This edition of our Travel Traditions Series covers our regular routine for the day we arrive on the island of Maui, which after a long flight and 5 timezones, is a rather short one after we land.
Whether it’s your first trip to Maui, or you go every year; whether it’s been 10 months or 25 years since you last visited the Valley Isle, that first day is special. And regardless of where on the mainland you may live, or any other country for that matter, that flight plan is going to do a good number on you one way or another.
We currently live in Chicago, and whether we take a direct flight or have to stop on the way, the journey to Maui is never shorter than 9 hours on a plane, and more time waiting in lines at the airport, sitting at the gate, the usual. We’ve always taken a morning flight out of O’Hare, which depending on delays, has gotten us to Kahului anywhere from 2:30pm to 4:00pm. Since our resort of choice is the Sheraton Maui Resort in Ka’anapali, we plan for about a 45 minute drive from the airport.
By this time, it’s usually around 4:30pm or so, but our bodies are telling us it’s 9:30pm Chicago time. Seeing as we had gotten up around 6:00am to get to the airport early enough, that’s already a long day, is it not? The Sheraton, like many resorts I assume, has a drive-up quick check-in. Being pros at the Sheraton, we know exactly where to go and where to park, so not needing the bell hop’s help is a time saver. The welcome attendant likes to greet you with a fresh flower lei, which we absolutely love, and that first deep breath with one of those around your neck is a good shot in the arm for getting through the next few hours.
Our Room
With our fresh leis, we head to our ocean front room. Although outrageously priced, we’re lucky enough to splurge for this option and truly enjoy it. Once in our room, we’ll usually just throw the bags on the bed and unpack just whatever we need to freshen up. After all, 9+ hours on a plane isn’t exactly a day at the spa. Anyway, with the beautiful lanai you see pictured here, we just have to step out for a moment and let it sink in that we’re finally back on Maui. In about 2-3 days, it will feel like we really never left the island in the first place.
It’s usually around 5:30pm or so by now, and time for us to head down to the Lagoon Bar at the Sheraton, right along the pool area if possible (shown above). Timing it accordingly, they will still be serving food, so we each grab a tropical drink of our choice and split a cheeseburger. Looking out towards the ocean from the Lagoon Bar after such a long travel day is such a release. We’re usually finishing up our light meal just in time for the Black Rock Cliff Dive Ceremony, which happens every night at sunset at the Sheraton. We’ll watch the cliff dive about 3-4 times a trip, but obviously that first one is the best.
Quick Shopping Trip
After the cliff dive, it’s about 6:30pm, although it’s starting to feel like midnight for us because of the time difference. We have one more stop before we retire for the night, so we hop in the car and drive over to the Lahaina Cannery Mall. Our mission there is just one stop (maybe two, if Cindy wants Starbucks). Since we stay for two weeks at a time, we like to stock up on all the essentials and a few snacks for our room by doing a little grocery shopping at Safeway. We like to make our first trip to the store this first night so that’s one less thing to do on our first full day of the trip.
There’s some initial sticker shock at first, seeing that the cost of living and everything else is so much higher on Maui than back home, but we’ll bring coupons and our savings club card to help soften the blow. If we were CostCo members and wanted to make a separate trip back to Kahului (without a car full of luggage), we could go down that route, too. For us, having a Safeway so close is good enough. We don’t necessarily have a list, so we just end up browsing all the aisles and getting what we feel like. We’ll stop at Safeway a few more times during the trip, so if we forget something, it’s no big deal.
Calling it a Night
Coming back to the Sheraton with our groceries, it’s about 8pm and you can sometimes hear the Royal Lahaina Luau up north along Kahekili Beach starting to get underway from our parking lot at the Sheraton. At this time of night, there usually isn’t that great a choice for parking. Since we stay in the ocean front rooms, there is a dedicated lot in the back, which isn’t that large. Lugging the groceries up to our room and loading the fridge, we have little energy for much else by now. We may turn on the news if we’re still awake enough to follow it, but the goal at that point is just to get some serious shuteye, and to wake up the next morning fully refreshed for our first full day in paradise.
The Travel Traditions Series here at the blog features our habits and rituals that we have for various aspects of our frequent trips to the island of Maui. Getting to know the island so well after all these years, having a few traditions adds a little continuity to our visits, while still giving us so much flexibility to enjoy many new things each trip.
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