top of page

Maui, HI

Updated: Sep 16, 2023

Our itinerary

Way back in June when Southwest had their 50% off 50 days of fall travel discount we decided to head back to Maui one last time before moving back to Texas, because why the heck not! During these 2 years in CA we have also become super close with Alec’s coworker & her fiance, Jade & Cameron. So when we decided to go on this trip who better to ask to join us than the traveling bugs themselves!

Day 1

Thursday morning we got up at the crack of dawn & headed for the airport. Luckily we were able to schedule an Uber & arrived at LAX around 6am. We made it through security & the Hawaii precheck super quickly which made for a very low stress travel day (if you know us at all you know how rare this truly is lol). We highly recommend filling out the Hawaii pre-check forms online prior to arriving at the airport, it makes for a super seamless process.

After grabbing coffee from The Coffee Bean (had to get my first Pumpkin Spice Latte of the season) & a quick breaky from Chick-fil-A, we headed to our gate to begin boarding. We haven’t flown Southwest in a while but man, did we love it! They have such friendly crew members + amazing service. Shortly after takeoff they came around to take drink orders (non-alcoholic) + pass out these pre-made snack packs which included a snack mix, crackers, cheese spread, fruit snacks, & tic tacs. I mean what more could you ask for?!

Once we landed at OGG, we headed straight for the Uber pick-ups. Since we did the Road to Hana (highly recommend) on our last trip to Hawaii, we really didn’t need a rental car. After checking into our Airbnb we headed to Whalers Village to grab some lunch. Luckily our Airbnb was only a 3 minute walk over to the village which is filled with lots of restaurants, convenient stores, & shopping. We decided to stop in their food court area at Joey’s Kitchen & got the Island fish taco plate + a side of rice. After lunch we popped into the ABC store to pick up some snacks & drinks before heading to the beach.

It was a pretty windy day so we didn’t stay at the beach too long (plus we had a super secret surprise event happening that evening so we didn’t want to be late). Around 5pm we headed back to our Airbnb to get ready for drinks at The Sandbar located inside of the Sheraton hotel, which was right next door to our place. After we walked over there the boys secretly slipped away in preparation for the big surprise! Unfortunately none of us had great cell service (minus me, go Verizon!) so we all had a slight panic attack & just hoped everyone was on the same page & in the right space. Once Jade finally got texts from Cam, she went to meet him inside the Sheraton while I sprinted to meet Alec on the top of a cliff. He was in charge of pictures & I was in charge of videos. After he popped the question & she said yes, they took some gorgeous beach sunset pictures and we headed back to The Sandbar to start celebrating!!

We ordered a bottle of champagne (of course, because how else do you celebrate the most stunning engagement ever) + 2 apps to tie us over until dinner. After we finished up there we walked over to our reservation at the new restaurant in the hotel, Huihui. I cannot say enough good things about this place; the food, the ambiance, the views, it was all to die for. To drink Alec got the chocolate espresso martini & I got the rosemary watermelon crush. Both were so tasty & mine was super refreshing too! For dinner we decided to do a bunch of apps & share them amongst the group. So we ordered Hawaiian lollipop wings, bao buns, dumplings, pork belly skewers, & pasta. Our personal faves were the dumplings + bao buns, we literally can’t stop talking about how delicious they were! After dinner we were exhausted, with the time change we had experienced one of the longest days ever, 20 hours to be exact, and were ready to call it a night.

Our trip was already off to the best start & we are both just so thankful to have had the opportunity to be a part of the future Kennedy’s beautiful engagement. We wish you both all the best, marriage is seriously the sweetest gift!!

Day 2

Friday morning we slept in as much as we possibly could but the 3 hour time change from California had us up super early. After we grabbed complimentary coffee from our lobby, we sat on the pool deck & enjoyed the calm morning while sipping our cups of joe. Once we were all finished we decided to walk over to Choice Health Bar, in Whalers Village, for some acai bowls. Alec ordered the Lil’ Powabunga & I got the Kaanapali Point, both were super tasty & had the freshest fruit ever.

