How to Book a Hawaii Trip on Points & Miles

A Hawaii vacation can seem out of reach, but by using points and miles to cover the major expenses in getting to and staying in this far flung Polynesian destination, it becomes doable for even those just starting out with credit cards.

This summer my family and I vacationed in Kauai and Oahu, with a week in stays covered with points and most of our flights with credits/miles. As a bonus, I’ll be sharing some paid experiences that were worth it and other tips on making Hawaii an affordable trip.

Flights to Hawaii

There are many different approaches to getting cheap or free airfare to Hawaii. We’ve used a mix of strategies and the best option might depend on where you are departing from. Be sure to check airfare to the several airports on the Hawaiian islands, as they are only a short flight away from each other. Always check for cheap cash rates, as I’ve seen deals like $400 round trip from the East coast.

Transferring credit card points to partner airlines

Transfer Capital One Miles to Turkish Airlines to fly United economy for 10,000 miles + $5.60 in taxes. If the layover is too long then it will price higher. Business class availability is rare to find, but a steal at 15,000 miles.

Use seats.aero or seatspy to find all available dates or search for specific dates using the Turkish Airlines website. If you see availability through Aeroplan to book United, then it might be available to book through Turkish for less.

Fly Hawaiian Airlines or Alaska Airlines in economy from 25,000 miles or in business class from 45,000 miles, when available. Should see more availability as they enable mixed partner awards in the future. Sign up for a Hawaiian Airlines personal card for the 70k after one purchase offer to quickly and easily get a stash of Alaska/Hawaiian Miles.

Remember that right now you can transfer Amex points transfer to Hawaiian Airlines, which you can then transfer those Hawaiian miles to Alaska Airlines to book flights. It is expected that this indirect Amex to Alaska transfer will be discontinued in the future.

Check PointsYeah if you are looking at traveling on specific dates to see what multiple award programs have available in one search. Sometimes dynamic pricing can work in your favor. As you can see here are some sample searches with Delta flights from 17,000 points, and American Airlines from 22,500 points in economy or 50,000 in business.

Earn American Airlines points through the AAdvantage Shopping portal, or sign up for the Barclays Aviator Red card for 70k after one purchase, plus the $99 annual fee.

Use my master list of transfer partners to determine what your options are for booking based on what points program you’ve been accumulating in.

If you want more information on the award prices of different programs then grab my FREE ebook.

Redeeming in the Amex Business Platinum Portal

If you have an American Express Business Platinum, then you can essentially get a rebate on points. Pay with points in the travel portal for a business/first class flight or any class of service on your chosen airline and you’ll get 35% of those points back.

This works well when cash prices are low for your chosen airline or for a business/first class seat. We used this strategy when a Delta flight was $800 in business, so it came out to around 50,000 points for the one way flight from the East coast to Hawaii.

Using Airline Credits & Passes

Use canceled/delayed flight credits toward your flight. We had $150 per person in credit from a delayed United flight. This covered a significant portion of a one way ticket to Hawaii.

Some credit cards offer an annual airline fee credit, which in some cases might work for airfare. Check data points for the Chase Ritz card and for the Amex Platinum here.

Earn a Southwest companion pass through flying or credit cards to have a companion come with you for only the cost of the taxes and fees.

Accommodations in Hawaii

World of Hyatt

Hyatt points are best accumulated using a World of Hyatt credit card or a Chase card with transferrable points. Award stays get waived resort fees. Opening just one business or personal card could get you several nights at one of these resorts.

• Grand Hyatt Kauai Resort– From 25,000 points/night
  • On the beach in Kauai, expansive resort with pools, slide, restaurants. Everything you would expect from a Hawaiian vacation with leis on arrival and the cute towns of Poipu and Koloa a few minutes drive away.
  • We would definitely stay here again and it is very well suited for families. Go for the club access rooms for more points or use a club access award. This gets you free breakfast and snacks throughout the day.
• Hyatt Regency Waikiki Beach– From 20,000 points/night
  • A great deal for being directly on Waikiki beach and in the middle of all the action. The iconic towers are attached to an outdoor mall on the lower level.
  • I had my parents booked here, but unfortunately their stay coincided with the union hotel workers protests. The unavailability of clean rooms or staff at all the major hotels on Waikiki Beach led to our decision to relocate to the Hyatt Centric. The staff at the Centric really saved the day!
• Hyatt Centric Waikiki Beach– From 20,000 points/night
  • A few minutes walk from the beach and close to lots of shopping and dining. We really enjoyed our stay here in the spacious updated rooms and enjoyed amenities like the free use of beach chairs we were able to take on our drives around the island.
  • The pool is more like a sun shelf with a hot tub, but it is stylish place to relax. I think this is all you really need from a hotel in Honolulu, a great base to explore the rest of the island.
  • If you can’t find availability, try playing with the dates and length of stay, I found that you needed to stay a minimum of a certain number of nights for availability to show.
• Hyatt Place Waikiki Beach– From 15,000 points/night
  • A solid option that includes breakfast and a swimmable pool in Waikiki.
• Andaz Maui at Wailea Resort– From 35,000 points/night
  • A stunning modern resort in Maui.
• Hana Maui Resort– From 25,000 points/night
  • A boutique hotel with bungalows along the the road to Hana.

