Our Family Trip To Hawaii - Cupcakes & Cashmere

Our Family Trip To Hawaii

My biggest takeaways (and favorite photos!) from 11 days in paradise.
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A couple of months back, we decided to take a family trip to celebrate my dad's 70th birthday. Initially we'd envisioned someplace in Europe—a coastal spot in Italy or perhaps the French countryside. But since we waited until the last minute to plan, everything was either exorbitantly priced or booked, so we pivoted to something much simpler: Hawaii. We decided on the North Shore in Oahu, which couldn't have been more idyllic, especially since it was our first real trip with Sloan outside of California. Here's what our trip looked like, my favorite things we did, my top recommendations, and biggest takeaways:

At the fruit stand with Sloan

At the fruit stand with Sloan

Going on an 11-day trip with our extended family was much more intimidating than I'd realized. My parents have stayed with us for long periods of time over the holidays and I'm incredibly close with them, but traveling is a different story. I wanted to find a place that appealed to all five of us, which felt like a lot of pressure, but in the end, we couldn't have planned a more flawless trip. We stayed at Turtle Bay Resort, which was kid-friendly without being obnoxiously so. We spent a loooot of time hanging in and around their wading pool, perfect for toddlers, and equal parts digging holes for Sloan at the nearby beach. The resort is on the North Shore, which is a lot quieter and more removed from some of the busier parts of the island, which we loved. We rented a car with a carseat and made sure to get out at least once a day for small excursions. Mainly we ventured out in search of great food (more on that below) and found it in small poke stands, unassuming bakeries, and roadside fruit stands. 

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Most of our days looked pretty similar - we'd get up around 7am and we took turns grabbing coffee and snacks from the little cafe downstairs to bring back to our room. It's funny - but since we make coffee at home every day - even the idea of enjoying it in a to-go cup in bed felt so luxurious. We'd then get lathered up in sunscreen (I swear it was like a full-time job ensuring we were all adequately covered and not getting burnt) and then head down to the pool or beach for a few hours. At lunch was when we'd typically head out to get food - as either a group of five or we'd divide and conquer. Though Sloan's naps are becoming more inconsistent at home, on vacation she slept like a champ - sometimes 2-3 hour stretches, since playing so much in the sun was so exhausting. While she napped, someone would stay in the room with her, which was dark and cool and a nice reprieve from the harsh sun outside. That's when I'd get the majority of my reading done (I tore through 'And Then She Was Gone' and 'Something in the Water,' both which I enjoyed). Occasionally one of my parents would stay with Sloan while she napped so G and I could take advantage of the beachside bar. It was the best of both worlds—getting to spend so much quality time with Sloan, but also being able to slip away, just the two of us. The afternoons looked similar - hanging in and out of the water, eating fresh fruit, and listening to live music by the pool. In the evening, we either went to one of the restaurants on the property or to one of the nearby food trucks for a casual environment that allowed Sloan to run around while we ate. And though my parents offered to watch Sloan each night after she went to bed so that G and I could stay out, we were both very content slipping into bed early to read and relax.

Dinner dates. (I'm wearing a Billabong Jumpsuit (similar here), a Donni Charm bandana, and my favorite OneStory earrings.)

Dinner dates. (I'm wearing a Billabong Jumpsuit (similar here), a Donni Charm bandana, and my favorite OneStory earrings.)

It was also our first time on a long-ish plane ride with Sloan and I'm still blown away by how well she handled it. We're pretty careful about the amount of screen time she has (she's only allowed to watch videos on the weekend), but I still remember something her pediatrician said to me a while back: "On trips, all rules go out the window." So that was kind of the motto we abided by while traveling—she got to watch all the movies she wanted on the plane (we got her a kid-friendly tablet loaded with her favorite movies) and I had my bag filled with fun snacks, i.e. things she's normally not allowed to have. We also had "in case of emergency" items—little toys, new coloring books, and an electronic lollipop holder (apparently with toddlers, the more random, the better) that we'd occasionally whip out whenever she got antsy or irritated. 

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When we first arrived, there was a bit of a mishap with our rental car that we'd reserved in advance that was at another location, forcing G and my dad to go on a long adventure in search of it, while Sloan, my mom, and I waited behind with all of the bags. I tried to keep Sloan as distracted as possible, playing "store" in and around a deserted baggage carousel and when the guys finally returned nearly two hours later, I apologized to her for all the time we'd had to hang out in the airport and thanked her for being so patient. It was only then that I realized that she'd had a ball running around the airport with me. All of the inconvenience and annoyance the adults had experienced were completely lost on her. It's so rare that I have that much uninterrupted time when I'm not working, trying to get some place on time or attempting to balance daily tasks, that I didn't immediately realize she'd been just as happy to be with me. It was a nice reminder that as parents, we play such a big role in our kids' experiences and that we have the ability to really shift their perspective. It's my biggest takeaway from the trip for sure: Even now that we're back home, I need to remember to allow myself the time and space to be much more present. The juggling act is real—for all of us, but particularly for working mothers, and instead of feeling constantly guilt-ridden, I just need to do a better job at compartmentalizing, so there's always room to play "store."

