Every Christmas break we take a vacation with the kids to a warm climate just as the temperatures in New York drop. The past few years we have taken a trip to Cabo. Last year, the weather was super iffy with high winds, cold temperatures and rain. Not only the weather put a damper on our precious time away together but we also learned that our kids have reached an age where they need a little more adventure in the mix of our travel versus sitting on a beach and swimming at the pool all day. With this in mind, Adam and I decided to take them on a real trip this year…to Hawaii. Given the long distance we worked it out so we could travel for two weeks (we normally go away for one week).

I don’t normally use a travel agent because travel is so easy to book online however when I take a trip that requires a lot of transfers, car rentals and various hotels, I find it more effective to get some help. A friend of mine once recommended Tate Escapes and I’ve been using Tate for these types of trips ever since.

Tate nailed it with this one. The itinerary that she put together was absolutely perfect for my family. I would not have known how much time to spend on each island and I found it very helpful having Tate arrange all of our flights, hotels and car rentals throughout Hawaii.

I so enjoyed sharing our trip on Instagram stories while traveling and got the most wonderful feed back and messages from my followers. I have added the trip as a highlight on Instagram now, look for the rainbow to watch anytime 🌈.

I’m listing an overview of our itinerary here and a full recap of our travels below.

December 21st: Flew American Airlines from JKF to LAX, LAX to Honolulu
Rented a car.
12/21-25th: Turtle Bay Resort on the North Shore of O’ahu
December 25th: Flew Hawaiian Air from Honolulu to Maui
Rented a car.
12/25-28th: The Ritz Kapalua Maui
December 28th: Flew Hawaiian Air from Maui to Kona
Rented a car. Drove 2.5 hours to our next accommodation. If you want a closer drive, fly into Hilo airport.
12/28-30th: Volcano Rainforest Retreat
December 30th: Drove 2.5 hours to the other side of the island, drove along the coast for breathtaking views and scenery.
12/30-1/3: Mauna Kea Beach Resort
January 3rd: Flew American Airlines from Kona to Dallas, Dallas to JFK
We had one day home (Sunday) before the kids went back to school and us to work. This was SO KEY to getting us all back on track with sleep, laundry and prepared to going back to reality…

Now here’s how the trip went down….

My kids happen to be well seasoned travelers so the long flights were a breeze for them. We’re always well stocked with books, movies on our ipad and snacks.

12/21-25th: Turtle Bay Resort on the North Shore of O’ahu

December 21st - Travel Day

We arrived in Honolulu late in the day and drove one hour to our hotel. The kids passed out in the car on the drive over but woke up when we got in and I was starving so we ordered room service (my absolute favorite part of a trip, always, weird, I know). We ate BLT’s and chicken nuggets in bed then passed out, hard.

December 22nd

Our room at Turtle Bay was awesome. It’s an old hotel but they’ve been doing work on it and the room we got was a new one. It was a “beach cottage” located right on the ocean so when we woke up in the morning we would go onto our deck to hang out with the waves crashing right in front of us.

After breakfast, we hit the pool that had a water slide for the kids. They loved it. Adam and I got to hang out on the lounge chairs while the kids slid down that thing 1000 times. It was blissful.

We wanted to get out of the resort for lunch and found a spot that wasn’t too far away called Haleiwa Beach House. It was so quaint, across the street from the beach and the food was delicious. A great find. We were heading to our friend’s house for a Hanukkah party shortly after lunch and wanted to pick up some wine to bring. We took a drive and wouldn’t ya know it…right across the street from the cutest wine shop ever was an Aviator Nation! Gosh I love that store. Naturally, I did a little shopping while in there.

Adam and I went to Hawaii back in 2005 for our friends Jon + Erin’s wedding. Erin is from Hawaii so before we booked the trip we confirmed they would be in the area over the holidays. Erin’s parents have a beach house in the North Shore and invited our family over for a Hanukkah Celebration which could not have been sweeter or more perfect. Hanukkah is not always so late in December so we normally celebrate at home with our family. It was so incredibly amazing to have close friends to celebrate with while traveling instead of skipping the holiday. Erin’s parents went above and beyond with the food, gifts for our kids and making us feel right at home. We had a lovely evening with them and it was so fun reconnecting with Erin, Jon and their kids who live in DC so we don’t get to see as much as we did when we were all younger (pre-kids!).

December 23rd

On our second day in the North Shore, we ended up having breakfast with some of the folks we met at the Hanukkah party who were also staying at our hotel for the night and then hit the tennis courts and swam for a little bit (well the kids and Adam did all this activity…I sat by the ocean reading, once again, blissful).

For lunch, we met back up with our friends at the Kahuku Sugar Mill where they park a variety of food trucks in between our hotel and their house. There were soooo many great trucks to choose from! I wanted them all. Gavin and I decided to share a bunch of different truck dishes so we could do a good sampling while there:
1. Huli Huli Chicken: the juiciest chicken I ever did eat.
2. Cheesus Chrust: Does a play on words get better than this? AMAZINGLY Delicious pizza!
3. Seventh Brothers: Some crazy fry + pineapple + onion ring dish - don’t ask. Was a bit heavy for us! But worth trying.