Hilton

Get Hilton Points through a co-branded card, transferring 1 to 2 from American Express, or buying points when on sale for half a cent each. Remember that all stays on points get the 5th night free and waived resort fees. There are 26 hotels and vacation clubs under the Hilton Honors program in Hawaii, here are the ones that offer the best value and reviews:

• Hilton Hawaiian Village Waikiki Beach Resort– From 70,000 points/night
  • Large resort on a lagoon/beach with resort style pools. Watch the Friday night fireworks from your room. Geared toward families.
  • My parents stayed here our last night in Hawaii, and remarked that the hotel could use significant updating. While the hotel is worn and the layout could be difficult to navigate, the view was breathtaking and the room was spacious. Breakfast options were not well rated, so they opted for the Starbucks on property.
• Hilton Garden Inn Waikiki Beach– From 50,000 points/night
  • Central Location near restaurants and shops in Waikiki, with a pool. Credit toward beach chair and boogie board rental.

Marriott

Points prices are dynamically priced in relation to cash price so book five nights to get a free night and more bang for your points. Resort fees are not waived on award stays. The best way to get Marriott points is through co-branded cards or by transferring from Amex 1 to 1. Marriott has 41 properties in Hawaii, here are the ones that offer the best experience:

• The Ritz-Carlton Oahu, Turtle Bay– From 94,000 points/night
  • Beautiful beachfront resort with pools in a popular snorkel spot.
  • We stayed here and booked through Amex Fine Hotels and Resorts to include breakfast and resort credit. The property was nice with an inviting lobby and pool area, but snorkeling was disappointing. Check in was slow and did not feel luxurious. For being a similar price point, we very much preferred our stay at the 1 Hotel Hanalei Bay in Kauai.
  • Read my full review of our stay before booking!
• The Laylow, Autograph Collection– From 62,000 points/night
  • Stylish hotel in Waikiki, by the international marketplace.
• The Royal Hawaiian, a Luxury Collection Resort, Waikiki- From 65,000 points/night
  • Historic Hotel right on Waikiki Beach and in the center of shops and restaurants.
• Sheraton Waikiki Beach Resort– From 64,000 points/night
  • Oceanfront Resort near Diamond Head
• Moana Surfrider, A Westin Resort & Spa, Waikiki Beach– From 62,000 points/night
  • Iconic hotel on Wakiki beach
• Courtyard King Kamehameha’s Kona Beach Hotel– From 42,000 points/night
  • Beachfront hotel in a casual setting in Kona
• Sheraton Kauai Coconut Beach Resort– From 57,000 points/night
  • Beachfront hotel with games and activities in Kauai.
• Sheraton Kauai Resort– From 74,000 points/night
  • Beachfront hotel near Poipu, Kauai
• Mauna Kea beach hotel, Autograph Collection– From 80,500 points/night
  • Secluded beachfront property being updated on the big island
• The Westin Hapuna Beach Resort– From 70,000 points/night
  • Beachfront property with impressive lobby and large pools on the big island.
• The Ritz-Carlton Maui, Kapalua– From 80,000 points/night
  • Older luxury property in Maui with great service and beach access
• Sheraton Maui Resort & Spa– From 53,000 points/night
  • Beachfront property with lazy river pool at the Black Rocks, Maui
• The Westin Maui Resort & Spa, Ka’anapali– From 67,000 points/night
  • Luxury beachfront resort
• AC Hotel by Marriott Maui Wailea– From 50,000 points/night
  • Walkable to shops and beaches with infinity pool
• Wailea Beach Resort, Marriott, Maui– From 64,000 points
  • Large resort with pools and slides on the beach
• Residence Inn Maui Wailea– From 52,000 points/night
  • Complimentary breakfast and local shuttle

Wyndham/Vacasa

Wyndham has a relationship with Vacasa that allows you to book vacation home rentals using Wyndham points. The cost is based on the average price per bedroom, per night of your stay, inclusive of fees. The cost is either 15,000 (up to $250) or 30,000 ($250.01 to $500) points per bedroom per night.

