Aloha from Hawaii! With March Break upon us, we headed to the Paradise of the Pacific for our first family trip of 2022.

This trip had actually been planned for 2020, but because of the pandemic, we had to push it back a few times. Needless to say, I’m glad that we finally made it here.

For this trip, we visited Maui and Oahu and made use of two timeshare preview packages, which we were very grateful we had, given the current prices of accommodations in Hawaii. We also had a chance to visit a couple of aspirational properties along the way too.

In this post, I’ll cover the basics of our trip, the itinerary, and the activities we did in Maui, with the next few posts covering more detailed reviews of the properties we stayed at and what we did in Oahu.  

COVID-19 Restrictions in Hawaii

Throughout the pandemic, Hawaii has been the state with perhaps the strictest travel restrictions compared to the rest of the USA. Recently, Hawaii has also relaxed their COVID measures. 

For entry from international destinations, including Canada, Hawaii follows the US federal requirements. This simply requires a negative COVID-19 antigen test within one day of your flight and proof of vaccination (children under 18 years of age exempt from the vaccination requirement).

For more information on Hawaii’s travel requirements, refer to Hawaii’s official travel website. All passengers who are not in quarantine are free to travel between islands without restrictions.

Currently, mask mandates are still in effect for indoor spaces, but as of March 26, 2022, this will no longer be required. 

The Itinerary

We really didn’t want to rush our time on the islands, and given that our kids were blessed with two weeks of March Break, we spent a total of 13 nights between the two islands, split up as follows:

• 2 nights: Kapalua, Maui at the Ritz-Carlton Kapalua
• 5 nights: Kā‘anapali, Maui at the Marriott Maui Ocean Club
• 2 nights: Wailea, Maui at the Grand Wailea,  Waldorf Astoria Resort
• 4 nights: Waikiki, Oahu at The Grand Islander by Hilton Grand Vacations

We stayed at a mix nicer properties and timeshare properties. We found this to be a good balance, allowing us to have relaxing days to enjoy the pools and amenities at the more luxurious resorts, while using our time at the timeshare properties to explore the islands.

It would be a waste to stay at the Ritz-Carlton and Waldorf Astoria otherwise!

The Flights

To get to Maui, we flew from Toronto to Maui in economy class on WestJet. WestJet doesn’t have direct flights, so we had an overnight layover in Calgary, which was fine to break up the almost 10-hour journey. 

Why go with WestJet when Air Canada has a direct flight? Well, both my husband and I had companion vouchers and WestJet Dollars to burn, so it made sense. We essentially paid cash on only the taxes for our flight. 

One thing to keep in mind is that unless you’re on WestJet’s Dreamliner, there is no screen on the seat to keep kids entertained, so bring tablets for them to watch stuff through the WestJet app or some books and activities to keep them occupied (this is what we opted for).

Coming back from Honolulu to Toronto, we booked a direct flight with Air Canada through an Aeroplan points redemption. Aeroplan is now a great program to redeem flights to Hawaii with.

We booked early on and were able to secure three one-way business class redemptions for 33,100 Aeroplan points each.

I booked the remaining two tickets in Economy Latitude for 27,200 Aeroplan points, with hopes that eUpgrade space would open up closer to our trip. About two months out, the “R” space opened up, so we were all now in business class for our nine-hour red-eye flight back.  

For our 40-minute inter-island flight between Maui and Oahu, I booked with Southwest for US$39.10 per ticket. The cost was covered by my annual US$200 airline fee credit from my Amex US Platinum Card.

The Car Rental

We rented with Hertz on both islands, mainly for the Ultimate Choice program that’s available at both locations.

The gist of the program is that if you have Hertz Gold status or above, book any midsize car and up and you can have your choice of vehicle from your designated parking lot (based on status and availability) when you arrive.

The choices at Maui’s airport were slim pickings, but we were able to grab a Dodge Caravan for US$607 for 10 days. In Oahu, we grabbed a Ford Explorer for US$303 for four days. For these rates, we used an eligible corporate code to unlock some savings. 

Another tip is that if you are booking with Hertz in Maui or Oahu and need a car seat or booster, do not add it to your initial booking online. Rather, just ask for one when you arrive. Both times the agents just told us to grab one from the back and did not charge us anything extra. 

Of course, if you want to guarantee there is car seat availability, then book beforehand. However, availability wasn’t an issue when we were travelling during the peak season of March Break.

Kapalua

Kapalua is the located in the north end of Maui. It is a bit far removed from many of the activities on the island, and everything here is a bit more spread out. 

If you still want to be in touch with civilization but want to be a little further removed from the the busyness of the other parts of the island, then this can be the perfect destination for you, even if it’s just for a couple of nights. 

To be honest, we weren’t planning on staying here initially until I learned that our good friends would be in the area staying at the Ritz-Carlton. We decided to join them, and had no regrets. Stay tuned for a future post of my review of The Ritz-Carlton, Kapalua. 

In terms of activities in the area, there is a nice Coastal Trail that’s an easy hike for even the youngest mobile kids. The beaches around here are smaller, but still quite picturesque. 

Snorkelling around Kapalua Beach is quite popular.

Should you be snorkelling with younger kids (and even adults) I would highly recommend purchasing a full face mask off Amazon.ca for ease of use. 

As for restaurants, there are few noteworthy places, including The Gazebo for breakfast or brunch (they’re well known for their fried rice and pancakes).

