Ready for Adventure: A Family Journey in Oahu and Maui

Ready for Adventure is a weekly series designed to help readers like you discover the best methods for planning post-pandemic getaways using points and miles. If you need advice on arranging your own trip with miles, please email us with your travel plans and current mileage balance.

Hawaii is an in-demand travel spot right now, as Americans can visit without significant entry restrictions. The COVID testing requirements for travelers from the mainland have been eased recently thanks to increased vaccination rates and lower case numbers. With this in mind, reader LaKeisha Batts contacted us for the best ways to arrange a trip to Hawaii for her family:

"Hello! I’m looking to reschedule our post-COVID vacation to: Hawaii (Maui & Oahu). My departure airports are: HOU or IAH and there will be 4 of us in total (2 adults, 2 kids). I would prefer to fly First Class, but I’m fine with economy as well! Thank you for your assistance!"

LaKeisha has a collection of Chase Ultimate Rewards, Marriott Bonvoy, and Southwest Rapid Rewards points to utilize for this journey. Let’s examine their balances and how they can maximize their points for a trip from Houston to Hawaii this summer.

Current Points Overview

LaKeisha has amassed a substantial collection of points across three programs, more than sufficient for a family of four to travel to Hawaii. Additionally, her points allow for stays at several nights in four- and five-star accommodations on both islands. Here’s a breakdown of their current point balances:

• 347,770 Chase Ultimate Rewards
• 280,059 Marriott Bonvoy points
• 148,812 Southwest Rapid Rewards

Airfare to (and within) Hawaii

This itinerary consists of two parts: flights from Houston to Hawaii and inter-island flights within Hawaii. Here’s how LaKeisha can utilize her points and miles to book every segment of her Hawaiian trip using her Chase and Southwest points.

Routes: HOU-PHX-HNL, HNL-OGG, OGG-LAS-HOU

LaKeisha didn’t provide specific travel dates, so we assumed she is flexible with flying any time before summer ends. Unfortunately, securing business class award seats to Hawaii for four during the summer can be quite tricky. However, I explored all available options and discovered that Southwest offers the most competitive award pricing for economy flights to Hawaii this summer. The good news is that booking with Southwest points allows LaKeisha to preserve her Chase and Marriott points for accommodations in Hawaii.

LaKeisha can book flights from Houston-Hobby (HOU) to Honolulu (HNL) for as low as 14,962 Southwest Rapid Rewards points per person, one way, depending on the chosen date. Most flights connect through Los Angeles (LAX), Las Vegas (LAS), or Phoenix (PHX).

Additionally, return flights from Maui (OGG) to Houston begin at the same rate, with the most affordable option connecting through Phoenix (PHX).

I also suggest utilizing Southwest points for booking flights from Honolulu (HNL) to Maui (OGG). Nonstop Southwest award flights can be found for as little as 2,240 points per person this August.

If LaKeisha opts for the least expensive flights, she would spend only 32,164 Southwest points per person for this Hawaiian getaway. This totals 128,656 Southwest points for the entire family, assuming they do not hold a Companion Pass.

How to Redeem Points for This Award

Booking Southwest award flights is straightforward, but there’s one limitation. When planning multi-city trips with Southwest, you can only include up to two cities in your itinerary. Therefore, LaKeisha will need to reserve her HOU-HNL, HNL-OGG, and OGG-HOU tickets as individual one-way flights.

This process is simple. Just visit the Southwest website and input your desired itinerary into the search box in the center of the page. Don’t forget to choose the "points" option at the top right corner of the search box to use your Southwest points. You can also click the Low Fare Calendar button to view a month’s worth of award pricing at once.

You’ll find all available award flights and their corresponding prices in the center of the screen. Browse through the options and click on the price for the flight you wish to book. Each flight displays three fare options: Business Select, Anytime, and Wanna Get Away. I recommend choosing Wanna Get Away fares for the best value, as the other two options offer limited advantages for most travelers.

Next, follow the on-screen instructions to finalize your award ticket bookings. Complete this process for all three segments of the trip, and you’ll have your airfare sorted!

How to Accumulate Enough Miles for This Award

LaKeisha has more than sufficient Southwest points to secure these flights. If you’re interested in doing the same, there are multiple ways to earn Southwest Rapid Rewards points, including transferring points from Chase Ultimate Rewards. The quickest method to accumulate them is by applying for a Southwest co-branded credit card and taking advantage of the welcome bonus.

Here’s a glance at current offers:

• Southwest Rapid Rewards Priority Credit Card – Earn 50,000 bonus points after spending $1,000 on purchases within the first three months of account opening.
• Southwest Rapid Rewards Premier Credit Card – Earn 50,000 bonus points after spending $1,000 on purchases within the first three months of account opening.
• Southwest Rapid Rewards Plus Credit Card – Earn 50,000 bonus points after spending $1,000 on purchases within the first three months of account opening.
• Southwest Rapid Rewards Premier Business Credit Card – Earn 60,000 points after spending $3,000 on purchases in the first three months of account opening.
• Southwest Rapid Rewards Performance Business Credit Card – Earn 80,000 bonus points after spending $5,000 on purchases within the first three months of account opening.

