15 Hour Stopover in Oakland, California

On a trip to Kona Hawaii (from my home in Virginia), I opted to make an interim stopover. I arranged the itinerary to fly into San Francisco and leave from Oakland the next morning. This allowed us to arrived relatively fresh in Hawaii (in early afternoon, after one long six hour flight) rather than frazzled late at night after two long flights.

Here is what I did on a 15 hour stopover in Oakland, California.

First, we had to get to Oakland from San Francisco airport. There are several ways to do so but I opted for BART. The 45 minute train ride set us back $8.95 each.

San Francisco Airport Tower from train
new San Francisco Airport Tower from train

We exited BART at 12th Street in downtown Oakland because it is the closest station to the hotel I booked. I was offered (via Twitter) a great rate and two category room upgrade at Waterfront Hotel. After exiting the station, I called the hotel for a shuttle, which arrived about 15 minutes later. I debated taking a taxi, which online sources estimated would cost $7.

While waiting for the Waterfront Hotel shuttle, I took this picture of the Oakland Tribune tower.

Oakland Tribune Building - from 12th Street Station
Oakland Tribune Building – from 12th Street Station

I selected Waterfront Hotel because it seemed to be in a great location and is a JDV property. Indeed, the location is fantastic; right on the waterfront (true to the name) and in the vibrant Jack London Square area. JDV operates the largest collection of boutique properties in California, with additional properties in other locations. I had wanted to try a JDV hotel since I learned about them when I visited San Francisco a few months ago.

How about this sunset view from my room’s patio balcony?

Sunset at Waterfront Hotel, Oakland, California
Sunset at Waterfront Hotel, Oakland, California

We arrived just in time for sunset but also just in time for Happy Hour. After a lightning fast checkin and quick stroll around the property, we headed back to the lobby for a full-pour glass of wine and plate of cheese and crackers.

Jack London Square offers a great mix of dining, recreation, and shopping options. During the warmer months, the open spaces host events and markets galore. I prearranged dinner with a second cousin at Bocanova. Bocnova specializes in locally sourced Pan-American cuisine and our group shared many tapas dishes (and, of course, wine). We dined outside, made possible with glorious heat lamps.

Bocanova, Jack London Square, Oakland, California
Bocanova, Jack London Square, Oakland, California

After dinner, following a suggestion from Waterfront Hotel’s Twitter account, we visited the recently opened Plank. Plank is a beer garden with fun activities; outside is bocce and inside is bowling, billiards, and other games. We opted for drinks around a fire pit then moved inside to watch some bowling fun.

Plank, Jack London Square, Oakland, California
Plank, Jack London Square, Oakland, California

It was now about 10pm but our jet lag was setting in. We headed back to the hotel and re-examined the amazing gift bag. Complimentary items included many snacks and souvenirs. Being the carryon aficionado I am, we could not take complete advantage of the hotel’s hospitality but we did pack the wonderful tote bag. It was very convenient for our many beach visits in Hawaii the following five days.

After a great night sleep in their amazingly comfortable bed, we were treated to a magnificent sunrise.





During a morning walk, I passed commuters walking to the ferry and then I watched the ferry leave for San Francisco. I saw the marine patrol begin their day and early bird workers preparing their shops for opening later that morning. A very peaceful time of the day.

At checkin the previous afternoon, I mentioned to the assistant manager our desire to leave at 8:30 for the airport. Oakland airport, we confirmed, as most guests use San Francisco airport. Bryan said he would take care of it. That led to my wife and I speculating what “take care of it” would mean.

When we checked out just before 8:30 the next morning we discovered a lovely town car waiting for us. The fare was the same as a taxi ($35). McCool Travel tip: ask your hotel about transportation options. They might have negotiated discounts unavailable to general public.

Once we arrived at Oakland airport, I considered our 15 hour stopover complete. We spent nearly half of our time sleeping and were in great spirits for the Alaska Airlines flight to Kona.

Advantages of our Oakland stopover:

  • break between two long (5-6 hour) flights
  • maximize time in Hawaii, arriving in afternoon instead of late at night
  • fly Alaska Airlines to Hawaii instead of United Airlines (personal preference)
  • experience a new destination
  • relaxing waterfront hotel room at a third the price across the Bay (in San Francisco)

How about you? Have you visited Oakland, California? What did you do?

Do you like stopovers? Or want to try a stopover on a future trip?

Also see what I did during other stopovers: 3 hours (Boston), 6 hours (Salt Lake City), 12 hours (Long Beach).

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17 thoughts on “15 Hour Stopover in Oakland, California”

  1. Great tips and pictures. I have never been to Oakland but I have a lot of friends from the Bay area. I will get there soon and take these tips into account.

  2. I love the photos thanks so much for sharing your adventure never thought to do an overnight layover great idea

  3. I love the BART and used it extensively when I visited SF. I didn’t have a chance to head over to Oakland while I was there, though. Looks like it’s worth checking out!

  4. I love squeezing in stopovers, especially on long-haul flights. It makes the journey so much more pleasant and you get two see two destinations rather than one.

  5. To be honest, Oakland has never really been on my radar, but it looks like you had a great time… and I’m a sucker for a sunset on the water. I may have to reconsider.

  6. I love these stopover posts! The only time I really used a stopover was on a flight from BOS – JFK – CDG – LHR, where I managed to hit the MoMA, Centre Pompidou, and Tate Modern in under 72 hours. I’m still pretty proud of that!

  7. I’m fairly new to the stopover concept, but I love it because you get to squeeze in one short stint somewhere and get to taste a flavor of the city. 🙂 I’ve done one stopover in Seoul so far and it was great!

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