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Hawaii is only a five-hour plane ride from the West Coast, and with so many flight and hotel options, the destination is an all-you-can-book buffet of points and miles. For those of you interested in planning your own trip to Hawaii, TPG Contributor William Morse shares how he booked a luxury trip to Maui and the Big Island almost entirely on points and miles.
I’m based in Los Angeles, and up until recently had never been to the points-and-miles haven of Hawaii. To right that wrong, I pulled the trigger on a six-day, five-night trip to the Hawaiian Islands over the Fourth of July holiday. My first challenge was deciding on which island(s) I wanted to visit; seeking the perfect mix of relaxation, nature and adventure, I chose to spend part of my time on Maui, and the rest on the Big Island. My second challenge was to actually book the trip on points and miles.
Since Hawaii as a whole is a massively popular international tourist destination, you can find plenty of available flights in and out of Maui’s Kahului (OGG) and even more into Honolulu (HNL), but I wanted to fly nonstop and leave from the Big Island (Kona-KOA or Hilo-ITA). I was flying in on July 1 and out on July 6 or 7, so award space was at a premium — and especially limited due to the holiday.
I’ve racked up a lot of points on my United MileagePlus Explorer Card and on my CitiBusiness AAdvantage Platinum Select World Master Card, so I naturally started my search on United and American. Neither airline was offering the dates I needed nor nonstop flights at the MileagePlus Saver or Economy MileSAAver rates, so I was looking at paying 67,500 miles with United round-trip or 62,500 miles with American. However, when I searched for one-way awards, I was able to find a one-way ticket from LAX to Maui (OGG) for 22,500 miles and a one-way MileSAAver award ticket from Kona (KOA) direct to LAX on American for 17,500 miles. Plus, by using miles I earned with my AAdvantage Platinum Select, I knew I’d receive 10% of my miles back at the end of the year (up to 10,000 miles). All told, I was headed to Hawaii for only 38,250 miles on nonstop flights that would have totaled ~$650.
The big domestic carriers offer plenty of options to get there, but if you’re looking for who can get you there for the least amount of miles, look no further than British Airways. It takes only 25,000 British Airways Avios for a round-trip from the West Coast using British Airways’ partners American/US Airways and Alaska. (British Airways bases award rates on distance, so you’re out of luck, East Coasters.) If you’re short on Avios, be aware that British Airways is also a transfer partner of Chase Ultimate Rewards (you can currently earn 40,000 bonus Ultimate Rewards points with the Chase Sapphire Preferred). Singapore Airlines (also a transfer partner of Chase Sapphire Preferred) is another good option, charging 35,000/60,000/80,000 miles from the mainland.
After an easy five-hour flight, my travel companion and I landed in Maui and went to pick up our rental car. A car is a MUST unless you plan on never leaving your resort. Cars are expensive to rent in Hawaii — and I wanted something fun — but I was surprised that I actually found the cheapest rates looking through Chase’s travel portal, where redeeming directly earned me 1.25x my points’ value. I used ~17,000 points I earned with my Chase Ink Plus to rent a convertible from Enterprise for three days and was upgraded to a Jeep. This was a solid deal, considering Jeep rentals for the same weekend were hovering between $130-$150/day — and by renting through Chase, I was still able to earn Enterprise Plus points.
Staying on Maui
A few months back I signed up for the Chase Hyatt Visa which gives you two free nights at any of its properties, along with Platinum status and plenty of other benefits. Unfortunately, the Andaz Maui (a Category 6 property with rates starting at $466 or 25,000 points per night) was booked for the dates I needed, but the Hyatt Regency Maui (see below), which starts at $259 or 20,000 Gold Passport points per night, had space. I considered using my two free nights here, but instead transferred Chase Ultimate Rewards 1:1 to Hyatt Gold Passport points and booked two nights using 40,000 points. After receiving an upgrade to a suite per my Platinum status and factoring in the $30-plus-tax per-night resort fee, this redemption proved a savings of approximately $900.
The Hyatt Regency Maui has a large open-air lobby and lanai filled with trees, parrots and even some penguins. Yep, penguins roaming around in tiny Hawaiian shirts. (I’m kidding, they were naked.) The lobby sits atop the rock-lined pool, tricked out with waterfalls and even a grotto with a swim-up bar. Though the rooms here were nice, and the 100,000+ square-foot resort had much more to offer, from yoga and sushi-making classes to snorkel and scuba lessons, tennis and golf. I tried some poke (a delicious Hawaiian dish made with cubes of raw, sashimi-grade fish) and the fish tacos at ‘Umalu, one of the resort’s five restaurants, and was more than impressed.
