Exploring MAUI, HAWAII in 4 DAYS! A NEW Travel Itinerary Challenge Series

In the third video as part of our Travel Itinerary Challenge series, we explore Maui, Hawaii in 4 days and try our best to eat, see, and do as many things as possible based on a prepared itinerary list! Open this up to learn more and see our itinerary ↓


If this is your first time viewing our videos, welcome and thank you! For some background about this series: in our years traveling together, we found our travel style involves cramming as many things into an itinerary as our body can handle. We plan a rough itinerary or list of things we want to do, see, and eat at our destination.

Below is the original itinerary we set out to complete. In our Itinerary Challenge Series, we will see how close we get to checking off each item on our list.

📝**Preston & Krista’s Original Itinerary for 4 Days in MAUI**
(If there is a checkmark ✅next to the attraction that means we were able to do it. We also included those completed attractions in the full actualized itinerary list too. )

1. Haleakala National Park Sunrise ✅
2. Hosmer Grove Loop Trail — Haleakala National Park
3. Keonehe’ehe’e (Sliding Sands Trail) — Haleakala National Park ✅
4. Kalahaku Overlook — Haleakala National Park ✅
5. Pu’u’ula’ula (Red Hill) — Haleakala National Park ✅
6. Haupa’Akea Peak (Overnight Camping) — Haleakala National Park
7. Twin Falls — Road to Hana ✅
8. Maui Moon Farm
9. Na’ili’ili-haele Stream & Waterfall — Road to Hana
10. Garden of Eden — Road to Hand ✅
11. Aunty Sandy’s Famous Banana Bread ✅
12. Nahiku Marketplace
13. Waianapanapa State Park ✅
14. Hana Bay — Hana
15. Hasegawa General Store
16. Wailua Falls ✅
17. Pipiwai Trail & Waimoku Falls
18. O’heo Gulch (Seven Sacred Pools) ✅
19. Ono Organic Farms
20. ‘Iao Valley
21. The Mill House ✅
22. Sam Sato’s
23. Da Kitchen
24. Nakalele Blowhole & Heart Shaped Rock ✅
25. Dragon’s Teeth – Makaluapuna Point
26. Star Noodle ✅
27. Makena Beach ✅
28. La Perouse Bay
29. Molokini Crater Snorkeling
30. Maui Kayak Adventures
31. Black Rock Beach
32. Turtle Town
33. Wailea Beach Park
34. Kaanapali Beach
35. Banyan Tree Park
36. Leoda’s Kitchen and Pie
37. Tin Roof
38. Paia Bowls
39. Mama’s Fish House
40. Aloha Surf Hostel
41. Ho’okipa Beach Park ✅
42. Ali’i Kula Lavender Farms
43. Maui Ocean Center
44. Horseback Riding (Makena Stables, Ironwood Ranch, Triple L Ranch or Piiholo Ranch)

📋**Preston & Krista’s Actualized Itinerary for 4 DAYS in MAUI**
1. Haleakala Observatory & Pu’u’ula’ula (Red Hill) — Haleakala National Park
2. Pa Ka’oao (While Hill Trail) — Haleakala National Park
3. Keonehe’ehe’e (Sliding Sands Trail) — Haleakala National Park
4. Kalahaku Overlook — Haleakala National Park
5. Kula Lodge — Kula
6. Ho’okipa Lookout — Hana Highway – Mile Marker #8.8
7. Twin Falls — Hana Highway – Mile Marker #2.1
8. Garden of Eden — Hana Highway – Mile Marker #10.5
9. Kaumahina State Wayside — Hana Highway – Mile Marker #12.2
10. Ke’anae Peninsula — Hana Highway – Mile Marker #16.9
11. Aunty Sandy’s Famous Banana Bread — Ke’anae
12. Coconut Glen’s Ice Cream — Hana Highway – Mile Marker #27.5
13. Waianapanapa State Park — Hana Highway – Mile Marker #32
14. Hana Bay — Hana
15. Koki Beach — Hana Highway – Mile Marker #51
16. Huli Huli Chicken — Koki Beach
17. Wailua Falls — Hana Highway – Mile Marker #45
18. Kipahulu District of Haleakala National Park — Hana Highway – Mile Marker #42
19. O’heo Gulch (Seven Sacred Pools) — Kipihalu Area of Haleakala National Park
20. The Mill House —  Waikapu
21. Mushroom Rock – Kaheliki Highway – Mile Marker #42
22. Nakalele Blowhole & Heart Shaped Rock — Kahekili Highway – Mile Marker #38
23. Honolua Bay – Honoapi’ilani Highway – Mile Marker #32
24. Napili Bay — Kapalua
25. Star Noodle  — Lahaina
26. Eco Skyline Haleakala Sunrise & Bike Ride & Zipline Adventure — Haleakala National Park
27. Makena (Big & Little) Beach — Makena State Park
28. South Maui Fish Co. — Kihei
29. Yee’s Orchard & Fruit Stand — Kihei
30. Flatbread Company — Paia

