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Maui Itinerary

7 Days In Maui With A Toddler

7 Days In Maui

There’s nothing a new parent needs more than a vacation. To celebrate keeping our son alive for a full year, my husband and I decided we’d treat ourselves to a relaxing vacation in Maui. Since it was Declan’s birthday, we figured he should get to go too so we all experienced the joy (read: horror) of traveling with a toddler. Here’s our 7 day itinerary with a points & miles round-up at the end.

Maui Trip Report 1Photo by Karma Hill Photography


Day 1 – Travel Day

For our first flight with Declan, we chose an early morning flight for two reasons. One, we knew he’d be in a good mood in the morning. Two, we knew he would probably take a nap because a portion of the flight was during his normal nap time. To encourage sleep, we dressed Declan in his pajamas so he’d be cozy and comfortable. We wheeled him through the airport using the wonderful car seat caddy and compact car seat that I talked about here. We stashed extra formula and snacks in our carry-on bags. And we made it to the gate with plenty of time to spare.

Too much time as it turned out. Our plane had a mechanical issue that resulted in a four hour delay. Luckily, I overpacked formula, snacks, and the diaper bag, but any longer and we might have started to run out. We were able to keep Declan entertained by walking him around the terminal to look at all the planes taking off and landing.

While the delay was frustrating, Alaska Airlines gave us each a $150 travel voucher for a future flight. Not bad for tickets we booked entirely with British Airways Avios. This is one of the reasons why Alaska Airlines is my favorite airline!

The flight was pretty uneventful and Declan slept for a good portion of the flight since he was tired from the delay. When we landed in Maui, we quickly got our rental car from Hertz and headed to our first stop: Target.

Here’s a great tip for traveling with a toddler: Order necessities online for pick-up in store at your destination.

We ordered diapers, wipes, and formula from Target before we ever left California and they were all waiting for us when we arrived in Maui. Read more about shop online pick up in store here. This saved us time on our first day and ensured we would be able to find the specific brands and supplies we needed without having to pack an extra suitcase full of diapers. (Which we did anyway. Be prepared, you know?)

We had a fantastic lunch/dinner at Da Kitchen which is located near the airport. The food was excellent. We loved it so much that to this day we occasionally have a box of their teriyaki sauce shipped to us in California. Then we set off for the Grand Wailea Resort Hotel & Spa where we stayed for the first four nights of our vacation.

Grand Wailea Resort and Spa Maui

The Grand Wailea Resort Hotel & Spa is a Waldorf Astoria resort that is part of the Hilton Honors program. It’s insanely beautiful. There’s something for everyone at this resort: fitness classes, an adult pool, a kid’s pool, a gorgeous spa, and great restaurants. Our Garden View King was very spacious with plenty of room to fit a crib. All of the rooms have a lanai or balcony which is wonderful to have in Maui.

Here’s another great tip for traveling with a toddler: Get yourself a room with a balcony.

By the time we arrived at the resort, it was Declan’s bedtime so we put him to sleep and sat out on the lanai to watch the sunset. It’s so nice to be able to sit outside where you can chat with your husband without being afraid to wake-up the baby. In Maui, it’s hard to find a lanai or balcony with a bad view. I’ll be talking more about this with my top 10 hotel hacks for traveling with a toddler on Sunday.

Day 2 – Relaxing in Wailea

Since there is a three hour time difference between Maui and California, the best day for early morning activities is your first full day on the island. We were all awake and well-rested by 4am Maui time. This made for the perfect opportunity to take some family photos.

I booked a family photo session with the ladies at Karma Hill Photography and they did not disappoint. We had a hour long photo shoot with Sasha who did an excellent job getting Declan’s attention for photos. I also hired Maui Makeup Artistry to do my hair and makeup before hand. Sarah and Shelby showed up at our hotel room well before dawn and got me camera ready in no time. I absolutely love these photos and I would not change a thing.

Maui Family PhotosPhoto by Karma Hill Photography

(Style tip: The mermaid color tutu I’m wearing is from Society-Plus. Head over there and get one for yourself!)

