Hello! Welcome (finally!) to the second edition of our travel series!
I'm editing this from my couch in Brooklyn, as much of the U.S. is being pummeled by an epic winter storm. Needless to say, I would much rather be in Hawaii!
This guide is written by Christine Amorose Merrill, who writes the What Say Christine newsletter. Last summer, Christine took her three-year-old daughter on an epic adventure to Oahu, which makes this the perfect guide for anyone looking for a solo trip with their young kids. But Christine shared so many great tips that apply to anyone who's looking to take a trip to Hawaii. (I especially love the advice to pick up souvenirs at Costco!)
I hope you enjoy her travel guide as much as I did! It's taken a lot of willpower to not just go ahead and book tickets for the next flight to Honolulu!
Want to pitch your travel guide? Learn more here!
Now, let's go to Hawaii—at least in our daydreams! -Lindsey
The Oahu Travel Guide
Who went on the trip: I went to Oahu with my three-year-old daughter, Jojo. My husband stayed home with our two pugs. We were in the final stages of a home renovation, and my husband wanted to stay close in case there were any issues. (That turned out to be a good decision—there ended up being a lot of loose ends for him to tie up in person!)
The impetus for the trip was that my daughter’s preschool was closed for the week. I was not thrilled at the prospect of entertaining her in our home amidst all of the construction dust (and the interior painting that was scheduled). I love to travel and have traveled solo with her a fair amount, so I was determined to go somewhere fun with her for the week!
How long were you gone: We flew out on a Sunday and flew home the following Saturday—six nights away, five days of fun, and two full travel days.
What was your budget: While I didn’t have a strict budget for this trip, we were in the midst of a very expensive year (see: home renovation). I definitely wanted to have fun and enjoy being in Hawaii, but I tried to focus on finding free activities and keeping our food budget to a minimum. I’ve been to Oahu a couple of times before, so I felt pretty familiar with the island, and I was very aware that food and drink (both in restaurants and even at grocery stores) can add up really quickly. I ended up spending about $1,800 total on the trip—definitely more than a standard week at home, but not too bad for a tropical vacation.
Why did you choose your destination: We pretty much chose this destination because of the accommodation. We joined Kindred*, a home-swapping service, last year, and we’re big fans. There’s an option for straight home swaps, but you can also earn credits by letting members stay in your home when you’re gone and then use those credits to stay elsewhere. Guests pay for professional cleaning before and after the stay (and Kindred provides insurance for any damages), so it really takes a lot of the stress out of home swapping. I love it because it makes longer stays a lot more affordable, and it’s really nice to stay in homes where kids live. (Twin beds! New-to-you toys!)
When I spotted a two-bedroom apartment in Oahu available for the week of my daughter’s summer break, I immediately jumped on it! Being able to spend six nights in Hawaii for a total of $250 was just too good to pass up.
*Editor's note: The link to Kindred includes Christine's referral code.
How did you pay for the trip: We used Southwest points for my flight, and I had a companion pass for my daughter ($11.60). We put everything on our Southwest Rapid Rewards card, which I pay off every month—it’s great for earning points for future travel, as well as maintaining the companion pass. I did Venmo the babysitter we hired during the stay–she preferred cash, but I didn’t realize that until I asked the day before, and there were no Chase ATMs or banks on the island!
Where did you stay (and any details you want to share about the accommodations): We stayed in a two-bedroom apartment in a quiet neighborhood near Punchbowl Crater in downtown Honolulu. The best part was the ocean-view balcony! It was located up a steep hill, so it wasn’t very walkable, but there was a free parking spot included, and it was very centrally located to Waikiki and downtown Honolulu. It cost $250 for the week through Kindred: $41 a night in Hawaii, with parking, is truly just too good to be true. It was so cheap, in part, because we had Kindred credits available, since we had previously hosted in our home, and we paid $600 earlier in the year for a Kindred Passport, which covers all service fees for any trips booked within 12 months. (It definitely paid for itself with the number of times we used Kindred over the year.)
Who is this itinerary good for (families, solo travelers, big groups, etc. and why): Best for families, especially for those with young kids! I also love a “mom-Jojo adventure day.” If you’re up for a mother-daughter trip, this is also perfect for that.
