Itinerary: Hawaii – Maui and Oahu

August 2020

Itinerary: Hawaii – Maui and Oahu

After an unforgettable 2020 travel year (thanks COVID) and an insane start to 2021 (whoop COVID vaccines), we were both itching for a trip. When I was able to get some time off, I knew exactly the rough draft itinerary to resurrect. An outdoor playground awaited us and we could not wait to explore it. Since we had ten days, we decided to add a few nights in Oahu staying at a bucket list resort – Aulani, a Disney resort and spa! While a week is certainly not enough to time see everything, it was certainly plenty of time to appreciate paradise.

Now, our itinerary changed quite a bit from what I had planned to what we actually did. This came down to a few factors but mostly it was not a problem with not having the time but the weather! Since so much is outdoors, our trip was plagued with a lot of rain – and that is ok – just had to be a bit flexible. The week after we got back there was mass flash flooding over both islands so we were grateful to not have had that! Do not be discouraged if things do not go as planned. Be flexible and adjust your day to things you can do, and stay positive – you are on vacation after all!

Here was our ten day itinerary!

Day 1MorningTravel
AfternoonArrive in MauiTin Roof
EveningEarly Bed
Day 2MorningHaleakala Summit
Lahaina Pali Trail
Paia Coffee
Leoda’s Kitchen
AfternoonMaluaka BeachUlulani Shave Ice
Sugar Beach
EveningKalepolepo Beach (sunset)Paia Fish Market
Maui Brewing
Day 3MorningExcursion: Whale Watching
Excursion: Molokini
Akamai Coffee
Beach Street
AfternoonWaihee Ridge TrailPiko Cafe
Day 4MorningExcursion: KayakingAkamai Coffee
AfternoonBeach / Pool timeTamura Fine Liquors
Tin Roof
Ululani Shave Ice
EveningMama’s Fish House
Day 5DayRoad to Hana
Day 6MorningRoad to Hana
AfternoonFlight to OahuPaiai Bowls
Paia Coffee
EveningExplore resortMakahiki
Day 7MorningMa’ili (Pink) Pillbox TrailIsland Vintage Coffee
AfternoonResort relaxingResort snacks
EveningResort relaxing‘Olelo Room
Day 8MorningDiamond Head Crater Trail
Halona Blow Hole
Makapu’u Point Lighthouse Trail
Skipped due to weather:
Hanauma Bay
The Curb
Leonard’s Bakery
AfternoonPearl Harbor National MonumentIsland Vintage Coffee
EveningResort relaxingOff the Hook
Day 9MorningNorth Shore – surf lessons Haleiwa Bowls
AfternoonNorth Shore – paddle boarding
Skipped due to weather:
Ehukai Pillbox Trail
Waimea Valley
Banzai Pipeline
Ka’ena Point Trail
Giovanni’s Shrimp Truck
Matsumoto Shave Ice
EveningResort relaxingMonkeypod Kitchen
Day 10MorningResort relaxingIsland Vintage Coffee
AfternoonFlight home

This was certainly not a comprehensive trip of both Maui and Oahu but we definitely hit the highlights and know areas to focus on when we return.

For all the details of our Maui portion, click here!

For all the details of our Oahu portion, click here!

For other posts related to our trip to Hawaii, including the preparation and packing- click here!

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