By the time our photo shoot was over, we were all tired so we decided to just enjoy the pool at the Grand Wailea Resort Hotel & Spa. We splurged on a cabana near the beach entry kiddie pool and spent the day relaxing in the shade.

Grand Wailea Cabana Maui

Day 3 – Birthday in Wailea

By day 3 we decided it would be best to keep Declan on his sleep schedule based on California time so we were up again before dawn. That day was Declan’s actual birthday so we spoiled him with some McDonald’s hotcakes for first breakfast. Hey, there’s not much open at 5am in Maui!

Grand Wailea Maui Buffet View

After McDonald’s and a nap, we hit the Sunday morning buffet in the Grand Dining Room at the Grand Wailea Resort Hotel & Spa for second breakfast. You can make reservations for this on OpenTable and I highly recommend it to anyone traveling to Maui. You don’t have to be staying at the Grand Wailea to make reservations. This was easily one of the best brunches I have ever had. The view was phenomenal (see above), the food was stellar, and atmosphere could not be beat. Reese gorged himself on the best sushi and sashimi he’s ever had so it’s a good thing we spent the rest of the day relaxing in an ocean front lawn casabella.

For dinner, we went over to Monkeypod Kitchen in Wailea. Since we were on California time, we arrived during their early happy hour which meant great food and cold beer for cheap. This was also one of my favorite places to eat in Maui.

Day 4 – Makena Beach and Snorkeling at Ulua Beach Park

Makena Beach Park Maui

After two days of relaxing by the pool, we finally decided to leave the resort and start enjoying some of the many fine beaches throughout Maui. We visited Makena Beach State Park (aka Big Beach) and then Ulua Beach Park where I saw my first sea turtle swimming in the wild. Aside from the turtle, Ulua Beach had decent snorkeling, a nice little area for kids to play in the water, and a small parking lot with facilities. But taking an infant to a beach is no cake walk so we gave up before we hit our third beach due to lack of parking and exhaustion.

We spent our final night at the Grand Wailea Resort Hotel & Spa enjoying take-out from Fabiani’s. Again, we just sat out on the lanai and enjoyed the view while Declan slept.

Day 5 – Upcountry & Ka’anapali

We planned on hitting the Road to Hana on Day 5, but ultimately decided it was too risky with a infant so we settled on exploring Upcountry Maui instead. We had a wonderful lunch at the Hali’imaile General Store and took Declan to see the goats at the Surfing Goat Dairy. This was a really fun activity for kids. Declan was a little too young so I took a turn milking the goats instead. Keep in mind that Upcountry Maui is very hot so be prepared for the weather and wear lots of sunblock.

Surfing Goat Dairy Maui

That evening we checked into our second hotel the Westin Ka’anapali Ocean Resort Villas. We had a Deluxe Studio Island View Villa with a full kitchen and more than enough room for our little family. We booked this resort using Cash & Starpoints from my Starwood Preferred Guest Credit Card. I’ll write more about redeeming Starpoints and Cash & Points nights in a future post.

Day 6 – Snorkeling at Kahekili Beach Park

We went searching for more great snorkeling spots on day 6, but we gave up after the second beach with no parking and headed back to our hotel. Well it’s a good thing we did because it turns out the best snorkeling was right outside our hotel!

Turtles at Kahekili Beach Park Maui

It’s called Kahekili Beach Park on Google Maps. If you’re not staying at the Westin Ka’anapali Ocean Resort Villas, there is a large parking lot, bathroom and shower facilities, and even a pavilion with picnic tables. We had a view of the facilities from our room. There’s not much sand between the grass and the water’s edge, but the reef starts almost immediately upon entering the water. We took turns snorkeling while the other took care of Declan in our room. We saw sea turtles (four!) and lots of colorful fish. It was really a great place to snorkel and I guarantee we will be back even if we don’t stay at the resort again. (I’ve been having trouble finding those Cash & Points nights that I love so much.)