After breakfast, we decided to explore the area a little bit & walk along The Boardwalk (which runs between the resorts & ocean). Once we went all the way up & down the path, we had worked up quite the sweat. We decided today was our pool day so we lathered up with sunscreen & soaked up all the sun we could get. For lunch we went to one of our favorite restaurants in the area, Monkey Pod! If you ever have the opportunity to go to Maui, this place is a must. We all started with their famous Mai Tais & couldn’t stop talking about that lilikoi foam all trip long. To eat Alec & I split the Maui Cattle Co. cheeseburger + garlic truffle oil fries. That is actually what he got last time we came & it was just as good as we remembered it to be.

We seriously got SO lucky with the weather, it was perfect. Not too hot but just hot enough to be able to get in the water comfortably. Once we finished lunch, we went down to the beach for a bit. The waves were super big & we all had so much fun just hanging out & splashing around. After we had our fill of sand & sea, we decided to end our day back at the pool. Around 3:30pm, we headed back to our place to change + freshen up for the evening. We decided to walk over to the Grotto Bar, which is located at the Hyatt Regency, for a drink during happy hour. This is such a cool bar located between 2 waterfalls in a cave by the hotel’s pool. Once we finished our drinks we walked back to Whalers Village for our dinner reservation at Leilani's On The Beach. To drink I got the Kaanapali sunset & Alec ordered a local beer. Yet again all the food looked so tasty that we couldn’t help but just order a ton & split it between the group. So we started with the macadamia nut hummus then ordered the beachside nachos, sriracha guava chicken wings, & the parmesan crusted mahi mahi. All of the food was incredible & left us full & satisfied! After we paid our bill, we headed back to our Airbnb for the dance party of the century. Well Jade & I had a dance party while the boys chilled on the patio listening to country music, but to each his own right?!

Day 3-

Saturday morning we got up and headed to Lahaina for the day, which is only about 15 minutes from Kaanapali. We first stopped to eat breakfast at Betty’s Beach Cafe which was the cutest little local spot. Alec ordered the chilaquiles & I got the chicken club wrap. After breakfast we walked down to the Lahaina Historic District to do some souvenir shopping & sightseeing. On our way we stopped by the Banyan Tree Park which is a must see. In the center of the park is a tree that is over 150 years old. Now this is not an ordinary tree, this tree grows down towards the ground, reroots itself, & continues growing another tree. So as you could imagine it is the most beautiful & unique tree ever, we highly rec stopping here to admire & learn more about the history of how it came to be!

After we finished exploring Lahaina we got in an Uber & went to Napili Bay, which was about 20 minutes away. We took the Kapalua Coastal Trail down to the water & did some cliff jumping & swimming. I was super nervous to jump in (more from my fear of the ocean/sharks than the height) but of course Alec did it so I just had to join in on the fun too! About 30 minutes into our eventful afternoon, a huge storm rolled in & out in the span of about 5 minutes.

After the storm passed, we headed up to have a drink & app at the Hana Hou Bar which is located by the pool of The Montage hotel.

After our snack & drink break, we headed back to our place to get ready for the evening. Thank goodness for Jade & her love of planning otherwise Alec & I would have yet again missed out on the best experience of our lives. Literally seconds after booking our flights for this trip, Jade hopped on OpenTable & made reservations for Mama’s Fish House. At first we thought she was crazy but now we completely understand the hype! Man, it sure is a journey to get there but it is so beyond worth it. We had a reservation for 5:15pm but ended up showing up around 4:45pm and getting seated right away. We were told to over indulge during this meal & that is exactly what we would recommend to anyone going in the future. To drink I ordered the celebration punch & Alec started with the paps whiskey sour. After our drinks came out they brought us each a lobster bisque bowl & honey butter + bread to share. Once we finished that started we ordered 2 more apps because why not! For dinner Alec got the Mahi Mahi & I got the Mama’s fish curry. His fish was so good but my curry was to die for. I was literally so full but had to keep eating because I couldn’t let a drop go to waste. At the end of our meal the waiter also brought out a celebratory house made ice cream & sorbet for us to share in honor of the newly engaged couple. All in all we would give this restaurant a 10/10! From the staff to the food and the most incredible beach sunset, we couldn’t get enough!!

