Matt and I have been very fortunate to have gone to Maui a few times. We are als2016-02-18 10.19.58o super lucky to have gone there twice with kids…and babies. We really love Maui. It’s our happy place other than the farm. The ocean, beach, whales, views, food, smells….the list goes on about why we love it so much. This trip was very special to us because it is our ten-year anniversary in a few months. We laugh at how each of our trips have changed so much, from honeymooners, to one kid, and then to two kids. But Maui can be for everyone, at every age.  Jennings, 3 was so excited to go to “Moowee” to see the whales and Nemo and Copeland, 10 months old came along for the ride.

This time we stayed in Maui just shy of a month. We were able to take the extra time because I’m currently on mat leave and my family generously took over Matt’s responsibilities on the farm. Because we were there for that length of time, we split up our trip at two different locations on the island, which I’m so glad we did since different parts of the island offer different things to do and even the weather is a bit different.

We tried to travel on a budget because Maui is an expensive trip and our Canadian dollar is about 70 cents to the US dollar. I got a US MasterCard to use while we were there to save a bit on the conversion fee.

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We booked our vacation for the month of February. Their busy months are from December to April (like most hot destinations), which also coincides when humpback whales come to the islands.  I booked all of our flights about six months before we flew using points, which saved us about $2000 CAD.  The total taxes we owed for the three flights was $700 CAD

We didn’t pack a lot of clothes because we had laundry facilities at both of our condos. If you are travelling with small children, I would highly recommend having laundry in or near your place.

Other than the standard items like clothes, swimsuits, sandals, and toiletries, I also packed:

  • Nightlight and baby monitor
  • Electronics like Apple TV (which we didn’t use because we hardly watched TV), Ipod for running, and Ipad for movies while on the plane and in the condo.
  • Couple new toys for Jennings to play with at the condo
  • DSLR (which I’m glad I took but I was too scared to take it out when we were at the beach because of the sand – it gets everywhere!)
  • Swim diapers for Copeland
  • Life jackets
  • Pool diving toys and goggles
  • Go-Pod for Copeland at the beach, and also a swimming float and tent. You can purchase or rent these last two items but because we already had them and they fit in our suitcase, I decided to bring them along.
  • Car seats. We took both because they are used to their own and I feel safe knowing they are using their own car seats.

The great thing about being in Maui is that there is a Costco, Wal-Mart and Target close to the airport in Kahului so you can pick up all the items you need after you get off the plane.

The biggest tip I can give you as an essential item to pack in your carry on is children’s medicine like Tylenol, Gravol, and Benadryl because you just never know.  When we went to Maui when Jennings was a baby, he was sick on one of the flights. This time around, he was sick in the airport during our layover.  The other thing is to pack a change of clothes for everyone 😉

The Bumbleride stroller was the most used item during our travels and time in Maui.  We checked it at the gate so we could use it in the airport. It’s a life saver when you have a long layoverIMG_1034.  I purchased a “skateboard” attachment for Jennings to hop on and off and it is one of the best kid’s gadgets I have bought. He likes to walk around when we are out so I didn’t think a double stroller was the best option for us.


If you are planning on going to Maui during their busy season, I would highly recommend booking your accommodations about a year in advance. The highly rated accommodations can sometimes book up to 18 months in advance.

We stayed in Kihei at the Kam Sands during the first part of our trip. Kihei is located on the South West part of the island. We really liked this resort because it is directly across from one of the main beaches in Kihei, it’s close to many restaurants and stores and the resort has many kid friendly features like a kiddie pool and elevators so you don’t need to haul all your luggage up one to three flights of stairs.  While in Kihei, the weather was pretty consistent: hot and sunny the whole time. The wind gets up in the day but dies down during sunset. It only rained once during the night for a short period of time.

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The second condo we stayed at was the Kuleana up on the North West side of the Island near Kaanapali.  We have stayed at this resort every time we have come to Maui. We really like it here because the views are amazing. Whales can be seen right off your lanai. When we’ve gone down to the beach, we’ve watched sea turtles swim up to the shore. Pretty amazing! We also like the location because everyone there is so friendly, the grounds are beautiful and it is close to Lahaina where there are some awesome shopping and restaurants and some pretty incredible beaches like Baby Beach, Napali Bay and Kaanapali Beach.

