Marvelous Maui: Eating Our Way Through our First Day

Our third day in the Hawaiian Islands was our First Day on Maui!

As I’ve mentioned, we don’t like to sit still for long, and we recognize that with our crazy work schedules, we only have a limited amount of time for vacations, so we choose to make the most out of that little time wherever we go. With that being said, if you are planning your own Hawaiian Vacay, do not-by any means- feel the need to stick to our itinerary! Know yourselves, the kind of vacation you’re after, and plan accordingly. Our general rule of thumb:

1 fun-tivity + 1 relaxing thing + 1 dining experience = the perfect day!

Leaving O’ahu & Traveling to Maui


We narrowed our stuff down to 1 big suitcase and 1 carry-on tote-size bag each. We were staying with friends on O’ahu, so it was easy to pare down like that, and leave the suitcase on O’ahu. If you plan on island jumping, I recommend speaking with the concierge at your hotel to see if you can check any spare bags with the bell hop.

Note: We wanted these smaller bags so we could throw a good bit of stuff in our rental car and take it with us. We knew that once we left our hotel in the morning, we would be out and about most of the day and would need a change of clothes, water bottles, towels, sun screen, and chargers.

Island Air 6:00 am flight to Maui.

  • This super early was totally fine because, once again, we woke up before dawn. It was an easy uber, two seconds through security, and we were off to the romantic part of our trip. It was just a 22 minute flight and the flight attendants were really cool because they gave us tropical juices, local coffee, and pointed out things outside the windows! Other islands, the history and formation of the state, etc. It was fun 🙂 Checked bag: $25.00
    • *Note: Island Air has since shut down, however Hawaiian Airlines also offers inexpensive island-hopping flights!

We got our car and first thing we did was drive through Kehei towards Paia (town). We rented a Hertz car using a vacation package booked through Expedia. For 3 nights at the Grand Wailea, 4 days of our rental car, and two round-trip plane tickets, we paid about $1500!!!

Breakfast in Paia


Breakfast: Paia Bay Coffee.  

  • This place was cute because it had a gorgeous mural across the street and all of the seating looked like it was in the middle of a jungle
  • Cheap, fairly basic coffee. The most froo-froo coffee drink would probably be a latte or cappuccino. We also got a nutella/cream/strawberry stuffed fresh croissant, and it was delectable!
  • The croissant was so yummy! IG.

*Note: We should have gone to Wal-Mart or Costco immediately when we landed, but we weren’t thinking about it. We stopped at the local gas station & bought a bottle of Aleeve (should have brought some, but we knew we’d want it after the hike) and a bottle of sunscreen (we just didn’t have the weight in our suitcase before!)

Funtivity Time!

Funtivity: Twin Falls hiking trail at Mile 2 on the Road to Hana


We chose not to drive the road to Hana because that would have taken at least 1 full day, if not two and we just didn’t have that kind of time when there were so many things we’d rather have done.

There was a great farmer’s stand at the entrance & we got a smoothie! (At the exit, we also got some more fruits for the drive/ to make drinks at the resort)


This hike was cool, we wore gym clothes, brought the gopro and hiked the first bit in to the little fall. But, if you go up farther, through the gate that says “experienced hikers only” you’ll find a bigger fall. Most people don’t jump off that one. We did, and it was truly exhilarating. Be careful though, scope out your landing spot first so you know you’ll have a deep enough place to land!The jump off the big falls.IG.

Cost.Parking. Free. Smoothie. $5. Fruit. $2. Postcards. $2. = $9 BRING CASH.

*I wish that I’d had a fanny pack or small hiking backpack with me. I did have a good-size (mid?) fairly water-proof crossbody purse that we managed just fine with on the hikes, but a backpack or fanny pack would have been easier since the crossbody moved a lot and sometimes pulled me in funny ways

This is my first attempt at a YouTube video… Enjoy the screams!

Fruit stands on the sides of the roads.

  • Yeah. We stopped at every single fruit stand that we found.
  • BRING CASH- they mostly work on the honor system.



Tour: Surfing Goat Dairy Farm.

Kyle was really skeptical about this because he really doesn’t like goat cheese. I love it, so i was excited.

It was fun though! We got to feed baby goats, see where they milk the goats and watch the process of making the cheese! Then we also go to do a tasting, and it was super good! A lot of restaurants on the islands use their cheese.

Cost: Tour. $26.04. Postcards. $5. = $31.04


Lunch. Paia Fish Market.

  • We went back to Paia for lunch! This place had some super yummy fresh fish options (good grilled fishes too!). Excellent fish and chips and excellent Definitely cheaper at lunch than at dinner, also from what we’ve heard, people didn’t have as good of experiences at dinner as we did at lunch.

