4-Day Maui Itinerary

Apr 22, 20200 comments

Some of our good mainland friends we’re coming back for a Maui vacation, and they asked us what they’d do with 4 days.  We thought we’d share our recommendations since it might help others planning 4 days on Maui.  First, you’ll see their message to us, then our recommendations below that.


“I hope that you and the family are happy, healthy, and doing well!”

We fly out next Wednesday to Oahu. We are staying a night at the Moana Surfrider then we fly to Maui and we are staying at the Grand Wailea.

Grand Wailea

I am sitting at my desk planning the week. The girls are so excited and we feel much-needed rest mixed with lots of fun.

This is a flexible schedule I have planned, but I would love some feedback:


DAY #1: Snorkeling at Molokini Crater.  The girls want to scuba dive, but we’re not certified.  Is there a legal way to do it without going through all the courses, or are there quick courses?

Molokini Crater Maui

DAY #2: Road to Hana – Last year we did Twin Falls and the place where the trees look like they are painted. I do not feel up to doing the whole road, do you have any suggestions? My girls mentioned the Venus Pools? Not sure how far down that is.

Road to Hana Hawaii

DAY #3: Paia and helicopter. Who do you recommend we fly with?  We know of Blue Hawaiian Helicopters, Air Maui, and Sunshine Helicopters.  Which is best and has the best prices?

Paia helicopter

DAY #4: Maybe Parasail, the girls want to do it. Cliff jumping for sure. Kapalua Bay? We all have never been. Is it worth going, maybe snorkeling there?

Maybe Haleakalā crater? We have never been.

Haleakala Crater

I hope the kids are doing well and enjoying the end of Summer. If you have time when we are out we would love to see you all.

Love, your mainland friends


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“Woohoo! Glad you’re coming out to Maui again!”

The Grand Wailea is great. Love that spot. Fun pools and dangerously fun grotto bar. I’ve found myself in there for far too long. Fun bartenders, tasty drinks, shade, and fun tiered pools with slides.  You can’t beat that.

Here’s how I would personally plan the 4 days:

Day 1

Helicopter: I suggest the West Maui & Molokai trip. It’s amazing! Blue Hawaiian is my favorite.  Check out all of their Maui helicopter tours.  The trip to Molokai is truly A TRIP!  You get to see a bunch of Maui, cross the channel twice, and get to see some of the highest sea cliffs in the world.  Oh, and there are waterfalls from the cliffs.  It’s unreal!

helicopter in Maui Hawaii

My favorite part of our last trip to Molokai was when the pilot landed on the edge of the sea cliff.  He started fiddling with the stereo, the theme song for 2001 came on.  When it hit that dramatic part of the music, he dropped us off the sea cliff straight down.  WHAT A RUSH!  We loved it.

Paia Town is just down the street from the heliport.  As you know, we live here and love it.  The shopping is great, the restaurants AWESOME, and the people watching legendary.  Grab some grinds and walk around.  As far as dining recommendations, I suggest Cafe Des Amis, Flatbread Pizza, Maka by Mana, or Mambo Cafe.  Those are my regular spots.

Paia Town


Day 2

Cliff jumping: Black Rock on Kaanapali Beach or the Cliff House in Kapalua. When cliff diving, watch someone else go first.  It can be dangerous depending on the height of the tide and possible debris on the surface or just below it.  Kapalua is beautiful but can get crowded. Napili Bay is a favorite for snorkeling. 5 Graves is my favorite closer to you in Makena. I’ve never Parasailed on Maui before, but I’ve done it in Mexico. Super fun!

cliff jumping in Maui

Again, for snorkeling on Maui, you don’t need to go all the way to the west side. You’ll find great beginner snorkeling at Ahihi Bay in Makena, which is a shallow reserve with TONS of fish. We got married about 30 feet from it at the Sugarman Estate. So many fish. If you snorkel from the shore, make sure there’s no swell. The south swell season is in summer, but sometimes winter swells will wrap around or an unexpected south swell will hit. Swell can make snorkeling dangerous.  I’m a big fan of Molokini Crater, which has an inner protected area for snorkeling.  You’re safe from swell and the water clarity is far better than off the shore.  Molokini is also a reserve, so ocean life is diverse and abundant.  We love making the trip to Molokini, which is only a few miles offshore.


