I had difficulty finding a sample itinerary for a self-drive day trip to Upcountry Maui that takes into account logistical efficiency, which tells me a couple of things: 1) it’s a road less traveled 2) I should write one
As a luxury travel specialist in SoCal, Maui is a top requested destination due to ease of direct flights and a variety of high-end accommodations. And yet, I rarely have takers when I suggest my clients go on an Upcountry Maui day. I get it, you go to the islands to beach/pool/veg; but I hope this guide will help those seeking off-the-beaten path experiences, and possibly, even convince the loungers to veer off a bit.
What is Upcountry?
Upcountry Maui geographically is the highlands surrounding Haleakalā volcano, comprised of a handful of high elevation towns and a lot of open space. But it’s also a way of life, defined by its history as an agricultural region and home to the paniolo – Hawaiian cowboys. As a visitor, you get a sense of it by tasting products borne from the volcanic soil, seeing how they’re made, and meeting the people behind them.
Why You Should Go
- It’s beautifully uniquely scenic
- Experience Hawaiian history and culture
- Delicious food and booze
- Do something different
Sample Self-Drive Itinerary
There are resources listing things to do and see in Upcountry but as I was planning my own day, I soon discovered that the towns and attractions can be quite far apart. I wanted an easy stop-by-stop guide like the ones for the Road to Hana but couldn’t find one that routed it to minimize drive-time/backtracking so I made my own, like a Tetris game of Google Maps and a bevy of guides, reviews, and blogs.
And since there are too many places to visit in Upcountry, I had to narrow it down to my ideal itinerary:
- Depart the Ritz-Carlton Kapalua early AM
- Upcountry Farmers Market
- Backtrack 15 mins to Tin Roof in Kahului for an early lunch
- Hali’imaile Distillery Tour
- T Komoda bakery for cream puffs
- Ocean Vodka Tour
- Elk burger at Ulupalakua Ranch
- Vineyard tour and tasting at Maui Wine
- Pretend to be a social media influencer by taking cliche photos at Ali’i Lavender Farm
- Get to Haleakalā summit by 4pm to do some hiking at Sliding Sands Trail and watch the sunset (see my post on sunset here)
In retrospect, this list shows that I’m a true optimist, but more so, how terrible I am at time management because of it. In reality, I got through 4.5 of them.
Recap and Routing
Kahului
Departed the hotel super late, like 10am, and was going to miss the Farmers Market since it’s a little over an hour away and ends at 11am so stopped in Kahului first. If you’re coming from a tourist area like Lahaina, Wailea, or Kapalua, you’ll pass Kahului (airport area) on your way upcountry.
Tin Roof
This casual takeout spot by Chef Sheldon @chefwonder from Top Chef (I’ve never seen a single episode) is only open 10am-2pm Mon-Sat. It was my only opportunity to eat here but if you can do it another day like airport arrival/departure, do that because there are great places to eat in Upcountry.
Tip: call in your order ahead since there’s always a line and go early. Chef Sheldon also has a more upscale establishment Lineage in Wailea.
Hali’imaile
Hali’imaile Distillery
Home to Pau Vodka, Paniolo Whiskey, FIDStreetGin, and Mahina Rum. The distillery tour is $10 p/p, and lasts about 40-45 mins, 7 days a week 10am-4pm, runs every half hour, online reservations recommended during high season.
If you’re not super into distillery tours or have sophisticated tastes, I would skip this and go only to the Ocean vodka tour (and/or Maui Wine).
Other To Dos in Hali’imaile
Maui Gold Pineapple Tour
On the same site as Hali’imaile Distillery, they also do a pineapple tour which takes you out to the fields. It’s $65 p/p, lasts about 1.5 hrs, and runs daily at 9:30am, 11:45am, 1:30pm – make reservations since it sells out a few days+ in advance. I’ve done pineapple tours on other islands and thought they were kitschy so I didn’t have it on my itinerary but I hear this one is quite good.
Dine at Hali’imaile General Store
Chef Bev Gannon was one of the OGs of Hawaiian Regional Cuisine (along with Roy Yamaguchi, Alan Wong, etc.) and it’s just across the street from the Distillery. From their website: “Chef Bev Gannon’s original and most acclaimed restaurant featuring eclectic American food with Asian overtones – the essence of modern Hawaii food. Founded in 1988, ‘The Store’ has been a Maui destination for both visitors and locals that appreciate fresh local ingredients.”
Makawao
T Komoda
Drove to T Komoda, a local tradition since 1916 in Makawao town, for cream puffs and other pastries but they were on vacation. It was a sad moment for me but I love that they just closed for 3 weeks and gave no notice aside from a sign on the door. That’s gangster.
Upcountry Farmer’s Market
The Farmers Market is about 10 minutes from Makawao town and open only on Saturdays 7am-11am, rain or shine. I saw people with snacks and goodies they bought there and got FOMO. But sleep was nice, too.
Kula
Ocean Vodka Tour at Hawaii Sea Spirits
Quick overview of their sugar cane field – used to make the spirits, followed by a walk-thru of the warehouse and packing plant. The tour ends with tastings at the outdoor bar with beautiful views of the island. Cost $15 p/p and includes a souvenir shot glass, runs every 30 mins, lasts about 35 minutes. The grounds are really pretty and Ocean vodka is smooth so I’d do this over Hali’imaile.
Surfing Goat Dairy
I don’t like goat cheese so this didn’t make my list but it’s supposed to be a yummy snack stop and farm tour with cute goats. They make a goat cheese chocolate truffle that you’re supposed to try and it’s just down the road from Hawaii Sea Spirits.
Kula (past Haleakalā)
Ali’i Kula Lavender Farm
It’s close to the entrance to Haleakala but I decided to skip it to get to hiking. I imagine there are a lot of people taking pictures of the back of their floppy hats.
Ulupalakua Ranch
Their variety of burgers are supposedly superb, especially the elk burger. And even though it’s still in Kula, it’s much further south – an extra 20 mins away from Haleakalā entrance (40 since it would require backtracking).
Maui Wine
Close to Ulupalakua Ranch so for sure combine the two. Open daily 10am-5pm for tastings and vineyard tours. I’m pretty bummed to have missed this. Next time 🍷
Haleakalā
Sunset
Most come for sunrise but I had heard from locals that sunset is better so I wanted to check it out. Obv, they were right. I wrote a blog post on it and how to do both sunrise and sunset here.
Hiking Sliding Sands Trail
It’s an 11 mile out and back trail inside the crater of a volcano. I mean, just think about how cool that is, but also extremely challenging.
There are tons of resources that will be more useful for those wanting to do the full trail (like All Trails, NPS). I only made it about 2 miles in the short time I had before the sunset. And those 2 miles were seriously no joke with the high altitude and changing weather conditions. You’ll want to pack layers and be prepared to be out of breath. The landscape inside looks like Mars and it’s incredible so I encourage hikers of all levels to attempt it, even if just for a mile.
I know it seems like a high opportunity cost to take a day away from the water in Maui but Upcountry provides such an interesting perspective and it’s totally worth it!