Escaping to Maui
For those with a sense of adventure – and willingness to bear the brunt of a long red-eye, there are some absolutely gorgeous budget-friendly beaches in the world. Hawaii is not one of them. Nevertheless, Americans are obsessed with Hawaii. It is on every American’s bucket list.
Hawaii has its charm and its beauty. Certain parts of the islands evoke a sense of nostalgia. Driving is relaxing, without worry of traffic jams or police soliciting bribes. Sure, there is also Mexico, where one can find a more affordable slice of beachside paradise…but it’s not Hawaii. And thanks to Southwest driving down market prices, good deals on flights are easier to be found.
A week in Hawaii is ideal. But let’s be honest, work schedules and life don’t always allow such luxuries. It is possible to make a long weekend work, allowing 4 full days and 4 nights, which was the case for our post-New Year’s trip in January of 2020. After working a 21-day stretch, it was time for a break, even if it was short. (Had we known what was to come, we would have figured out a way to stay longer!). Yes, for 2020, Maui’s all we’ve got. And, we loved every second of it.
Maui at a glance:
Maui sample itinerary:
| Day 1 | Flight Arrives in afternoon Early dinner at Mama’s Fish House. Overnight near airport. |
| Day 2 | Haleakala Sunrise (early!), followed by hiking and exploring Haleakala. Visit Surfing Goat dairy and lavendar farm on your way back to town. Overnight: near airport, or in Wailea. |
| Day 3 | Option 1: Relax, rejuvinate in Wailea. Consider an evening luau. Option 2: Drive the road to Hana (~3-4 hours each way with stops). Consider overnight in Hana if you have an extra day. |
| Day 4 | Ali’i Nui Sailing Charter for snorkeling/whale watching, vs relaxing on the beach or poolside at Wailea – consider renting a paddle board and swim with the turtles. |
| Day 5 | Morning strolling in Lahaina, then head to Kaanapali beach. Visit I’ao state park in the late afternoon, just before closing. Dinner at The Mill House. Catch red eye flight home. |
With the time change working in your favor and the departing flight being an overnight flight, a trip to Hawaii can work for a quick getaway. Four to five days is a bit of a tease and not enough to see and do it all, especially when part of the goal of your trip is to spend some time doing nothing, but a wise person once told me to travel with the intention of returning again. Always save something to do, to look forward to, on that future trip.
Details of our trip:
In most of our travels we utilize VRBO or AirBnB to save on expensive resort rates, and usually only stay in big box hotels if we can stay on points; on this trip, we had Marriott free night award certificates and Marriott points to burn. Since our flight arrived in late afternoon, and we had hopes of experiencing sunrise at Haleakala, we opted for one night at an airport hotel. To catch the sunrise at Haleakala involves getting up very, very early for (keep in mind it is a good one hour drive from the airport up the narrow winding road to the park entrance, and then another 30 minutes from park entrance to the summit), so we thought we would use the time change to our advantage, going on our first morning in Hawaii knowing we would be up before dawn. Reservations are required for sunrise and unfortunately, reservations sold out too quickly for us to snag one. ‘Iao State Park is a good back-up plan, less than 25 minutes from the airport, and is best in early morning before the throngs of tourists – follow it up with a beachside picnic near Lahaina.
We like the Courtyard Marriott Kahului Airport for its clean rooms, friendly staff, local live music in the lobby in the evenings, and close proximity to awesome local dining. I am a little bitter that Marriott increased the number of points required for a free night at this property so it is less of a bargain now, but it can be a great use for a 50k point free night certificate if you have the Marriott Bonvoy Brilliant card.
For the remainder of the trip, we chose the Wailea Beach Resort for 3 nights (which, unfortunately, has been devalued since our stay and Marriott free night certificates can no longer be used here). The resort has extensive waterfront and a beach area as well as several pool areas (including an adults-only infinity pool and another pool with a water slide). The location was perfect for us to walk to many restaurants, and there was a small market next door to stock up on picnic necessities. The resort had many free activities, from yoga waterside to lei making classes. Wailea seemed to be a bit more sheltered from the rain that pummeled the rest of the island during our stay, though we certainly experienced our fair share. Some of the best turtle habitats on Maui are right in front of the resort, and we were able to swim and paddle board with the turtles – so fun! We also found ourselves hanging out a lot at the Andaz resort, and if I was splurging, this would be my pick to stay (they are a Hyatt property, and in theory might be an option for a free night on points, but searching on several occasions I have not seen any awards nights available).
A long waterfront walking path stretches along Wailea, and made for a lovely sunrise run (for a 4 mile out-and-back, take the sidewalk south to the Polo Club hotel, cut through their parking lot, and continue along Makena Rd, passing some jaw-dropping houses as well as some local beach access points that offer peace and quiet; turn around where Makena Rd. intersects with the main road. Head back, end at the Andaz for a stretch, and then treat yourself to a sumptuous breakfast at the Andaz). At night, an evening stroll allows for sneak peaks of the various luaus. We didn’t go to any, but we walked so much I felt like I had seen the highlights by the time we left!
Whale-watching is a highlight in Maui from January through March. Based on a well-guided recommendation from a friend, we opted for a combination snorkeling-whale watching excursion through Alii Nui Sailing Charters. Pick up is early (no sleeping in on Maui!), but included in the price – so you can nap on the way back. The service on board is phenomenal. Breakfast is served immediately upon boarding. Lunch was a lavish spread with a huge open bar. The homemade ginger ale was delish. Tours are kept small, and there is plenty of room on the boat to relax and stretch out. There was a photographer in scuba gear on board, so a camera was not necessary. Most importantly, the bathrooms were very nice and clean. Our tour stopped at two different areas to snorkel (ironically, we were right near our resort!); we had to cut snorkeling short due to high winds, but we were able to whale watch on the sail back to the dock. I can’t recommend this company enough.
