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Maui Itinerary

Because Maui was my favorite vacation, I want to share what an incredible place this is and what we did, so hopefully, you can have a similarly great or even more amazing experience.

Why Maui?

While you might go visit other islands, if you’re only going to one, this is probably it. Maui is a fantastic blend of tourist amenities (great restaurants, etc) and nature, so it’s really a perfect blend of how amazing Hawaii is.

Region to stay: The best regions are the west side of the island and the south side of the middle of the island. Both are basically deserts because the mountains block all the clouds and rain, so it’s perfect to be able to have dinner, sunrises, and sunsets without any rain but be a 60-minute drive from a rainforest on the other side of the island.

Tourist regions to stay: west side and middle-south side

A few things to note:

  • Rent a car. You’re going to want to do this far, far in advance. When we went, we tried to reserve a rental a week before arriving and they were all sold out. We ended up getting a car through Turo, but the daily car rental rate was more expensive than our hotel. Still, it was worth it. If you want to experience Maui, you need a car. Most of Maui has one-lane roads; if someone is driving behind you and likely wants to drive faster, the courteous course on the island is to pull over and let them go past.

On the top of Haleakala in our rented jeep
  • Most of the best restaurants are booked months in advance for dinner reservations. If you have a premium travel card that provides you with Concierge service, then this is the perfect time to use it: tell them what restaurants you want or just tell them a region of the island, what type of food, and/or a price range, and they will make all the reservations for you.
  • Bring suntan lotion, obviously, but try to wear “Reef Safe” sunscreen here to help preserve the surrounding coral reefs.
  • I can’t speak for the other islands but, on Maui, you’ll only need to bring bug spray if you’re going to hike in the bamboo forest. Besides that, we didn’t see any mosquitoes, which was great!

Day 1

Road to Hana Tour

  • A tour is by far the best way to travel the road to Hana because this road is one of the top 5 most dangerous roads in the world, so you don’t want to be driving it yourself.
  • Why day 1? Because the tour van will likely pick you up a 5am, but it’s especially easy to wake up that early on the first day because, if you’re on east coast time, that’s 11am your time. Also, this will give you quite a large geographical understanding of the island, which is nice to have from the outset.
  • Time: 6am to 6pm. Lunch and snacks are provided.
  • We used Stardust tours for ours. Very happy with the experience.

On the hiking path at the far end of the black sand beach

Approximate Road to Hana Tour map

Day 2

Sunrise on Haleakala

  • You have to reserve a spot (because there is limited parking). Reservations become available at 7am two days in advance. You have to be quick, though, because reservations fill up by 7:02am.

Hike around Haleakala

  • There are a few short hiking trails and a very long hiking trail at the top. If you are hiking, bring sunscreen and apply liberally. Because of the elevation (above 10,000 feet – and above the clouds), there is less atmosphere above you to protect you from UV rays, so you will get burned almost twice as quickly.

At 10,000+ feet on Haleakala, you are literally hiking above the clouds.

Ocean Organic Vodka Distillery

  • The distillery is near the base of Haleakala on your drive down from the summit, so it’s the perfect stop. The liquor tasting is good but not amazing.
  • What’s amazing? Their cocktails, food, and incredible view. Their food easily competes with the best lunch spots on Maui, so lunch at the distillery is perfect, and it was never crowded when we went (we liked it so much we went twice). Their “Fy” gin is incredible even on its own.

Maui Winery

  • If you’re not too intoxicated from the distillery and if you have made a reservation at least a few days in advance, you can head to the winery, which is about a 15 minute drive from the distillery. The wine and snacks are good – not amazing, but good.

Haleakala, Distillery, and Winery Map

Day 3

Sunrise at Waikeakua Gulch

  • This is a nice place to watch the sunrise.

Sunrise at Waikeakua Gulch

Nakalele Blowhole

  • After the sunrise, you can hike down to see the blowhole.

Hiking and/or Beach

  • If you want to hike more (which I would), then you could head to the Waihee Ridge Trail (the road from the blowhole to the trail is pretty dangerous though, so you might want to actually go all the way around the west side of the mountain rather than the relatively short distance east along the coast to this trail). Even if you have to drive all the way around the west side of the island, this trail is worth it. Beautiful views.

View while hiking the Waihee Ridge Trail
  • Or, if you prefer an easier walk, you could do the Kapalua Coastal Trail, which is a nice, easy, beautiful walk.
  • Head to the beach. Like anywhere. Our favorite beach, though, was Kaanapali Beach because the restaurants (and Starbucks) were literal feet from the beach, so anytime we wanted we could get a drink, go to the restroom, etc without having to walk far. Very enjoyable afternoon. All the beaches on Maui are public, so just look for the free public parking lot, and there will be signs to the public access path to the beach (since the beach is lined with resorts that would otherwise block your access to it). I also recommend going to Leilani’s, which is on the beach. They have fantastic fish tacos.
Fish tacos at Leilani’s

Map to Leilani’s:

Kaanapali Beach map
Map of long (safe) route from Waikeakua Gulch to Waihee Ridge Trail
Map of short (dangerous) route from Waikeakua Gulch to Waihee Ridge Trail

Day 4+

  • Maybe head to the rainbow eucalyptus trees or bamboo forest (you’ll have passed both of these on your Road to Hana tour). For parking, when you get to mile marker 6.5, there is space to pull off the road. There were a lot of unofficial signs saying “No Parking,” but no official signs. We parked there, walked a few hundred feet further down the road to the eucalyptus trees, saw those and took pictures, and then walked back and headed into the forest. We didn’t find the primary falls (there was a path that headed downwards that was too muddy to traverse), but we hiked around for a bit and found our own waterfall. It was amazing. A few hours of lounging about in our own private waterfall. Bring bug spray though!
Hiking in the bamboo forest
Standing in front of a rainbow eucalyptus tree
  • Check out Wailea Beach. Although we didn’t make it to this beach so I can’t speak from personal experience, it is considered to be one of the best beaches in the world. (You could also do this on Day 2 after the Distillery and/or Winery.)
  • Go see the Banyan Tree. You can do this on another day instead (it’s in downtown Lahaina on the west side of the island). But, if you couldn’t fit it in, make sure you check it out. This tree puts down multiple tree trunks and covers over an acre. Amazing.
  • Near the Banyan Tree (a few blocks north of it) is a location of Ululani’s Hawaiian Shave Ice. It was about an hour wait just to get the shaved ice, so we didn’t get it, but it’s supposed to be some of the best shaved ice.
A small glimpse of the massive Banyan Tree
  • Also near the Banyan Tree (all in Lahaina), maybe visit the awesome art galleries along Front St. (the main street) – our favorite was Sargent’s Fine Art. There are a lot of historical sites on this street as well.
  • Excursions (day cruises, surfing, snorkeling, diving, whale watching – if you go in the winter months, but then you also risk more rainy days). 
  • Maybe a beach day. 
  • Maybe more hiking.
  • Maybe revisit your favorite places (we went back to the Ocean Organic Vodka Distillery for lunch and drinks).

Good summary of Maui: standing under a perfect rainbow on a dormant volcano.
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