Hotels in Hawaii

Hawaii offers a wealth of fantastic hotels that can be booked with points. Most major hotel chains have locations in both Oahu and Maui, and with LaKeisha’s Chase and Marriott points, she enjoys considerable flexibility. Let’s briefly explore some of the top options available to her.

How to Reserve Hotels Using Points

I suggest the family utilizes their stash of over 280,000 Marriott points to secure a five-night stay at one of the island's Category 7 hotels. These accommodations require 60,000 points per night (or 70,000 during peak times), but the family will benefit from Marriott's fifth-night free promotion.

Here are some of the top choices:

• Moana Surfrider, A Westin Resort & Spa, Waikiki Beach — 60,000 points per night
• Sheraton Waikiki — 60,000 points per night
• The Laylow, Autograph Collection (Category 6) — 50,000 points per night
• The Royal Hawaiian, a Luxury Collection Resort, Waikiki — 60,000 points per night
• Waikiki Beach Marriott Resort & Spa (Category 6) — 50,000 points per night

Chase points can be instantly transferred to World of Hyatt at a 1:1 ratio, allowing the family to use them for hotel stays in Maui. Hyatt offers numerous excellent redemption options on the island, some of which can provide the family with over $500 in value per night.

Here’s a glimpse at some of the top Hyatt options in Maui, along with their nightly award rates:

• Andaz Maui at Wailea Resort — 30,000 points per night
• Hana - Maui Resort — 30,000 points per night
• Hyatt Regency Maui Resort and Spa — 25,000 points per night
• Kaanapali Alii — 30,000 points per night
• Wailea Ekahi Village, A Destination by Hyatt Residence — 20,000 points per night
• Wailea Grand Champions Villas, A Destination by Hyatt Residence — 20,000 points per night

If the family chooses to book the highest-priced option — the Andaz Maui — at 30,000 points per night, the total for a five-night stay would be only 150,000 points. In comparison, the same stay this summer could reach up to $5,700, translating to an impressive 3.8 cents per point in value for their Chase points.

How to Reserve a Marriott Hotel Using Points

To book Marriott hotels, visit the Marriott website. Input your itinerary in the center of the page and check the "Use Points" box in the lower right corner of the search box to view award rates.

Browse through the available hotels and select one you'd like to reserve. Then, click on "View Rates."

Next, choose the room you wish to book and follow the on-screen instructions to finalize your reservation.

When booking a five-night stay, the fifth-night free benefit will automatically be applied during checkout.

How to Reserve a Hyatt Hotel Using Points

To book a Hyatt hotel, visit the hotel group's website and input your itinerary in the center of the page. Be sure to check the "Use Points" box to view award rates.

Locate the hotel you wish to book and click on "View Rates" to see the available award rooms. For hotels in high demand, you may need to adjust your travel dates, as award availability can vanish quickly.

Choose the room you want to book and follow the on-screen instructions to finalize your reservation.

How to Accumulate Hotel Points

Fortunately, the family has ample points to cover their hotel accommodations in Hawaii. If you want to earn Marriott points quickly, consider using a cobranded credit card from American Express or Chase. Here’s a summary of the available cards and their current welcome bonuses:

• Marriott Bonvoy Boundless Credit Card: Earn 75,000 Marriott Bonvoy bonus points after spending $3,000 on eligible purchases within the first six months; plus, earn 50,000 bonus points after staying six eligible paid nights at Marriott hotels through Jan. 31, 2024. Offer ends August 10.
• Marriott Bonvoy Brilliant® American Express® Card: Earn 150,000 Marriott Bonvoy bonus points after spending $6,000 on eligible purchases within the first six months; plus, earn 50,000 points after staying six eligible nights at Marriott hotels through Jan. 31, 2024. Offer ends August 9.
• Marriott Bonvoy Business® American Express® Card: Earn 75,000 bonus points after spending $3,000 on purchases within the first three months of card membership.
• Marriott Bonvoy Bold Credit Card: Earn 50,000 Marriott Bonvoy bonus points after spending $1,000 on eligible purchases within the first six months; plus, earn 50,000 bonus points after staying six eligible paid nights at Marriott hotels through Jan. 31, 2024. Offer ends August 10.

For earning points at Hyatt hotels, consider the following cards:

• World of Hyatt Credit Card: Earn 30,000 bonus points after spending $3,000 on purchases within the first three months of account opening. Additionally, earn up to 30,000 more bonus points by earning 2 bonus points for every $1 spent on purchases that typically earn 1 Bonus Point, on up to $15,000 in the first six months.
• Chase Sapphire Preferred Card: Earn 60,000 bonus points after spending $4,000 on purchases within the first three months of account opening.

Conclusion

LaKeisha has more than enough points for an unforgettable family trip to Hawaii. Although securing business class tickets for a family of four can be challenging, the value of points for luxurious hotel stays compensates for the economy flights. If your family is dreaming of a summer escape to paradise, consider mirroring their travel plans.

If you have a specific destination in mind and need assistance with your points strategy, reach out via email to potentially be featured in the next edition of Cleared for Takeoff.

Feature photo by Pierre Leclerc / Shutterstock.com