How to Book Your Low-Risk Hawaiian Vacation

June CasagrandeAugust 19, 2020
How to Book Your Low-Risk Hawaiian Vacation Right Now

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The best time to visit Hawaii is … no one knows. The coronavirus pandemic didn’t come with an expiration date, so it’s impossible to foresee when travel will be safe again. But the time to book a trip to Hawaii is far easier to answer: It’s right now.

Airlines and hotels are offering some of the easiest terms ever seen for cancellations and changes. Some airlines will give you up to two years to change your plans with no penalties. Hawaii hotels that required you to cancel several days prior to arrival have switched to easy 24-hour cancellation terms if you don’t choose a nonrefundable rate, and in some cases even if you do. Car rental companies continue to offer the same friendly cancellation terms they always have.

These easy outs mean you can start deal hunting right now and book your entire trip with little to no risk you’ll lose money if, as your trip date arrives, you decide you don’t feel safe.

Excursions like snorkel tours, Pearl Harbor visits, whale-watching trips, zip lining and luaus are another matter, of course. Operators of these attractions could take much longer to get back up and running. But that’s the beauty of Hawaii. The breathtaking beaches and stunning emerald-green mountains are free and wide open. It’s business as usual for the sea turtles, spinner dolphins, coral reef-dwelling fish and sunbathing monk seals. So you can have a trip of a lifetime without a single organized tour.

Note: Hawaii has a 14-day quarantine requirement in effect for all arrivals until Oct. 1 (and then required COVID-19 testing and evidence of negative result to avoid quarantine after Oct. 1).

Flights to Hawaii on points

If you’re a member of any of the major airlines’ frequent flyer programs, run some test searches for award flights to see whether you need to earn more miles. Remember that you can book one airline outbound and a different one on the return flight. So if you have only half the American miles you need for a round-trip flight, you can get a credit card that earns United, Delta, Alaska, Hawaiian or Southwest points and, with the card’s welcome bonus, quickly accumulate enough miles for the return trip.

If you’re in the Western U.S., New York City or Boston, consider signing up for the Hawaiian Airlines® World Elite Mastercard®. It has a lower spending threshold than many other cards to reach the welcome bonus: Limited Time Offer: Earn 60,000 bonus miles after spending $2,000 on purchases in the first 90 days.

That’s more than enough miles to get you and a companion a one-way flight. A nonstop one-way trip to the islands from Los Angeles, San Francisco, Phoenix, Las Vegas or other Western departure points starts at 17,500 HawaiianMiles. The two East Coast airports Hawaiian serves, New York-John F. Kennedy and Boston Logan, have nonstops starting at 26,250 miles. American, United, Alaska and Southwest are also offering credit card welcome bonuses with enough or nearly enough points to get you and a companion to or from Hawaii.

Flexible options

With the airlines’ easy COVID-era cancellation policies, you can pick a date for your trip, book and, assuming you read the fine print, change your mind if you decide you’re not comfortable traveling.

For example, Hawaiian Airlines is waiving the fees it usually charges to redeposit your HawaiianMiles if you cancel a flight you booked through Aug. 31. Normally, they charge $150 to redeposit miles when you cancel a flight from the mainland U.S. to Hawaii. As the pandemic continues, we expect to see similar friendly cancellation terms extended into the future.

Buying your ticket with cash? Hawaiian’s coronavirus-era policies help you, too. Hawaiian tickets bought before Aug. 31 can be traded in for a travel credit extending a full two years from the original purchase date.

You’ll find equally eager-to-please terms with all the major airlines that fly to Hawaii. American has been waiving change fees for cash tickets and award tickets, as have United, Delta and Alaska.

Southwest Airlines, which never charges change fees, now flies to all four major Hawaiian islands. Southwest’s four credit card options from Chase let you earn Rapid Rewards points good toward a Hawaii flight.

Hotels and vacation rentals

If you’re a member of Marriott’s Bonvoy loyalty program, you’ll find dozens of great properties at every price point. Looking for luxury? Check out the Mauna Kea Beach Hotel on the Big Island of Hawaii, a Category 7 Bonvoy property where rooms range from 45,000 to 70,000 points per night.

