Last Updated on September 8, 2025 by Lauren Belzer Sanford
Sometimes when life hits you like a ton of bricks, you have to crawl out from under them and go on a vacation!
In June 2022, I was laid off from my job and forced to start the hunt for a new role. Anyone who knows what it’s like to be unemployed knows that the job search is a full-time job in itself. After months of interviews, being ghosted, and endless rejection, quite frankly, I needed a break.
Max and I had been wanting to go to Hawaii, specifically the island of Maui, for a while. Both of us had been before with our families, but never together. We thought what better time to do it given he had “unlimited” PTO, and I didn’t have to worry about taking off time from work at all. We planned it only a month or so out, so if a job opportunity came along, I’d just push my start date to after our return, or just let them know that I had prearranged travel that I’d need off.
So, on November 1, 2022, we made our way to Maui! I’m going to warn you that this was primarily a relaxation trip, so we spent most of our time at the beach, at the pool, drinking tasty cocktails, trying delicious restaurants, and being low-key. There was not a ton of adventure on this trip, but hey, when you spend money on a resort, you want to be able to enjoy it! This was our 6-day itinerary:
Day 1: Arrival & Pool Day
If you’ve been to the Hawaiian Islands from the West Coast, you know that it takes several hours to get there. We flew out of LAX instead of John Wayne because, sadly, John Wayne didn’t have any direct routes from Orange County to Maui.
The best part about traveling to Maui is the “time traveling” you get to do. We took off around 8:00 am Pacific time, and although we were up in the air for roughly 5.5 hours, we landed close to 11:00 am, so it didn’t feel like we “lost” that much time.
Once we grabbed our bags, we called an Uber from the OGG airport to our resort, Wailea Beach Resort – Mariott, Maui. Something Wailea Beach Resort does (and many hotels of a certain caliber) that I think all resorts and hotels should implement is essentially a “locker room” that guests can use if they arrive before check-in or are going to be staying on the property past check-out.
It was so nice to be able to be greeted with our fresh POG juice, put our swimsuits on, and enjoy the pool/beach while the front desk held onto our luggage! We also spent a little bit of time getting acclimated to the property—walking around, and taking in the views!
Once we were able to make it up to our room, we freshened up for dinner at Spago at the Four Seasons Resort Maui at Wailea. The Four Seasons was just a short stroll down the beach from us, so we decided to walk over a bit early and enjoy a drink with a view at their bar. Spago was easily our favorite restaurant of the trip, a great way to kick it off, and maybe even one of our favorite restaurants ever! If they have it, be sure to order the Seafood Red Thai Coconut Curry…it is incredible!
The Four Seasons property is gorgeous, so it is definitely on our list for a Maui trip in the future!
Day 2: Resort Day
On our first full day, we pretty much didn’t leave the resort until it was time for dinner. We had breakfast on-site at Humble Market Kitchin by Roy Yamaguchi. They have both a buffet option and a la carte for breakfast. Either is a good choice. Regardless, make sure you order the Coconut Macadamia Nut Pancakes made with haupia cream, toasted coconut, and brûléed pineapple…they are insane. Don’t skip out on the fresh tropical juices, either!
It’s safe to say we spent nearly all day at the Maluhia Pool, their infinity-edge, adults-only pool on-site. You can rent a cabana at the resort’s various pools, but we were never sure if we were going to be popping from the pool to the beach and back, so we just went out shortly before or after breakfast to claim our chairs and we had no problems. We didn’t get to experience it, because they were building it while we were there, but they have since opened their Olakino Wellness Experience. You do have to pay extra for an experience, of course, but if you’re looking to treat yourself, it may be nice! The best part about visiting Maui and specifically the Wailea area when we did was that it was off-season, so we were not competing with as many people on or off the resort!
In the afternoon, we took a quick jaunt down to Ulua Beach to take a dip in the ocean for a bit before heading back up to the pool! We loved this spot because it’s a smaller beach so there were not many people.
After a day of relaxation, sipping on mai tais and mojitos, we ended the evening by walking up the hill to Matteo’s Osteria. Wailea Beach Resort has a shuttle that you can call down to that will take you where you need to go within Wailea (if they’re available), but we decided to walk. I’m not going to say it was a terrible experience, but it was a little bit further than it looked on a map, and the way there was 100% uphill.
All-in-all, it was a great first full day!
Day 3: Beach Day
The next day, we slept in as much as we could given we were three hours behind our usual time zone and still adjusting a tad, then got up and grabbed a quick breakfast and coffee at Whale’s Tale on the Wailea Beach Resort property.
We spent the first part of the day at Wailea Beach. We did not rent any beach chairs from the resort, because you have to reserve them early, and we forgot to do that, so we just posted up with our towels and enjoyed the sand and nice warm water!
This beach was a little more crowded because it’s shared with a few of the resorts so we ended up only spending a part of our day there. We then headed back to our resort to spend the last part of our day at the Maluhia Pool.
