Taking a family trip to Maui over Christmas week sounds expensive, and on paper it is. Hotels in Wailea run $700 to $1,200 a night during the holidays. Business class flights from Salt Lake City aren’t cheap either. But when you’ve been stacking points and miles all year, a trip like this becomes a completely different conversation. This is how we pulled off six nights in Maui, flying business class, staying at two Hyatt properties, and landing back home on December 28 with most of the big-ticket items covered entirely by rewards.

Getting There: Hawaiian Airlines Business Class on Alaska Points

We flew out of Salt Lake City on December 22 with a connection through Honolulu before landing at Kahului (OGG). The routing was Hawaiian Airlines, booked with Alaska Mileage Plan miles. If you haven’t explored this redemption yet, it’s a strong one. Hawaiian is a partner with Alaska, and business class seats to Hawaii can be excellent value depending on when you search. Business class on a Hawaiian flight to Hawaii isn’t the lie-flat product you’d find on a long-haul international route, but the extra space, priority boarding, and better meals made a real difference on a holiday travel day when the airports were absolutely slammed.

One thing to plan around: we couldn’t get a rental car at OGG. Over Christmas week in Maui, airport rental inventory gets wiped out fast. We booked a VIP private transfer instead, an Escalade pickup through a local service, and it got us to the Hyatt Regency without any hassle. We arrived relaxed, nobody was fighting over luggage, and we didn’t have to navigate unfamiliar roads after a long travel day. After checking in, I shopped around and found an SUV at a reasonable price through an Avis location connected to the hotel. So while there was nothing available at the airport, options did exist nearby, and I’m glad I looked instead of defaulting to several thousand dollars in rideshare costs for the week. The lesson: book your rental car months in advance or budget for a private transfer. Don’t count on grabbing one curbside when you land.

The return flight was on Delta, departing OGG the evening of December 27 and arriving Salt Lake City the morning of the 28th. A late departure on your last day is worth arranging if you can. It gives you most of the day to enjoy the island instead of spending it in an airport.

Nights 1–2: Hyatt Regency Maui at 25,000 Points Per Night

We checked into the Hyatt Regency Maui on December 22 and stayed through Christmas Eve. The rate was 25,000 World of Hyatt points per night. When cash rates at this property are running several hundred dollars a night over the holidays, that’s a redemption worth making.

The hotel was completely full. As a World of Hyatt Globalist, I normally expect a suite upgrade, but I went in with realistic expectations and didn’t get one. That’s the reality of peak holiday travel at one of the most popular resorts in Hawaii. The property itself is genuinely beautiful, and it’s easy to see why families flock here. The grounds are well-maintained, the pool is excellent, and the views are hard to complain about.

One Globalist benefit worth knowing before you arrive: the 4 p.m. late checkout does not apply at the Hyatt Regency Maui. The property is classified as a resort and spa, which carves it out of that perk. They offered access to the Ohana Lounge after we vacated the room, but it’s essentially a comfortable waiting area with no food or drinks. Not a hardship, but not a real substitute for late checkout either. If that benefit matters to your travel day, know going in that you won’t have it here.

Club lounge access was a genuine win. The lounge ran out of food a couple of times during our stay, which is probably inevitable at a property this busy over the holidays, but the hotel proactively handed over a $100 food credit to make up for it. That kind of service recovery without having to ask for it goes a long way.

The oceanfront walking path in front of the hotel is worth making time for. It connects several Kaanapali resort properties along the shoreline and adds a real sense of place to the stay. I walked it multiple times.

Christmas Eve: Whale Watching and the Giving Machine

December 23 started with a whale watching tour out of Maalaea aboard the Quicksilver at 10:30 AM. Humpback whale season in Maui runs roughly November through April, and December puts you squarely in it. The Quicksilver is a large catamaran with knowledgeable guides, and if you haven’t done a whale watch in Maui, it’s a genuinely memorable way to spend a morning. All activities on this trip were paid in cash. We reserved points and miles for hotels and flights, so experiences like this were where our real-dollar budget went.

