Rough Draft: 5 Day Itinerary for Maui, Hawaii

Rough Draft: 5 Day Itinerary for Maui, Hawaii

April 2020

Rough Draft: Maui, Hawaii

While it was not on our radar for 2020 travels, when we were invited to a friend’s destination wedding, we could not think of a better reason to make it out to Hawaii! As I learned more about the island of Maui, the more excited I got that we had this opportunity to visit.

Today was supposed to be our first day in Maui. And this thing happened called COVID-19. We already had to cancel our trip to Vietnam that was scheduled for March 2020 – our big two week trip of the year. And it ended up being the absolute right decision given the spread and progression of the virus. That being said, I at least was hopeful that our domestic trips later in the year could be saved. No so my friends! The US had every advantage to get ahead of the spread yet here we are, escalating quicker than China.  Ok, rant is over. When we got this message from the airline, we knew it was game over.

Screenshot 2020-03-25 at 8.20.50 PM

Fortunately we got an airline credit – not ideal but better than losing all the money. Still waiting to hear back from Airbnb about getting a full refund, and our car rental through Turo was fully refunded. I feel so bad for the couple that had to cancel their wedding – I cannot imagine!

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Since I have the leg work of an extra long weekend planned, I can at least share with you for whenever regular travel plans can resume. This itinerary is easy to extend by visiting some of the other Hawaiian islands (*Aulani*) or even California as well, which we may do since all the travel plans for 2020 have been wiped clean until further notice. Who knows, we may just continue flying onto New Zealand and stay for awhile… Anyway, enjoy daydreaming with me!


Thank you to my brother for photos of Maui!

Here is how I would structure a five day trip to Maui!

Day 0Arrive in Maui
Day 1

Papawai Scenic lookout

Leoda’s Kitchen and Pie Shop

Ululani’s Shaved Ice

Beach time
Dinner at Mama’s Fishhouse
Day 2Sunrise Haleakala Summit
Hiking at Haleakala
Kihei Cafe
Maui Brewing
Beach time
Day 3Molokini snorkel excursion
Day 4Road to Hana
Camp at Wai’anapanapa
Day 5Depart

I had the following beaches tagged for the various beach times throughout the trip:

Kaanapali Beach

Kamaole Beach Park

Keawakapu Beach

Makena Beach

Palauea beach

And no trip to Maui would be complete without the journey of the Road to Hana! There is so much to do that I was determined to spend two days of the trip dedicated to a leisurely exploration of everything the Road to Hana has to offer.

Day 1Paia 
Ho’okipa Beach  
Twin Falls 
Food Stop: Huelo Look Out 
Rainbow Eucalyptus trees
Waikamoi Waterfalls
Food Stop: Ka Haku Smoke Shack
Garden of Eden Arboretum
Honomanu Bay
Food Stop: Aunty Sandy’s Banana Bread
Keanae Pennisula Lookout
Food Stop: Half Way to Hana
Upper Waikani Falls
Food Stop: Nahiku Market Place
Waiʻānapanapa Campground
Day 2Hana
Kaihalulu Red Sand Beach
Food Stop: Braddah Hutts BBQ Grill
Waioka Pond
Wailua Falls
Pipiwai Trail
Waimoku Falls
Kuloa Point Trail
‘Phe’o Gulch

If you have been to Maui, let me know what I missed and what your favorites are!

We got this chance to try this rough draft in real life! Check out all the details of our trip to Maui here!

Don’t forget to check out all DESKRIB itineraries here!

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