First Flight: Traveling with a Five-Year-Old

An early morning wake-up call couldn’t dim our enthusiasm for taking my five-year-old great-nephew Elijah (we call him Eli) on his first plane trip. I’m not sure who was the most excited — Eli or us.

SFO watching planes

Mr. TWS and Eli at San Francisco International Airport

Eli has had a love of airplanes since before he was two. Whenever he visited us, he loved watching them take off and land at San Francisco International Airport. Mr. TWS and I encouraged that interest and talked to him about the joys of going places by plane. When Eli asked if we would take him on a plane ride someday, our brains went into planning mode. First, we checked with his mom (my niece) for her permission. Then, we checked Eli’s kindergarten schedule, our schedules, airfares, and accommodations. We came up with a short getaway that was perfect for sharing this momentous travel experience with a special five-year-old boy.

 Destination: San Diego 

La Jolla, California

La Jolla, California

Just a one-and-half-hour flight from San Francisco, San Diego seemed to us the perfect choice for a young first timer. Because we hadn’t been there in many years, we thought San Diego would be a great place for us to revisit and we knew that there would be plenty of activities for kids.

Getting ready for take-off

Since we were going to have only one night, we scheduled an early morning outbound flight and a late evening return to make the most of two days for the trip. When we woke Eli up, I said, “I’m sorry to get you up so early” and he replied reassuringly, “That’s OK.” Then he looked outside and seeing it was still dark said, “Do people really go places at night”?

We had spent a little time letting Eli know what to expect at the airport, particularly about airport security, and he handled the whole process very well. After we told him our gate number, he was eager to help us find it calling out the number of each gate we passed and excitedly letting us know when we reached ours.

On our way to the gate at San Francisco International Airport

Although Eli wanted to carry his own backpack, it got a little heavy as he explored the airport

Just watching the planes take off and land and pull in and out of the gates at such a close vantage point was exciting for Eli. But there is no shortage of other things at the airport, particularly for a five-year-old first-time traveler. Mr. TWS took him on a walk through the terminal pointing out planes at the gates, shops, and art. He enjoyed it so much that he asked me to go with him again so he could show me the same sights.

Eli was proud as he carried his own ticket and gave it to the gate agent. The simple act put a big smile on her face (and his) and made him feel quite grown up.

Boarding his first flight, Eli hand the agent his ticket, walks down the jetway, and gets to meet the pilot

Boarding his first flight, Eli hand the agent his ticket, walks down the jet way, and gets to meet the pilot

On board

Mr. TWS told Eli that the first thing he should do when he gets on the plane is to look to the left and see the pilots in the cockpit. He did exactly that and was greeted by the pilot with a big “Hi Buddy!” He was a little shy and serious, but also thrilled about the meeting. The next adventure was finding our seats. We pointed to the number on the ticket and where to look in the plane for a match. He easily located the seat, sat down and immediately fastened his seat belt, an important part of the instruction from Mr. TWS.

Reviewing the safety card and getting familiar with airplane features

Reviewing the safety card and getting familiar with airplane features

In flight

Eli felt very special to have the window seat, and it was a big part of his enjoyment and excitement during takeoff, landing, and the flight between.

Soon after takeoff, we experience a bit of turbulence. When we first hit a pocket that shook the plane, Eli was surprised and said, “What was that”? Mr. TWS calmly explained how it was just like riding in car when you hit a bump on a rough road or if you’re on a boat and riding on the waves. Eli understood that and continued to enjoy the flight, never worrying about any further turbulence (which was fairly minor during the rest of the flight). We think that with his first bumpy ride behind him (and reassurance about and an understanding of turbulence), he’s prepared for future flights without fearing turbulence.