Here’s our itinerary!
Sunday
Our flight left San Diego at 8:45 a.m., so we woke up a little earlier than normal, had breakfast at home, and then headed to the airport. One of the perks of my husband not coming with us is that he drove us to the airport—a lot less stressful than dealing with an Uber (and saved us $40). The flight was fairly uneventful. Jojo just hit the age where she’s pretty stoked to watch a movie, so we both ate the (many) snacks I packed, watched some content, and took an occasional coloring break.
We landed in Honolulu around 1 p.m. Our first stop was to change out of our sweaty travel clothes and into our swimsuits and shorts. Next we picked up our rental car ($351.74 for the week). We headed straight to Magic Island—part of an oceanfront public park (with free parking!). The man-made lagoon is perfect for a toddler, with calm and shallow water. My Oahu-born-and-raised acupuncturist recommended it to me, and it didn’t disappoint. We picked up a Katsu chicken plate lunch at the L&L Hawaiian BBQ ($14.64) in the park and had a picnic next to the beach. We were starving, and it did the job!
We did some swimming and sandcastle building, and then I decided to try and force a car nap in order to adjust to the time difference. It was going to be a long day if Jojo didn’t sleep at all. We did a little drive up the coast—she fell asleep, hooray!—and I listened to a podcast via Airpods before we headed back to a grocery store.
We stocked up on groceries for the week (bread, peanut butter, jelly, milk, yogurt, eggs, shredded cheese, etc.) including a few of my Hawaiian favorites, like a fresh pineapple and fresh poke for dinner. I was somewhat shocked at how much one bag of groceries costs ($108.30), but I knew that it would save us money overall. I also bought a six-pack of Maui Hard Seltzer (POG flavor!) so that I could have one fun drink every night at home.
We checked in at our Kindred just after 4 p.m. The hosts left an ocean life coloring book and crayons for Jojo (very sweet!), so she happily did some coloring while I unpacked and settled in. Jojo had some leftovers from our plate lunch, and I ate the grocery store poke (delicious!!) on our balcony. We both went to sleep early and slept well!
Monday
We ate breakfast at home—eggs, POG juice, and a glass of cold brew for me—and then headed back to Magic Island. We stopped by an ABC Store on the way to pick up some sunscreen, sand toys, and a plastic inner tube for the week, as well as an emergency energy drink for me ($40.28). The joy of a three-year-old is that she’s pretty happy to hang out at the beach as long as I’ll let her, so we spent the morning at Magic Island—a totally free activity, including free parking! We headed back to the Kindred for lunch (PBJs made with the bread, peanut butter, and lilikoi jam we picked up last night), and while a nap time isn’t in the cards, Jojo had some quiet playtime (and an episode of Gabby’s Dollhouse) while I answered some emails.
In the afternoon, we went over to the Waikiki Aquarium ($12 for adults, free for 3 and under). We found free street parking right outside the aquarium. It is tiny and fairly dated, so we moved through it pretty quickly. Then we walked along the water to DECK. Waikiki. I found it on a list of best happy hours on Oahu—a great option for dinner deals, especially when you’re already eating early with a toddler. I treated myself to a beer, Jojo sampled a pineapple juice, and we shared french fries and beef sliders ($46.15). The food was good, and the outdoor seating had a very nice view of Diamond Head crater. On our way home, I took Jojo for her first shave ice at Waiola, a spot that is low-key but very popular. A passionfruit-guava for me and a rainbow shave ice for her ($10.24). We were both happy with our choices!
Tuesday
We had breakfast of instant oatmeal at home and then hopped in the car to explore the north side of the island (about a 90-minute drive). I decided to break up the drive with a stop at the Dole Plantation. I knew it was going to be touristy, but it was a solid stop for a clean bathroom. We did the Pineapple Express train ride ($15 for adults, free for kids 3 and under), which only took about 20 minutes but provided some novelty. We walked around the gardens and watched people feeding the koi in a pond before getting back on the road. I’m not sure how much I can recommend the Dole Plantation. It’s absolutely a tourist trap, and it’s crowded and pricey. But if you have a kid who loves a train or a kid who is a good age for a maze, it’s not a bad place to stretch your legs.
