Are you planning your first trip to Hawaii? Want to know the best tips and tricks to help get you started? Keep scrolling to learn about the secret advice you need to know when going to Maui!
This list of things to know before planning a trip to Maui was written by Marcie Cheung (a Hawaii travel expert) and contains affiliate links which means if you purchase something from one of my affiliate links, I may earn a small commission that goes back into maintaining this blog.
I’ve been to Maui about a dozen times now.
As a teenager with my family, solo in my twenties, pregnant and waddling around at seven months, and later chasing toddlers on the beach.
I’m also a Certified Hawaii Destination Specialist who used to dance hula professionally for over 20 years.
So when people ask me how to plan a Maui trip, I have… opinions.
Some of this advice comes from experience. Some comes from mistakes (like the time my family spent 12 hours stuck on the highway during a wildfire trying to reach our Ka’anapali hotel).
And some comes from just paying attention to what works and what leaves travelers disappointed.
If you’re planning your first Maui trip, or even if you’ve been before but want to actually enjoy it this time, these are the things I wish someone had told me.
Nobody Warns You That the Road to Hana Is Actually a 12-Hour Commitment
Your guidebook says the Road to Hana is 64 miles and takes two hours. That’s technically true if you never stop and there’s zero traffic. But that’s not how this works.
The reality? You’re looking at a full day. Maybe 10-12 hours round trip.
One-lane bridges mean you’re waiting for oncoming traffic. Rental car drivers who’ve never driven a winding coastal road are going 15 mph.
And every single waterfall has at least three tour vans parked in front of it.
But honestly, that’s okay. The Road to Hana isn’t a commute. It’s the whole point of the day.
Those fruit stands selling banana bread that’s still warm? The random beach where you’re the only people there? The waterfall where you can actually swim without 50 strangers photobombing you? That’s what you came for.
When I did this pregnant at seven months, we left at 7 AM and got back around 6 PM. We stopped at maybe eight places and still felt rushed.
Now when I take people, I tell them: clear your entire day. Bring snacks. Stop when something looks interesting. Let other cars pass you if they’re in a hurry.
Worth it if: You like road trips, don’t mind driving on winding roads, and want to see Maui’s jungle/waterfall/black sand beach side.
Skip it if: You get carsick easily, hate driving, or only have 3-4 days on Maui (there’s too much else to see).
I did a whole podcast episode on how to actually enjoy the Road to Hana instead of suffering through it. That’s episode 31 if you want the details.
One critical thing: Waianapanapa State Park (the black sand beach everyone wants to see) now requires reservations up to 30 days in advance. You can’t just show up.
It’s $10 for parking plus $5 per person. Book ahead at the state parks website or you’ll be disappointed.
Wailea Is Where Regular People Go to Pretend They’re Rich (And It’s Amazing)
I’m just going to say it: Wailea is expensive. But if you can swing it, or if you’re celebrating something special, this is where you want to be.
Twenty-five minutes from the airport, you’re suddenly in a completely different world.
The Grand Wailea has pools that look like they belong in a resort commercial. The beach access is pristine. The restaurants actually require you to wear real shoes (not just flip flops).
When my husband and I did our babymoon before our first kid, we stayed in Wailea and ate at the hotel restaurant every night because we were too relaxed to leave.
The walking paths between resorts have ocean views that make you stop mid-step just to stare.
But Wailea isn’t just about the fancy hotels. You can book surfing lessons, play golf, kayak, or do a sunset dinner cruise.
There’s high-end shopping if you’re into that, and honestly some of the best restaurants on the island are walking distance from the main resorts.
The luaus in Wailea are also top-tier. The Feast at Mokapu at the Andaz Maui is one of my favorites after dancing hula for 20+ years.
It’s smaller and more intimate than the big productions, and they source everything from local farms. You’re not sitting in rows of 300 people. You actually feel like you’re at a gathering.
The Grand Wailea also has a luau that’s solid if you’re already staying there.
Worth it if: You want the full resort experience, you’re honeymoon or celebrating something, or you just want to be pampered for a few days.
Skip it if: You’re on a tight budget or you want to explore Maui’s less polished side.
If you’re torn between Wailea and other areas, I compared Wailea to Ka’anapali in episode 56 of my podcast.