Another fantastic recommendation from a friend was splurging on the Chef’s Table by The Mill House. The Mill House is worth a visit on the own, but the dinner offered incredibly unique and interesting “chef-y” plates, while diners could walk around and ask questions. Live music topped off a wonderful ambiance. We truly enjoyed getting to meet our table-mates, and before long, we were sharing memories and bottles of wine. Click here for other Maui restaurant recommendations.
The Wailea Beach Resort is kind enough to allow guests resort access on the day of departure, which worked great for our red-eye. We spent our last day at the pool, and had access to a locker room, restroom, and showers as well as a TV lounge area.
Plan your own trip:
Craft your itinerary:
Make a list of activities you want to do (a day of doing nothing should be part of the plan), and prioritize – you may not have time to do it all, or weather may limit how many bucket-list items you can tackle. Plan your time to minimize time spent driving or in transport. On the day of and day prior to your flight home, plan for meals and activities in close proximity to the airport; you don’t want to chance a delay on the ferry from Lanai or traffic on the road to Hana preventing you from getting to the airport in time. If you are visiting multiple destinations, I always recommend ending your trip with activities and meals near a large airport hub in case your flight this is cancelled (i.e. best not to take the day trip to Lanai on your last day, in case the ferry breaks down – Maui has plenty of flight options, Lanai for example does not).
Decide where you will stay:
On Maui, there are three general regions most people stay; scan your list of activities and priorities and see which area makes the most sense to stay in. To minimize driving, consider dividing your nights between the airport area and one of the resort areas. Tours, cruises, snorkel excursions, and whale watching trips can generally be arranged from any location, but check in advance to see if they provide transportation.
- Near the Airport/Central Maui: the beginning of the road to Hana (consider spending a night in Hana if possible), Haleakala, lavender farm and goat farm (on the way to Haleakala), I’oa State Park. Depending on when your plane lands, you may or may not have some time for the beach. There are several beach parks along the North coast near the airport – start down the road to Hana and you will find plenty of spots. These parks can also be a great way to spend a few hours catching some final rays of sunshine before your flight home.
- Wailea: beach activities, paddle boarding, snorkeling with sea turtles, whale watching. The beaches are frequently punctuated with rocky outcroppings (where, of course, you will find the turtles), but quiet without any motorized watercraft, and I find the mix of landscape beautiful. Resorts are more modern – tiered infinity pools with ocean views are the standard.
- Kaanapali/Lahaina area: innumerable beach parks and beach activities including sailing, jet skiing, paddle boarding and whale watching – the beaches are longer and more expansive than Wailea. Stay here if you have plans to jet ski or paraglide. Pool areas at these resorts seemed more geared towards kids and are set further back from the beach and waterfront. Cliff diving occurs on black rock next to the Sheraton. Other activities: and seeing the Banyan tree in Lahaina, day trips to Lanai on the ferry (the ferry can also be a great way to see whales). Lahaina itself is limited to older hotels, but could be an option for a night (the historic Best Western Inn is bookable on points and has clean rooms, balconies overlooking the banyan tree, and talking parrots to greet you, but one night is plenty).
House/condo rentals and resorts are both options on most parts of the island. Consider your budget, whether or not you want to stay beach side or in a walkable area, and how much driving you are willing to do.
Reserve in advance:
Many activities book up in advance – the sunrise at Haleakala being one reservation that may be tough to get (reservations open 7 days in advance at the time of this writing.). Make dinner reservations a few weeks in advance (or months in advance when it comes to Mama’s Fish House!) if there are particular places you want to go. Open Table makes it easy, and it is free to cancel if you change your mind. Same goes for your car rental. I used to be a big proponent of the Name Your Price feature on Priceline to save money on car rentals; nowadays we either book free car rentals through Chase using Ultimate Rewards points, or book direct through National car rental as the convenience of their Emerald Aisle program is second to none. Who wants to spend a precious hour of vacation time in a rental car line when you can just walk up, pick your car yourself from their lot, hop in, and go? (And also, why *does* it take so long in those car rental lines?)
Lastly, if you are staying at a resort, many of the poolside chairs and lounge areas are free for guests to use but must be reserved in advance – or you can show up at 11am the day of and take your chances, or cough up money for a private cabana. Ask the hotel in advance about reserving.
Neccessities
Stocking up on hiking/beach snacks or supplies for your rental is best done near the airport, there is a Costco next to the airport, and several large grocery stores in the area. Wailea has an island market that isn’t far from most of the resorts. For short trips, we often just bring our own snack items (nuts, etc) in our luggage to avoid the hassle of having to waste time shopping for supplies.
How to structure each day:
Organize your day around the ebbs and flows of island life. Not all vacations require sleeping in, so ditch that mindset. Sunrises and sunsets are the best times of day, so rather than forcing your jet-lagged body to sleep in, which it will not want to do anyway, embrace the time change to become a morning person – waking up by 5am or 6am to grab your coffee, enjoy the sunrise and the cooler temperatures of the morning for a run or a walk. The best hours to paddle board or snorkel are before 11 am, when the winds typically increase. Plan dinner around 6:30 or 7pm after enjoying sunset, so that you can be in bed by 9-10pm. I also realize I am sounding old here…but getting good sleep and optimizing daylight hours will make your vacation more enjoyable and leave you with less jet lag since you will have less of a time shift on returning home.
At the time of this writing, Maui is open for business, but travel to Maui requires a negative COVID-19 test from an approved testing partner within 72 hours of boarding (I recommend Vault Health if you can’t get an appointment locally) and completion of a health screening. Please check the State of Hawaii website for details on current requirements and advisories. Maui has limited health care resources, so please respect the current requirements and mask mandates. Mahalo!