I have a long list of places that I love to visit in Maui’s upcountry, but I think Maui Wine in Ulupalakua is my #1.

The drive out to the winery is one of the best on Maui
The property is incredibly beautiful and historic
The aloha hospitality is alive and well
There are snacks. And drinks.

Do you need any more reasons to go? I don’t think so, but here’s everything you need to know before you go:

Maui Wine

Maui Wine is situated on the slopes of Haleakala above Wailea and Makena, but you’ll have to take the long way around to get there and that’s part of the charm. From Wailea/Kihei, it’s about an hour back up towards the middle of the island and then up Haleakala Highway through the upcountry.

But it’s about the last 20 minutes or so that is INCREDIBLY SCENIC. From Keokeo onwards, plan to slow down and spend a little extra time at some of the pullouts to take in the views down below.

You can show up, poke around the property, and check out the gift shop anytime you want, but if you want to do a tasting, you should definitely make a reservation in advance. They try to accommodate walk-ins, but there’s pretty limited seating so if this is something you’re serious about experiencing (it should be!), plan ahead.

Reservations (make them here) get you a table for 90 minutes (this isn’t the kind of place where they’re standing over you with a stopwatch) and you can order anything you want from the menu including flights, wine by the glass, cocktails, and small bites.

I can’t really comment on the quality of the actual wine here (it’s not something I’m really into or knowledgeable about), but the experience is great.

My favorite is always the Lokelani, but this time we did the pineapple tasting and rose ranch tasting, plus a brie tray and had an overall fantastic time sitting out on the lanai sampling and taking in the views.

And the views are GREAT. Besides looking out and being able to see the ocean, the winery is located on a beautiful tree filled estate with historic buildings and beautifully landscaped grounds.

They aren’t currently offering tours, but you can do a self guided tour around the grounds plus there’s a room where you can read a lot about the area’s history.

The tasting room is open Tuesday through Sunday from 11AM to 5 PM.

***Want to save major $$$ on your trip to Hawaii? I get asked ALL the time how I’m able to travel so often to Hawaii and stay at really nice resorts. Well, my favorite travel hack is cashing in points to score free airfare and free nights at some of Hawaii’s most high end resorts. Read my full guide on the exact system I use to max out credit card rewards here. Seriously, it’s going to save you soooo much money.

Ulupalakua Ranch

While you’re out at the winery, you’re definitely going to want to stop in at the Ulupalakua Ranch Store across the street. Not only do they have great souvenirs that represent this part of the island, but it’s a great place to get lunch.

The grill on the porch is open from 11AM to 4PM and they serve up local grass fed burgers (beef, elk, venison, lamb) straight from the ranch. They also have fresh made sides and fixin’s and the perfect place for a little picnic.

Another great option if you want a more substantial meal than what they offer at Maui Wine is Grandma’s in Keokea. Their breakfast is my favorite but they’ve got an amazing dessert case (plus they’re famous for the banana bread) that you can stop in for all day long.

P.S. One of the reasons I’m able to travel to Hawaii so often is because I get free flights with my Southwest credit card AND I can fly someone with me for free with my Companion Pass.

I have this Southwest Premier Rapid Rewards Visa card through Chase. The current sign up offer is 50,000 points. Depending on where you live and fly from, that’s at least one completely FREE ticket to Hawaii and it could be two depending on the time of year (or more if you catch a crazy sale).

But the real pro travel hack is getting the Southwest Companion Pass.

If you acquire a certain amount of annual points with Southwest (either through flying or credit card spend), you get a companion pass where you can bring someone with you on every flight you take FOR FREE for the entire year. I can’t tell you how many thousands of dollars I save using this every year.

What makes this doable is that the sign up bonuses from Southwest credit cards goes towards the point requirement.

By far the quickest way to qualify for the companion pass is by signing up for a personal AND business card through Southwest.

**Besides being a business owner, if you’re self-employed, a freelancer or contractor, a gig economy worker, if you own rental properties, etc…you qualify for a business card.

And you’ll be most of the way towards qualifying for a Companion Pass PLUS you’ll have 110K points to book flights to Hawaii. That’s enough points to book 3-4 flights to Hawaii! AND you can take someone with you for FREE.

P.P.S. Here’s one more really important thing you need to know before your Hawaii trip…

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii and a lot of state and national parks have instituted reservation systems at some of the island’s most popular spots to help manage the crowds and make things a little more sustainable.

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan.

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too.
Get that info >> HERE