Five Days on Maui – The Valley Island Guide


The final island on our Hawaiian vacation was Maui.  Maui is known as the Valley Island, because it features a valley in its center, between the volcanic mountains to the northeast and southwest.  It is the second-largest Hawaiian island, and has a very easy-going vibe.  After the hustle and bustle of Honolulu, we were ready for some relaxation at the Waldorf Grand Wailea on beautiful Wailea Beach!

Air Travel/Transportation

  • Hawaiian Airlines – $5/ea (Used 4,500 American Airlines miles to island hop)
  • Rental Car, 5 days – $0 (Used 16,829 Citi ThankYou Points)


Just like the flight from Kauai to Oahu, we used 4,500 American Airline miles to book island-hopper flights on Hawaiian Airlines.  These flights are available on for 5,000 AA miles, and we got a 10% rebate because of our Citi AA Platinum cards.  Availability was a bit spotty for award seats, but we were able to make it work with some careful planning.  If you can’t find award seats, the flights are inexpensive at $80-$100.  Our return trip to Kansas City was covered as part of the open jaw on our Korean Air booking.


We definitely wanted to drive the famous Road to Hana and see the top of Haleakala Crater, so we opted to rent a car.  This time, we used our Citi ThankYou points to book a Jeep Wrangler with Alamo through the Citi Travel website, at a rate of 1.25 cents per point.  At the rental counter, Brooke spotted a beautiful, bright-red, 4-door Jeep Wrangler Unlimited and I asked if we could get an upgrade.  Without hesitation, the agent offered a complementary upgrade!


  • Waldorf Grand Wailea Resort, 5 nights – 280,000 Hilton Honors Points

We booked five nights at the Waldorf Grand Wailea Resort using our Hilton Honors points and the 5th night free promotion.  This resort was incredible, with excellent customer service, top-notch dining, and a fantastic pool/beach area.  As we pulled up to the front of the resort, we were greeted with flower leis.  At check-in, we were upgraded to a Deluxe Ocean View room due to my Diamond Status.  I also asked if the front desk agent could waive the $30/day valet parking fee, to which she happily agreed.  Breakfast was not included with our stay, but the agent noticed my diamond status and included that as well… normally $30/person!)  As if that wasn’t enough, she handed us a packet with complementary drink tickets and a voucher for a bottle of champagne to celebrate our anniversary!  Wow… just wow!

The average nightly rate for our room with a breakfast package is $987 (after $30 resort fee, $30 valet fee, and taxes)!  Hilton waives the resort fee on point stays.  This gives us a point redemption value of 1.41 cents per point!!  ($987 x 4/280,000)  This is much better than the average Hilton Point value of 0.4 cents per point.  Our room was very nice, with a comfortable king bed, spacious bathroom, and a balcony facing the ocean.

The pool area was awesome, with water slides, a swim-up bar, a lazy river, a rope swing, an adults-only section, and the world’s only water elevator!  I was particularly impressed with the water slides.  When I read that there would be slides, I pictured a couple boring, short slides for the kids.  The actual slides were more like what you find at a water park!  Check out my video below.  We spent quite a bit of time lounging at the pool and floating around the lazy river… ahhhhh, relaxation!

The resort also features a few excellent restaurants.  As I mentioned earlier, we were given free breakfast, which was a full buffet with an omelet station.  We enjoyed our daily meal while sitting on the Grand Dining Room’s main balcony overlooking the beach.  The casual dining restaurant, Bistro Molokini, is situated near the pools.  It has an excellent menu, but you absolutely must try the Ahi Poke Nachos… they are incredible!  Finally, no visit to the Waldof is complete without eating dinner at their featured restaurant: Humuhumunukunukuapua’a.  Named for the state fish of Hawaii, this restaurant is definitely a fine dining delight.  We enjoyed a three-course meal, including seared scallops, filet mignon, and a 3lb Hawaiian spiny lobster!  Our waiter paired an excellent bottle of wine (which we used our Champagne voucher), and he presented us with a celebratory chocolate cake for our anniversary.