Buy Two Maui Gold Pineapples, Not One (Trust Me On This)
Regular mainland pineapple is fine. Maui Gold pineapple is a completely different fruit.
I’m not exaggerating when I say the first time I tried one, I questioned every pineapple I’d eaten before. It’s sweeter, juicier, and has this brightness that grocery store pineapples just don’t have.
You can find them at any Safeway or Foodland on Maui. Get two. The first one will be gone in 24 hours and you’ll regret not buying a backup.
We cut ours into spears and sprinkle li hing mui powder on top (you can find it at ABC Stores or any grocery store). Sweet, salty, tangy, and slightly addictive.
If you want to take pineapples home on the plane, the easiest way is to buy a case at the airport after security.
They’ve already been through agricultural inspection, they don’t count as a carry-on, and you don’t have to deal with the hassle.
Way simpler than trying to bring pineapples from a grocery store through inspection yourself.
Not All Maui Luaus Are the Same (Especially After the Fires)
People think luaus are interchangeable. Go to one, you’ve seen them all. As someone who danced hula professionally for over 20 years, I can tell you that’s completely wrong.
Each luau has different energy, different focus, and tells the story differently.
Some are educational and traditional. Some are high-energy theatrical productions with fire dancing and special effects. Some are intimate and cultural. Some are dinner shows that happen to be Hawaiian-themed.
The 2023 Lahaina fires changed the luau landscape on Maui. Feast at Lele, which used to be my top recommendation for people who’d already done a traditional luau, is gone.
Old Lahaina Luau survived but had smoke damage. It reopened in March 2024, and while it’s operating again, half their staff lost homes in the fire.
Recent reviews say the quality isn’t quite what it used to be, which makes sense when you consider what that team has been through.
I still recommend Old Lahaina Luau for first-timers who want the traditional Hawaiian cultural experience.
You’re sitting on the ground (or at low tables), the focus is entirely on Hawaiian history and hula, and it’s very educational.
Just know that you’re supporting a business and community that’s rebuilding. Book Old Lahaina Luau here.
My other top pick is the Feast at Mokapu at the Andaz in Wailea. It’s smaller, more intimate, farm-to-table food, and still has that cultural depth without feeling like you’re in a giant auditorium.
This one has become my go-to recommendation, especially for couples or honeymooners.
The Grand Wailea Luau is also solid if you’re staying on the south side and want something convenient.
For first-timers: Old Lahaina Luau or Feast at Mokapu
For families with kids: Royal Lahaina (Myths of Maui) has fire dancers and is more theatrical, which keeps kids engaged
For repeat visitors: Try Grand Wailea Luau or one of the newer resort luaus like the Ritz-Carlton’s Kapa Moe
Skip if: You’re only on Maui for 2-3 days and would rather spend that evening doing something else. Luaus are worth it, but they’re a 3-4 hour commitment.
Ka’anapali Looks Close to the Airport But Geography Has Other Plans
On the map, Ka’anapali is 16 miles from Kahului Airport. Looks like nothing, right?
But Maui isn’t laid out like a grid. That 16 miles takes 40 minutes on a good day. With traffic, an hour. Sometimes two.
Ka’anapali is on Maui’s west shore, and there’s basically one highway that connects it to the rest of the island. When something goes wrong on that highway, you’re stuck.
I learned this the hard way. We had a hotel reservation in Ka’anapali one trip, and halfway there, we hit a roadblock.
Wildfire had jumped the highway (not the devastating 2023 Lahaina fire, this was an earlier one). The road was completely closed. No alternate route.
Twelve hours later, after sitting in our rental car, eating gas station snacks, and entertaining a restless kid, we finally made it to our hotel.
Twelve. Hours.
Even without wildfires, Ka’anapali is geographically isolated. If your plan is to do the Road to Hana, visit Haleakala, check out the south shore beaches, or explore upcountry Maui, you’re adding at least an hour of driving to every single activity.