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We booked both of our condos using VRBO.  I have used this site many of times and have never had any issues or concerns. This site has many affordable accommodations versus staying at one of the hotel resorts.  Two bedroom condos typically range from about $150 US to $400 per night versus hotel resorts can start at $500 US per night. Our costs were:

  • Kam Sands – approx. $200 US per night
  • Kuleana – approx. $350 US per night

Sleeping schedules: There is a five-hour time difference from Maui to Regina so the first few days the boys’ schedules were a bit off and there were some temper tantrums and tears. They were tired and wanted to go to bed at 3pm and then were up for the day at 3am.  But after those first few days, we got the hang of it and everyone adjusted well.

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Routine: Our routine didn’t venture too far off from our routine at home. Sunrise was around 6:30 am so I would go for my run and by the time I came home, the boys would be up and having breakfast. After breakfast, we would go for a walk to a park, beach, or store. We would come back, have a snack and get ready for the beach. We usually got to the beach around 10-10:30 am before it got too hot. The boys would be ready to go back to the condo for lunchtime and naps around noon. After naps, we would head to the pool or go shopping. We would cook supper at the condo and be down at the beach for sunset around 5:30 pm. Everyone would be ready and in bed by 8 pm.  This is so different from our first trip where we would go out for supper after sunrise versus being in bed 🙂

Baby Gear Rental: We rented a pack n’play and a booster seat for Copeland from Maui on the Fly (MOTF), but there are plenty of businesses that offer this service.  We have rented from MOTF before and have always got great service. Plus, they will set up the items and have them ready for you before you arrive. The total cost for those two items for the month came to $200 US. We would have liked to have rented a crib but it was too much of a hassle taking it down and moving it to our second condo. You can rent a variety of items such as strollers, high chairs, exersaucers, toys and games, and beach essentials too.

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Vehicle Rental: You will need to book a vehicle a few months before you travel if you have children and want to go and do some site seeing on your own. We used the remainder of our points to book the vehicle and it only got us about ten days. The taxes and extra fees for that was about $400 US. We then booked the remainder of the trip using Discount Hawaii Car Rental and saved a few dollars. We rented a van and it was about $70 US per day with taxes included.

Things to Do

IMG_1494There are so many awesome things to do in Maui. On our previous trips, we have done the road to Hana, Iao Needle, snorkeling, etc. Since this isn’t our first rodeo and travelling with a baby and toddler, we spent most of our time at the pool and beach. Plus, being at the beach and pool doesn’t cost anything 🙂 When we did venture out, we went to places that only took a couple of hours so we could somewhat maintain the kids’ schedules.

Beaches: Maui offers some of the best beaches and every view is breathtaking. We really enjoyed Kam 3 at Kihei because it was right across from the condo in Kihei and is close to some amazing take out restaurants. While up north at Kaanapali, we really liked Baby Beach because it’s in a cove so there is hardly any wind and waves which is perfect for a toddler and baby. This beach doesn’t have a shower or washrooms though.

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Whale Watching: Jennings had to go twice on the Pacific Whale Foundation tours because he loved it so much. Plus, the tours are only a couple of hours long so on the second trip, Copeland and I stayed back in Lahaina and walked around and shopped. We went on the Ocean Spirit which is a large catamaran that seats about sixty and every spot on the boat is a good one. Children under 12 are free and an adult ticket cost about $60 US. If you do choose to go on a whale tour, I would highly recommend PWF as they are a non-profit and all the money raised through tours and merchandise goes towards whale conservation, education and research.

