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Travel Diary: Maui

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In case you’ve tuned in to my social media accounts recently, you already know that we just returned from a weeklong couples’ trip to Hawai’i… and it was the absolute best!!

This was my first time ever visiting Hawai’i because getting there from Florida (where I grew up) is an incredible endeavor and, of course, super expensive. Because of this, most Floridians just opt to visit the (much more accessible & affordable) Caribbean instead. 😂 Needless to say, this trip was such an amazing treat!

At the beginning of our trip, we spent two full days (and nights!) on Maui where we crammed as many adventures in as we possibly could and then made our way over to the neighboring island of Lana’i for the remainder of our trip for maximum relaxation. It was the most chill and fun vacation that I didn’t realize that I needed.

Keep reading for all of my tips and recommendations for Maui and Lana’i!
(Buckle up, this is gonna be a long post!)

Saturday: 1/18 — Our friends flew from Florida to meet us in Seattle and together the four of us flew to the Kahului Airport (OGG) on Maui.

Immediately after landing we picked up our cute rental Jeep from Avis and drove down the western coast of Maui to the Andaz Wailea resort where we stayed for two nights! If you plan to drive around on Maui to explore, I would definitely recommend renting a Jeep — some of the roads are unpaved so you may need the Jeep’s “offroad capabilities”. 😉

After checking in, we quickly changed into our swimsuits, hopped into one of the resort’s gorgeous infinity pools and each enjoyed a Lava Flow Piña Colada to kick off the trip!

After our quick dip in the pool, we went back to the room, freshened up and walked over to the neighboring Wailea Marriott resort to take part in their Te Au Moana Luau (which is set up to look out onto the water!).

(My dress is this Lilly Pulitzer maxi; it’s currently sold out, but you may be able to find it on Poshmark!)

We decided on this particular luau (there are SO many to choose from!) because (1) they had a stunning backdrop, (2) they had the traditional food items buffet-style instead of a set plated meal (because we had a couple of picky-ish eaters in our group), (3) they greet each person with a fresh lei upon arrival, and (4) it had great online reviews!

We loved watching the pig roast revealed from the traditional underground oven (which we learned is called an “imu”)!

The space had a great flow, the food was tasty (I encourage you to try the poi! It’s a traditional dish that’s an essential part of the Hawaiian diet), the performances were awesome, and before dinner they had a lot of little stations set up to do a few simple crafts with kiddos or offered cute souvenirs for purchase. The sunset behind the stage was stunning and we had the best time!

After the sun went down it got a bit chilly from the wind coming off the water, so I recommend bringing a light jacket or sweater with you! After the show was over, we walked the short distance back over to our hotel and immediately went to bed because we had an early morning adventure the next day!

Sunday: 1/19 — We woke up early to drive up to the Lahaina Harbor to secure our boat boarding position with Ultimate Whale Watching. We had purchased our tickets ahead of time for the 6:50am slot, but the sooner that you check in for the excursion the faster you can board the vessel so that you can choose an optimal seat! We arrived to check in at 6:20am and we ended up having to board after a group of 8 people; lesson learned (read: get there even earlier!).

The whale-watching boats with this company are relatively small so technically everyone has a decent whale-viewing seat, but we wanted seats where we would be able to move around if necessary. I also recommend sitting in the first row of seats under the bimini top — the seats in the very front of the boat were exposed to the sun as well as a bit bumpy as we zoomed from one place to another.

(The left image is an adolescent whale doing a slap on the water’s surface with it’s pectoral fin and the image on the right is a snap of a baby whale’s tail wave as it dove into the water.)

We chose the 2 hour excursion and I would highly recommend that length of time for this whale-watching experience. The boat’s captain will drive the boat right over to whales to get as close as is safe (and respectful of the animals), but the whales were alllll over the place so sometimes it took a little while to get from one whale to another; we spent a decent amount of time with each whale buddy, but the getting to and from each one takes a bit of time so the full 2 hours was the perfect amount of time (I think any less wouldn’t have been long enough and any longer and I feel like most people would have been ready to head back to shore… lol).

We were shocked at how many whales we saw both up close and in the distance; they were so active! We’ve been whale watching before (in Maine) and didn’t get to see very much, but this experience was so magical! This time of year is pretty ideal for viewing humpback whales in Hawai’i because they migrate down to the warmer waters to breed and give birth so we got super lucky and were able to see a few mama whales with their calves. Baby whales can’t hold their breath as long as full grown whales can (their capacity just isn’t even close yet!) so they tend to stay pretty close to the surface, which is perfect for those of us wanting to admire them!

After our whale-watching excursion we drove our Jeep from Lahaina over to the town of Paia to have lunch at the famed Mama’s Fish House. This meal was a bit of a splurge, but SO worth it! I also recommend (1) making a reservation WAY in advance because spots fill up quickly, and (2) going for lunch because the views are so gorgeous during the day!

Other than at sunset, you really don’t get to enjoy the oceanfront view at night so I think that having lunch at Mama’s was pretty ideal. Half of the menu rotates according to what’s fresh and caught earlier that day and the other half of the menu is made up of Mama’s staple menu items; you really can’t go wrong with your selections!

We also thought that Mama’s had the best Mai Tai’s on the island, so if you’re into rum beverages you should definitely give (at least 😉) one of theirs a try!

