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Baby’s First Flight: San Diego

I originally published this to a different blog site I hadn’t used in years. Then I realized there is no way I am keeping up with a number of blog sites, so I am re-posting here. It was originally posted May 2018.

I recently started working for a major U.S. airline and hope to travel more, often with my husband and baby daughter. I won’t use my daughter’s name to protect her privacy, but her initials are M.O.B., so we refer to her on social media as our little mobster or just by her first initial, M.

Memorial Day was this past weekend. The key advantage of working for an airline is that I decided Wednesday I didn’t want to stay in Chicago over the long weekend, and I was in San Diego with my family two days later! My trip goals were:

  • Practice flying as a non-revenue passenger (airline employees travel free on a space available basis, meaning we don’t get reserved seats, so we only fly if there are still seats after everyone else boards)
  • Fly with my daughter for the first time to better understand her tolerance for air travel
  • Travel someplace with relatively high flight availability so we wouldn’t get “stranded” on the return flight without reserved seats
  • Go someplace new, sunny/warm (rain was forecast in many major cities for the weekend), and family friendly
  • Pack as light as possible, given the baby

Tiffany Travels View from Airplane


Let me start by saying non-rev travel (non-revenue standby) is not for the faint of heart! Instead of booking a flight, you “list yourself” for a seat, meaning you add yourself to the list of standby passengers. My employer/airline seats people based on seniority in terms of time with the company. Since I’m new, I’m at the bottom of the list.

I checked numerous destinations before finding one with sufficient availability to make travel likely. My co-workers tell me you can never assume you’ll get on a domestic flight because 50-100 people could easily join the day of, but international flights are a little more certain since people are less likely to book an international flight the day beforehand if they’ve taken time off from work, selected hotels, etc.

When I selected a flight and listed my family on Wednesday evening, there were just shy of 50 seats available, 9 of which were in a priority cabin (first class). I was number 6 on the list, so it seemed like even if I didn’t get a great seat, all three of us would at least get on the flight. By the next morning, there were half as many seats. For awhile, I was number 11 on the list, then 9, then 6, then 8 again… All the while, seat availability declined, making my place on the list more important. The numbers changed every half hour or so. I decided not to check again until just before I went to bed the night before our trip. (Didn’t quite happen that way, but it would have been much smarter, and I had the best of intentions!)

I expected that waiting at the airport would be even more stressful than the listing process. When you’re a non-rev passenger, the ENTIRE PLANE might board before you find out whether you got a seat. I’m the sort of traveler who likes to board early in my boarding priority level so I can stow my things, get settled, and mentally run though a checklist to see whether I need to send any last-minute info to work, friends, or family. However, since I had chosen flights with decent seat availability, the gate agents had the flexibility to assign our seats while the first class cabin was boarding instead of at the end of the boarding process. On the flight home, we even got a row to ourselves!

I am so grateful to co-workers who made our first family vacation stress-free and memorable. Mobster loved watching other planes and baggage carts at the gate, and the cutest moment of all was when she smiled and waved at an O’Hare ramp service employee and he waved back!

Tiffany Travels Mobster Plane Window


I read lots of online posts and checked with friends to collect advice in advance of our trip. Here were some that helped us:

  • My daughter, under age 2, was listed as a lap infant. My plan was to bring a car seat and check it for use at our destination. I read this series about flying with car seats because I’d never done it before. In the end, we elected to rent a toddler car seat (the convertible size for babies about one year or older) from our rental company, Hertz. Hertz delivered the car seat as promised, but I did not feel remotely as comfortable with that seat as with our own, and I do not expect I will travel without my own car seat in the future.
  • To alleviate pressure to babies’ ears, it’s a good idea to have them drink a bottle or chew/suck on things during both takeoff and landing. This can be tricky if a flight is delayed and you’ve tried to time things perfectly, so be sure to plan alternatives (pacifiers, Cheerios, etc.). Mobster loved drinking from her sippy cup once she was done with her bottle, and we let her eat some crunchy puffs, which she loved. It’s worth waking the baby up as the plane’s descending to repeat the process; my mom quoted an article over the phone that said many babies who cry on flights were woken from naps from ear pain.
  • I accidentally packed M’s blanket in my checked bag, but I had several sweaters with us to keep her warm on the plane.
  • We had quite a few toys with us, including a few new ones. Fortunately, the hum of the plane’s engine meant noisy toys weren’t audible beyond our row. (We didn’t pack anything especially loud, but one of her toys made a gentle beep if pressed just right.) We also said yes to an extra drink cup and a crinkly bag of pretzels, which M found delightful. – By the way, do you have any idea how many bags of pretzels airlines go through? Our CEO said during orientation that many people drop him a suggestion to use company XYZ for gourmet pretzels, and he says he would be happy to consider those companies if they can produce 14 million bags per year!