Overall, I highly recommend this resort to anybody who plans to visit Maui.  Of all the resorts we have visited, this one most completely represents luxury.  From the warm welcome, to the expansive pools, to the delicious dining, this resort has it all!


First Night

We arrived at the OGG airport around 4pm, so we grabbed our rental car and headed toward Maui Brewing Company for dinner and drinks.  Unfortunately, when we arrived, we discovered they were hosting a private event.  We consulted Yelp, and discovered Cow Pig Bun next door to the brewery.  Oddly located in an office building, this restaurant has an excellent menu.  We shared the Bahn Mi and really enjoyed it.

After dinner, we headed to our resort to check in and enjoy the gorgeous sunset.  Once the sun went down, we walked down to Bistro Molokini for a nice chocolate cake to celebrate our official wedding anniversary.

Day 1 – Sea Turtles and Local Brews

  • Molokini Crater & Turtle Town Snorkel Tour

One of our goals during our trip to Hawaii was to see some giant sea turtles.  With this in mind, we researched snorkel tours on Maui.  Many tour companies came up on our search, but Redline Rafting caught our eye.  They offer smaller, more private tours, with a maximum of 22 people on their boat.  Other tour companies use large ferry boats and cram hundreds of people on board.  Redline Rafting also departs earlier than most tours, so you get to experience the Molokini Crater without hundreds of other people splashing around.  We arrived at the dock in Kihei at 6:30am to check in and meet our tour guides.  They were a lot of fun, and very knowledgeable about the history of Maui and its surrounding islands.

Our first stop on the tour was the Molokini Crater, a volcanic crater off Maui’s west coast.  The waters around the crater’s inner bowl are teeming with colorful aquatic life.  We saw a variety of tropical fish, including the state fish of Hawaii (the Humuhumunukunukapua’a).  Next, we rode around to the back wall of the crater, which the US Army used for target practice in the past.  The wall itself is incredible to behold, and some people have even found artillery rounds embedded there.  You can swim directly up to the massive crater wall, and feel the waves gently lift and lower you 10-15 feet at a time!

We departed the crater and headed toward the coast of Maui to visit two more areas, known as Turtle Town and Turtle Arches.  As you may have guessed, the primary highlight on this portion of the tour is swimming with sea turtles!!  We spotted five different turtles, and literally came within inches of these graceful animals (see video).  Definitely a bucket list item checked off!  After we finished snorkeling, our guides from Redline Rafting provided lunch, and we returned to the dock.  I definitely recommend booking this tour during your visit on Maui!

After our tour, we headed back to chill at the resort.  We kicked back at the pool with some cold drinks and floated in the lazy river.  (Bonus tip: Pack an inner tube in your carry-on, and inflate it upon arrival.)

For dinner, we ventured out of the resort to get some local fare.  We discovered Maui Fish & Chips, a newly re-opened restaurant in Kihei.  It is a very unassuming spot, with a limited menu.  However, what it lacks in flair, it makes up for in quality fish & chips!  We opted for grilled Mahi with Garlic Fries and fried Ono with Furikake.  Both were fantastic, and our bellies were full for under $15!  We also met the owner, Colin, who is passionate about making sure everyone enjoys the best fish & chips they’ve ever had.  Keep up the great work, Colin!

Our second attempt to visit Maui Brewing Company was more successful than the first.  The facility is very impressive, and they offer over 20 unique beers on tap, all brewed on site!  We sampled 15 of their offerings, and our favorites were the CoCoNut PorTeR and the Double Overhead IPA.  Quick tip: On Thursdays, you save $1 per pour if you wear Maui Brewing gear… just in case you were going to buy a tank top or hat.


Day 2 – Road to Hana


We spent our entire second day on Maui driving the famous Road to Hana.  This scenic drive is an absolute must-do on Maui.  The “Hana Highway” is approximately 50 miles long, and it is a narrow, twisting, sometimes one-lane road with an estimated 600 turns and 54 (mostly) one-lane bridges, and no shoulder!  Make sure that you carve out an entire day for this challenging drive, because you will want to stop often to visit the following list of sites (and more).  Also, before you depart for Hana, make sure to download the Gypsy Tours App for Maui.  It provides an excellent audio guide for the Road to Hana.  Your narrator will point out all noteworthy stops along the road and tell interesting stories about Maui’s past.