Ka’anapali works great if:
- You’re planning a resort-based trip
- You don’t mind the drive to other parts of Maui
- You want to be close to Lahaina (though much of Lahaina is still rebuilding from the 2023 fires)
- You like the west side’s calmer waters for snorkeling
Consider Kihei or Wailea instead if:
- You want central access to everything
- You’re planning to drive to multiple parts of the island
- You want more restaurant and activity options within walking distance
- You’re on a budget (Kihei has way more affordable condos)
I covered where to stay on Maui in detail in episode 71 of my podcast.
Rent a Car or Miss Half of What Makes Maui Special
Maui’s public transportation is basically nonexistent. There are some buses, but they’re slow, infrequent, and don’t go anywhere tourists actually want to go.
Most tours won’t pick you up from your hotel. They’ll tell you to meet them at a central location, which means you need a car to get there anyway.
Without a car on Maui, you’re stuck at your resort.
You can’t do the Road to Hana. You can’t see Haleakala. You can’t drive up to the cute upcountry towns. You can’t hit the good beaches that aren’t right in front of hotels. You can’t try the restaurants everyone raves about.
I always book through Discount Hawaii Car Rental because they aggregate all the major companies and their prices beat booking direct.
But book early. Rental cars on Maui get expensive fast, especially during peak season, and sometimes they straight-up sell out.
Once you have a car, download the Maui Shaka App. It’s basically an audio tour guide that talks to you as you drive.
Way better than trying to navigate using your phone while also not missing the turn for that waterfall everyone said you had to see.
One exception: If you’re truly doing a resort-only trip and someone else is handling all your transportation (wedding, group travel, whatever), you can skip the rental car. But for 95% of Maui visitors, a car is non-negotiable.
You Can Do Maui as a Day Trip (But Should You?)
If you’re island hopping and trying to hit multiple islands, you can technically do Maui as a day trip from Oahu or another island.
I wouldn’t recommend it as your only Maui experience, but if you’re short on time, it’s doable.
The strategy: take the earliest interisland flight (usually around 6-7 AM), pick ONE activity that’s unique to Maui, and catch a late evening flight back (8-9 PM).
What counts as unique to Maui?
- Snorkeling at Molokini Crater (can’t do this anywhere else)
- Watching sunrise at Haleakala (Big Island has volcanoes, but this is different)
- Driving part of the Road to Hana (do the first section, turn around at Hana town)
Or skip the big activities and just hit one or two Maui-specific spots like Ululani’s Shave Ice or Mama’s Fish House.
Worth it if:
- You’re already island hopping and want to say you visited Maui
- You have a specific activity you want to do that’s only on Maui
- You’re comfortable with a packed, exhausting day
Not worth it if:
- This would be your first time in Hawaii (stay longer, enjoy Maui properly)
- You want to actually relax (running around for 12 hours isn’t relaxing)
- You’re traveling with kids or elderly family members
I covered the full strategy for planning any length Maui trip in episode 47 of Hawaii Travel Made Easy.
Costco Travel Has Better Maui Deals Than You Think
If you have a Costco membership, check their travel packages before you book anything else. I know it sounds random, but Costco Travel consistently beats other package deals.
They bundle flights, hotels, and rental cars, and often throw in extras like resort credits or free breakfast. Their price comparison tool actually shows you the best value, not just the cheapest price.
The best deals are during shoulder season: mid-April through June, and September through mid-December. If you have flexibility and no school-age kids, this is when to go.
Just know that Costco Travel packages work best when you’re booking far in advance. Last-minute deals are rare.
Haleakala Sunrise Requires Full Winter Gear (Yes, In Hawaii)
Watching sunrise from the top of Haleakala is one of my top three Maui experiences.
The view is breathtaking in a way that photos don’t capture. You’re above the clouds, watching the sun light them up from underneath.
But I need you to understand something: it is COLD up there. Not “oh I should bring a sweatshirt” cold. Actually cold. 30-40 degrees. You’re standing outside in the dark at 10,000 feet elevation waiting for the sun.
I’ve watched people show up in shorts and tank tops because “it’s Hawaii.” They’re shivering so hard they can’t enjoy the sunrise. Don’t be that person.
Pack like you’re going to a winter morning in the mountains:
- Long pants (jeans work)
- Multiple layers on top (tank top, long sleeve, hoodie, jacket)
- Closed-toe shoes
- A blanket if you can grab one from your hotel
The temperature drops three degrees for every 1,000 feet of elevation. Do the math.