Wandered Paia. Went into little shops, explored.


  • I repeat. We should have gone here sooner. But we stopped by for a few essentials:A case of water, a cutting board, a knife, 2 towels, some spray sunscreen, a pineapple. (we needed the board & knife to make cocktails :p)

Relaxing. Makena Beach.

Not really any photos from Makena on day 1, we just really wanted to relax and soak it all in.

Time to Check-In to the Resort.

Resort: Grand Wailea.

  • Back at the hotel, after we got checked in and settled in our room, we chilled and popped a bottle of champagne that we’d brought…. From Atlanta. Yes, we were willing to go all out on the resort, but wouldn’t pay their prices for the alcohol. Haha. We toasted and got ready for our photo shoot.
  • I cannot possibly write enough good things about this resort. The pools were amazing, the beach was private, it was walking distance to the nearby shops and happy hours, Humuhumu is one of the best restaurants that I’ve ever eaten at… They even provide sunscreen at the valet stand so you can re-apply before hitting the road for adventures!
    There is the first (only?) water elevator in these pools, and the pools connect through water slides and lazy rivers, in the middle of which is a swim-up bar behind a waterfall. Heaven! I’ve also had one of the best mojitos of my life here! I’ll post a video later in this series about the resort and pool!
  • So. While I LOVED this resort. It was gorgeous, so affordable with our Expedia deal, in a fabulous location, had restaurants, was breezy, open, and included a deluxe sunset photoshoot. If you decide to book here, be aware that there is a resort fee of $30/day and (if you rent a car- which you pretty much have to) a valet fee of $30/day. Additionally, anything that you spend will have an excise tax. So each of those are really $31.25
  • Cost:Resort Fee. $31.25. Valet Fee. $31.25. Bellhop tip. $5.

Photos with Pacific Dream Photography.

  • Our stay came with a free photoshoot. (We had Anna, she did a fantastic job).
  • The shoot was a ton of fun, and really captured “us” nicely. The pictures cost ~$80/piece, sadly.
  • But even Kyle walked into the sales pitch thinking that we would, at max, buy 1, and that they would try to sell him really hard. They didn’t at all!
  • They also made a beautiful video of our shoot that captured not just the still shots, but also video clips (similar to a “live” picture on an iPhone). That was really expensive. But we both admitted that if we were there to get engaged, go on a honeymoon, or were there with our kids (or if I’d had a job at the time), we definitely would have bought it, that’s how awesome it was!
  • However, the only negative was that they changed our time of the photoshoot (so we only got 30 minutes) because the sun was setting earlier in September than it was in May when we had scheduled the appointment. It was frustrating that they emailed us when (1) we were staying in the hotel and they had that information, so they could have communicated that way; (2) they had our phone number and could have called; (3) we don’t check our email while on vacation and they emailed us that morning, so not even a few days in advance when we might have seen. However, 30 minutes with Anna was plenty as she took fabulous photos!
  • CostFree-$160
  • Tips:Wear a flowy dress. IG.
    • Check out HeatherKCookPhotography for tips on doing your make-up for a photoshoot.
  • The photos turned out amazing!

Sunset cocktails in the room.

Dinner. Humuhumunukunukuapua’a (aka Humuhumu)

  • This is the restaurant at the Grand Wailea.
  • We got a seat with a view of the sunset and had one of the few truly fantastic service experiences that we’ve ever had. It was tapas style, (or at least that’s what we focussed on).
  • I think our waiter’s name was Justin. And we could not sing his praises enough.
  • He even timed our small plates so that they came out in the order that optimized our experience. (e.g. even though everyone around us had already gotten bread, he brought out our crudo small plate first because you should have crudo before). He guided us with a kind but firm hand through the menu and it was a very pleasant experience actually!4 cocktails, 2 crudo, seeevvverrrallll other dishes, dessert. $171.67.
  • We’re honestly scared to go back because we don’t want to not have the same impeccable service! Justin- if you ever read this, please know that you made our dinner experience truly magical.
  • Kyle’s Review:
  • Overall- 4 Stars
  • Food- 5 Stars; Service- 5 Stars; Ambiance- 4 Stars
  • “A little empty since we were there at the beginning of the slow season, but the great food made up for that. What really put our experience over the top was the outstanding service we received from our waiter, Justin. He was perfectly attentive without being overbearing, which is a hard balance to strike. He gave great advice after taking the time to get to know our taste, and paced our meal perfectly even though we chose to order a bunch of small plates and one entree instead of a more traditional coursing. I’d come back just to experience his service again.”

Read more about our adventures in Hawaii.

Read more adventures and eats on Maui.

Read more from our visits to O’ahu!

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