Eli uses ear-clearing techniques on descent into San Diego

“What’s happening to my ears?” Eli uses ear-clearing techniques on descent into San Diego

As frequent flyers, we all know how sensitive ears might be during descent, so we gave Eli a piece of gum to help his stay clear. Sure enough, shortly into the descent, he said, “What’s happening to my ears?” and while he continued to chew his gum, we gave him some additional tips. Mine — to hold his nose and blow a little (usually works for me) and Mr. TWS’s — to yawn wide and often. Since we told him that this was normal, he calmly tried both and was able to keep the unusual sensation from becoming a painful problem. Once on the ground, he let us know that he could hear better again.

When we deplaned in San Diego, Eli thanked the pilot for flying him to San Diego and had a nice little chat with him.

Where we stayed: Room with a view

View from 14th floor of Hyatt Regency Mission Bay, San Diego

View from 14th floor of Hyatt Regency Mission Bay

The big hotel was a new experience for Eli as well and there were many things at the Hyatt Regency Mission Bay hotel and grounds to explore. Overlooking Mission Bay, the view was fabulous and the boats and other activities we could see from the balcony of the room were fun to watch. But the pools were the big attraction for Eli as he looked down during the day and also at night. We hadn’t planned for time in the pool to be part of the trip activities because of the cool weather forecast but with a heated pool and an adjoining hot tub, it made sense to indulge Eli’s desire to spend time in the water. He really enjoyed it, particularly the slide into the pool and making new friends in the hot tub.

Sunset view from Hyatt Regency Mission Bay, San Diego

Sunset view from Hyatt Regency Mission Bay

Keep it simple: What we did in San Diego

There are many things to do with kids in San Diego and on a short trip you should be selective, practical, and flexible. There are excellent resources for San Diego activities for kids such as the comprehensive list of activities in our friend’s blog, The World is a Book. However, we decided to keep it simple in the short time in order to eliminate any stress around commitments, time constraints, reservations, and waiting in lines.

A favorite thing -- Mr. TWS gives Eli a piggyback ride on a hiking trail

A favorite thing — Mr. TWS gives Eli a piggyback ride on a hiking trail

Head to the beach!

Playing with the waves on the beach in San Diego

Eli playing with the waves on the beach in San Diego

As it turned out, the biggest hit for Eli was spending time in the water despite the cool temperatures. He had a blast playing with the waves and running around in the sand. So we ended up maximizing that aspect of the trip. On the first day, Eli was still wearing his jeans as we got to the beach, so we took off his shoes and socks and rolled up his pants, and he headed toward the shore to chase the waves outward and then let them chase him back. Of course, his jeans got a bit wet, and then wetter, and finally he did a face plant and his shirt and everything else was soaked so we got him into his suit and he played for hours.

On the beach in La Jolla

On the beach in La Jolla

Old Town San Diego

We didn’t plan to spend much time exploring Old Town San Diego but Eli, camera always at the ready, found many things of interest including buildings of the old west, shops, restaurants and floral and cactus displays. And so, we spent a bit more time than expected before and after dinner in the area.

Point Loma and the Cabrillo Monument

On Saturday morning, Eli had the pool at the top of his activity list, but it was too cool in the early morning (though I’m sure he would have thought nothing of it). So we had a quick breakfast and decided to go for a drive to explore Point Loma. The views were spectacular, and we all enjoyed visiting the lighthouse and the Cabrillo Monument.

Lighthouse at Point Loma, San Diego

Lighthouse at Point Loma

But the highlight was hiking on the rocky trails many right on the water’s edge such as those near the Point Loma tide pools. My favorite moment happened a bit after I warned Eli to be careful of slipping as we walked up a sandy path. As we were headed back down, he stopped to tell a family coming up, “Be careful up there; it’s slippery!”

Hiking the rocky trails at the Point Loma tide pools, San Diego

Hiking the rocky trails at the Point Loma tide pools

La Jolla

We took a drive around beautiful La Jolla (north of San Diego) and had lunch there on our second day. Nearby the restaurant was an area of the beach (La Jolla Cover) where the sea lions gather. Eli didn’t seem to be bothered by the rather unpleasant smell as he walked among the sea lions to see them up close on this glorious afternoon. Then it was time for him to hit the beach again where he would have gladly stayed much longer if we hadn’t had a plane to catch.