For a taste of historic Hawaii in the heart of Waikiki, bask in the laid-back Victorian elegance of the “First Lady of Waikiki,” Moana Surfrider, A Westin Resort & Spa, opened in 1901. Or stay just steps from Waikiki’s famous shopping and nightlife at the famous “Pink Palace” — The Royal Hawaiian, A Luxury Collection Resort, which “Mad Men” fans will remember from Don and Megan Draper’s drool-worthy Hawaiian vacation. Both are Category 7 properties in the Bonvoy portfolio, with rooms starting at 45,000 points per night.

If you have a Bonvoy credit card that offers an annual free night certificate, there are several properties in Hawaii where you can redeem it. On Oahu, the no-frills Sheraton Princess Kaiulani is right across the street from the Moana Surfrider. On the Big Island, the Sheraton Kona Resort & Spa at Keauhou Bay and the Courtyard King Kamehameha's Kona Beach Hotel are both well-positioned to serve as a base for exploring the island. And on lovely Kauai, the Sheraton Kauai Coconut Beach Resort is a well-priced option right on a beach. These are all Category 5 Bonvoy properties, making them the only places in Hawaii where you can redeem a 35,000-point free night certificate.

Hilton Honors members have 19 hotels to choose from spread across the four major Hawaiian islands. These include the sprawling and spectacular playground that is the Hilton Hawaiian Village, located on the widest stretch of beach in Waikiki; the Grand Wailea, A Waldorf Astoria resort on Maui; and the modest Hilton Garden Inn Kauai Wailua Bay on the "Garden Isle" of Kauai.

World of Hyatt loyalists will find seven Hawaii properties in the program, including the stunning Grand Hyatt Kauai Resort & Spa. IHG Rewards members have just two places to earn or redeem points. The Holiday Inn Express Waikiki makes up for its small rooms with free breakfast and a pleasant location removed from the hustle and bustle. On the Big Island, the Holiday Inn Express & Suites Kailua-Kona is a little short on charm but is conveniently located for exploring the island and also offers the brand’s famous free breakfast.

The vast majority of hotels in Hawaii come with resort fees that can break the bank if you don’t budget for them. For example, at Hilton Hawaiian Village the nightly resort fee is $50 and does not include parking, which is an additional $49 per day if you park your own car and $59 if you valet. So read up on your hotel’s policies before you book, and plan accordingly.

Hawaii is also home to lots of vacation rentals at both ends of the price and luxury spectrum. Browse the offerings on HomeAway or VRBO, but be sure to look at the total price, not just the nightly, to see how much you’ll be paying in cleaning fees and management fees.

Rental cars

Most major car-rental companies have locations in Hawaii — many of them offering both airport and in-town locations — where you can pick up your car in the morning, go exploring, then return it at the end of the day to avoid those outrageous parking charges.

Nerd tip: Be warned — what you save in money doing this, you lose in time spent waiting in line at the car rental counter. If you plan on doing lots of exploring every day in Hawaii, it’s better to just take the hit on the parking. To find good deals, start at Discount Hawaii Car Rental, which can often get you a deal on major brands including Thrifty, Dollar, Avis and Enterprise.

Picking your island

Banish these two words from your mind: “island hop.”

Yes, getting from one Hawaiian island to another takes just a very short flight. But checking out of one hotel, driving to the airport, going through security, standing in line at a rental car agency, then getting to your new hotel and finding out you can’t check in for several hours can take a big bite out of your vacation. For trips of eight days or less, pick one island and rest assured it will be all you need.

So, how to choose?

Look at the four major destinations as these are the only islands with flights directly from the mainland:

  • Big Island of Hawaii: Ideal for on-the-go adventure seekers. It offers the largest diversity of experiences and climates, from stunning beaches to a sometimes-snowcapped Mauna Kea mountain to the surreal moonscape that is Volcanoes National Park.

  • Maui: Great for families who enjoy long, scenic car rides like the Road to Hana.

  • Kauai: The “Garden Isle.” May be the most beautiful, with lots of genuine aloha spirit.

  • Oahu: It gets a bad rap for being too touristy and developed. Perish that thought by skipping through an aerial video like this one showing off Oahu’s many charms.

The bottom line

By making it easy to change your plans, Hawaii travel providers are offering peace of mind for bookings you make today. Start exploring options online, read the fine print, follow local developments about when they will open for tourism, then reserve your easy-out Hawaiian vacation as soon as you’re ready.

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