My husband has been to San Diego several times before, but it’s been on my bucket list for years. I knew it would be a quick trip (just a day and a half + travel), so all I really wanted was a decent hotel near a beach where we would spend the day. Booking at the last minute as I did, many of the city’s hotels had astronomical holiday weekend prices. Placed I’d seen listed only the day before at reasonable rates climbed $200+ per night overnight! In the end, I chose a hotel overlooking the bay on Shelter Island. The view was perhaps not quite as advertised, but it was quiet and clean and perfectly peaceful from our balcony. If I were to visit during a non-holiday weekend, I would review this San Diego hotel site, which I found useful in understanding the different parts of the city from the perspective of hotel locations.

Tiffany Travels Bay Club Hotel and Marina

We spent two nights at the hotel but had just Saturday in the city. We started with brunch near the Ocean Beach pier. We loved the palm tree-lined street, which had the California feel I remembered from my business travels almost a decade ago! Mobster tried wearing sunglasses for the first time and surprisingly didn’t try to take them off. She has often cried when the sun faces her while she’s riding in the car, so it made sense in hindsight.

Tiffany Travels Mobster Sunglasses

After brunch, we stopped briefly at the beach to watch the surfers and introduce the baby to sand, which she hated. (She also hates grass and pretty much anything that’s not a hardwood floor, haha.) After the beach, she fell asleep in the car, so we took the opportunity to drive through some cliffside neighborhoods and wend our way to Fort Rosecrans National Cemetery, which had a beautiful view of the city and was also a fitting place to visit in its own right, given the holiday.

Tiffany Travels View from Fort Rosecrans National Cemetery.JPG

Next, we drove to La Jolla and walked down to La Jolla Cove, where M enjoyed watching the sea lions a little bit and the other kids a lot. I knew I could count on her love of people watching even if she didn’t appreciate the other experiences!

Tiffany Travels La Jolla Cove California SealsTiffany Travels La Jolla Cove California Sea Lions

Her daddy held her down near the sand, but she tried to pick her feet up every time the ocean water came near her. She hated it! Eventually, she did enjoy sticking her little feet in the protected tide pool area.

Tiffany Travels Mobsters Beach Feet

As someone who grew up in the rural Midwest, I am dying over the fact that my daughter’s very first trip to a beach was to the PACIFIC OCEAN! I was shocked to hear people refer casually to one of the Great Lakes (Lake Michigan) when I moved to Chicago as “the lake.” Where I grew up, “the lake” was an often-murky body of water, small, used primarily for fishing, boating, and ice fishing. Kids braved the water when algae levels weren’t toxic. Now I live about 30 minutes from Lake Michigan but still took little mobster to the ocean first! I found this website about different San Diego beaches helpful in selecting a beach to visit.

We went for an early seafood dinner (around 4pm!) and stroll in a park in the Gaslamp Quarter to end our day. While M napped in the car, we started driving to a lookout point in the nearby mountains, but frankly, it didn’t go well. I got carsick on the drive and found the dry landscape depressing. Fortunately, my husband is a good sport and took the opportunity to point out that some “balls” on telecommunications wires were probably placed there to make the wires visible to helicopters, and given the proximity to various military bases, it was very likely a helicopter training area.  Following his comment, I immediately recognized the landscape as similar to dozens of war movies. It made the return drive much more interesting. Then we headed back to the hotel since it was already “late” for the baby, accounting for time zones.

It was a whirlwind trip for sure, but it was an absolutely perfect first family vacation. San Diego treated us well. I can’t wait to go back and also to find the next great family destination!