranes in Oakland’s port. He didn’t.

The Crucible Glass Class Oakland 2013 1The Crucible
Another fun thing I did was go with Natalie to get hands-on at for one of their classes. This industrial arts organization is home to innovative classes in mediums such as welding and neon sign-making for community events and festivals such as the Fire Arts Opera and Burning Man. The organization promotes collaboration and expression through materials and innovative designs. We took a three-hour where we made paperweights. When we walked in, Natalie had the same feeling as I did—we weren’t really jazzed about doing the class but it turned out to be a lot of fun and was surprisingly relaxing. The three-hour introductory class costs $125.

Oakland Gondola 4Gondola Servizio Gondola Cruise
Yes, my brain had to work overtime when I was told that we could go on an authentic Gondola experience without traveling to Venice. The Italian owners brought their two boats over from the Floating City in 1999 and started offering gondola cruises for two to four people soon after. (1520 Lakeside Drive; 510-663-6603) operates on Oakland’s Lake Merritt where they offer 50-minute rides that begin at just $70. Of course, you don’t have the same views as Venice but it sure is unique and a lot more private. The Gondoliers even sing, which they don’t in Italy.

Oakland Art Murmur 2013Art Murmur Walk
If you happen to be visiting at the beginning of the month then be sure to visit Oakland’s free monthly First Friday gallery walk, known as the . Twenty-one member galleries and nine mixed-use venues are open to the public and hold artists receptions. The event takes place on the first Friday of the month from 6 pm-9 pm and the streets are packed. Each Art Murmur draws up to 10,000 people and includes food trucks, street vendors and other exciting installations.

Grand Lake Farmers Market Oakland 3Farmers Market
I love farmers markets and Oakland has one of my favorites. There are 11 of them in total each week. Arguably the biggest and best is the at Splash Pad Park. It’s been voted the best of the East Bay for several years in a row. The market is held every Saturday from 8 am-2 pm and takes place near the Grand Lakes Theatre.

Localite’s Maker Tour in Temescal
I didn’t get to go on the —an insider’s tour to Oakland’s Temescal neighborhood—but it’s supposed to be the city’s best. You meet artisans, enjoy a light lunch (among other treats) and gain a deeper understanding of the city of Oakland’s history. Wear comfortable shoes and warm clothes. It takes place every Saturday from 10 am-12:30 pm and costs $45 per person. Starting Location: Frog Park, near Claremont Ave and 51st Street map.

Oakland CathedralCathedral of Christ the Light
One thing I wanted to do but didn’t find time for (sorry, God) was attend mass at . From the street it looks like a funky office building but once I found out what it was, I popped in to see this $172 million treasure. They have free docent-led tours, every Monday-Friday at 1 pm.

More on Oakland, the “new Brooklyn”:
Where to Eat in Oakland, California
Where to Stay in Oakland, California


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I used to be afraid to fly and at times even leave the house! I conquered my fear (long story) and now I travel to 20+ countries a year sharing my firsthand knowledge, tips and deals with friends, family and readers. Please sign up to our free newsletters and tell your friends!

11 Comments on "Oakland: What to Do, Where to Eat and Sleep"

  1. Thanks for the great article. I have lived in Oakland for 5 years after living in San Francisco for 28 years. Everything you said is so true and what I say to my ffriends, especially the weather and the value. Really appreciate you spreading teh good on oakland. Come back anytime. BTW love your website and your great posts.

  2. That “Historic House in Oakland” is the Camron-Stanford House which is on the shores of Lake Merritt…

  3. Too bad I didn’t bump into you! I arranged the great weather for you! ;) I live dtwn and work by the lake. I’m a 2nd generation Oaklander and quite happy to be here. As you could see, it would be very difficult to be bored!

  4. thanks. my daughter lives there and it’s a lovely place. where did you stay?

  5. Thank you, Johnny! Even though we are entering winter, East Bay Winery Bike Tours will schedule some rides during our slow season to accommodate your readers. Enter ‘Rooster’ for 10% off on any scheduled tour or us for private group tours!

  6. New and Old Brooklyn! Ironically enough – way back in the day (like pre-earthquake) parts of Oakland were actually a unincorporated township called Brooklyn.

  7. Oakland is a cool place. I have been going there for years because my family lives in the Bay Area. I prefer flying into Oakland Airport because it’s less crowded, easy to get to by Bart and security lines are always shorter. I think it totally is the new Brooklyn.

  8. Oakland is home of the Raiders – ’nuff said. I’ve lived in the Bay Area for 40 years and I still can’t say much good about Oakland. Most of the town is a dump. They built two high rises with towers on top and are affectionately known as the “needles” (as in drug needles) – an appropriate symbol for Oakland. It’s downtown is pitiful – bunch of government brown baggers make it feel deserted even at lunchtime. Oakland is the place you drive past on your way to somewhere nice.

    • I beg to differ!!! I have lived in Oakland for 45 years and I LOVE it here. (Maybe you should move…?) I know NOTHING about the “needles”. Are you referring to the Federal building? There are office buildings higher than that. AND they are quite squat. I drive downtown all the time. I see all types of folk…which is why I LOVE my town… No place else in the world has such diversity!

  9. Sounds like Paul hasn’t been in Oakland for 40 years. Great restaurants, music and arts. Great natural beauty and a city that speaks over 130 languages.

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