Kid-friendly restaurants don’t have to be typical family restaurants. Adults and kids can have the food they want in a comfortable ambiance. We enjoyed two restaurants for lunch and one for dinner that had great options for adults and good kids’ menus. The ones that we tried and would recommend:

Draft Mission Beach
3105 Ocean Front Walk
San Diego, CA 92109

Lunch at Draft on the Mission Beach waterfront

Lunch on the waterfront at Mission Beach

Cafe Coyote Restaurant
2461 San Diego Avenue,
San Diego CA 92110

Cafe Coyote in Old Town San Diego

Cafe Coyote in Old Town San Diego

Brockton Villa
1235 Coast Blvd.
La Jolla, CA  92037

Lunch at Brockton Villa in La Jolla

Ready for lunch at Brockton Villa in La Jolla

Mission Bay restaurant tip: Despite appearances, not all restaurants allow kids. We heard that the Sandbar had awesome fish tacos. I’ll bet they do, but after we sat down at a table near the open windows, we were told that we would have to leave because customers must be 21 years old. When we stepped outside, Eli asked, “Did we just kicked out of that place”? It became a running joke with the three of us during the rest of the trip that Eli was going to get us kicked out of a place again. He loved it, and when we dropped him off with his mom the next day, he said (and he said it proudly): “I got us kicked out a restaurant!”

Coming home

Back at the San Diego airport, Eli was now like a pro — helping move our bags onto the conveyor belt, walking through the scanner, and patiently waiting for bags on the other side.

Sleeping on the plane ride home

On a late flight home, Eli sleeps after a busy day of fun in the sun

When it comes to flying, Eli seems like a natural. He found himself a fairly comfortable spot to lay his head and promptly fell asleep soon after takeoff as he watched the lights of San Diego disappear below. Mr. TWS in the adjacent seat was asleep as well. Wide awake, I contemplated how much fun our San Diego excursion had been.

Eli unfiltered! 

We thought that it added significantly to Eli’s experience to provide him with a camera so that he could take pictures of his own for the trip. We let him use (and have complete charge of) one of our old point-and-shoot cameras and gave him only a single direction — to take pictures of things he liked. He took 180 photos! We’ve included some of his photos below.

Window seat view on our descent into San Diego

Window seat view on our descent into San Diego

There were excellent views of the Hyatt pools from our room, and Eli got a lot of photos of them at different times of day.

View of the Hyatt Regency Mission Bay's pool area from our 14th floor room

View of the Hyatt Regency’s pool area from our 14th floor room

He seemed to have a particular fancy for cacti, stopping to shoot several close ups, especially during our evening in Old Town San Diego.

Cacti in Old Town San Diego

Cacti in Old Town San Diego

Cacti garden wagon in Old Town San Diego

More cacti catch Eli’s eye on a wagon in Old Town San Diego

He also loved taking photos of Mr. TWS and me in various locations — the car, the elevator, walking along a sidewalk, etc. Of course, he couldn’t resist a selfie either.

People pictures by Eli

Mr. TWS and I as photo subjects and an Eli selfie

I hope that Eli will make it back to San Diego someday and that he’ll smile as he remembers our time with him there.

Our tips for traveling with a five-year-old:

Based on this experience, we share these recommendations. We’d love to hear tips from those of you who have traveled with children, too.