Day 4-

When Alec & I came to Maui last time we did a snorkeling excursion & absolutely loved it. So when we came back with Jade & Cam we decided we just had to go again! Unfortunately the tours start super early so we had to get up at the crack of dawn to Uber to Maalaea Harbor. Of course we thought we were all prepared & ready to go but as we checked in the captain noticed that we had booked for Monday instead of Sunday. Luckily he was SUPER sweet & let us get on the boat & go on Sunday instead. Afterwards Alec & I apologized to Jade & Cam and explained how we are always cursed with bad luck when traveling & sadly this trip was no exception lol.

Once we finally made it on the Aqua Adventure and grabbed all of our gear, we got some breakfast & found a seat. They were serving muffins, fresh fruit, & coffee which was the perfect start to the day. It took about an hour to get everyone on & ready to go, then about another hour to get from the harbor to Molokini Crater. Of course the captain had to inform us that a shark has been spotted here frequently & to keep our eyes peeled. This FREAKED me out but after talking to the captain more & Alec basically dragging me into the water, we snorkeled together & had the best time. The water is such a clear blue with so many colorful fishies & cool coral reefs. After about an hour or so we all hopped back in the boat & headed to Turtle Town. Unfortunately the water isn’t nearly as clear here & the turtles were not out to play but it was still fun to hop in for a bit & swim around. One of the Aqua Adventure employees actually found & picked up a Lipstick Urchin for everyone to hold. After spending about another hour snorkeling here everyone got back on the boat again to eat lunch before heading back to the harbor. If you are looking for a wild ride we recommend you sit on the front of the boat but be warned, that is THE splash zone!!

Once we made it back to the harbor, we got in our Uber & went straight to our pool. We soaked up as much vitamin D as we could before going back to our rooms to get ready for sunset pictures + our last dinner on the island. We had reservations at Hula Grill which is located in Whalers Village on the sand. To drink Alec had to get one last Mai Tai (however not as good as Monkey Pods) and I got the world famous woo woo. To start, we ordered Hawaii ceviche & kabocha pumpkin hummus for the table. For dinner I got the Kiawe roasted chicken & salt & pepper ribeye. It was the perfect last meal for one of the best trips we’ve ever taken.

Day 5-

When Monday morning rolled around we were all so sad to be leaving the beautiful state of Hawaii. Once Alec & I got up, we grabbed coffee from the lobby, & walked on The Boardwalk one last time. After we cleaned & packed up our Airbnb we did have some time to kill, so we decided to do the Tiktok Neon Moon Dance Challenge (and no I did not have to force or bribe Alec to do this it was actually his idea lol).

Maui, you will be so dearly missed & we have loved being so close to you these past 2 years. Thanks for all the memes, amazing food, & beautiful views! We can’t wait to come back again one day soon!!


What to wear

Thursday’s travel outfits-

Thursday’s evening outfits-

Friday’s evening outfits-

Saturday’s evening outfits-

Sunday’s evening outfits:

Monday’s day + travel outfits:



Where to stay

Located right by Whalers Village & only 100 steps from the beach!

We also had access to a wonderful pool that overlooked the ocean.

Other places


Where to eat


Choice Health Bar (Whalers Village)

Swan Court (Hyatt)

Waicoco (The Westin- breakfast & dinner)


Cliff Dive Grill (Sheraton)

Food truck

Joey’s Kitchen (Whalers Village)

Mai Tai (Sheraton)


Hula Grill (Whalers Village)

Huihui (Sheraton)

Lelani’s On The Beach (Whalers Village)

Monkey Pod (Whalers Village)

Pau Huakai Tiki Bar (Hyatt- HH only)

The Sandbar (Sheraton)



What to do

Parasailing (depending on the time of year, they don’t allow it during whale season)


the stegalls

35 views0 comments

Recent Posts

See All


bottom of page