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!

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!

Activity Food
Day 1 Morning  Flight to Maui
Afternoon Pick up Car  

Drive to Paia

Mama’s Fishhouse
Evening Check into Airbnb

Explore Kihei

Papawai Scenic lookout

Leoda’s Kitchen and Pie Shop

Ululani’s Shaved Ice

Day 2 Morning  Sunrise Haleakala Summit

Nap on a beach

Kihei Cafe
Afternoon Maui Brewing 


Day 3 Morning  Molokini snorkel excursion
Evening Beaches
Day 4 Morning  Road to Hana (See below!)
Evening Camp at Wai’anapanapa

State Park

Day 5 Morning 
Evening  Flight Home

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.

Road to Hana Itinerary

Day 1


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

End of Day 1

Day 2


Kaihalulu Red Sand Beach

Food Stop: Braddah Hutts BBQ Grill

Waioka Pond

Wailua Falls


Pipiwai Trail

Waimoku Falls

Kuloa Point Trail

‘Phe’o Gulch

Drive Back to Airport

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

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

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