Make sure to arrive before 7:30am if you want to be seated quickly. Otherwise, you could be in the line for up to two hours.

If you do need to wait, there’s a beach below to to keep the kids busy, and if during whale season, you can try spotting breaching humpback whales from here (we saw quite a few). 

For a bit more of a fine dining experience, try out Merriman’s, which also features live music a couple of hours over dinner each night.  

Kā‘anapali

Kā‘anapali is a busy resort area on the west side of Maui, located on a 5km stretch of sandy beach. The beaches are nice here, although some would argue that the scenery is not as picturesque as that of Wailea. It is quite a popular destination among vacationing families. 

Maui’s historic town of Lahaina is less than a 10-minute drive away. Here you will find a variety of shops and restaurants. If you walk around the historic town, you can visit the oldest Banyan tree in Hawaii, located in Lahaina’s Courthouse square.

The most famous luau in Maui, Old Lahaina Luau, is also located here and features nightly performances. Tickets sell out at least a month before, so book early. Note that they do not have any fire dancing, just in case your kids were looking forward to this like ours were. 

Other fun activities for families include a chocolate tour by the Ku’ia Estates Chocolate Factory.

You’ll be taken to their cacao farm, where kids can see cacao plants and sample a variety of chocolates along the way. Best yet, all the proceeds go towards charity. 

If your kids love snorkelling, then a trip to Molokini crater may be a good option. It is a five-hour excursion, including a 45-minute boat ride there and back. At times it can be rough, so it’s not good for those prone to seasickness. 

Four Winds II & Maui Magic are companies with a good reputation with families. They have a slide on their boats for some added fun. The Four Winds boat has a glass bottom so toddlers can join in the fun too.

If your child is scared to use the snorkel mask, then ask for their See Boards (large flotations with a clear bottom viewing window).

If your kids love aquatic life, then check out the Maui Ocean Center, Maui’s aquarium. I wouldn’t say it’s an aquarium worth raving about, but their sea turtle display and humpback whale exhibits are unique.  

Some popular and good eats we had in this area were Ululani’s’s shaved ice, Leoda’s Pies, MiSo Phat Sushi, poke from Tamara’s and Foodland, Star Noodle and Paia Fish Market. For a fine dining experience, check out Lahaina Grill. 

Here we stayed at the Marriott Maui Ocean Club, which I will soon have a review of, including my experience with their timeshare presentation.

Wailea

Wailea is the posh, high-end, and expensive resort area of Maui. Here you will find the Four Seasons, Andaz, Fairmont and the Grand Wailea where we stayed at.

Sandy beaches are interspersed with rocky formations along its scenic coastline. Like Kā‘anapali, there is a nice coastal boardwalk that connects the various resorts. 

One of the bucket list things to do on Maui is to watch the sunrise from the summit of the dormant volcano, Haleakalā.

Of the three regions we visited, Wailea is the closest to the Haleakalā National Park, but it will still take slightly over an hour to get to the summit. The kids found being above the clouds to be pretty cool.

Reservations for entry at sunrise need to be made online beforehand. They are released 60 days in advance, and again two days in advance.

The best time to do this is probably shortly after you arrive in Maui, when you’re still jet-lagged, as you’ll then need to leave the hotel no later than 4:30am to 5am. Pack a light breakfast to eat in the car and dress warmly, as the ambient temperature at the peak is a good 10 to 15 degrees cooler.

After hitting up sunrise at the summit, you can head down to nearby Grandma’s Coffee House for a casual breakfast, or you can pick up some fresh baked goodies from Komoda Store and Bakery.

If you can’t make it for sunrise, then try for sunset and hit up the Hali’imaile General Store for dinner on the way down.

The one thing we didn’t have time to do this trip was the Road to Hana. Guess that means we’ll be coming back sometime in the future.

If you plan to do it, be sure to book tickets to the famed Black Sand Beach at Waiʻānapana State Park at least 24 hours beforehand, as tickets can only bought online (and even a few weeks before if you want a choice of entry time).

If you’re headed to Hana or even as a short day trip, head into the town of Paia to eat at the famous Mama’s Fish House. It was one of our best meals in a beautiful setting, but you’ll have to book a few months ahead if you want to score a reservation here.

They also have a sandy area just outside the restaurant which is great for restless kids to play in as you enjoy the rest of your meal.

Just a few minutes down the road from here is Ho’okipa Beach Park, where you can find plentiful sea turtles coming out of the ocean and lounging on the beach  – between 4–6pm is the best time to see them.

Other good eats include Kihei Kaffe for breakfast and Lineage for lunch or dinner.

Conclusion

Two weeks seems like a lot of time to spend in one state, but there is so much to do on just the island of Maui alone.

With sunny and warm weather year-round, sandy beaches, a variety of accommodation options, and great food (endless shaved ice for the kids and poke for the parents), Maui makes for a wonderful family destination. 

Having stayed in three different areas in Maui, I can say that whatever location you choose, you won’t regret it.

Each one has its charm and its advantages and disadvantages, depending on whether cost is an issue, whether you prefer to be in the centre of the action or prefer a quieter setting, and where you plan to spend most of your time. Plan out what you want to do first and let that guide you, or just hop around like us!

Lastly, staying in Hawaii can be pricey from both a cash and points perspective, so have a look into timeshare packages as another way to save big. Stay tuned for the next few posts on Oahu, my timeshare experiences, and a review of the properties we stayed at on this trip.