February 21, 2022
It’s time for our annual Hawaii recap. We’ve been back for a couple of weeks now and we are still reeling from our time in Maui. Feeling truly grateful for such a wonderful vacation. We went for 28 days and it felt like the perfect amount of time. My sister and her daughter came for 9 days during the beginning of our trip and they had a blast! As you might already know, I’m a planner. I like to plan out most of our vacations – day by day – even planning for do-nothing days. I planned out the days my sister and niece were there, but we didn’t really stick to a schedule after they left. I’m going to walk you through the trip and include as much as I possibly can – with links! In the past, we’ve visited Kauai, Oahu, and Maui but the last couple of years we’ve stuck with Maui only. We’ll probably go back to Oahu next year for a few reasons, but most importantly for Seven Brothers burgers.
Our travel to Maui was quite uneventful. We flew from Boston to Dallas and then on to Maui. The first flight was about 4 hours and the second flight was 8. We had just enough time in between our layover to grab some breakfast in the airport. The girls are incredible travelers so we are spoiled in that department. They both put on their headphones and watched a bunch of movies. They slept about 4 hours between the two flights. I had also bought them some coloring books so when they weren’t watching movies, they were coloring. We landed in Maui at about 4 pm and headed straight to Target to get the things we didn’t want to pack – bathing suits, sunscreen, etc. Then we were off to check out the condo. This year, I let Jon take over the accommodation arrangements and he absolutely knocked it out of the park. He found a beautiful condo in the most convenient location. Here’s the link! It had everything we needed and was very spacious. The best parts were 1. the pools – we were usually the only ones swimming and 2. the location – every morning I would walk from the condo down to the Honolulu Coffee Company at the Shops at Wailea. 3. The sunset view from our deck – it was gorgeous! Another favorite was the washer and dryer – what a game changer! We usually have to pack up our stuff and take it to a local laundromat but to have one right in our condo was really nice.
During the first couple of days, we mainly caught up on sleep and time zones. Jon and Poppy got sick during those first two days so they stayed in and soaked up the sun at the pool while Willow and I explored the area. When Jess and Bella arrived, it was time to break out the planner. I don’t like to overdo it so I usually only plan one or two (or three lol) things a day and obviously, I make sure they’re up for everything we have on the list! After I picked them up at the airport, we drove straight to the beach to watch the sunset. The perfect welcome to Maui. Here’s what our schedule for their time in Maui looked like…
Sun: Walk | Pool | Beach | Dinner
Mon: Calypso trip 6 am – 1 pm (snorkeling at Molokini Crater, boat jumping, turtle town) | Pool | Lava field
Tues: Hana – Surf spot, Garden of Eden | Paia – açaí bowls | Beach for sunset
Wed: Breakfast at Kihei Caffe | Market shopping | Beach and pool all day | Beach for sunset
Thurs: Ioa Valley | Beach | Mom & Dad dinner out
Fri: Sunrise at Haleakala
Sat: Beach | Girls dinner
Not bad right? We got it all in too! It never felt like too much. As I mentioned, the weather was just perfect. Our go-to beach is Big Beach (Makena). I would NOT recommend it for families with young children as the waves are HUGE, but if you have good swimmers with you it’s the best in our opinion. Ioa Valley is a very easy hike and a fun one. We walked down to the water and found a perfect little rock pool for swimming. It’s great for a short morning trip before a beach day.
This year, we did not go all the way to Hana. Last year we did and we actually stayed for 3 nights out there. It was amazing and so peaceful but we didn’t want to head all the way out there this time around only to turn right around. Instead, we decided to go about halfway to the Garden of Eden with some fun stops on the way. The Garden of Eden is a must stop in our opinion – with a bamboo forest, a view of the Jurassic Park opening scene and lush gardens thorughout, it’s a peaceful place where peacocks and other birds follow you while you explore the many paths and trails. This was the first year that we went to Twin Falls which is not far into the drive. We were all so glad we did! My niece Bella and Jon did some cliff jumping into the water and the girls and I stayed below playing in the rock pools. We would definitely go back next time. Every time we head towards Hana, we make stops at Ho’okipa Beach and the town of Paia. Jon always takes some great drone shots of the surfers at Ho’okipa and we always get something tasty in Paia.
A first for us this year, we visited Haleakala for sunrise – well, just after sunrise. It’s almost impossible to get a reservation for sunrise as they sell out so quickly. We tried multiple times but the second the slots become available, they sell out. We decided to go just after sunrise and it was absolutely breathtaking. We were 10,000 feet up looking into a dormant volcano – above the clouds. Highly recommend this trip, but keep in mind it’s a little farther than the map tells you it will be.
This was our second year doing the trip out to the Molokini Crater on the Calypso. It’s a great time. After some whale watching on your way out to the crater, the boat parks and almost immediately we’re all jumping off for snorkeling through the crystal clear water. After snorkeling, we head up to one of the top decks for jumps and slides into the water. After a couple of hours, we pack up and they take us over to turtle town where you can snorkel more and swim with the turtles. Poppy had passed out by the time we arrived in turtle town so I skipped that part but the rest of the group had a blast and saw some huge turtles! It’s the perfect morning/mid-afternoon trip and the crew is always fun and so sweet!
