Here’s How We Book our Hawaii Travel (and beyond)

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Booking a trip to Hawaii is expensive and it can be time-consuming. But we’ve had a lot of practice that we’re here to share with you to help make your booking process easier. 

After booking numerous trips for family while we were living in Hawaii and now booking our own trips to go back to Hawaii multiple times per year, we’ve picked up some strategies. From getting the best rates to making sure we have the best experience, here are our best strategies and tips to help you book like a pro.

We have some quick links to help make your trip planning easier:
1. Avoid choice overload with our Where to Stay database.
2. Pick the best credit card for Hawaii travel to start racking up points for your next trip
3. Book your rental car with peace of mind here.
4. Grab an itinerary and check out our Activities database to make the most of your vacation!

Booking a Trip to Hawaii: The FAQs

Before I jump into the strategies that we diligently use, let’s get some basic questions out of the way. These are the top questions that float into our inbox weekly. 

How much does a trip to Hawaii cost?

It depends on when you go, what island you visit, and whether you plan to stay in a luxury resort or stick with a value vacation rental. 

To give you an idea of how much a trip to Hawaii costs, we estimate a trip to Oahu for a family of four for a week will cost $13,493 for everything. We track this cost annually, which you can see in that article. And you’ll see how we came up with that cost so you can adjust the numbers to whatever your trip will look like. It is not a cheap trip, but there are strategies that can help make it less expensive, which we cover below. 

Should you use a travel agent to book your trip to Hawaii?

Weekly, we get an email from someone who is using a travel agent to book their Hawaii trip. We’ve used travel agents in the past, so I am not trying to throw shade here, but I wouldn’t advise using one for Hawaii travel for two reasons:

1. The accommodations that I usually see them put people in are sub-par. Not terrible, but not great, considering the nightly rate. That’s why we created our Where to Stay section. 
2. They usually don’t know a whole lot about Hawaii. Every month or so we’ll get an email from a travel agent asking for advice on planning a trip for their client. Usually these travel agents cover a number of different locations, including Hawaii, so it’s understandable that they haven’t been able to go deep on all the different options with a trip to Hawaii. We’ve gone deep and we give you the information on this site, for free! 

Go with a travel agent for your trip if you really can’t be bothered to get into the details of trip planning. But if you’re here reading this article, I’d guess you are the type of person who likes getting into the details and planning your best trip. 

Should you book a vacation package to Hawaii?

You can, but we don’t. Aside from the fact that I just don’t like booking everything at once, I like to have more flexibility to change reservations, dates, or other options (and to take advantage of strategy #6 below). Booking a package makes that difficult. 

Aside from my love of keeping plans flexible, I don’t think they actually save much (or any) money. I just priced out a 10 day trip to Maui over Thanksgiving 2023 with a 1 bedroom unit at Honua Kai, direct airfare, and a rental car. Here’s the price discrepancy I found: 

• Expedia: $14,384
• Costco: $14,099
• Booking directly myself: $12,448 (flight: $5,830, accommodations: $6,132, car: $526)

So booking the trip myself, rather than using Expedia or Costco for a package deal, will save me over $1,500. That’s a lot of mai tai’s.

And booking multi-island travel gets tricky when you book a vacation package. Our island hopping guide can help.

Bottom line: we book our travel separately and don’t book vacation packages. 

Booking a Trip to Hawaii: the timeline

People often ask us, when is the best time to start booking a trip to Hawaii. Our answer is always: book early. What does that look like? In an ideal world, it would be:

• Book airfare, accommodation, and rental car: 6 – 12 months in advance
• Book restaurants: 1-2 months in advance (note: book Mama’s 6 months in advance)
• Book a luau: 2-3 months in advance (a luau is not a required activity, see our thoughts)
• Book other activities: 1 month in advance

Are you reading this in May and you want to plan a trip in June? Cool. Just read our Hawaii Trip Planning article and follow the strategies below. 

While in an ideal world it’s best to book ahead, life happens! We’ve booked a trip 2 weeks before leaving and it worked out great. We’ve also tried to book a trip two months in advance and couldn’t find a hotel we liked so we had to reschedule. 

If you’re planning a trip to Hawaii, you’re going to want to buy our itineraries. Whether you’re planning a year in advance and you have the time to nail down every little detail, or you’re leaving for Hawaii tomorrow with nothing planned, these itineraries will help you. Just download and off you go on your epic adventure. 

“We returned home from our family vacation to Kauai on Monday and wanted you to know how helpful your Wayfinder Itinerary was. We used it throughout the trip and it never failed us. Thank you for providing such a thorough and thoughtful guide. We are certain to return (hopefully to other islands) and will, once again, rely upon your insights and advice.”