One of the things I was prepared to deal with was jet-lag since Hawaii is three hours behind L.A. And while I was hoping that Sloan would sleep on the plane, she didn't, but ended up taking a quick nap on the hour-long car ride to the hotel, which was a blessing since she was tired enough to go to sleep at 8 p.m. (and miraculously slept until 7 a.m. the next morning). We just made sure to all adjust to Hawaii time as soon as we landed and didn't deal with any issues the entire time. As for sleeping arrangements, we got Sloan an air mattress that was right by our bed. And while a separate room would have been ideal, just so G and I didn't have to tip-toe around whispering in the dark, it worked out fine. 

Another thing I made sure to do with Sloan was stock up on food for her since she's such a picky eater and it's not always easy to find things she'll want at a restaurant. So each morning, we gave her a bowl of Cheerios with banana (we had all of the ingredients in the room) and we'd pack a bagel and cream cheese to take with us for lunch. Beyond helping alleviate some of my anxiety that we'd get some place and not have anything she could eat, it also allowed us to try out places she wouldn't normally go (aka out for poke, grilled shrimp trucks, etc.). I also had lots of snacks for her on hand at all times—mangoes, granola bars, etc. since the only times she had meltdowns were when she was hangry. At night, we could usually find items on a kid's menu that she'd eat—like a quesadilla or chicken tenders— that felt okay to get since the rest of the day she'd eaten (relatively) healthily. 

I came home feeling absolutely and whole-heartedly refreshed. It had been a while since we'd taken a proper relaxing trip and it's funny how it makes you appreciate even the smallest things. I noticed aspects about our house I'd forgotten I loved—the breeze that comes in our bedroom at night, the smell of the rosemary outside the front door, and light in our kitchen each morning. I look forward to incorporating some of my favorite parts of the trip, like drinks enjoyed outside and lots of after-dinner walks, as the best way to fully appreciate the fullest extent of our vacation. Read on for some of my favorite photos from the trip, and reader recommendations:

The view from our room after sun showers

The view from our room after sun showers

Our final sunrise

Our final sunrise

Hanging in the pool with 'Gaga'

Hanging in the pool with 'Gaga'

My new obsession (plus the branding is just so cute)

My new obsession (plus the branding is just so cute)

At the beach with her dad

At the beach with her dad

'Fifi' holding up Sloan's head while she napped in the car

'Fifi' holding up Sloan's head while she napped in the car

The Haupia Pie at Ted's Bakery

The Haupia Pie at Ted's Bakery

Sweaty after a hike 

Sweaty after a hike 

Shave ice at Matsumoto's

Shave ice at Matsumoto's

The pulled pork breakfast bomber at Kono's

The pulled pork breakfast bomber at Kono's

Showered and cleaned-up after a long day at the beach

Showered and cleaned-up after a long day at the beach

Ran into a girl wearing one of our jumpsuits at dinner—she looked gorgeous in it!

Ran into a girl wearing one of our jumpsuits at dinner—she looked gorgeous in it!

More shave ice 

More shave ice 

After a hike with my mom near the hotel

After a hike with my mom near the hotel

Our daily order: coconut, mango, papaya, and pineapple

Our daily order: coconut, mango, papaya, and pineapple

Strawberry daiquiri (for me), Mai Tai for G

Strawberry daiquiri (for me), Mai Tai for G

My favorites, on our way to dinner after our first day

My favorites, on our way to dinner after our first day

Ready for the pool

Ready for the pool

My go-to breakfast at Ted's

My go-to breakfast at Ted's

Eating fried fish and poke at Ken's

Eating fried fish and poke at Ken's

The poke at Pupukea Grill

The poke at Pupukea Grill

Pre-dinner shot from our balcony

Pre-dinner shot from our balcony

After completing the Pillbox hike

After completing the Pillbox hike

Dinner near the food trucks

Dinner near the food trucks

Sunrise Shack's açai bowl

Sunrise Shack's açai bowl

Additionally! When I asked for some Oahu recommendations over InstaStories, I received hundreds of incredible responses. I tried to condense the list as much as possible, and I've included the most-recommended spots below!

Key: Places with multiple recommendations are bolded and spots we visited have an asterisk (whenever possible, specifics have been added). Also I created an Oahu Highlight on my Instagram profile that you can refer to as well.