We headed north and stopped by Farm to Barn Cafe for a watermelon juice ($9.86) before going to the Waialua Library. I love libraries and bookstores, and I always make a point to stop in them when traveling (and buy a book to support the bookstore!). It’s a petite library, but it has a nice section of Hawaii- and ocean-themed kids books displayed, so we took a little reading break. We grabbed two books from the library book sale ($2) on the way out as some extra vacation reading material.
We stopped at Laniakea Beach, hoping to see some sea turtles but no luck. We continued on to the North Shore food trucks, where we stopped for lunch at Seven Brothers for a salad for me and a grilled cheese for Jojo ($30.68). After lunch, we drove to Tracks Beach Park, which is about an hour away. Part of my plan for the day was a big midday drive in the hopes of a car nap, which happened! The waves at this beach end up being a little more intense than I love for Jojo, but we built a lot of sandcastles and even saw a seal swim by. (FWIW my husband and I snorkeled here on a trip pre-baby and saw SO many fish. I would recommend it more if you have two adults and can trade off snorkeling or actually swimming in the water.) We drove home and had a low-key dinner of cheesy eggs.
Wednesday
We woke up and—surprise!—had breakfast at home. This is one of the reasons I like staying in vacation rentals with kitchens instead of hotels: You save so much money on coffee and breakfast! We drove to Lanikai Beach, which was recommended by our Kindred host, and WOW. It was absolutely beautiful. We parked the car (for free on the street), and there was a “beach toy library” on the path in. Jojo picked out an extra bucket, shovel, and Barbie to play with for the day. The beach is not only beautiful, but it’s the perfect type of shallow water and calm waves for little kids. We had a ball playing here all morning—just a truly perfect beach morning.
We went over to Nalu Health Bar for lunch where we split a turkey pesto sandwich and both got a smoothie ($35.82). It’s on a super cute stretch of little shoppy shops, so we popped in to a few. We picked up some fun stickers and matching mother-daughter temporary tattoos at Sugar Sugar ($6.28). We also stopped by a post office to pick up stamps so that we could send postcards home ($6.10). I love sending and receiving snail mail, and I am trying to raise Jojo to be the same way!
The Hibachi is a favorite hidden gem stop for poke—a friend who was living on Oahu introduced me to it when I visited a few years back—so I knew I wanted to pick up some poke here to bring home for dinner ($19.90). I also stopped by my favorite roadside stand for a fresh coconut and an absolutely delicious and perfectly sliced pineapple ($22).
Since we got a lot of sunshine all morning, we spent the late afternoon playing in the apartment. I’m very glad we packed the MAGNA-TILES, as they got a lot of use! I enjoyed my poke for dinner and made some cheesy pasta for Jojo, and we popped back to Waiola for a shave ice treat after dinner ($6.15). We also stopped at Safeway to stock up on a few more grocery items, like yogurt and granola bars ($14.03).
Thursday
To give myself a true vacation experience, I hired a babysitter for the day. This did not come cheap ($320 for eight hours plus tip), but it was 100% worth it. I love to snorkel in Hawaii, and I realized that it’s impossible to do this while traveling solo with a toddler. It’s possible I could have found a cheaper option, but the babysitter was a friend of a friend, and she was absolutely fantastic.
I left Jojo at the apartment to play with a new face, and I headed to Hanauma Bay ($25 entry fee, plus a $5 cash parking fee). Note that you have to buy a ticket online two days in advance. On Tuesday, I had set my alarm for 7 a.m. so I could snag mine! It’s beautiful, but since they limit entry every day, it’s a rigamarole to get in: several different lines, a video explaining the rules and how to keep the reef safe. It all seems like a bit much, but then I immediately saw people breaking the rules, which is a bummer. (If you go, follow the rules! Be good to the reef!!!).
I spent all morning alternating between snorkeling and reading on the beach. My dream! I saw lots of colorful fish and at least one turtle, so I was satisfied. Eventually, I realized that I wished I had packed a lunch so that I could stay longer, but I was hungry and getting a lot of sun, so I called it a day and headed to lunch at bEASTside Kitchen. The guava fried chicken is delicious but definitely heavy ($33.05). I had some work to catch up on, so while it’s not the most idyllic, I went to the Waikiki Library to send emails while I had childcare coverage.