After Jess and Bella left, we did another hike and some fun kid stuff. My favorite hike of the trip was the Kapalua Coastal Trail – stunning views and gorgeous beaches along the way. There’s a great beach for snorkeling (Kapalua Bay Beach) but it is slightly crowded and another peaceful and secluded one that is worth the trip (Oneloa Beach). Poppy celebrated her 3rd Birthday while we were there and we decided to go to the Aquarium with her after some whale watching at our favorite lookout. Speaking of whale watching, I might need to write an entire post just on that because we saw so many incredible things this year, including a rarely captured heat run! Mamas with their babies, lots of breaching – it was unreal. We also made it over to the new Maui Golf Sports Park – this was a blast for the kids. It had a rock wall for climbing, bumper boats, mini-golf, and an awesome shave ice stand!
After day 17, it was time to check out of our Airbnb condo, and honestly, it was a sad day. We had fallen in love with that little place! We were excited to head north up to Kaanapali for the more luxurious part of our trip. This was also the part of our trip where Brie Shelly of The Experience by Brie took over. We’ve never had a vacation like this one before. It turned a great trip into an experience we will never forget filled with surprises along the way. We headed back to our favorite spot for R&R – the Westin Maui Resort and Spa. Last year, the hotel was finishing up a huge renovation and this year it was completed. Since we booked through Brie, we had so many incredible perks, one of which was an upgraded room in their new Hokupa’a Tower and exclusive access to the Lanai. As Hokupa‘a guests we were treated with panoramic views, daily artisanal Hawaiian small bites at breakfast and dinner, a private bar, infinity edge cocktail pools, and cultural experiences. To give you an idea of the “small bites” – filet mignon over a bed of rice and Haagen Daz ice cream for dessert or scallops and tiramisu. It was really extravagant and also the perfect place to relax, take a break from the sun and watch the whales breaching from above the resort. We also had breakfast credits for every morning of our stay at their top-of-the-line restaurant, Waicoco. After checking in and catching our breath after hearing about our upgrades, the girls were greeted with special gifts, and then it was pool/slides time!
The girls made some friends pretty quickly and spent most of their days playing with them. You really don’t need to leave the resort after you arrive due to the 6 pools, two slides, three restaurants, market, Starbucks, etc., but we did sneak away a couple of times – once to explore the town of Lahaina, and another day we spent an afternoon at Slaughterhouse Beach with some beached sea turtles. Back at the hotel, Jon rented a complimentary go-pro and we made our reservation for their famous Luau. Highly recommend the Luau if you’re staying at the Westin – it was an amazing experience. Our friend Hannah from California was staying in Lahaina so we got to hang with her during our time in Kaanapali which was extra special.
After a week at the Westin, we were headed back to Wailea to finish our trip at the Andaz – one of our favorite hotels in the world! The same day we were scheduled to check-in to the Andaz, it was also Poppy’s Birthday so this was the day that we visited the Maui Ocean Center, mentioned above. We checked in just before dinner and thanks again to Brie, we were upgraded yet again and asked to meet back in the lobby after exploring our room. We arrived back in the lobby and a sweet man met us there and took us to a room for a private Hula dance lesson. We NEVER would have done something like this on our own, but it was one of the biggest highlights of our trip. We spent an hour with him as he explained the history behind Hula and the instruments used for this special dance. By the end of our lesson, we felt like Hula pros – although we probably did not look like it! The girls received the ultimate gift basket when we returned to our room which even had a framed photo of our family included! Talk about feeling special.
We spent the final few days of our trip swimming, eating, drinking pina coladas, and walking the beach. It’s always hard to leave Maui, but after a trip like this one, it was extra hard. We set aside a little time every day for a gratefulness circle and also to remind the girls how lucky and blessed we were to have spent this time together in such a beautiful place. The girls were troopers during our busy season and it was an especially hard year for them as we had almost double the amount of work due to covid the prior year. This was our time to be fully present and just be together every day. We cherished every single beach walk, every swim, every dinner together. I did bring my professional camera, but I also brought three different polaroid cameras to capture live moments. I’m so glad that I did because these photos and the memories we made are really all we have to remember this time we spent together in paradise. Our flight home left around 10 pm and the girls slept just about every second of both flights. The way back is always a breeze compared to the way there.
I know that many of you are planning your Hawaii adventures and I would love to answer any questions you might have, so please reach out! If you don’t know where to start, I highly recommend reaching out Brie – she is the best and I was absolutely blown away by her planning and attention to detail. We already can’t wait to start planning our next trip with her soon! I know I missed a ton, but this is getting quite long so I’ll wrap it up here! Here are some of our favorite photos from the trip. We already can’t wait to be back on our OTHER favorite island!