  • Rainbow Trees at the Arboretum

Along the road to Hana, you will see trees with rainbow-colored vertical stripes.  You will think that they must be fake, but I assure you that these are naturally occurring eucalyptus trees.  Don’t try to stop along the roadside, because it is dangerous.  Pull into the Arboretum (free) and walk down the path to see these multi-colored trees up close.  DO NOT CARVE YOUR INITIALS INTO THE TREES… DO NOT.IMG_9167

  • Caves & Black Sand Beach at Wainapanapa State Park

Wainapanapa State Park offers some walking trails, water caves, a lava tube, and a black sand beach!  Stop here and explore for a bit.  The black sand/pebbles at Pa’iloa Beach are as picturesque as can be.  The loop trail will take you down to the freshwater caves where some powerful legends live.  I decided to jump into the freezing water of the cave and swim deep into the cavern, beyond the reach of daylight.

  • Wailua Falls Swim

There are many waterfalls along the Road to Hana.  Our favorite was easily Wailua Falls, because we were able to swim in the waterfall!  Drive just a bit past the falls to a parking area and walk back across the bridge.  On the far side of the bridge, you can access a narrow trail leading to the falls!  We followed this trail and dove in!  The water was a bit chilly, but well worth the plunge.

  • Seven Sacred Pools

The Seven Sacred Pools are actually past Hana, but worth the additional drive.  About half an hour drive past Hana, you will reach Haleakala National Park.  When you pay $10 to enter the park, save your receipt.  This will allow you to enter the park at Haleakala Summit (see below) within three days without paying again.  The Seven Sacred Pools are part of Hawaiian lore, and they are beautiful to behold.  We were forbidden from swimming in the pools during our visit, because excess rain had made the waterflow quite dangerous.  Hopefully you have better luck!


  • Fruit and Banana Bread Stands

Food options are a bit sparse along the Hana Highway.  For this reason, I recommend bringing snacks for your drive.  However, you should stop to sample some rare fruits if you see a fruit stand!  We tasted dragonfruit, starfruit, fresh mango, and some berries that tasted exactly like peanut butter!  We also stopped to buy some coffee and fresh banana bread.  Coffee makes the long day of driving more enjoyable.

  • Additional Tips

Take your time and really enjoy the drive.  Do not get in a hurry.  Do not get frustrated with slow drivers, and move to the side (when possible) for locals… they drive FAST!  Get gas in Paia Town before you get onto Hana Highway, because you will not find anymore until Hana.  Get going early, because the road will get crowded later in the day, and you will want plenty of time for stops along the way.  Driving in the dark would be a major challenge!

After the long day of driving, we returned to the Waldorf to feast on the aforementioned Ahi Poke Nachos!  What a great day!

Day 3 – Haleakala Sunset & Mama’s Fish House

Our third day started out with pool and beach time in the morning.  Roll out of bed, flop onto a pool chair, drink in hand.  Ahhhh, luxury!  We spent the morning this way until lunchtime.

South Maui Fish Company is a local food truck near the beach in Kihei.  We found some great reviews on Yelp and decided to give it a shot.  We arrived just before noon and ordered the ahi poke and fish tacos with pineapple coleslaw.  While we waited, we heard the owner tell the next people in line, “We’re out of poke and tacos!”  Apparently, this is normal.  The truck opens for lunch and closes when they run out of food.  Fortunately, we arrived just in time to order!  The food was incredible, so get there early, or you may miss out.

  • Haleakala Crater Sunset

Haleakala Crater is a popular spot on Maui.  Most people recommend going for sunrise, but after a long day driving the Road to Hana, I was not ready to wake up at 3:30am and drive 1.5 hours to the top of Haleakala.  Instead, we drove up for sunset while our Gypsy Tours app taught us the history and genesis of the crater.  Our receipt from the prior day’s visit to the Seven Sacred Pools got us into the National Park for free.  Word to the wise – the temperature at the top was FREEZING!  We were literally in the clouds, and the temp dropped from the mid-90’s to the mid-30’s!  The landscape at the top was much like I would imagine the surface of Mars – rocky, desolate, cold.  We had really entered into an entirely different ecosystem.