After a late afternoon refresh in the room, we got ready to head up to Monkeypod Kitchen for an early dinner. Since we had already experienced the uphill trek to get to Matteo’s the night before, we planned ahead and called the concierge for the resort’s shuttle service to take us up to Monkeypod. It was a nice change being chauffered up there!
All we were feeling was appetizers so that was our plan…but we ended up befriending people at the bar and the bartender, so we stayed and spent time enjoying far more than just their famous mai tais! The seared ahi is amazing!
After that, we called the shuttle to come back and get us and spent the evening walking along the beach path.
Day 4: Pool Day & Sunset Sail
After breakfast, we went on a morning walk along Wailea Beach Path quite a ways down to where it turns from hotels into residences. It was a stunning morning with lots of gorgeous viewpoints on the walk, especially up the hill. The best part about our little stroll was the cats in the bushes! One even came out to say hi!
For the majority of the day, we spent time at the resort’s other pool(s), the ‘Ohi Pools. The ‘Ohi Pools are family-friendly pools, so there were kids, but not many given the season and it was still very peaceful! We also went back to Ulua Beach for a little bit since it was so small, quiet, and restful on our first day.
That evening, we got ready for our sunset sail with Kai Kanani, which we had booked on our first day with our hotel concierge. Most boats tend to go out of Kaanapali or other more northern towns, but we were lucky to find room on Kai Kanani as it was a beach-loading boat out of a beach south of where we were staying. They arranged pick-up and drop-off to and from our resort which made it extra convenient!
The staff on the boat were amazing – wonderful service, delicious small bites, drinks…they even took us out to see Molokini Crater! The sunset was stunning from out on the water, and despite getting a little bit wet with the beach loading and unloading, it was an otherwise perfect experience.
Since we only had small bites on the boat, we decided to grab dinner at Humble Market Kitchin for something before heading to bed. Unfortunately, I was so tired from my Dramamine that I almost fell asleep at the table, so we ended up rushing through dinner to go to bed – oops!
Day 5: Day Trip to Lahaina & Black Sand Beach
On our last full day, we quickly grabbed Starbucks at our resort for a coffee and breakfast before we rented a Turo for the day to drive up to Lahaina! We called a quick Uber from Wailea Beach Resort to the Turo’s location at a parking lot in front of an ABC Store in Kihei. Once we figured out where the keys were from our Turo “host,” we headed on our way up to Lahaina!
We found street parking and walked around for a bit, popping into some shops and walking along the water. We ended up stopping for lunch at Paia Fish Market before shopping around Lahaina Town, where I got my all-time favorite pale yellow sweatshirt that I wear all the time!
Unfortunately, much if not all of of what we saw, did, and ate in Lahaina is no longer there, as it was tragically lost to the August 2023 wildfires. If you’d like to support businesses like Paia Fish Market, they do have two other locations on Maui (Paia and Kihei) and also on O’ahu (Waikīkī and Kailua).
After our time in Lahaina, we stopped for an afternoon coffee in Kihei at Lava Java Coffee Roasters for an afternoon pick-me-up, which is coincidentally right next to Paia Fish Market’s Kihei location.
Since we still had a little bit of time before we had to return the Turo to the ABC Store parking lot, we drove down to One’uli Beach (also called Naupaka Beach) to see the beautiful black sand beach. It was a bit crowded in the area, so we ended up having to park on the side of the street and walk in, but it was cool to see!
Before our final dinner reservation of the trip, we got ready, took some pictures just before sunset & got drinks at KAPA Bar & Grill where we used our free “welcome” drink coupon from the front desk. They gave it to us upon check-in, but we forgot about them until our last night, so we ended up using them for a “farewell” drink instead!
After our appetizer and drink, we had some time to kill, so we strolled by the luau. We did not book a luau for this trip since both of us had experienced one prior with our families, but we happened to walk right by the Te Au Moana Luau that was happening at our resort, so we were able to catch a glimpse as we went on our walk!
By the time our short stroll was over, we still had a little bit of time before our later dinner reservation at Nick’s Fishmarket Maui at the Fairmont Kea Lani Resort. We ended up getting on the shuttle and heading down there early and had a drink at their bar. The meal was wonderful and the perfect end to our trip. The waiter was phenomenal and full of energy and excitement, and we were seated in a way that we could look out at the vast property toward the ocean, with a warm breeze, and delicious food!
We strolled the Fairmont property to soak in our last night in Maui before getting picked up by the shuttle to head back for a nightcap at Wailea Beach Resort.
Day 6: Shopping & Departure
Our flight wasn’t until the afternoon, so we headed up to The Shops at Wailea for some coffee and last-minute shopping (Honolulu Cookie Co. + a home store where I originally saw a cute market bag in).
From there, we said “a hui hou kākou” to this beautiful island, called an Uber to the airport, and went on our way!
We both love the island of Maui so much and can’t wait to venture back and explore more of it!