Our Family Trip To Hawaii _Breakfast

Moke's Bread and Breakfast (banana pancakes)
Leonard's Bakery (malasadas)
*Ted's (haupia pie + large Hawaiian breakfast plates)
*Kono's (breakfast burritos with kalua pork and awesome milkshakes)
Diamond Head Grill ("go for the blueberry cream cheese scones")
Heavenly
Kona Coffee Purveyors ("amazing kouign amann in Waikiki")
Over Easy 
Koko Head Cafe ("great place for brunch - get the cornflake french toast!")
Liliha Bakery
Cafe Haleiwa
Green World Farms (best coffee)
*Sunrise Shack (acai bowl, monkey bowl, blue dream)
Boots & Kimo's
Coffee Gallery (get: pumpkin and cream cheese muffins)
Haleiwa Bowl
Hukilau Cafe
Waialua Bakery & Juice Bar
Paalaa Kai ("you have to get the snow puffies!")
Island Vintage Coffee
Eggs and Things ("best pancakes")
Cinnamon's
Da Cove 

Our Family Trip To Hawaii _Lunch-Dinner

Arvo
Fete
Brick fire Tavern (best Neopolitan pizza)
*Pupukea Grill
Giovanni's Shrimp Truck ("and the corn stand nearby for their baja corn!")
Marukame Udon
Seven Brother's
(best fish burger)
Ono seafood (poke)
Morio's Sushi Bistro
Kahuku Grill
Mike's Huli Chicken
Kahuku Superette (like a local 7-11 but with great poke, get with rice and bring to beach)
*Elephant Shack ("good spot for Thai")
*Ken's Fish (we went three times and they're only open on Fridays and Saturdays)
Sprout Sandwich Shop
Surf N Salsa
Noi Thai (Obama used to eat there)
Mama's fish house
The Pig & The Lady
(this got the most recs of any spot for "Vietnamese fusion with great banh mi")
Yama's (quick stop for amazing Hawaiian food, great to take to the beach)
Mahina and Sun's
Ahi Assassins ("hole in the wall with the freshest fish")
Alan Wong's ("get the coconut cream dessert")
Rajanee Thai (in Haleiwa, best Thai despite the wait)
Side Street Inn ("get the pork chops and fried rice")
Haleiwa Joe's Seafood and Grill ("their prime rib is the BEST")
Storto's ("a sandwich shop with Hawaiian sweet bread and papaya seed dressing")
Impossible's Pizza Truck
Banzai Sushi
Beet Box Cafe
Papa Ole's (bomb cookout style burgers)

Our Family Trip To Hawaii _See-Visit-Do--

Dole Plantation ("touristy, but great for kids")
*Haleiwa ("cutest little beach town")
Laniakea Beach or Papa'iloa Beach ("turtles basking in the afternoon!")
*Pillbox Trail Hike
Lanikai Beach

Makapu'u Lighthouse Trail
Kualoa Ranch (Jurassic Park)
Makapu'u Tidepools
Ka'ena Point Trail (gorgeous views)
Makapu'u Lookout (30 minute hike)
Manoa Falls (favorite easy hike)
Hamama Falls Trailhead
Mau'umae Trail 
Koko Head Crater Trail
Ho'omaluhia Botanical Gardens
Maunawili Falls
Kailua (cute little town and nice beach - check out Kalapawai Cafe and Deli. Nearby hike: Maunawili Falls)
*Shark's Cove (a bit tricky to get to, but worth it for the snorkeling - plus there are lots of great food trucks right across the street)
Waimea farmers' Market (Thursdays 2-7pm)
Buddhist Byodo (temple in the mountains)
Ko Olina (3-4 lagoons with super calm water)
Hanauma Bay Snorkeling
China Wall/Koko Kai Mini Beach Park
Mermaid Secret Caves

Our Family Trip To Hawaii _Shopping

Owens and Co. 
Roberta Oaks
Here The Store
Paiko Hawaii
*Guava Shop
Fighting Eel
Olive & Oliver
Tini Manini (in Haleiwa town locally made children's clothes)
Kalakaua Ave (high end shopping)
Barrio Vintage
Bailey's Antiques and Aloha Shirts

Our Family Trip To Hawaii _Dessert--

Banán (banana frozen yogurt)
Waiola Shave Ice
*Matsumoto's Shave Ice
Island Vintage Shave Ice
Via Gelato
Bubbies ("best hot fudge sundae and mochi ice cream")
Island Snow in Kailua (Obama's favorite)
Duke's (hula pie)
Monsarrat Shave Ice

Our Family Trip To Hawaii _Drinks

Kaneohe Bay Sandbar
Lanikai Juice 
Wow Wow Lemonade
Bar Leather Apron ("cool speakeasy")
Royal Hawaiian ("go for the original Mai Tai")
Banyan Tree Bar at Moana Surfrider
The Hideout at The Laylow ("a cool mid century modern hotel")
Myrna Bird
Tchin Tchin Bar
Kona Brewing Company