A Professional’s Guide for How to Plan a Trip to Maui

In theory, planning a trip to Maui is easy. You simply go to an online travel website such as Expedia or Travelocity and pick the Maui vacation package that looks good and meets your budget needs.

In reality, this step alone would only give you a regular, ho-hum vacation at best. And at worst, it could be a complete disaster.

You are investing quite a bit of money in your trip to Maui, why would you settle for just ho-hum?

As professional a Travel Advisor, I have planned thousands of vacations. I’ve learned what works, what doesn’t, and what is a total waste of time. Through my years of experience, I’ve discovered seven essential steps that can help anyone create amazing vacations. Today I’m sharing them with you.

So are you ready? Let’s dive in.

Create A Vision of What You Want Your Vacation to Be

When working with a client we typically start with a “discovery” session. This is where I meet with them to learn more about what they want for their vacation. This helps me to understand their vision for what they’d like to experience, see, do, and feel on their trip. This process is vital to creating a great vacation.

This step is also key to helping me stay on target as I begin researching activities, lodging, and flights. If I know they are wanting to lay on the beach all day, I do not need to spend hours researching hiking trails and adventure tours.

Though you are planning this trip yourself, it is incredibly helpful to do this exercise before you begin your research. Take time to visualize what you are doing, seeing, and feeling on your trip (and if you are going with someone, be sure to get their vision as well). A few things to consider:

  • How active are you? Are your days filled with activities and plans?
  • Or is your vacation more about relaxation and laying on the beach all day?
  • Are you wanting to cook meals or eat out for every meal?
  • Do you want access to a ton of amenities and activities or would you prefer to be in a more quiet, secluded area?
  • Do you want to experience culture?
  • Do you want to hit the popular sights or the lesser-known, local sights?
  • What do you want your food experiences to be?
  • How do you want your days to go (leisurely mornings or early starts)?

Know upfront what you want to experience so that when you are planning you can stay on target and not get overwhelmed by the options.

Decide on Your Vacation Budget

As a general rule, a trip to Maui in the low season (late April through early June and mid-August to mid-December) can range between $1500 – $3500+ per person (including air, lodging, food, and some activities). In the high season (late June through mid-August and mid-December through late April) the same vacation can range between $2500-$4500+ per person.

Though this is a wide range of pricing and can fluctuate depending on your research strategy, it is a good rule of thumb when planning your vacation to Maui.

Let’s break it down by category so you can plan more accurately.

What Does a Flight to Maui Cost?

According to Google Flights, flights to Maui from the mainland can range from $300-$600 (depending on low or high season respectively) from the west coast and $600-$1000 from the east coast. From Canada, prices increase approximately $100 more than the pricing listed for the mainland USA.

For more accurate pricing information, see the Flight Research section below.

How Much Does it Cost to Stay in Maui?

Maui offers a wide range of lodging options for tourists. From camping and hostels to resorts and vacation rentals, they have something for every budget.

On average, you can expect the following pricing:

Type of Lodging Nightly Low Season Nightly High Season

  • Camping in a tent $ 15.00 $ 18.00
  • Camping Cabins $ 90.00 $ 90.00
  • Hostels Dorm Style $ 41.00 $ 75.00
  • Hostels Private Room $ 120.00 $ 150.00
  • 3-Star Hotels $ 200.00 $ 375.00
  • Luxury Hotels $ 865.00 $ 2,000.00

How Much Should I Budget for Food in Hawaii?

Though pricing will vary based on whether you are eating out every meal or cooking or preparing meals at your lodging, these are some average prices:

  • Breakfast Restaurant $10 – $20 per person
  • Lunch Restaurant $15 – $25 per person
  • Dinner Inexpensive $20 – $55 per person
  • Dinner Moderate $30 – $75 per person
  • Dinner Fine Dining $40 – $125 per person

When considering the cost of groceries, here are some averages to help you gauge these costs against what you currently spend at home:

The average cost of:

  • A gallon of milk $4.69
  • Dozen Eggs $4.49
  • Bottle of Water $2.34
  • Loaf of Bread $4.76

How Much Should I Budget for Activities on Maui?

