Maui: How To Plan A Dream Vacation

What is a dream vacation? We believe certain criteria must be present for a trip to be considered a dream vacation. Although we love to travel and see new places, there are some destinations that are on our bucket list. Places that, above all others, we have longed to visit. We typically plan on spending a bit more money when we go there since they are so desirable. While we never want to waste money, we want to make sure we are doing all the things we most want to do on any particular dream vacation. The reason for this is that a dream vacation may be a possible once in a lifetime trip so we make sure to do it right. Continue reading to find out all about our trip to Maui.

A peaceful beach scene on Maui at sunrise.
We were treated to beautiful sunrises right outside our hotel in Maui.

Location: Maui, Hawaii

When we started thinking about our next trip, we initially were thinking of going international. We love to explore new countries and we still have so many we want to see. However, we started to plan this trip in the Spring of 2021 and COVID was still an issue although travel restrictions were starting to ease up. We had only done a little bit of traveling over the last few years and mostly it was to see family. We, like most of the world, were ready to get out and explore!

Narrowing Our Search

With everything going on in the world at that time, we were a bit hesitant to travel out of the country. As I stated above, restrictions were easing up but things were still touch and go. We didn’t want to travel internationally and have issues returning to the country or having an extended quarantine period. Due to this aspect, we decided to stay in the US.

Cassandra and I always had a goal to visit Hawaii by the time I turned 45 and Alaska by her 45th birthday. We believe most Americans consider these states as highly sought after vacations. Even though I had some time before missing out on this goal it was fast approaching. We decided why wait on a trip we both wanted to do and agreed to plan for Hawaii. The only issue now was which island(s) to see?

Why Maui

Once we decided on Hawaii, we still had a lot to figure out. While there are well over 100 islands that make up Hawaii, most people travel to only 6 major ones. We had to choose between Hawaii (the Big Island), Oahu, Maui, Kauai, Molokai, and Lanai and each island is unique in its own way. We initially narrowed it down to the first three listed, which for most, are typically the islands that people plan to visit.

After doing a bit of research and asking friends that have traveled to Hawaii, we cut the Big Island from our list. For the time we planned on being there, the Big Island just seemed too busy for us and it wasn’t what we were looking for on this vacation. With Oahu and Maui left, we seriously considered splitting our time between the two islands. Typically, we try to see as much as we can while vacationing so this seemed a great option. After some careful consideration, we opted to thoroughly enjoy one location. This was after all a dream vacation and we wanted to do it right.

Deciding to pick only one island, we continued to do our research. When we travel, we really don’t look for places to shop and we aren’t big on going out at night. We love to hike, go to the beach (when applicable), and just enjoy the beauty of nature. With all these in mind, we found Maui to be the perfect fit for us.

We had a fantastic view of the island of Molokai from our room.
We had an excellent view of the island of Molokai from our hotel room.

Booking The Trip:

Once we decided on Maui, it was time to book the trip. As with many vacations, we had the option of booking everything piece by piece or looking into a vacation package. Packages are a great option because most of the work is already done for you. You have the option of adding or deleting some aspects to suit your needs and it really takes the hassle out of planning the vacation. However, that convenience comes at a price. Most times I have found that putting the effort in to look for the best deals on each of the major aspects (flights, hotels, rentals) you often find a significant discount on the price.

Shopping Around

After researching for this trip I found a great vacation package offered through Costco. At the time, we were members of Costco but I didn’t even realize they did vacation packages. The package did include all the major aspects we needed for this particular vacation. Also, the price for the package was very reasonable (for us anyway.) It helped that at the time I was researching this, Hawaii was just starting to open up to visitors from the mainland post COVID. Sometimes the right timing goes a long way to making your dream vacations a reality!