Erin’s parents house is on the water where the beach is private and the waves are huge. The weather was so incredible we decided to let the kids spend the afternoon playing in the waves. They could have been in there forever. It was pure heaven to them jumping those waves!

We left our friend’s place in the late afternoon and went back to the resort for dinner at Roy’s Beach House. Truth be told, we were quite TIRED! But the food was pretty good. We just fell asleep while eating it…ha!

December 24th (AKA Christmas Eve)

Another day in paradise…and another day with our dear friends. This time…we met up for lunch and a day at the Polynesian Cultural Center. This was such a cool spot for kids! Every way you turn there is something for them to do and learn (without them even knowing that it’s educational) about different Polynesian cultures. We watched a show, got tattoos, watched another show of dancers on boats in the water, made fish hook necklaces out of clay, played with our balls, walked under waterfalls…the list goes on. I highly recommend this place if you’re in the area. Bring sunblock, hats and make sure you drink a ton of water, it was HOT!

The day ended with another dinner at their house, more quality time, insanely delicious food and a bonfire on the beach. I mean c’mon! It was too perfect. (also a huge bonus to the trip: Erin + I were talking about how difficult it is to pack for 4 people for 2 weeks! That’s a lot of #@*%! Erin offered me to do laundry at her mom’s house. BRILLIANT! It was a total game changer to do 3 days worth of clothing. Got me 3 extra days on the back end!!) We lit the third night of Hanukkah candles and sang the blessings together. I mean….seriously. My heart was so full.

December 25th (AKA Christmas)

D-Day. Time to leave our pals and head to MAUI.

On our way to the airport we swung by Ted’s Bakery because so many of our friends (and strangers!) recommended it to us. Everyone said…you have to try the pie! So we tried the pie. Was good but I’m unclear on the hype. That may just be because I don’t have a sweet tooth. I think I was personally more excited by the roosters that roamed around while we ate whom I named after each of my family members. HA!

We boarded a flight to Maui (was shockingly easy on Hawaiian air). We got on that plane, off the plane and got our luggage with zero waiting time. Was pretty remarkable and not what we’re used to (ahem, Air Canada).

When we arrived at the Ritz Carlton in Kapalua we were pleasantly greeted with a fruity mocktail that was refreshing and cool. The boys and I walked around while Adam checked us in…and when Adam walked over with our keys he was like..um, you guys…look ! There is a rainbow! Well isn’t that special…..! The boys go: Now we understand why the license plates have rainbows!

We spent Christmas Eve at a buffet that I had signed us up for through the hotel.
Truth: Wasn’t worth it. Those hotel holiday buffets never are. We should have just eaten in a restaurant.

December 26th

We had a really fun and fabulous boat ride planned. I had planned this outting with Gavin months in advance…we were so stinking excited about it. This boat was going to be a 5 hour ride, a sick menu / bbq lunch was listed, unlimited bevs, water slide into the ocean, glass bottom, snorkling, etc etc.

We were on our way and got a call when we were just about 10 minutes away. Sorry ma’am, the boat ride has been canceled due to high surf. I was so bummed it hurt but I looked at the boys and said, This was G-d’s way of keeping us safe. The next morning, there was a helicopter missing in Kuai and I had hundreds of messages from friends and family wondering if it was me. Beyond scary and I am so grateful to be safe. I’m also sad. We had 6 different days on our 12 day trip where the water was too rough. Such a crazy thought isn’t it? It’s like the earth is mad at us…rightfully so.

Ditto for our luau, it had been canceled due to rain but for all of these lemons…life just handed them right on back to me. We rebooked boat rides (not as elaborate) that were just as fun as our original plan. We also rescheduled the luau to the next night and I must say, it was my favorite night in Hawaii.

December 27th

The boat rides that we re-booked truly made for the best day. I don’t even know where to begin…
We started the day with an express, 2 hour snorkel. The guys who ran this boat were a bunch of blondes from California who were very well trained and made me feel safe. We all got to go into the water to snorkel. I got in for about 6 minutes and then came out to enjoy champagne on the boat. Gavin was out shortly after me and joined me with a mocktail. Meanwhile Luke and Adam were swimming with the turtles. Luke got so close to one he could smell his breath! And he knew not to touch them….
Following this delightful boat ride, we walked through the beach town that we were in called KA'ANAPALI to a cliff that we heard you can dive off of…Gavin was way ahead, gunning it to this cliff. Luke ran behind and started to climb up with Adam. Before I knew it, Luke climbed back down with Adam and Gavin made it up to the top. I spotted his bright blue bathing suit and I yelled BE CAREFUL GAVIN! He jumped. I am so thankful he’s so fearless. I can do a lot of things, but I could not have done that.