At 4 p.m., I went back to Jojo, and I was thrilled to hear that she had a lot of fun all day, too! The reward that I promised was a visit to the cat cafe that we had walked by earlier in the week, so we headed there around 5 p.m. Hilariously, we were there for the cats’ dinner time ($29.93), which was very entertaining. We went home for a dinner of leftovers and fresh pineapple.
Friday
Our last full day! We had finally come to the end of the giant cold brew, POG, and eggs, so we had a special breakfast treat at Sunrise Shack. I had a delicious coffee, and we split an acai bowl (Jojo’s first—she approved!) and a peanut-butter-and-banana toast ($38.51). It was all fantastic, but the cost reminded me why I am so happy we had breakfast at home all week.
We decided to head back to Lanikai Beach since we just had such a lovely time, and it was just as pleasant the second time around. We spent the morning playing in the sand and swimming in the ocean. We stopped by Kalapawai Market to pick up a couple of sandwiches ($26.94) for lunch. We took them with us to Lawrence Lovestock Farm, a rescue petting farm ($60). We had a blast feeding frozen grapes and strawberries to the pigs, goats, cows, and bunnies, and it was a nice change of pace from the beach to be in the lush Oahu mountains. I was also very happy to support a local animal rescue organization!
Although we picked up stamps at the post office, I had a harder time tracking down postcards than expected. I decided to see if the art museum gift shops had anything to offer. Our first stop was the Capitol Modern, and while the gift shop was unexpectedly closed (a “back soon!” sign was up for quite a while), we discovered a delightful outdoor sculpture garden that ended up being an unexpected (and free!) highlight. We then popped over to the gift shop at the Honolulu Museum of Art and had some luck finding postcards ($12).
We headed back to the apartment to start organizing and packing, and I had Jojo do some coloring on the back of the postcards. Once I felt like things were in a good place for the next day, we headed to Costco to fill up the rental car with gas ($39.95) and to pick up some souvenirs to bring home, including 12 boxes of chocolate-covered macadamia nuts ($104.67). We had a lot of friends and neighbors help us out over the summer while our house was under construction, so I wanted to pick up some thank-you gifts. In general, Costco in Oahu is great for a lot of Hawaii-specific foods and snacks, and it’s conveniently located near the airport so you can stop by right when you arrive or before you leave.
We stopped by Magic Island for one last ocean swim on our way home. Jojo made friends with a local kid who happily shared all of his beach toys with her, and I chatted with the mom about the best things to do with kids in San Diego. (They’re thinking about booking a trip!) Back at the apartment, we did a fridge-clean-out dinner, and I let Jojo stay up late to see the Friday fireworks from our balcony.
Saturday
Our flight home was at 8 a.m, so we woke up super early, finished up our last breakfast at home, and headed to the airport. We had to drop off the rental car and check in our luggage, and then I grabbed a cold brew ($6.13) at the airport Starbucks. We walked through a gift shop, and Jojo spotted a stuffed mermaid doll. We hadn’t really bought many toys or souvenirs for her all week, so I decided to reward her for a week of great behavior with a memento of the trip. I also picked up some of our favorite Hawaiian hot sauce to bring home ($41.88).
And then we were back on the plane, with more movies to watch and coloring to do. It was a wonderful trip, but we were both very happy to see David waiting for us at the airport!
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Best money we spent on the trip: I’m very glad I hired a babysitter for a day. It was a big expense, but being one on one with a toddler (including two six-hour flights!) for a full week can also be a lot. I am very happy that I was actually able to snorkel and read on the beach (two things that I truly love!) in Hawaii.
Worst money we spent on the trip: The plate lunch at L&L Hawaiian BBQ wasn’t fantastic, but we were hungry. I wish I had done a little more research on what a good right-off-the-plane lunch would have been!
Money I’m glad we didn’t spend: I spent a lot of time looking up different kids activities on Oahu—indoor playgrounds, children’s museum, etc.—but I’m glad we focused on just going to the beach (a free activity with free parking!) instead. We live in San Diego (aka very close to the beach), but the beaches in Oahu are just so much better for swimming with a little kid.
Thank you so much, Christine! Remember, you can submit your travel guide here!