Also, you need a reservation to enter between 3 AM and 7 AM. This costs $1.50 per vehicle, and you can book up to 60 days in advance on Recreation.gov.
Book early because spots sell out, especially during busy season. You can only get one reservation per person every three days.
Separately, you’ll pay the Haleakala National Park entrance fee ($30 per vehicle for a 3-day pass, or free if you have an annual national park pass).
If you’re coming from the west coast, the time difference actually helps. Hawaii is 2-3 hours earlier than Pacific time, so your internal clock will wake you up early anyway. Schedule this for one of your first days on Maui.
Worth it if: You can wake up at 3 AM, don’t mind cold temperatures, and want one of the most memorable experiences on Maui.
Skip it if: You’re not a morning person, you get altitude sickness, or you’d rather sleep in and relax on vacation.
Or book the Haleakala Sunrise Tour and let someone else handle the driving while you doze in the van.
I did an entire episode on how to actually enjoy Haleakala instead of just suffering through the cold. That’s episode 10 of Hawaii Travel Made Easy.
Whale Season Is December Through May (February Is Peak)
Humpback whales migrate through Hawaiian waters every winter. If seeing whales is on your list, plan your trip between December and May. Outside those months, they’re not here.
February is when you have the absolute best chance. The whales are everywhere. You can sometimes spot them from the beach, which is incredible.
But for the real experience, book a whale watching boat tour. You get way closer, the guides know where to find them, and you’ll see behavior you’d never catch from shore. Some tours use smaller rafts that get you even closer to the water.
One heads up: boat tours get canceled if the ocean’s too rough. Book this early in your trip so you have backup days in case weather doesn’t cooperate.
Worth it if: You’re visiting December through May and want to see whales up close.
Not relevant if: You’re visiting June through November (whales aren’t here).
What to Actually Do Before Your Trip
The logistics of planning a Maui trip can feel overwhelming. Start with these things:
Book these as early as possible:
- Rental car through Discount Hawaii Car Rental (prices go up, cars sell out)
- Haleakala sunrise reservation if you’re going (60 days in advance on Recreation.gov)
- Waianapanapa State Park reservation if you’re doing Road to Hana (30 days in advance)
- Popular luaus like Old Lahaina or Feast at Mokapu (these sell out weeks ahead)
What to pack:
- Reef-safe sunscreen (look for non-nano zinc oxide or titanium dioxide on the label)
- Warm layers for Haleakala and evening temperatures
- Comfortable shoes for walking and light hiking
- Download the Maui Shaka App before you go
Money-saving tips:
- If you have an annual national park pass, it works at Haleakala
- Check Costco Travel before booking anything
- Visit during shoulder season (April-June or September-December) for better prices
- Eat breakfast at your hotel or condo instead of restaurants
One thing that’s worth splurging on: Professional photos. I book Flytographer every time we visit Hawaii now.
You get $20 off through my link, and having actual photos of your family together (not just selfies) makes the investment worth it.
We have photos from Maui hanging in our house that I look at every day.
The Honest Truth About Planning Maui
Most people overthink this. You don’t need to have every hour scheduled. You don’t need to see everything. You don’t need to book 47 activities.
Pick the things that matter to you. Give yourself time to just be on the beach without a plan. Let yourself change your mind if you’re too tired to do that activity you thought you wanted to do.
Some trips, we do the Road to Hana and Haleakala and pack in activities. Other trips, we spend half the days doing nothing but reading on the beach. Both are good Maui trips.
If you want more help, my Maui Travel Guide has complete day-by-day itineraries, restaurant recommendations, where to stay for different budgets, and all the activities I actually recommend after visiting a dozen times.
And if you want one-on-one help planning your specific trip? I do Hawaii travel consultations where we figure out exactly what makes sense for your dates, interests, and budget.
Whatever you decide, Maui is pretty forgiving. It’s hard to have a completely terrible time when you’re in Hawaii.
Looking for more Maui travel resources? Find out my best Road to Hana tips, how many days in Maui you need, Maui vs Big Island, cheap and free things to do on Maui, budget Maui restaurants, and the best things to do in Maui with kids.