After the big jump, we did a bit of shopping, I bought my first ever swim shirt from Lily Pulitzer and then we had lunch at Monkey Pod Kitchen which was amazingggggg. They have a few locations around Hawaii so make sure to check the location you make a reservation at if you go.

Following lunch was boat ride #2 by PacWhale Eco Adventures also recommended by our friend. We came up very close to whales and Luke + I also took a 90 minute nap. Hey! It’s that ocean water. Again, blissful.

Believe it if you can, but after TWO boat rides and a long day of adventure, we rushed home to change for our rescheduled Luau! Man was it worth it. The luau was an infusion of culture. It was beautiful, delicious, fun and my children loved it. They had so much fun with the theme (they bought shirts at the beach), they loved their leis, Luke came up with a mocktail called: The Lukey Luau (orange juice with a splash of sprite). There’s something about a dinner show that is just so cool! Thanks to my friend Minh-Ha who suggested this one which I highly recommend: The Feast at Lele

December 28th

We had our last buffet breakfast at the Ritz and spent the morning by the pool. We checked out around lunch time and hit up Paia Fish Market that we had heard of through a friend for fresh fish tacos before our flight to Kona.

Once we got to Kona, we had a 2.5 hour drive to the Volcano Rainforest Retreat. I cannot put into words how much I love this place. I found this place back when Adam and I were in Hawaii in 2005 and when we decided to take the kids this was the first place I booked. I could not wait to bring them here! There are only a few cottages on the property so it’s very private and you’re completely immersed in the rainforest. Our guest cottage had a glass ceiling, fireplace, kitchen and Japanese hot tub in the back. When you wake up in the morning, it’s always raining so you hear and see the rain drops coming off the trees above and around you. By 9am the sun comes out (if you’re lucky…which we were!) and the whole place fills up with beautiful, natural light.

December 29th

For the one full day that we had in this part of the island, we went to the National Volcano Park. The volcanos are no longer active. All the lava has erupted and created new land around the island, even into the ocean. The kids were in awe of everything that they saw in this park from the natural steam vents to the lava rocks that they hiked and climbed all over. We were all pretty taken by the lava that spilled into the ocean that we got to walk on. At one point, the kids turned to us and said, “Mom & Dad, Thank you so much for taking on this trip, this is the coolest thing we have ever done.” Tears filled up in my eyes from their gratitude, their appreciation of our earth and for all the questions that they were asking with genuine curiosity.

We took a Volcano Park break and had lunch at a hidden gem referred to us by the owners of the Volcano Rainforest Retreat called Cafe Ono. The owner opened this cafe within his art gallery / gift shop and made every place to sit unique with pieces of art that you could buy if you wish, bright colors and lush gardening. The food was vegetarian (scared me at first because we are hard core meat eaters) but we all found something delicious on the menu. Was perfect.

For dinner that night we went to Ohelo a darling restaurant right down the road from where we were staying. The food was delicious and the service was wonderful especially for a family of 4 pretty exhausted folks.

December 30th

The boys woke up and were dying to get one more hike in at the Volcano park before check out. Adam took them while I cleaned up the cottage before having to check out.

Around 11am we left the Rainforest and took an incredibly stunning drive over to the dry side of the island. Driving along the coastline was mesmerizing (and nauseating) and fascinating to see so much untouched, lush land once again making us realize just how beautiful our planet is and how lucky we are to be living on it.

Along the way we made a pitstop at the black sand beach where there were large, adorable turtles sunbathing and we got to gawk at them…

On our way to the next hotel, we stopped at another spot recommended by a friend called Lava Lava Beach for lunch. It was FABULOUS! Such a fun scene right on the water, tons of games for the kids to play while we waited for our table and a delicious menu. Highly recommend this place.

Once we got to our hotel we settled in at our final hotel, The Mauna Kea (one of our faves ever) and got ready for an adults only dinner with a different set of friends who were staying at this hotel with their family. We ate at Red Water Cafe, nothing to write home about but a lovely night out.

December 31st - January 3rd

The rest of the trip, we HIT THE POOL AND BEACH and even got in some R&R! It was so amazing to get all the activities done in the first part of the trip and then have this beach + chill time planned for everyone to take a breath and relax.

The best part of traveling with our kids now is that they are old enough to go off on their own in the hotel. At the Mauna Kea there was an activity center (mostly outdoors!) where the kids could play pool, ping pong and bocce ball. They felt such a great deal of independence going off to play games on their own and bonded as brothers using each other to play with instead of constantly asking us. Of course we spent all our family time together in the water and it was the best. Jumping waves with our kids (mostly Adam because I’m a nervous Nelly who screams when I think a wave is gonna break on me and kill me!!) is the absolute best. They are so fearless it’s insane.

I think I’ve talked long enough about this trip. There are certainly a few things I may have missed but I know I covered all the really good stuff. Of course if you have any questions please ask in the comments below! I’d be so happy to answer.

Aloha!