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Shopping in Lahaina: Lahaina offers a wide range of shops from museums, clothing, jewellery, souvenirs, spas, an outlet mall and restaurants.  The area has rich history dating back to 300-700 AD from when the Polynesian settlers arrived to the famous Banyan tree planted in 1873. We really enjoy getting some Kona Coffee at Bad Ass Coffee and browsing along the main street, Front Street where all the action is at.2016-02-16 10.25.55

Maui Tropical Plantation: We wanted to get in a bit of agriculture while we were there and this seemed to fit the bill. The plantation offers a 45 minute tram ride through the
park and they show you various trees, plants, flowers and food that are grown on Maui like coconut, pineapple, banana, dragon fruit, avocado, and papaya. Adult tickets are $20 US and children (ages 3-12) are $10 US.2016-02-10 15.45.45

Where and What to Eat

We only ate out once as a family while we were there.  Not as much as I hoped for but it’s hard with two young ones that may or may not want to sit and wait for a table and then to eat. It’s also expensive to eat out regularly as a family of four. Our one meal at an average restaurant was $110 US (with tip) and that was only a lunch.

IMG_1976So what we did this time is take out. We did a take-out lunch every few days and this was great as we usually had leftovers for supper.  We liked to cook and eat supper at the condo because the kids would normally be getting quite hangry by that time and we enjoyed walking down to the beach to take in the sunset and watch the whales and sea turtles.  We scoped out some highly rated restaurants on Trip Advisor and these were our favourite spots:

  • Cocunuts (Kihei) – they are famous for their 17 ingredient fish tacos. A must in Kihei!
  • Kinaole Grill Food Truck (Kihei) – the calamari wedges melt in your mouth and Jennings couldn’t get enough of the coconut shrimp. The side salad with feta and macadamia nuts is fresh and delicious along with their side rice pilaf.2016-02-10 12.10.25
  • 808 Deli (Kihei) – Matt ordered the Toasted Wasabi sandwich (roast beef, onions, pepperjack cheese, etc) and I ordered the Chicken Pesto Panini. The servings are huge and everything is so fresh and so yummy. I also ordered the Chocolate Banana pudding and I didn’t feel bad that I didn’t share 🙂2016-02-12 13.24.14
  • Cinnamon Roll Fair (Kihei) – We went here a few times in the morning. The rolls are baked every morning and there’s always a line up.  They are gooey, moist, fluffy, caramely, and creamy. Heaven in your mouth.  Matt and I would each order a roll, along with the macadamia nut and icing sides (because you have to go all out).2016-02-08 09.11.31
  • Ululani’s Shave Ice (Lahaina and Kihei) – This is hands down Jennings’ favourite stop. He didn’t care about all the flavours they offered; he only wanted a blue, green and purple shave ice cone. The shave ice is fluffy and melts in your mouth. Plus, you get to choose between a few different kinds of ice cream to put on the bottom. He always chose coconut ice cream.2016-02-08 13.25.34
  • The Fish Market (Kaanapali) – Since Jennings loves coconut shrimp, we ordered that along with the Fish n’ Chips and side homemade chips. All of our food was fresh and it was one of the best fish n’ chips I have had in a long time. I would highly recommend this place if you are wanting to buy fish to take home. They have plenty of fresh fish (and some ready to cook options like crab cakes) to choose from and they are so helpful.

To also help the wallet, we shopped at Wal-Mart, Target, and Costco for the majority of our food and liquor. We also loved buying locally grown and made products at the Kaanapali farmers market like pineapple, mangos, papayas (I liked the strawberry papayas the best), apple bananas, banana bread, macaroons, pineapple salsa, guacamole, and guava jam.  If you want to take time and browse locally made products, gifts and some food items, check out the Maui Swap Meet in Kahului. You can get some pretty unique items there but I went for the food of course 🙂 I’m a big fan of coconut candy. They soak coconut in sugar-water and then roast it. Sooo good.  Our other favourites are salt water taffy, dried papaya and mango, roasted and salted macadamia nuts and coffee.2016-02-06 11.58.20


We got family pics when we were there. I’m so glad we did because they are such a treasure. I love taking pictures but that means I am not in many of them so it was awesome we got photos professionally done. Plus, our pictures were taken at one of our favourite beaches, Baby Beach.







More pictures of our trip can be found on my Facebook and Instagram pages.

Stay tuned for an upcoming post on our tour of the Maui Monsanto farm site.

If you are planning a trip and need some further information, please let me know and I would be happy to help.