  • When renting a car — remember the car seat. Although we had seen reviews warning about problems with the condition of car seats available at rental agencies, we decided to have one provided by Budget at the airport in San Diego rather than have to travel with one. We’re glad we did because the car seat we were given was clean and of good quality and having one provided really simplified things.
  • Think about your transportation to the airport. Normally, Mr. TWS and I take a taxi to SFO. One of the deterrents this time was that with a five-year-old we were going to need a car seat for him in the taxi. Already having decided not to bring one on the trip, we looked for another way. Our decision to drive to an off-airport parking lot and then take their shuttle (no car seat required) to the airport worked out well. It was economical, convenient, and service at De Anza Parking was great. I would consider this option in the future for short trips, with or without a child in tow.
  • Prepare the child for travel. Spend time prior to the trip explaining some of the processes involved such as rental cars, shuttles, aircraft information, security procedures, and in-flight activities. Then explain things as you go along. Eli was totally paying attention to everything that was happening and was like a sponge picking up the information.
  • Enjoy the airport. There’s always much to see at the airport outside the windows and in the terminal — shops, art, and people from around the world.
  • Get them involved. Give the child responsibilities such as helping to find gates, presenting tickets, and carrying appropriate luggage or other items. Eli enjoyed these, he learned, and he will be able and willing to do these in his future travels.
  • Maximize activities on the plane. Looking in the cockpit when boarding, finding seats, fastening the seat belt, pointing out airplane features, reviewing the safety card, watching activities on the tarmac, and keeping excitement building for the first-ever take off were all part of the adventure and added to Eli’s fun.
  • Explain common in-flight experiences. This demystifies things that might be otherwise alarming, such as turbulence and the effect on the ears of changes in cabin pressure, and makes them seem commonplace rather than a reason to be anxious about flying.
  • Capture the moments. Buy an inexpensive disposable camera or let the little traveler use an old one of yours to enable him/her to capture the special moments through their his/her eyes.
  • Enjoy the ride. Whether on a road trip or high in the sky, encourage children to observe and appreciate the scenery along the way. Although I can understand that games, movies, and other distractions are sometimes necessary (for many of us on long flights), a child can be just as interested in the real world around him and seeing new sights.
  • Plan an agenda but be prepared to be flexible. Anticipate and be flexible spending time on whatever might turns up.  Serendipitous activities can often be the most fun.
  • Share the excitement of travelConvey your excitement about traveling. Be part of opening a young person’s mind to travel whether to see distant lands or to explore close to home.


Note: This post may contain affiliate links. If you make a purchase through these links, I will earn a commission at no extra cost to you. Thanks!

16 thoughts on “First Flight: Traveling with a Five-Year-Old

  1. Suzanne Fluhr

    You guys are the best great aunt and uncle and Eli is a truly adorable little boy. Looking back, I think 5ish is a great age to travel with children. They’re old enough to understand explanations, but they’re still full of wonderment. They really allow you to see the world through uncynical eyes. I bet this trip will be one of Eli’s special life memories.

  2. Terry

    I love this – such a fresh approach to travel, seeing it from a kids-eye view, and good tips for anyone contemplating their own version.

  3. Janice Chung

    What a wonderful adventure not only for your grand-nephew, but for you too! I’m sure all of you will never forget the trip. Providing Eli with a camera was a fabulous idea and your tips are great, not just travelling with a 5 year old, but travelling with any “youngster”!

  4. Betsy Wuebker

    How adorable! He will long remember this experience and I’m sure you will, too. It sounds as though you planned things perfectly and timed them to take advantage of attention span and interests!

  5. Donna Janke

    I really enjoyed this post. I like everything you did to make this trip special for Eli. And it sounds as if he made it special for you. When we travel a lot we take a lot of things for granted and forget what the experience might be like for someone who hasn’t done it. You had to think through that to help Eli. I chuckled at the pool and water time – always a favourite with kids regardless of temperature.

  6. Jo ~ Lifestyle Fifty

    I can imagine you were almost as excited as Eli! I loved this post, so many tips and a tone of excitement throughout as if discovering things all over again for the first time. Hmmm, I can’t wait to be a grandy!

  7. Sue Reddel

    What a marvelous story and adventure for Mr. Eli. I loved that he took his own photos as well. Sounds like his first flight was a wonderful experience and hopefully the first of many.

  8. Pingback: The Sweeneys in Scottsdale Part Two - Traveling with Sweeney

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.