On Christmas Eve itself, we stopped at the Light the World Giving Machine at Whalers Village in Kaanapali. It runs noon to 1 PM and lets you select a charitable donation on someone else’s behalf. A small thing, but it fit the day well with the kids along. Dinner that evening was at Tommy Bahama Restaurant and Bar in Wailea. Solid food, relaxed setting, and one of the easier holiday reservations to secure on the island.

Nights 3–5: Andaz Maui

We transferred to the Andaz Maui on Christmas Eve and stayed through December 27. The Andaz is a noticeably different property. It’s quieter, more design-forward, and the atmosphere skews toward couples and honeymooners. We made it work with the family, and the Wailea location put us close to some of the better restaurants on the island.

The Ka’ana Kitchen breakfast buffet here is genuinely one of the best hotel breakfast spreads I’ve had in the US. The catch during peak season is the wait, which stretched to 45 minutes on some mornings. Get there early.

The Globalist late checkout issue came up again. The hotel was fully booked and asked us to be out by noon. As a Globalist, that’s a frustrating ask, especially on a day with a late evening flight. The 4 p.m. checkout is one of the most useful benefits in the program, and a sold-out holiday week is exactly when you’d want it. They offered the Ohana Lounge as an alternative, same as the Regency, a place to wait with no real amenities attached.

None of this is a reason to avoid the Andaz. The property is excellent and I’d go back, ideally on a non-holiday week with one of the suites. But if late checkout matters to your travel day, understand that during peak periods at these Maui resorts, it may not be available regardless of your status.

Christmas Day and the Rest of the Activity Lineup

Christmas Day was a 7-line zipline tour on the North Shore, starting at noon. The terrain is lush, the views are excellent, and doing it on Christmas morning is exactly the kind of memory that makes a Hawaii trip stick. Worth planning around if your group is up for it.

December 26 was dinner at Matteo’s Osteria in Wailea, a polished Italian restaurant that requires some advance planning during the holidays but delivers. Our last full day, December 27, started with a sea scooter snorkeling tour at Wailea Beach at 8:00 AM. Sea scooters let you cover significantly more ground than standard snorkeling and lower the barrier for people who aren’t strong swimmers. Wailea Beach has calm, clear water and good visibility, and it made for a great final morning.

On the Regency versus Andaz question, which comes up a lot: the Regency is the better choice for families with young kids. It’s lively, there’s a lot going on, and it’s built for that energy. The Andaz is more intimate and couple-focused. I’d happily return to either, but for a holiday family trip, the Regency is probably the right call.

The Points and Miles Breakdown

Here is how the redemptions broke down:

• Flights: Hawaiian Airlines business class SLC-OGG via HNL, booked with Alaska Mileage Plan miles

• Hyatt Regency Maui (2 nights): 25,000 World of Hyatt points per night, 50,000 points total

• Andaz Maui (3 nights): World of Hyatt points redemption

• All activities and dining: paid in cash

• Airport transfer: VIP private Escalade, paid in cash

The strategy was simple: use rewards for the two biggest line items, flights and hotels, and spend cash on the experience. Activities, restaurants, and ground transportation are real costs, but none of them individually are what makes a Maui trip feel out of reach.

The Bottom Line

Maui at Christmas is a significant cash outlay if you’re paying for everything. It’s a different trip entirely when you’re not. We flew business class, stayed at two excellent Hyatt properties, watched humpback whales, zipped above the North Shore on Christmas morning, and ate well every night. The trip wasn’t free. We spent real money on activities and meals, and the rental car situation added cost that better advance planning could have avoided. But the flights and hotels, the parts of the budget that would have been most painful in cash, came out of rewards accounts we’d been building all year.

A few things to take away if you want to do something similar: lock in your rental car when you book your flights, not a week before you leave. Know which Globalist benefits apply and which don’t at resort-classified properties. And consider splitting your stay between Kaanapali and Wailea. The two areas feel different, and two nights plus three nights gave us a good read on both.

The broader point is straightforward. Points and miles programs exist so you can travel better than your cash budget alone would allow. A Christmas week trip to Maui in business class with two Hyatt hotel stays is exactly the redemption that makes the effort of building these accounts worthwhile. If you’ve been sitting on Alaska miles or World of Hyatt points and wondering whether the payoff is real, now you have your answer.

Maui at Christmas: How We Did It Almost Entirely on Points