🎧We recommend downloading The GyPSy Audio Guide if you end up driving around the island (

🌅Online reservations required to view the sunrise @ Haleakala National Park:

💻It was helpful to us to know the status of Parks & Beaches in Hawaii before we visited — Hawaii Division of State Parks website (

⚠️For the Nakalele Blowhole @ Kahekili Highway please use extreme caution if going down. Adhere to guidelines set by the Maui Department of Fire & Public Safety! There have been serious injuries and deaths at the location: (

We hope the itinerary lists and tips are helpful!

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  1. We hope you enjoy the third video in our Travel Itinerary Travel series where we spent 4 days exploring Maui – the Magical Island! We'd love to know about places you have been to in Maui on your past travels or let us know about places that you're inspired to visit! We are always eager to learn more about things to eat, see, and do for the next time we visit Maui!

  2. Kind of a lame question – do you remember if there was parking at your stops on the Road to Hana? We are planning a trip and I'm starting to get nervous about driving, especially since there is apparently no parking. How do you navigate that?

  3. How was the skyline tour up to Haleakala? How many hours did it take and did anyone get car sick from all the twists and turns or altitude? I really want to do that tour!

  4. Maui is such a magical place. Spent 10 days there and it just wasn't enough. My favorite was probably the hidden red sand beach on the way to Hana. Had a blast snorkeling at the many beaches, with Slaughterhouse beach probably being my favorite snorkeling experience. Sunrise on Haleakala was pretty amazing too. Stayed in Napili-Honokowai. It was so sad to say goodbye. I can't wait to return. Planned on going again this August but we chose to cancel our summer vacations to Aruba and Maui this year because of the Covid. We'll hopefully reschedule for next year. Cool video by the way. Brought back some great memories. Aloha Mahalo 🤙🏽

  5. We love your shooting style, information, Mr Waffles and energy! The most informative and enjoyable series of Hawaiian vacation videos we have found planning our trip for next year. If you ever go back, upload another series! If you're ever headed to RMNP, give us a holler for tips. Aloha!

  6. Where is Molokini snorkeling? Anyway, awesome video guys! I've been to Maui over 5 times, and I still need to make it to Oheo Gulch. I love Star Noodles, Mama's Fish House for lunch, and Haleakala sunrise. I'll check out the restaurants you visited. My brother set-up a family trip to Maui September 2020 and I'll use some of the activities here to fill our itinerary. Thank you very much!

  7. Been to Maui 17 times so I know the drill but 44 activities in 4 days is insane. You are like young puppies and I am an old dog who just wants to relax. Good luck with your travels.

  8. When on Maui, May I suggest dropping into visit the happy Maui Humane Society off the highway back towards the airport in Kahulie….they place a lot of dogs and 🐈. They doa great job!🌴🌴🦜

  9. Great vid, makes everything look attractive, but folks, please, please stay away fro Kahekili highway. Very dangerous, especially when you can't tell when some one else's fear kicks in, causing them to do something that puts you at risk. There is no room for error. Everybody there will tell you not to take that road, so don't.They know what they're talking about.

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