About this Trip
We took this trip for Spring Break 2025—two adults and two kids, ages 9 and 13. Overall, there wasn’t a lot of advanced planning involved beyond booking our flights, accommodations, and a rental car. We did lock in our fishing expedition a couple of weeks ahead, and if you’re planning to visit Waiʻānapanapa State Park during your drive on the Road to Hana, I’d recommend reserving your spot at least a day or two in advance.
If catching the sunrise at the summit of Haleakalā is on your list, be sure to reserve that well ahead of time—like months in advance. I’d also suggest booking a luau early since, while there are plenty of options, they tend to fill up quickly.
Everything else we did was super easy to book, often the day of or just a day or two before. (Oh, and we ended up skipping the sunrise at Haleakalā this time around. Next trip!)
Stay & Flight
We flew Southwest Airlines from Dallas on a 4-hour flight to OAK, where we had a quick connection before heading on to Maui. It actually worked out well, giving us a chance to stretch our legs and grab a real meal before the longer 5-hour flight from OAK to OGG. We departed Dallas at 6:00 a.m. and arrived in Maui at 11:35 a.m. local time, right on schedule – no delays, hooray!
By the time we landed in Maui, we were all pretty travel-weary, but we decided to stop by the Walmart near the airport to stock up on supplies. It was super crowded, low on stock, and not the most fun experience, but it was more affordable than shopping in town. If you have a Costco membership, that might be a better option. We picked up sunscreen, water, coffee, beach snacks, breakfast items, drinks, and a few other things to stock the house before heading over to the Airbnb.
We stayed at an AirBnb (linked here if available!) in the Maui Kamaole Condominiums in Kihei, Maui. This complex is a popular spot for visitors, offering a peaceful atmosphere with beautiful tropical gardens and well-maintained grounds. Kihei is located on the leeward side of Maui, which means it gets less rainfall and enjoys more consistent sunshine compared to other parts of the island. It’s also known for its calm waters, making it a great spot for snorkeling and other water activities. The area tends to be less windy than the northern side of Maui, but still close to everything you need, including beaches, restaurants, and shops. We especially enjoyed how easy it was to walk to places like Coconuts Fish Cafe (for the best coconut shrimp) and nearby shaved ice and ice cream spots. Another plus, parking at all of the nearby beaches was no problem at all, even on spring break.
The Airbnb itself was clean, quiet, comfortable, and spacious, with multiple patios to enjoy the surroundings. The bedding was incredibly comfortable too - a big plus. It was also well-stocked with everything we needed, including a cooler, beach chairs, umbrellas, and 4 sets of snorkel equipment — a nice bonus that made our beach days even better. The property offered great amenities as well, including two pools, a hot tub, and grill access.
Day 1 Friday - Travel
First day was mostly travel. We flew out of Dallas at 6:00 a.m. and arrived in Maui at 11:30 a.m. We powered through, did some shopping, checked into our place, and then checked out one of the beaches nearby. Beaches near us included:
Charley Young Beach – Just north of Kamaole Beach Park 1, it’s a quieter, scenic spot.
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Kamaole Beach Park 1 – The largest and northernmost of the three Kamaole beaches, known for its soft sand and gentle waters.
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Kamaole Beach Park 2 – Located just south of Kamaole 1, it’s smaller but equally beautiful with great swimming and snorkeling.
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Kamaole Beach Park 3 – The southernmost Kamaole beach, popular for family picnics, a grassy park area, and bodyboarding.
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Keawakapu Beach – Just south of Kamaole 3, a long and peaceful stretch of sand that’s perfect for walking, swimming, and snorkeling.
Day 2 Saturday - Pineapples and Southern Beaches
We toured the Maui Gold Pineapple Plantation in the morning, and it was definitely a fun time. The tour was pretty interesting—you really come away with a whole new appreciation for pineapples after seeing how much effort goes into growing just one. They give you plenty of pineapple samples to try, and there’s also a little drive around the plantation, which gives you a good look at the fields. The best part? Your admission includes one pineapple per person. We brought ours back to our Airbnb and ate it throughout the week on our beach days—perfect snack! Price was a little high considering it was just an hour - but EVERYTHING in Maui is like that so you kind of just have to get used to it.
After the tour, we decided to hit up one of the beaches near our Airbnb. The kids had a blast boogie boarding, snorkeling, and just generally running around in the waves. It was a great way to wind down the day after learning all about pineapples.
Day 3 Sunday - The Road to Hana
The Road to Hana is one of Maui’s most famous drives, but it's important to know that it’s impossible to do it all in one day without making some trade-offs. If you want to see everything, you’ll need to plan for an overnight stay in Hana. However, if you're okay with skipping some stops in favor of others, it’s still a long but doable day trip. Just be ready for a full day of driving and sightseeing!
Here are some tips for making the most of your Road to Hana adventure:
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Get the Shaka App – This app is a must-have! It’s an audio tour of the Road to Hana for $22, and it’s well worth it. It works offline, so you won’t miss anything while driving with no service. It provides great history and info, and tells you exactly where to stop and park. The kids thought the guide’s voice was a little "corny," but they ended up loving it. Bonus - on the way back, they give you history lessons.
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Prioritize your stops and start early – There’s a lot to see along the way, so plan ahead and focus on the spots that interest you most. Starting early is key to making the most of your day, and it also helps avoid the crowds.
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Get tickets for the Black Sand Beach – The Black Sand Beach at Wai'anapanapa State Park is one of the highlights of the drive. It’s a popular spot, so make sure to book tickets in advance. Same-day reservations are hard to get, and late day reservations impossible in busy season. We decided to head straight there, skipping other stops, and it was totally worth it—the black sand and turquoise water are stunning.