Scuba Diving: No, you can’t skip the courses, but you can go Snuba Diving.  Snuba is a similar concept, but it requires zero experience and only a short lesson before entering the water.  It’s a ton of fun and offers you the chance to stay below the surface and see more fish for a longer period of time.  Check out this video to understand it better.

Day 3

The Road to Hana is great, but you don’t want to plan anything else that day either. Best to stay the night, but I’ve had a blast on day-trips many times. Venus Pool (Waioka) is past Hana. Pretty far.  We don’t recommend it because it can be a little sketchy to get down to, doesn’t take too many people to make it crowded, and there’s no warning for flash floods.  The Seven Sacred Pools at Oheo Gulch is a far better option for swimming in pools, plus there are many waterfalls (Venus Pools doesn’t have waterfalls.)  Another reason we like Oheo Gulch is that it’s managed-well, meaning they’ll shut down access if water levels become dangerous upstream.  You’re not going to get killed from a flash flood with this system in place.  It can also handle a large volume of people, so you never feel crowded. Skip Venus Pools for all these reasons and also because it requires trespassing.

hana maui hawaii

If you do the full loop (which is AWESOME), I suggest doing breakfast in Paia or grab something quickly, and check out the falls along the way. Waikani Falls and Hanawai are right off the road. Then definitely stop at Wai’anapanapa for the black sand beach and check out the caves. Wailua Falls (right off the road), and maybe Kipahulu if time. Kapahulu (Seven Sacred Pools or Oheo Gulch) has one of the most epic hikes EVER! You hike to Waimoku Falls. See the video we made from the hike below. If you do this, I would not stop too much on the way. A few waterfalls, Wai’anapanapa, and then the hike. It takes time to do the full hike, so leave for Hana very early.

So much to see. Don’t rush it. Stay at the coolest spots and skip the rest. You want to drive back before sunset. I like doing the full loop, though it’s bumpy for a good portion on the backside. Driving the dry backside with the windows down, the sun setting, and still having the chill of waterfalls in my bones is pretty epic.


Day 4

Grand Wailea pools

Day after the Road to Hana, hang out at the Grand Wailea ALL DAY. Pool, beach, chill. You’ll want to do nothing. Maybe reserve a gazebo if they’re not too crazy expensive. Forget what they charge, but it’s nice having shade and home base. End the day with a sunset, cocktails, great food, music, and a show at the Grand Luau.

Haleakala Maui Hawaii

If you feel like you have the energy, definitely try to squeeze in a trip to Haleakala. Because it takes a decent chunk of time to drive up and down, I recommend taking a guided sunrise tour to the 10,000-foot summit (if you don’t mind waking up about 2 am). Meals and comfy seating are included, and since you’re not doing the driving, you can get plenty of relaxation time while also enjoying the marvelous views from the oversized shuttle windows. Either way, it’s epic. Lots of cool stuff to see going up and coming down, too. Kula is BEAUTIFUL, and Makawao has great shopping.

Maui Hawaii

For those up for one last Valley Isle thrill, we love the Haleakala Sunrise & Zip Tour from Skyline Hawaii, which includes a guided tour up to the summit of Haleakala in time for sunrise (including warm jackets!), as well as a continental breakfast break before the final portion of the tour: a 5 line zipline ride over canyons and through remote areas of Upcountry’s fragrant eucalyptus forest, a swinging bridge a la Indiana Jones, and a ride on the only pendulum line in the state. Guests must be 8 years and older, weigh between 60 and 260 pounds, and be able to hike a 1/2 mile at elevation.

haleakala combo tours

See you soon, Your Hawaii Ohana

Thank you, Natalie Brown Photography, for most of the photos.  MAHALO!


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