Other great options for points-redeemable hotels on Maui include the Grand Wailea, a Waldorf Astoria Resort, a Hilton Category 10 property that starts at $439 per night in August or between 70,000-95,000 HHonors points per night; and the Sheraton Maui Resort and Spa, a Category 5 property that boasts some of the best snorkeling in Maui and rates that start at $289 or 12,000 points per night.
If you’re a Visa Signature cardholder, be sure to check out the Visa Signature Hotels & Resorts on Maui (including the Grand Wailea and Andaz Maui), and if you hold the Platinum Card from American Express or The Enhanced Business Platinum Card from American Express OPEN, know that you’ll also receive money-saving perks at several Maui properties (including the Four Seasons Maui) by booking through Amex FHR portal.
How to Spend 48 Perfect Hours on Maui
Here’s how my lovely companion and I spent some of the most amazing 48 hours of our lives — and I suggest you do some of the same. Wake up early and drive to see the banyan tree in the middle of Lahaina; one tree covering two-thirds of an acre and an entire city block, its limbs twist and spiral every which way, sprawling to take up new roots every hundred feet or so. When you’re done planning the world’s ultimate treehouse, walk up the street and catch some breakfast at Longhi’s. After breakfast, it’s time to get the blood pumping; walk a quarter-mile south to Maui Kayaks and hire a guide for a two-and-a-half-hour kayak and snorkel tour on the open ocean (~$70/per person).
From there we jumped into the Jeep, took off the top and jetted toward Mount Haleakala, a 10,000-foot-tall dormant volcano that rises well above the clouds. Starting from sea level, the Jeep drank a quarter tank to reach the summit and the topography changed every thousand feet.
Serving up farm-to-table meals since 1988, Hali’imaile General Store, which has received the Wine Spectator Award of Excellence two years running, was the culinary delight of our trip. I don’t want to over-hype this place, but I’m pretty sure the Horseradish Crusted Opakapaka in apple-brandy beurre blanc could simultaneously end wars and cure male pattern baldness in one bite. Lucky for me, it was the first Friday of the month, so I used my Chase Sapphire Preferred to earn 3x points on the bill.
Up next was the famous, 64-mile-long Road to Hana, which winds its way along the coast, then up through forest reserves high on cliffs that crash into the Pacific. Keep in mind this trip is about the journey, not the destination — 64 miles might not seem like a long trip, but you’ll rarely hit 30 miles per hour and there are so many places to stop (like Twin Falls and Wai’anapanapa State Park) that you should plan (at least) an entire day around this adventure.
With apologies to Tboz, Left Eye and Chili, you should go chasing waterfalls, and the backside of Haleakala National Park — and more specifically the Seven Sacred Pools (or Pools of Ohe’o) — is the perfect place to do so. Twenty minutes beyond the town of Hana itself, this lush mountain valley rainforest has a four-mile hike that leads you up to the 400-foot-tall Waimoku Falls.
This hike is hot and humid, so you’re going to need to cool off when you’re done. Continue half a mile past the ranger station and down the path to the Seven Sacred Pools to take a leap of faith. Be smart, though; paper beats rock and rock beats scissors, but rock also breaks bones. If you don’t want to risk injury, rest assured that there are plenty of places to wade in for a dip.
You could stay overnight in Hana at the luxurious Travaasa Hana (starting at at $350 per night), which shakes off the traditional resort vibe and spreads out over several acres dotted with cottages overlooking the ocean. We opted to save a bundle by renting a simple oceanfront duplex called Tutu’s (Grandma’s) House through VRBO for ~$170 per night; this cozy one-bedroom offered a lanai with the best stargazing views I’ve ever come across.
Still feeling the exhilaration of jumping 30 feet, we packed up and made the same beautiful drive back along the Hana Highway to Kahului (OGG) airport, ready to take on the Big Island. There are plenty of flight options to get from Kahului to Kona (KOA) on the Big Island, but I chose Mokulele Airlines because I could book directly through the Chase travel portal. Rather than spend $140 out of pocket, I used 11,200 Ultimate Rewards points for two one-way tickets on the 40-minute sunset flight. Hawaiian Airlines also offers five nonstop flights daily, starting around $100 each way.
Staying in Kona
You’ll find properties are much cheaper on the Big Island than on Maui. This limits the return you’ll get on redeeming your points, but there are still some solid options.
I used the two free weekend nights I earned with my Citi Hilton HHonors Reserve Card to book a room at the Hilton Waikoloa Village, a Category 6 property that starts at $189 or 50,000 points per night. Spread out amongst three main towers and set on the sunny Kohala coast, the resort was massive — so big that it has its own tram and a network of boats that take you from section to section. I have Hilton Gold status (which comes with the Citi Hilton Reserve), so we received $40 in food and beverage credits; our resort fee was waived; and we were given free spa access and upgraded to a room with a partial ocean view. Overall, my two free weekend nights yielded around $600 in value — a decent, if not quite amazing, way to maximize your Hilton Free Nights.