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Food Trucks in Hana – There are food trucks in Hana, but their hours can be a little unpredictable, so don’t count on them for a guaranteed meal. They’re a great option if you can time it right, but it’s a good idea to bring heavy snacks too.
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Bring towels and extra clothes – There are plenty of places to get in the water along the way, so be sure to pack towels and a change of clothes. You’ll likely want to swim at waterfalls or beaches, so it’s good to be prepared.
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Take Dramamine if you get motion sickness – The Road to Hana is full of winding, narrow roads, so if you’re prone to motion sickness, take Dramamine before you start. It’ll make the ride a lot more comfortable.
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Haleakalā’s Pipiwai Trail – If you plan on hiking the Pipiwai Trail in Haleakalā National Park, be ready for a 2-hour hike. It’s beautiful, with bamboo forests and waterfalls, but keep in mind that some stops may be closed by the time you’re headed back, especially if you’ve skipped things earlier to fit this hike in.
Day 4 Monday - Fishing Expedition
We kicked off the day with a fishing excursion through Action Sportfishing that included a little bit of everything—fishing, whale watching, and a sunrise on the water. We departed out of Maalaea Harbor which was about 20 minutes from our place. The tour started early, with the most incredible view of the sunrise over the ocean. The calm morning waters made for such a peaceful start to the day. (Make sure to take dramamine at least 30 minutes before departure if you are prone to motion sickness; our 9 year old was a little green around the gills the whole time.)
Once the fishing began, the kids had catching mackerel. Over the course of the boat ride, hey got to decide which ones we’d keep for bait and which ones to set free. We managed to reel in two amberjacks, but they went back into the water since they aren’t good for eating (apparently, they can have worms). We were really hoping to catch some mahi mahi to take back and cook, but no luck this time. Still, the process itself was exciting and kept everyone entertained.
While we were out on the water, we got to see so many whales! It was absolutely amazing to watch them breach and spout so close to the boat. The boat was super comfortable, and I’ll admit, I even squeezed in a couple of naps during the quieter moments. Overall, it was such a memorable experience—combining sunrise views, wildlife, and a fun (if not super fruitful) fishing adventure.
After fishing we visited another one of the beaches near our AirBnb to wrap up the day!
Day 5 Tuesday - Snorkeling and Whaler's Village
We started the day heading north to check out the Nakalele Blowhole. This natural wonder is a powerful spout of water created by waves crashing into an underwater lava tube. It’s a bit of a rocky climb down to get close, and none of us were wearing the right shoes for it—but we made the trek anyway. The views were absolutely stunning, with rugged cliffs and endless ocean in every direction. Unfortunately, the blowhole wasn’t spouting much while we were there, which was a bit of a letdown.
After that, we headed to Whaler’s Village for lunch. Whaler’s Village is an open-air shopping and dining center right by the beach in Kaʻanapali. It’s a lively spot with lots of shops, restaurants, and a bit of a resort vibe. Parking, however, was a hassle—it’s tight and expensive unless you get validation. We had lunch at Monkeypod, and honestly, it wasn’t great. Big thumbs down for the food, but they did validate our parking, so there’s that.
From there, we made our way to Kaʻanapali Beach. Pro tip: Drive to the Sheraton and valet park for $30. The fee is offset as long as you buy food or drinks at the pool bar, which we thought was a solid deal. From the Sheraton, it’s just an elevator ride down and a short walk to what has to be one of the best beaches in the world. The snorkeling here was incredible—crystal-clear water, sea turtles everywhere, and calm waves. There’s also cliff diving for the more adventurous types. It was absolute perfection.
The drive back to Kihei took about an hour on a one-lane road, and traffic made it a bit of a pain. For dinner, we stopped at Maui Brewing Co. The food and beer were solid, and the vibe was fun, but the ordering system? Super weird. When we arrived, they asked how many were in our group (four), then told us we’d need to wait 45 minutes—even though there were plenty of open tables. Apparently, those tables were “reserved” for parties of 15, but no one ever showed. In the end, we just scanned a QR code at one of the tables and ordered our food, so the wait didn’t even matter. It was odd, but we rolled with it. The boys had a blast tossing a football around outside while we waited, so it ended up being a fun way to wrap up the day.
Day 6 Wednesday - Maui Ocean Center and Luau
In the morning, we visited the Maui Ocean Center, an impressive aquarium showcasing Hawaii’s marine life. It’s beautifully designed and super family-friendly. Some of the highlights included the Living Reef, which has vibrant coral and tropical fish, and the Open Ocean exhibit, where you walk through a 750,000-gallon tunnel surrounded by sharks, rays, and other sea creatures. The kids especially loved the sea turtles and the interactive tide pool where you can get hands-on with some of the smaller critters. It was both fun and educational—a great way to learn about the unique underwater ecosystems of Hawaii.
After the Ocean Center, we headed back to our Airbnb for some downtime. We threw on Moana 2 (because why not?) and just relaxed for a bit—perfect after a busy morning.
That evening, we had tickets to a luau at South Maui Gardens. This venue is gorgeous—an outdoor garden setting with tropical plants, twinkling lights, and a laid-back yet festive vibe. The luau itself included traditional Hawaiian music, hula performances, and storytelling. There were a variety of food trucks here, offering everything from local seafood to savory dishes like grilled meats and refreshing tropical treats. It was a fun, casual twist on the typical luau dining experience. The show itself was short, but a lot of fun. We loved it.
Day 7 & 8 Thursday - Laid Back Beach Day and Travel Home
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