Even though the price was right on this package, I thought I could do better. At the time I worked for Sheraton Hotels and received an employee rate on rooms. Also, since I rented cars often for long road trips, I had a membership through Budget Rent-A-Car and received discounts as well. I also checked several websites for cheap flights to Maui around the times we were planning on visiting. After all the time I spent looking, the package was still the better deal.

Included In The Package

Round trip airfare from the SC to Maui with one layover in Dallas/Fort Worth.

4 night stay in Royal Lahaina Resort (3-star hotel) in an oceanfront room.

Economy rental car for the length of our vacation.

$100 excursion credit booked through the Costco website.

$25/day dining credit at the hotel.

Customizing The Package

As I stated above, you typically have the option of adding or deleting from a package to better suit your vacation needs. For this trip, we knew 4 nights wasn’t going to be enough. We added an extra night and to offset the cost, we changed our flights and room selection. We added one more layover to our trip which saved around $400 and changed to an ocean view room which saved almost another $200.

You have to be careful when changing your package however. By changing the room, we lost our $25/day dining credit. I didn’t realize this until after I paid the deposit, but in the end we were less concerned about this and we still kept our excursion credit which was more important to us. Also, make sure you pay attention to the details of the package. I wasn’t really paying attention to ocean “front” and ocean “view.” I assumed they were the same thing and when I found out different we were quite concerned. It ended up we still had a great view of the ocean but our room also provided amazing views of the West Maui Mountain Range!

Our view of the West Maui Mountains at sunrise was breathtaking!
Our view of the West Maui Mountains at sunrise was breathtaking!

Planning Our Maui Itinerary:

Once all of the major details were booked for our trip, it was time to plan the activities we wanted to do while in Maui. Although having an itinerary is not for everyone, we like to have a schedule for the things we most want to do while on vacation. Once we have these set, we can start researching some other activities to fill our time. The key to having an itinerary, make sure to plan free time throughout your stay. This allows you to be flexible to add to or change up your plans while on vacation.

Our Must Do’s

Our must do’s consisted of three activities. We wanted to make sure we did plenty of snorkeling, we wanted to eat at a Hawaiian Luau, and we wanted to hike on a volcano. Since these were what we wanted to do most, we planned them first. After careful consideration based on long travel days, nights out, and physical exertion we picked the days which best suited these activities. After this we were able to decide how we wanted to spend the rest of the time on our trip.

Snorkeling

Maui is fantastic if you like to snorkel. I researched several places that were great for snorkeling. However, we also chose to use our excursion credit on a snorkel tour. Through the Costco site, we found a great option for a half day tour through Aloha VIP tours. The tour included lunch and cocktails along with two different spots for snorkeling. It turned out that we arrived in Maui after a horrendous storm, so the water conditions were rough. Due to this, the travel time took a bit longer than normal and we only made it to one spot in Honolua Bay. With that being said, it was still fantastic. I’ll elaborate more on this later in the post.

We also found two other spots on the island that were known for great snorkeling. Black Rock Beach, behind the Sheraton Maui, a short walk from our hotel and Wailea Beach which was a further drive down south on the southwest of the island. Both areas did not disappoint with warm, clear water and dozens of different fish species to swim amongst.

A beautiful place to relax and snorkel, Wailea Beach did not disappoint.
A beautiful place to relax and snorkel, Wailea Beach did not disappoint.
Hawaiian Luau

No trip to Hawaii is really complete without attending a luau. Again, we researched some of the best luaus on the island and were happy to find that one of the best rated and longest running, Myths of Maui luau was located right next door to our hotel. We upgraded to the VIP package which included early access and preferential seating, complimentary leis, top shelf liquor selection, and earlier access to the buffet itself.

The luau buffet offered many items local to Maui.
The first of many plates, the buffet offered many selections native to the island.

When we arrived we got a cocktail from the bar and were shown to our seats right up front near all the action!! As we settled in we were in awe of the amazing views all around us. It was such a peaceful location to hold this event. As I stated before, we arrived as strong storms were moving through the area, but on a normal day you would have breathtaking views of the sunset. As we waited for the buffet to open and the show to begin, we opted (for an additional cost) to have our picture taken.