Mary B.

Our Strategies for Booking a Trip to Hawaii

Ready to jump into planning? These are our strategies to help you get the most for your money. 

Strategy #1: Earn & Use Credit Card Points

Jordan and I love to travel. A lot. We’ve each been to over 60 countries and we spent nearly a decade living abroad. 

Do I wish we could bankroll this level of travel without caring about the costs? Absolutely. 

Would that lead to financial ruin? Probably. (I like nice things).

Instead of emptying our bank account, we lean heavily on points and miles to help us defray the cost of our travel. And while we are members of every mileage and loyalty membership program and get points for our stay, miles that we earn by using our credit cards is what actually moves the needle to help us book our free or reduced cost trips. 

If you want to know exactly what credit cards we have and use, you can skip down to that section. 

Because we have been able to find such good airfare deals to/from Hawaii over the past couple of years, our credit card points have mostly been used on accommodations in Hawaii with Marriott or Hyatt properties. 

We’ve been learning a lot from Travel Freely when it comes to this. Their articles that have been most helpful include:

• Our ultimate guide to hotels in Hawaii using points
• The best credit cards for a trip to Hawaii
• Travel Freely members saved $9,500 on a trip to Hawaii

We know a lot of people love using miles & companion passes on Southwest to Hawaii to get their airfare for free. 

Strategy #2: Find a good deal on airfare

These last couple years, the airlines have had bargain basement fares to and from Hawaii. So finding a good deal on airfare can be incredibly easy, especially if you’re traveling from the west coast! We do have an article on finding cheap airline fares, but we haven’t had to use the tactics in it lately. 

Because airfare has been so reasonably priced lately, we haven’t used our credit card miles to book Hawaii airfare. If you want to know what we’ve been doing with all of our points, there is a general travel section at the bottom of this article. 

We do have our favorite airlines to fly to/from Hawaii and the rest of the continental US. Our go-to airlines (ranked in the order we check them) include:

• Alaska Airlines: whenever possible, we fly Alaska. Wherever they fly, we will almost always look at them first. Their planes aren’t the newest or shiniest, but their service is just so over the top excellent. We actually flew Alaska for the first time when we moved to Maui (they were the only airline that would allow our dog to fly in-cabin) and we have been hooked ever since. 
• United Airlines: truthfully, I don’t love United, but they have excellent Hawaii flight schedules and so many direct flights to all of the islands. If we can’t fly Alaska, we next check United to see if they have the flight schedule we’re looking for. 
• Hawaiian Airlines: we tend to book Hawaiian for most of our inter-island travel. Our son loves getting his mid-flight POG juice and it’s nice to support the local airline. We don’t love their online booking system: it can be difficult to cancel or make changes online and getting a customer service representative on the phone can be a challenge. But there is something about flying Hawaiian airlines to Hawaii that makes things a little more festive!
• Southwest: If we can’t find the inter-island flights that we want on Hawaiian, we go with Southwest. They offer competitive fares and our bags fly free! We haven’t used them to/from the mainland yet, but they offer extremely low fares at times. 

Strategy #3: Book rental cars early

I sound like a broken record, but ever since the great rental car crisis of 2021, we have been constantly telling people to book their rental car early. This is especially important if you’re heading to Hawaii during peak travel times, like Christmas/New Years, summer, or spring break. 

We almost always use Discount Hawaii Car Rental for our bookings. They offer excellent deals with national carriers and there is no prepayment, so we can change our reservation if we need to or if prices drop (we’ll cover this in strategy #6). Check out our full list of rental car company suggestions.

Strategy #4: Pick two places to stay

Our standard advice is to search for accommodations first before booking a flight. That’s because the nightly cost for a hotel or vacation rental in Hawaii is through the roof. Some islands are more expensive than others — Maui has the highest average daily rate while Oahu has the lowest. So your hotel budget might affect what island you choose to go to. 

People often ask if we prefer hotels or vacation rentals. And honestly, I think there is a time and a place for both! We stay in both, and usually on the same trip. 

We usually spend 70% of our trip in a pretty nice, but not too expensive vacation rental. While we’re staying at a vacation rental, we usually do more activities and spend time out exploring. 

We then stay in a resort for the other 30% of our trip and really soak in the amenities! As a (often tired) mom, I really appreciate the amenities of a hotel: the room cleaning, the restaurants on-site, and the pool where our kids will happily play for hours. 

We have a Where to Stay section that will help you search for places to stay by island. This is especially helpful if you’re overwhelmed with the sheer number of vacation rental options. We’ve picked some great ones to share. 