Amex Fine Hotels & Resorts

• Take advantage of special offers when booking through Amex Fine Resorts and Hotels (FHR). We used this to book our stays on the north shores of Kauai and Oahu to get free breakfast, room upgrades, and resort credit.
• 1 Hotel Hanalei Bay
  • A highlight of our trip and worth the splurge, as I go into in this review. A gorgeous property where you can snorkel right off the beach, paddleboard through a river, surf, and explore towns nearby. Breakfast was included and we had $300 in resort credit by booking through FHR, which resulted in some great food and drinks by the pool.

How to Make Your Time in Hawaii Affordable

Activities & Tours

Skip the hotel luau and go to a more authentic family run establishment like Toa Luau. It takes place in Waimea Valley, and you’ll have access to the grounds before the luau. Definitely make time to walk the trail to the waterfall.

During the luau there are interactive demonstrations on various Polynesian skills, and then there is the dinner show that features dances from all of Oceania. It was fun to give the skills a try, like working with the coconut, fire baton, and palm weaving. The entire experience balanced entertainment and education very well.

If you are going to Kauai, then you absolutely must experience the Napali coast. There are several ways to do that, from hiking, to boating, to helicopter tour. While I didn’t get to do the hike, I highly recommend this raft adventure tour and the no doors helicopter tour.

They both offered a completely different perspective, and we ended up having perfect weather for both tours. Be sure to pick Captain J’s boat tour specifically, because the competitor’s raft does not have seats, nor do you want to be seasick on a catamaran.

These tours may be on the pricier side, but they are completely worth it. Stack your discounts by checking your credit cards for offers on Viator and make sure you have an account with Viator to earn rewards to use toward your next bookings.

There are also plenty of things to do in Hawaii that are free or low cost. All the beaches in Hawaii are public, so you can take your pick of even resort beaches. Hiking may require an entrance fee, but do check if the park requires advance reservations. Here are some other free or low cost activities to consider:

• Ho’omaluhia Botanical Garden- Free, lush gardens and photo opportunities
• Dole Plantation- Free to enter gift shop, where you can buy a dole whip. You’ll see the pineapple fields while driving up.
• Koloa Rum Tasting Room- $5 per person for online reservation
• Kauai Coffee Company- Free tasting and self guided tour

Car Rental

Use a tool that searches multiple companies and rate types like Kayak or AutoSlash. We found the best rate with a Costco discount through Autoslash/Priceline. If you are booking last minute or want a specific car then try Turo, through which you rent an individual’s car from them.

The more ahead of time you can book your car the better. I booked ours a few months ahead of time and the rates only continued to go up as we got closer to the trip.

Food

Food can be very expensive in Hawaii, so try to eat like the locals do instead. Food trucks are very popular and offer an affordable lunch option, sometimes right by the beach! There are also lots of fruit and juice stands where you can get a freshly blended smoothie bowl.

Hit up supermarkets and casual cafes for sandwiches and snacks.

• Kuuleis Gourmet is in the town that inspired Lilo & Stitch, close to the boat departures for the Napali coast. Everything we ate here was delicious and homemade!
• Bocconcino in Waikiki or Kalapawai Market by Kailua beach for Italian subs.
• Konos (multiple locations) for pulled pork. Whisky Smoke 808 on Oahu for barbecue.

Go to locally owned establishments where you can put together your plate from a variety of prepared options.

• We loved the quick tuna poke bowls we got at The Fish Express in Lihue, Kauai while waiting for our tour timeslot at the Koloa Rum Tasting Room.

Take advantage of happy hours to have an early dinner at great restaurants. We took advantage of these two great deals while in Hawaii:

• Keoki’s Paradise on Kauai has a two course menu for $32, available daily from 4 to 5 pm.
• Herringbone Waikiki has a great selection of appetizers, cocktails, beer and wine at a significant discount from 4 to 6 pm, and 9 pm to close, daily.

Dinner reservations are highly recommended at most restaurants, especially when you are in smaller towns with limited options. Some restaurants that we really enjoyed and were luckily able to get into would be Waikiki Shokudo and La Spezia (Kauai).

When to book your Hawaii vacation

Don’t wait to book your trip to Hawaii! When I booked everything in 2024, points prices for everything were less. Booking United through Turkish was only 7,500 points one way. All the Hyatt hotels we stayed at were in a lower points category (they may change as they are reevaluated every March), so it was generally 5,000 points less per night than what it is currently priced at. Activities providers also tend to reevaluate their prices every season, and hint: they don’t go down. So don’t delay, use those points for better value today!