Just getting settled in at the Myths of Maui Luau.
Just getting settled in at the Myths of Maui Luau.
Dinner and a Show

Once the buffet opened it was time to try the traditional island cuisine. From local fish, to island produce to, of course, Pua’a Kalua (roast pig) and everything in between we couldn’t have asked for anything more. It was hard to save room for all of the delicious food but luckily you were able to return for most of the evening.

With full bellies, we settled in for an amazing show. What we did not know was that luaus are not strictly Hawaiian in their origin. The show discussed island customs and showcased dance from several cultures including Aortearoan, Tahitian, Hawaiian, and Samoan. All the music was done in house and was authentic to each culture. The show ended with an amazing Samoan fire knife display that was truly awesome! We would highly recommend this experience to anyone traveling to Maui.

Volcano Hikes

You have a few options when deciding on volcanoes to hike in Maui. If you want to stick near the west coast, the Iao (pronounced EE-ow) Valley is tucked in the West Maui Mountain range. This area is very lush and green and is a significant contrast to Haleakalā farther east. The valley was created by the Iao stream that cut through the mountains. The hike through the valley was short, .6miles, but was a wonderful way to end our visit. The highlight of the hike was the view of the Iao Needle, a 1,200 foot lava rock formation (from the valley floor) that juts into the air. The top of the needle is often covered in clouds! The hike up provides views of lush vegetation and gardens. Also, there are signs that discuss the rich history of the area.

The highlight of the Iao Valley, the Iao Needle towers 1,200 feet above the valley floor.

While the Iao Valley was lovely, the main volcano attraction on the island is Haleakalā. This volcano is popular among tourists that arrive early to be treated to breathtaking sunrise views. A reservation is required to see the sunrise and they fill up quickly! (I called 15 minutes after reservations opened and they were full.) Lacking a reservation, we were held at the gate until it opened at 7am.

Haleakalā National Park

Haleakalā is a massive volcano rising 10,023 feet above sea level in eastern Maui. It provides stellar views regardless of the time of day and many like to hike down into the crater from the summit. (Sliding Sands trail) This particular trail is 11miles and is, as its name suggests, over uneven, and unsure, footing. Remember that whatever you hike down, you will need to be able to hike back out so don’t over do it!

The trail can be seen winding down the side of the crater.
Sliding Sands Trails winds down the interior of the crater.

Favorite Maui Moments:

Our time in Maui was filled with so many wonderful memories. The island as a whole is absolutely beautiful. There wasn’t a single moment on our visit that we were unhappy about. We truly did fall in love with this special place, so much so, that we talked about living here permanently. Each of us did have a favorite moment that I’d like to discuss further.

Mike’s Favorite Memory

For me, the time we spent on Haleakalā was magical. I’ll admit, I was a bit upset over not securing the reservation for the sunrise. I do believe it would have been awesome to see that. With that being said, driving up to the summit in the dark would have been nerve-racking! We still were driving in the dark but once we hit the real twisty parts, the sun was starting to brighten up the sky. We arrived at the guard gate about 20 minutes before 7am so we just had to wait a little. After continuing on, we were treated to amazing views. There was still some heavy cloud cover but we could see some of the tops of mountains from the other islands jutting through.

We were above the clouds as we drove to the summit of Haleakalā.
We were well above the clouds as we drove to the summit of Haleakalā!

Once we arrived to the summit we started by checking out the shorter hikes to warm our legs up. It was a bit chilly, so hiking helped warm us up a bit too. After exploring the area and reading the information posted giving us some background on the park, we decided to tackle the crater hike.