Strategy #5: Book activities ahead of time

Part of our job is to find great activities with great companies. But the great activities often book up early. Gone are the days of showing up to the dock and hopping on a tour (for the most part). If there is a tour you want to do, book it early. 

We usually book our tours a month in advance of our trip, so we can get the time and day we prefer. Don’t feel like you need to go overboard on too many tours and activities, but if one or two really look interesting, book them! While we appreciate DIY travel, the tours we’ve done have really added to our vacation experience. 

You can check out our favorite Tours & Activities and search by island here. Some of the most popular on each island include:

• Manta Ray snorkeling on the Big Island
• This morning Molokini snorkeling tour on Maui
• A snorkeling tour on Oahu’s west coast
• A Napali Coast snorkeling tour on Kauai

We also will usually book one nice sunset dinner in advance. Even with two young kids, we prioritize having one really special meal together. And we bring these with us to pull out if we need to. 

Strategy #6: Re-check prices before our trip

This is such an annoying thing to do but we have saved so much money re-checking prices before our trip. We re-check airfare, rental car prices, and hotel rates one or two weeks before our trip to see if any prices on things we can cancel have changed. 

We usually find the biggest savings in our hotel rates! We’ve seen hotel rates fluctuate so much that we’ve been able to cancel our reservation and re-book it and save hundreds. It doesn’t always happen, but it has happened to us often enough that it’s been worth our time to check it before every trip. 

Strategy #7: Keep everything organized

We love to travel and we almost always have 3 or 4 trips booked at any given time. But I am not organized and not detail oriented. So I rely on technology to keep these trips organized. Here’s what we use:

• Google sheets: we have a day by day itinerary in a shared google sheet so Jordan and I can both see what the plan for the day is. Our travel is very much go-go-go, so we need this level of detail to make sure we’re seeing everything we need for this site!
• TripIt: I use this free app to keep track of the big reservations like our flights, hotel, and car rental. That way if I need a confirmation number, I can pull it up in a snap. I like that you can see your trip in a timeline, which helps me to see if I’ve forgotten anything. 
• Travel Freely App: since credit cards have become a huge part of how we pay for our travel, this free app helps keep us organized. We input our credit card details, like when we opened the card, bonus details, and due date. 

What’s in Our Wallet: earning and using credit card points

Like most people, we don’t have an endless travel budget. So we have taken a deep dive into how to earn and use credit card points to help stretch our travel budget further. I’m going to detail out our current strategies and some resources we’ve learned from. But before I do, I want to clarify that we responsibly use credit cards by paying them off in full each month and by not spending more than we are able to. 

Due to the nature of our job, a majority of our spending is on travel, so it was important to us to find cards that had travel perks and gave us extra points for spending on travel. 

Here are the cards we use and the cards we currently use or are planning to get in the next few months (note that these are cards for two people, and a business which is why there are so many).

• Chase Sapphire Preferred
• Chase Sapphire Reserve
• Chase Ink Business Unlimited
• Chase Ink Business Preferred
• United MileagePlus Explorer Card (we are canceling this card in 2023)
• Capital One VentureX
• American Express Business Platinum Card (we’ll be adding this card in 2023)

We picked these cards strategically. All of them had great sign up bonuses that we could meet with our normal spending. Many of them offer exceptional membership rewards.

Jordan and I don’t share credit cards or add each other to our cards as authorized users. Instead we use two-player mode to get sign up bonuses and our miles add up fast. 

Some of these cards have annual fees, but the sign up bonus and number of points we earn each year on spending make the card worth it for us. 

We are always in the process of planning multiple trips, so having a bank of points and miles we can use is incredibly valuable. We focus on earning points on travel rewards credit cards that let us transfer our points to travel partners, rather than specific travel cards like a Marriott 

Using credit card points and miles

There is an art to finding the best deals with credit card points and miles. We are not experts, but we like to learn from the experts. 

Our favorite free resources are: Travel Freely and the All the Hacks podcast. Both are excellent. 

Here’s a recent example of how we’ve used our points and miles to pay for travel: 

We have a big trip to Europe planned and we used my Chase points to book our tickets to Europe (business class!!) and we used Jordan’s Chase points to book our trip home (not business class). We’re using our Capital One points to erase a portion of the cost of our vacation rental. And we are using Marriott points for a one night stay in London. 

What would have been an impossibly expensive trip is now well within our reach. And while we used a lot of points to book the trip, we have continued to earn more points through sign up bonuses and spending, so we have plenty more in the bank for a big family trip in 2024.