After lunch, we decided to make our way down the Road to Hana making stops along the way for cool photo ops.  I had downloaded the GyPSy App to my phone prior to flying to Hawai’i and we were SO GRATEFUL to have that app since all of us had zero cell reception and the app guided you the entire way on the crazy road, sharing details and the significance of each stop, and helped you to gauge whether or not each point of interest was worth stopping for. We only had a couple of “must see’s” on the Road to Hana, so we spent most of the time in the car on one of the most treacherous roads I’ve ever been subject to. 😂 (HUGE props to my husband for being our driver both ways!!! 🙌🏼) FYI: the locals will speed past you on the road because they know it so well, but please keep to the speed limit and pull over for others to pass when you have an opportunity to do so.

We stopped to see Twin Falls, which were kinda cool (and a bit muddy for my shoe choice of sandals 🤦🏻‍♀️), but I wouldn’t say that they were the best waterfalls that we saw that day.

Since we had gotten a late start on our drive, there weren’t too many people on the road BUT that side of the island was very wet (as is expected!) so the roads were a bit more dangerous than they would have been otherwise… we took it pretty slow and admired the beautiful scenery around us.

After MANY hairpin turns and one-at-a-time bridge crossings (that showcased even prettier waterfalls, in my opinion!), we arrived in the town of Ke’anae to see the views and learn a bit about it’s history.

The Lookout from the peninsula was awesome and we had a good time pausing there to watch the waves crash dramatically on the lava rocks. We decided to move on when it started to sprinkle rain.

Then we continued on our drive to Wai’anapanapa State Park to see the Black Sand Beach which was so amazing to witness in person! We followed the signs from the parking lot to get to the stairs that led us down to the black sand / rocky beach. We even got to walk through a lava tube on the beach, which was super cool. If you walk back up the stairs and go around the cove, there’s a gorgeous lookout that provides some pretty awesome views (see last two photos). When we arrived it was raining fairly heavily, but only lasted about 10 minutes into our stop so we got a little wet, but the sky cleared a bit toward the end for some photos!

Afterward, we made it to the Hana town limits (just barely 🤣) and stopped at a pretty deluxe roadside stand called Hana Farms to buy some of their banana bread (SO yummy!). It was here that we turned around and retraced our path on Hana Hwy to get back to Kahului (where we were dropping the rental car off). The drive back from Hana in the dark added another level of terror, but we made it! 😂 (Please note the screengrab below which shows the crazy path through the mountains!)

We dropped our Jeep back off at the airport Avis and took an Uber back to our resort in Wailea. We ate a quick dinner at the hotel and fell asleep immediately, which was good because we had an even earlier start the next morning!

Monday: 1/20 — That 1:30am wakeup call was BRUTAL! We were all exhausted (my husband was actually so tired that he opted out of this adventure), but the rest of us managed to get to the lobby by 2:00am to meet our tour shuttle. Apparently, the best way to see the sun rise is to watch it from the edge of a dormant volcano and to get there before everyone else does (ya gotta get a front row spot, right?!). We were provided a small continental breakfast (coffee, fruit, and pastries) for an hour before re-boarding our shuttles and heading up to the Haleakalā summit. The ride up was roughly an hour and a half and I slept almost the entire time (trying to grab every minute of sleep that I could! 😂).

When we arrived at the summit, there weren’t many people there yet (sunrise was at 6:58am and we de-boarded our shuttles at 4:40am!). We followed our guides in the dark to the viewing railing and took our positions. I’ll admit that at first we were a bit annoyed at having to stand in the cold (it was ~35°F at 4:45am at the crater rim!) for two hours ahead of the sunrise, but after our eyes acclimated and we realized that we could see the night sky super clearly we forgot that we were even cold! We had so much fun watching shooting stars and meteors in the sky while we waited that we completely lost count.

(I know this image is dark, but if you have the opportunity to view it in a dimmer environment, you’ll get a good idea of our spectacular celestial view that morning!)

And then, just like that, it was time to greet the sun. As the light came up over the horizon and illuminated our surroundings, we realized what an incredible place we had been standing in for the past two hours! We had been hanging out above the clouds! 😍

To give you an idea of it’s enormity, the crater is large enough to fit the entire island of Manhattan inside it!

It was super chilly, and even though we had packed and dressed accordingly for the colder temperatures, the wind chill was overpowering our warm clothes! Luckily, the tour company offered insulated windbreaker / blanket / poncho-things(?) that helped tremendously! And after the sunrise we were greeted at our shuttle by hot cocoa, coffee, and tea! We absolutely loved our tour company and would definitely book experiences with them again!

On our way back down the mountain in our shuttles we learned more about Hawaiian history (and lore) which was super fun — our guides were awesome (ask for Everett and Jacob)! When we got back down Haleakalā (around 9:30am?), there was a breakfast buffet waiting for us which was perfect because we were STARVING!

I recommend dressing in layers if you can! When we got back down the mountain, we were all pretty toasty in the 85°F weather. (What a drastic temperature change to pack for! 😆) After we finished eating our breakfast, we hopped back on our shuttle which returned us to our hotel so that we could reunite with my husband (who, I might add, totally regretted not joining us for the sunrise… 😉).

There we quickly packed up our things in the room, changed out of the clothes that we had worn to the freezing summit, and took one last dip in the awesome resort infinity pools before checking out of the Andaz.

We crossed the street and visited The Shops at Wailea to do some retail therapy and then had lunch at MonkeyPod (everyone told us the Mai Tai was a must-try!) before heading up to Lahaina to catch the last ferry of the day to Lana’i!

*FYI: the Expeditions ferry is Passenger-Only, $30 each way, and only runs like 5 times in each direction, so plan your day accordingly!

Since this post is already incredibly long I am going to create a separate post for my Travel Diary from Lana’i, so look for that early next week!

Please let me know in the comments if you have any questions! We had the absolute BEST time and if you’re traveling to Maui soon, I hope that this post is helpful to you!

xx, Natalie





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