Hiking Into The Volcano

As I said earlier, the full Sliding Sands Trail was around 11 miles and we never intended to do the entire thing. Our plan was to hike down a comfortable amount, enjoying the views and the weather as we did so. We took our time so we did not overexert ourselves knowing the way back would really put us to the test. The trail had a fair amount of hikers on it but that thinned out the farther down we went. As we hiked, the clouds started to burn off so we really could see amazing views of the nearby islands.

We made sure to stop for plenty of pics while hiking at the high elevation.

The crater itself reminded us of what we thought hiking on Mars would look like. The reddish sands dominated the area with only some sparse vegetation popping up here and there. After about 2 miles, and plenty of rest stops, we decided to make our way back up. If I’m being honest, the ascent was less about enjoying the views and more about taking the appropriate amount of breaks to help combat the thin air! We did see a couple of folks with pack mules heading down into the crater. I imagine they were going to set up camp down in the crater for an extended stay. Once we completed the hike, we were ready to head back to the hotel to enjoy some relaxation!

The Haleakalā Crater is massive as seen from the summit.

Cassandra’s Favorite Memory

Cassandra is drawn to water and especially the ocean. It is no wonder that for her our snorkeling excursion was her favorite memory. In the morning we walked to our meetup location and were able to introduce ourselves to the other people taking this excursion. After a brief safety chat, we were able to head out to our boat.

On the way to our snorkeling destination, we were treated to amazing views of Maui’s north eastern shores. The weather was absolutely perfect and we spotted several pods of dolphins as we ventured out. When we approached one particular pod of dolphins we slowed down to admire them. As this happened, far off in the distance we noticed a spout of water rise from the ocean. Focusing on this spot, we soon saw a large fin breach the water and realized it was a humpback whale! The show didn’t stop there as a whale erupted from the water several times which was a sight we will never forget!

Arriving To Our Destination

Continuing on, we arrived at our destination in a protected cove in Honolua Bay. Sheltered from the current, the waters were calm, clear, and warm. It was the perfect location for snorkeling. After a quick discussion on the area and respecting the sea life, we got our gear on and ventured into the water. The cove was teaming with a variety of brightly colored fish of all shapes and sizes. The highlight of our outing was when a sea turtle joined in the fun.

Our view of the Maui Coastline from the boat.
It’s easy to see why people fall in love with this beautiful island!

Choosing to stray from the group a bit, Cassandra loved diving down into the blue-green water. Diving down near the 20-30 foot ocean floor, she was treated to teams of fish near the coral. She loved the silence of the ocean floor, and the greenish hue the water took at that depth. After plenty of time to explore the area, we headed back to the boat for our return trip.

Preparing For Our Return Trip

Before heading back to shore we were treated to a delicious BBQ lunch. There was ample food to go around, and after plenty of swimming, we all had quite the appetite. We enjoyed our lunch in this beautiful setting before pulling up anchor and heading back. The trip back was a bit rough due to the ocean conditions. Thankfully, the cocktails provided help ease our queasy stomachs along with the breeze. It was a bit more mellow on the way back because we all were tired and had full bellies. Once we made it back, we departed the boat and headed back to our hotel for a nice nap!

Final Thoughts:

Our trip to Hawaii truly was a dream vacation and it did not disappoint. We enjoyed every minute of the vacation and it was everything we always imagined Hawaii would be. As I said earlier, we really could see ourselves living here for the rest of our lives. It was hard to leave, but we know we will be back.

Below I will lay out our itinerary for this trip and an itemized budget to give you an idea of how we made this vacation a reality. It isn’t always easy to make these big trips a reality. We provided some tips on ways to make travel happen on last week’s post if you need a little help. Also, if podcasts are more your style, we’d love for you to check out ours. Thanks so much for spending some time with us. We hope we can inspire you to make that dream vacation a reality.

Complete Itinerary:

These were the things we looked into prior to coming to Maui. Any other time during these days was free time or time we could add specific things once arriving to the island.