Ultimately, the Waikoloa was a nice property for the wrong guests. If you’re looking for a place to bring the whole family in a Las-Vegas-meets-Disney-World setting, this is your place — but if you’re looking for an intimate escape or cultural immersion (as we were), then keep searching. Set over 62 acres with two championship golf courses, a (wonderful) 25,000 square-foot spa, multiple pools and even its own lagoon with water sports and a dolphin experience, the resort has plenty to do. To me, though, it just felt over-manufactured and out of place on such a beautiful island, and even with all of its space, the entire experience felt incredibly crowded.
Other points-redeemable hotels in the area include the Marriott Waikoloa, a Category 7 hotel that starts at $189 or 35,000 points per night, and the SPG Category 4 Sheraton Kona Resort, from $199 or 10,000 points per night.
If you’re a Visa Signature cardholder, be sure to check out the luxurious 540-room Fairmont Orchid, which has its own white sand lagoon, on the Visa Signature Hotels & Resorts portal. If you hold the Amex Platinum or its business version, you’ll receive some sweet perks here, as well as at the Big Island’s Four Seasons by booking through the Amex FHR portal.
Touring the Big Island
Excited to see what the Big Island had to offer, we drove to the other side of the island to the city of Hilo, where we again took to the skies — only this time on a 55-minute helicopter flight over Kilauea, one of the Big Island’s active volcanoes. For about $189 per person, Dave, our pilot at Safari Helicopters, took us around the island, hovering us over bubbling lava and showing us a spectacular chain of waterfalls. I used my Barclay Arrival Plus World Elite MasterCard to book — meaning I can redeem points to cover the cost and get 10% of my redemption back (that is, until November).
With our feet once again safely on the ground, we stopped at Pineapples in Hilo to grab some fresh island grub and a jalapeño margarita before making our way to Hawai’i Volcanoes National Park, a UNESCO World Heritage Site. With 323,431 acres to explore, it’s impossible to see the entire park in one day, but if that’s all the time you have, take a four-mile hike through the massive Kilauea Iki crater, still remaining from a 1959 eruption. Then check out the Thurston Lava Tube, a 500-year-old lava-formed cave that’s so wide, you could drive a car through it. Be sure to stick around the park into the evening, when the glow from the lava really brightens up.
When leaving the park, I’d suggest that you take the long way back, heading southwest along Highway 11. Stop at Punalu’u Black Sand Beach, where green sea turtles regularly take naps along the shore. The contrast of blues, blacks and greens coupled with some easily accessible turtles make this a photographer’s paradise.
When you start to get hungry again, pull over to the one of the many produce stands along the way to pick up some fresh fruit and banana bread; they’re everywhere. If the red and black sands didn’t do it for you, head south down South Point Road to Papakolea, the green sand beach at South Point; the southernmost point in the US.
We had one last stop in front of us: the Waipio Valley. Starting from one of the best vantage points a parking lot has ever offered, follow the path the down along Waipio Valley Road — often called the steepest road in the US — into the valley, which is cut in the middle by a small river going to sea and surrounded by 2,000-foot-tall bluffs. Out of the forest and onto the black sand, we sat down on a piece of driftwood, uncorked some wine and took it all in.
As we drove toward Kona airport to catch our red-eye, we were treated to one last Hawaii sunset. At KOA open-air terminal, long lines for security and overbooked flights served as a harsh reminder of mainland life — and I realized that I didn’t really want to leave. But as I boarded the 757 and wedged myself into coach, I was comforted by the knowledge that Hawaii’s many valuable ways to redeem points and miles will ensure it’s a destination I’ll be visiting again. Soon.
For more on Hawaii, be sure to see:
Planning a Hawaiian Vacation with Hilton HHonors Points Even after the introduction of the Chase Sapphire Reserve, the Chase Sapphire Preferred is still a fantastic choice if you want to avoid the Reserve’s $450 annual fee, earn 2x on all travel & dining and earn a 50,000 point sign up bonus.
AAdvantage Plans to Restrict Awards on Hawaiian Airlines
Our Dream Vacation to Hawaii: A TPG Reader Success Story
Credit Card Combinations for a Hawaiian Vacation
Best Transfer Partners for Flights to Hawaii
Maximizing HawaiianMiles Airline Partner Awards
How Do I Get to Hawaii Using Chase Ultimate Rewards Points?
Destination of the Week: The Big Island
Destination of the Week: Maui
Even after the introduction of the Chase Sapphire Reserve, the Chase Sapphire Preferred is still a fantastic choice if you want to avoid the Reserve’s $450 annual fee, earn 2x on all travel & dining and earn a 50,000 point sign up bonus.