At the very top, we parked the car to watch the sunset.  Unfortunately, as a tropical mountaintop, this area is prone to heavy cloud cover and rain.  We stood on the edge of the lookout point, shivering and staring into the grayness of seemingly endless clouds.  We watched the minutes tick by toward sunset with no discernible break in the gray.  Finally, Brooke whispered a brief prayer: “God, please break the clouds, if only for a second.”  I swear, as if He literally heard her and reached down, the clouds opened up to reveal a glowing orange ball half-way below the horizon!  The small crowd at the top gasped and quickly reached for cameras to capture the surreal event.  The sun slipped peacefully out of sight, and the clouds consumed us once again.  Seriously, goosebumps as I write this!

Screen Shot 2016-01-30 at 5.16.52 PM
Cloud Break Sunset

After making the dark drive down from Haleakala, we were excited for dinner at the world-famous Mama’s Fish House.  This restaurant is dubbed the best restaurant in the islands, and one of the top in America.  That said, be sure to make a reservation!  Brooke ordered the Taste of Maui, which comes with poke, ahi tuna teak, Kalua pork, rainforest bananas, coconut octopus, and poi.  I went for the less flashy lobster-stuffed mahi.  Both dishes were excellent, and they even offered a free dessert to celebrate our anniversary!

Days 4 & 5 – CHILL!

After two weeks of hiking, snorkeling, driving, exploring, touring, etc, we were!  We spent the last two days doing exactly that.  We floated the lazy river and enjoyed the water slides.  We took full advantage of the resort’s beach access, and we browsed the nearby Wailea Shops.  We did basically NOTHING and loved every second!  Make sure to build some time for R&R into your island adventures.

  • Dinner – Humuhumunukunukuapua’a

The only item of note over the last couple days was dinner on night four.  As I mentioned above, we visited the Waldorf’s feature restaurant.  Our dinner was unreal – bottle of Spanish wine, seared scallop app, 3-pound Hawaiian spiny lobster, filet mignon, and local ice cream with an oreo crust!  We enjoyed dressing up, and enjoying world-class fare in an open air restaurant at sunset.

Total Trip Cost Breakdown

The following table breaks down our transportation and lodging costs.  Our return flight to KC was covered in the Kauai post via the Korean Air strategy.

Item Points/Miles/Loophole Actual Cost
Airfare x 2 from HNL-OGG 4,500 AA Miles + $5 per ticket on Hawaiian Airlines $10
Rental Car – 5 Days 16,829 Citi ThankYou Points (1.25CPP) $0
Waldorf Grand Wailea – 5 Nights 280,000 HHonors Points (fifth night free promo) $0

Our time on Maui was very luxurious.  The Waldorf and its staff treated us like royalty!  Snorkeling with sea turtles, driving to Hana, and watching a Haleakala sunset made lasting memories.  Dining experiences were fantastic, and I already miss eating fresh fish daily.  I hope our experiences on The Valley Isle inspires you to plan a trip!  Cheers!


20 thoughts on “Five Days on Maui – The Valley Island Guide

  1. 280,000 Hilton Honors points?! How did you build up such a stockpile?? Great write-up series, I am using it as inspiration for our October trip to Kauii and Maui.


  2. Since you were in Maui 5 days doesn’t this mean you stayed at the resort 6 nights?? Great write-up overall though. Will use this as a basis for my Maui trip next year.


  3. Nice trip report. We are going to Maui in Spring Break w/ 3 kids. Do you recommend the Molokini Snorkeling tours for the kids (10, 11, 16)?


  4. Going to GW in May with my family of 5 using points. My wife and I are both diamond status. Seems like you just casually asked for the parking to be waived and free breakfast when you checked in. Any other advice on how to go about asking for this? That would be so awesome to have free breakfast every morning! Thanks for the great write up. We are really excited to go.


  5. Hi Jesse

    How did you book the hotel for 70000 points per night. When i search I see the point rate as 239000 per night… Am i missing something


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