Sunday– arrive at airport and drive to hotel (we arrived late and made it to our hotel after midnight)

Monday- Run errands (go to Costco/Walmart for groceries). Relax at the resort and see what’s near us, check out the beach. Visit Myths of Maui luau located next to our hotel.

Tuesday– Check out the snorkeling by Black Rock Beach located behind the Sheraton, a short walk from our hotel. The rest of the day was free time…short walks, beach day, and relaxing at the pool

Wednesday– Early morning rise to head to Haleakalā National Park. Dinner at Kobe Japanese Steakhouse & Oku’s Sushi Bar in Lahaina.

Thursday– Snorkel excursion. Beach time at the hotel. Cocktails out at Whaler’s Village

Friday– Checkout. Drive to Wailea Beach for snorkeling. Head to Iao Valley for last hike. Arrive at airport for evening departure.

Our morning view of the backside of Black Rock Beach.

Total Expense:

Below I have itemized our total expenses for our entire vacation. This includes every dollar spent other than gratuities. We tip very well, especially while on vacation, so I did not want to include these in the total. The amount tipped is a personal decision and we did not want ours skewing the numbers. The prices given are the totals for each item so you can judge what you would tip for those activities/meals. I’ll try to add some areas we could have saved money as well to make it easier to judge your spending.

Breakdown

$3800 Costco package- 5 night Hotel stay in ocean view room at Royal Lahaina Resort. Roundtrip airfare from SC to Maui with 2 layovers. Economy rental car for the entire trip. (parking was not included but the price reflects the $90 we spent for this.) $100 credit for an excursion booked through the Costco Travel website.

$200 Groceries- We did some shopping to keep our dining costs down. We like to go big when we dine out and make them special occasions not just necessary for survival! We mainly bought items for breakfast, lunch, and booze and snacks for our room. While we over spent here (lots of booze left over at the end of our trip) we saved money by not having to buy all of this out at a restaurant.

$375 Luau- We upgraded our Myths of Maui tickets to VIP entrance so the total was $175/person plus we opted for a photograph which was $25. We completely think it was worth it, however general admission tickets were $50 less per person. If you chose general admission and didn’t get the photo that’s a savings of $125 (for a couple.)

$200– Snorkel tour. After receiving our $100 credit, our total expense for the tour was $200. This included lunch and drinks. There was plenty of great snorkeling right from the shores of some of the beaches as well so this could be an area to pick another tour.

Dining Out

$175– Kobe Japanese Steakhouse & Oku’s Sushi Bar. We really wanted to check out Lahaina and knew we wanted sushi while in Hawaii. This was a highly rated restaurant that unfortunately was burned down during the wildfires that hit the area. We definitely overindulged and the price listed included Uber rides there and back. We wanted to treat ourselves and we didn’t want to drive if we had cocktails. Numerous places we could have gone to that were walking distance from the hotel.

$90– Hula Grill. We wanted to go out one night while we were there and Whaler’s Village was walking distance for us. We ordered delivery earlier after returning from our snorkel excursion. This was mainly cocktails and a few appetizers and we enjoyed talking to another couple at the bar on vacation as well.

$90– Takeout. After waking up from a post snorkel nap we were very hungry. We ordered Thai delivery but could have spent slightly less here and been ok.

$80– Waikiki Brewing Company. After snorkeling at Wailea Beach we went to the nearby mall for some final shopping and lunch. Great beers and food and with its proximity to the beach, was perfect for us.

Optional Costs

$200– Souvenirs. On the last day we picked up some souvenirs for family, friends, and us. This is another area to save money depending on what you would like to spend.

$50– Gas. Depending on how much driving you do, this could be lowered. The big trip was to Haleakalā National Park. However, we had to drive back to the stores the following day due to our late arrival. These were near the airport and that was a 90 minute round trip drive.

$30– Entrance Fee. This was the entrance fee for us into Haleakalā National Park.

$10– Parking Fee. There was a $10 parking fee for Iao Valley.

Total cost was $5300 or $2650/person

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