 Kahekili Beach Park Maui

Day 7 – Maui Ocean Center & Travel Day

On our final day in Maui, we packed up and headed towards the airport. On our way, we stopped at the Maui Ocean Center. It seemed like a great place to let Declan walk around for a little bit before he was cooped up on a plane for over five hours, but, honestly, it was pretty disappointing as far as aquariums go. We’re fortunate to have the incredible Monterey Bay Aquarium nearby so maybe we just had high expectations. I doubt we’d visit the Maui Ocean Center again and I don’t really recommend it unless you just need to kill some time.

Maui Trip Report Maui Ocean Center

After we left the Maui Ocean Center, Declan had a massive diaper blow-out that leaked all over his car seat. There was no way we could clean it up well enough to take the car seat on the plane so again I used order online, pickup in store to buy a replacement. We had to leave the old car seat in a shopping cart in the Target parking lot. Trust me when I tell you that while I regret leaving it behind, there was no other way to handle that situation.

Our last stop before the airport was Costco. Costco is the secret to cheap fuel on all of the Hawaiian islands. There is usually a Costco right near the airport and if you bring your card with you from home, you can take advantage of the cheapest fuel around before you return your rental car.

Our flight back to Oakland with Declan was a lot more challenging than our flight to Maui. Declan refused to nap the entire flight. Luckily, he didn’t cry much and we were able to keep him busy with the Fisher Price apps on my old iPhone.

Travel Curse Strikes Again

In an effort to get Declan to go to sleep, I kept feeding him formula throughout the flight. It did not help him fall asleep, but it did cause him to vomit all over Reese when we landed. Now there’s an easy way to tell who on a plane full of passengers are parents and who are not. How do they react to a baby throwing up? The aisle was full of people waiting to deplane when it happened so the only thing we could do was sit there as the fellow parents gave us those knowing looks of understanding and the non-parents tried to control their gag reflexes. Luckily, everyone had a change of clothes in our carry-on and Reese and Declan were able to get changed before we headed home.

Points and Miles Round-Up

We booked 3 roundtrip economy tickets from Oakland to Maui on Alaska Airlines using a total of 75,000 British Airways Avios from the British Airways Signature Visa. Fees for these tickets were $33.60 total. For more information on British Airways and Avios, read Redeeming British Airways Avios and Evaluating Value: British Airways Visa Signature Card.

We booked 4 nights in a Garden View King at the Grand Wailea Resort Hotel & Spa using two weekend night certificates from the Citi Hilton Honors Reserve Visa Card, 70,000 points Hilton Honors points for the third night, and $354 cash for the fourth night. The Citi Hilton card is no longer available. The Hilton Honors Surpass Card from American Express will completely take it’s place in January 2018. We had to pay the $30 resort fee on our fourth night plus $30 a day for valet parking for the whole stay. The Grand Wailea does not have a self-parking option so valet is your only choice if you rent a vehicle. The total for our stay was $504 plus tax. For more information about Hilton Credit Cards and Hilton Honors Points, read Wallet Wednesday: Hilton Honors Surpass Card and Hilton Honors Card and Redeeming Hilton Honors Points.

We also booked 2 nights in a Deluxe Studio Island View Villa at the Westin Ka’anapali Ocean Resort Villas for 10,000 Starpoints from the Starwood Preferred Guest Credit Card and $180 per night. Self-parking was $15 per day. The total for our stay was $390 plus tax. For more information about SPG and Starpoints, read Redeeming Starpoints and Evaluating Value: Starwood Preferred Guest Credit Card.

We rented our car through Hertz for $251 cash because we did not have Chase Ultimate Rewards points at the time.

The grand total for our 6 night stay: 75,000 British Airways Avios, 2 weekend night certificates from Hilton, 70,000 Honors points, 20,000 Starpoints, and $1178.60 cash.

Final Thoughts on Maui with a Toddler

I consider this to be a pretty successful points & miles trip. Sure, we still spent some cash, but we stayed at some fantastic resorts that were more than worth the reduced cost.

It was certainly not the dream vacation I envisioned when I thought of going to Maui, but that’s pretty much to be expected when traveling with a one-year-old. We all had a wonderful time and we got to see some incredible beaches and wildlife. But next time, I hope there are less bodily fluids.