Activities on Maui can vary in price as much as restaurants can. However, in general, pricing can range from free for things activities such as hiking, beach access, and walking tours to $800+ for private helicopter tours or fighter jet experiences.

Some moderate activities include:

How Much Does Transportation Cost on Maui?

As with all things on Maui, transportation can vary based on what you need. Here are a few average prices for a variety of transportation options:

  • Public bus system $4.00 per day pass
  • Airport Shuttle $11-$30 per person or $289 per group luxury
  • Moped Rental $85 per day
  • Car Rentals (2021) $140 – $280 per day (mid-size vs. premium)*

*Cars rental prices have skyrocketed in 2021 due to the surge in tourism post-pandemic and inflation. But may return to normal as we “return to normal.”

Decide When To Take Your Vacation on Maui

You may already have dates planned for your vacation. If that is the case, don’t worry, anytime you can get to Maui you will have a great time. Go ahead and skip to the next step.

However, if you would like to choose your ideal time to maximize your savings and avoid some of the crowds, please read on.

As I’ve already alluded to, there are low and high seasons on Maui. In general, the low season is from late April to late June and from late August to mid-December (exclusive of the Thanksgiving holiday). The high season on Maui is late-June to late August and mid-December to late April (with some lower time frames sprinkled into late January).

As a general rule, the best time to travel to Maui is in the low season with the best month being October. Pricing in the low season is generally lower and crowds are typically far lighter.

If you are seeking the cheapest month to travel to Maui, a great tool to use is Google Flights. To learn our tips and tricks for getting the best prices, see our YouTube video here.

Begin the Research Phase of Planning (But DO NOT Book Anything…Yet)

Now that you have your vision, budget, and timing established, now it is time to research the where and what of your vacation. Research begins after these other items because knowing these things will help you save time. How? By allowing you to cut through the thousands of options to the specific items that are ideal for your needs.

The research phase of vacation planning consists of looking into three main areas, flights, lodging, and activities. This does not need to be a long, drawn-out process. You already know what you want, all you need to do is find the options that best meet those desires.

SIDE NOTE: If there is still a possibility of the pandemic affecting your vacation, be sure to research the current restrictions and requirements before planning your trip. Should there be another outbreak, the restriction could be so prohibitive that you decide to vacation elsewhere.

How to Find the Best Prices on a Flight to Maui

The best website for pricing flights is Google Flights. They take all of the pricing information from every flight booking engine and present it to you in one easy list. This allows you to compare pricing and choose the option that works best for you.

There are some tips and tricks for finding even better prices. See our video on how to save more money on flights by CLICKING HERE.

How to Find Places to Stay in Maui

When it comes to lodging in Maui, you have quite a few options to choose from. As we mentioned in the budgeting section, you have your choice of everything from camping to luxury resorts. The video below covers all of the options and includes recommendations for each.

How to Find Things to Do in Maui

One of our favorite places to research things to do in Maui is YouTube. There are several videos that cover the top tourist attractions on the island. They include vlog style video, so you can see the areas they are speaking about. They also include pricing information and tips for going.

However, most of the videos talk about the same places over and over. So we created our own video that covers 16 places no one else is talking about. Between our video and one or two from other channels, you will get a really great idea of all the things you can do and see on Maui.

Create a Rough Draft of Your Itinerary and Make Adjustments

Once you’ve completed your research, you are ready to create a rough draft of your itinerary. This is where you plug all the different things you want to see and do into a calendar to make sure the flow, timing, and logistics will work for your vacation vision.

A few notes about this vacation rough draft:

  • Consider the time change. If you are coming from the mainland you will be a minimum of three hours earlier than you are used to. This typically results in you being awake SUPER early your first morning. Why not take advantage of that by scheduling your sunrise bike tour of Haleakala that morning? Sunrise tours can meet as early as 3:30a-4p in the morning, so every advantage you can give yourself to help get up that early will be worth it.
  • What was your vision for how busy each day of your vacation is? Were you running from activity to activity or did you have some relaxation in your day? Did you have leisurely mornings or were you up with the sun and out the door? Take your vision into consideration when planning your itinerary. If you want relaxation, do not schedule something first thing in the morning every day.
  • In general, your Maui itinerary should be limited to 1 to 2 activities per day. This will allow you to have more flexibility and relaxation time on your vacation. If you plan multiple activities every day, you risk being so exhausted by all the action that you don’t have an opportunity to soak it all in and enjoy the experience.
  • Check to make sure the activities, restaurants, beaches, parks, etc are open and available on the days you are planning to visit. Check for any unexpected closures due to construction, holidays, hours of operation, etc to make sure you can go as planned. You also want to check on availability. For instance, if you need to purchase tickets or make reservations, make sure they have openings for the times you are seeking.
  • When planning your itinerary, consider the transportation and the flow of your day. How will you get to the places you want to go? Did you give yourself enough time between activities to get back and forth, change, etc? If you need to take public transportation or rent a car, is there availability, and/or is the timing right?
  • Lastly, are there any adjustments that need to be made? Are all of your activities and restaurants on one side of the island and you are planning to stay on the other side? Should you maybe move closer? If not, is it worth renting a car instead? Do you need to move anything around to facilitate your plans? Do you need different flight times to get to the island in time for an activity or reservation or allow for one last activity before you leave?

Make Reservations and Book Your Vacation

At this time you should know fairly well exactly what you want for your vacation. Only now should you make reservations and bookings. Prior to this, things are still flexible so you can fine-tune your vacation itinerary. If you jumped in and made flight bookings and hotel reservations, you might be stuck with locations and times you don’t ultimately want.

Now that you are ready to book, go to the places you found the best pricing and reserve, book, purchase tickets, and schedule appointments everywhere possible. Solidify as many plans as you can to ensure you can go and experience everything you have planned.

Travel is back in a big way so things are booking up fairly quickly. Do not make the mistake of thinking you can simply show up somewhere and they will have availability. Unless they expressly say it is walk-in only, reserve or buy tickets for everything ahead of time.

Plan the Final Logistics of Your Vacation

You now have your itinerary planned and everything booked – that’s great! But you are not done yet. Now is the time to consider all the little details that will make your vacation even better than expected.

To get an idea of what I mean, take a look at this video:

Now is the time to think through every day of your trip and discover ways to make it better and/or protect against anything going wrong.

Here are some ideas to help you along:

  • Can you ship your luggage to your destination so it’s one less thing to worry about at the airport?
  • How early should you arrive at the airport? Though travel is back COVID is still causing nightmares at the airports. Plan plenty of time for TSA lines and arrival processes.
  • Can you get access to airport first-class lounges to make your experience more comfortable and luxurious? Check out PriorityPass, your airline members program, or LoungeBuddy (app on iOS and Android) for options.
  • Did you plan for transportation to/from the airport when leaving and on arrival? Do you need an airport shuttle? Would you like a Lei greeting on arrival?
  • What amenities/accessories would be nice to have in your hotel on arrival?
  • How early do you need to check in and is it possible? If you are on a red-eye flight, call ahead to ensure you will be able to check in as soon as you arrive (and get in a quick nap before you begin exploring the island).
  • What will you need for all of your dining and activities? Special gear? Warm clothes (if you are going to Haleakala early morning or late evening, it will be cold)? Nice clothes for dining?
  • Have you bought travel insurance yet? HIGHLY recommended for all vacations. Our favorite companies are TravelGuard and Allianz.
  • Do you have a plan for your luggage storage on your last day (if your flight is after check-out time)?
  • Have you called your hotel concierge or host yet? Calling ahead to get tips and ideas for your vacation can make all the difference. Ask about what to do, see, how you can make your vacation more spectacular, safety concerns, money questions, and more.
  • Ask a travel advisor. You can have a travel advisory make one last look over your plans to make sure you’ve remembered everything and give advice for things you may have forgotten. I recommend you do this before booking anything in case they can find better prices/options for you.

So there you have it! A basic overview of the seven steps professionals take when planning a trip to Maui. If you follow the guidelines, you will avoid the ho-hum and have an incredible vacation!

Need assistance planning? Whether you just want to ask a few questions, have us design just a piece of your trip, or do the whole thing we can help. You can take a peek at our services HERE.

Happy travels!

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