Traveling for leisure as a single parent with a kid in tow

My kid and I went to San Jose for the long weekend. Just because I am on my path to early retirement, I’m not depriving myself.

I went to San Jose I have a lot of friends there and it’s been a while since I’ve visited. When I worked in senior living, I used to travel to the Bay Area when I worked in senior living. My employer managed a few senior living communities over there.

My college friend and I ventured out to Oakland on Saturday to see a mutual friend from college. I have to be honest, I was a little hesitant to make my way up there because I was only going to be in the Bay Area for two full days. I wasn’t trying to see EVERYTHING in one trip. It’s like if they flew in from Los Angeles, I’m not going to take them to Disneyland and then lounge at a beach in San Diego.

Lake Merritt in the afternoon

My Bay Area friends were scratching their heads as to why I chose to land in San Jose. For the same price, I could have flown to San Francisco or Oakland. I chose San Jose because I wanted to test out traveling as a single parent — the flight is short but also far enough from home. Also, I wanted something laid back and slow-paced where I didn’t feel compelled to take Lana to see the sights like a checklist traveler (“we have to go here and here and here”). I would have been happy dining out, going to a museum, and taking a short hike somewhere. I did promise them I’d be back on future visits on other long weekends where I’d land in other parts of the Bay Area so I was in no hurry.

In the end, I am glad we made the drive to Oakland to enjoy brunch and the afternoon with friends. Considering how I have far more friends who have no kids, they were very understanding. I shared with my friends that up until the day of the trip, the idea of traveling with a kid as a single parent was incredibly overwhelming. I’ve had plenty of people planting doubts in my head if I could pull it off. Well…I love to travel. Considering how much has been taken away from me, I want to keep travel as part of my life. To me, this trip was a test to see if I could handle traveling with a small child. If I “failed” — basically have a meltdown at the airport — I would try again.

To those naysayers, I would consider this trip a success. Lana loved being on a plane. That was all she talked about.

She sure looks comfortable.

Note to self: I should have chosen a larger tote as my carry-on. It’s my airport survival kit. The one I brought was too small to carry a blanket, my sweater, her sweater (which she refuses to wear), emergency clothes for her, iPad, wallet, paperback book, headphones, and two empty water bottles. I felt my bag was going to explode.

Regarding those naysayers — it’s ironic that they have children and are coupled. They probably were projecting that they would never travel with their small children because they couldn’t pull it off. But now I can retort, “Well there are two of you to parent a kid, theoretically wouldn’t it be easier to travel with small kids? You each are doing half the load.”

Okay, I’ll stop shading. For the next trip, I am looking at going to Montreal in the wintertime. I know it will be very cold but they do have a large underground city.