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!
| Activity | Food | ||
| Day 1 | Morning | Travel | |
| Afternoon | Arrive in Maui | Tin Roof | |
| Evening | Early Bed | ||
| Day 2 | Morning | Haleakala Summit Lahaina Pali Trail | Paia Coffee Leoda’s Kitchen |
| Afternoon | Maluaka Beach | Ululani Shave Ice Sugar Beach | |
| Evening | Kalepolepo Beach (sunset) | Paia Fish Market Maui Brewing | |
| Day 3 | Morning | Excursion: Whale Watching Excursion: Molokini | Akamai Coffee Beach Street |
| Afternoon | Waihee Ridge Trail | Piko Cafe | |
| Evening | Relax | ||
| Day 4 | Morning | Excursion: Kayaking | Akamai Coffee |
| Afternoon | Beach / Pool time | Tamura Fine Liquors Tin Roof Ululani Shave Ice | |
| Evening | Mama’s Fish House | ||
| Day 5 | Day | Road to Hana | |
| Day 6 | Morning | Road to Hana | |
| Afternoon | Flight to Oahu | Paiai Bowls Paia Coffee | |
| Evening | Explore resort | Makahiki | |
| Day 7 | Morning | Ma’ili (Pink) Pillbox Trail | Island Vintage Coffee |
| Afternoon | Resort relaxing | Resort snacks | |
| Evening | Resort relaxing | ‘Olelo Room | |
| Day 8 | Morning | Diamond Head Crater Trail Halona Blow Hole Makapu’u Point Lighthouse Trail Skipped due to weather: – Hanauma Bay | The Curb Leonard’s Bakery Helena’s |
| Afternoon | Pearl Harbor National Monument | Island Vintage Coffee | |
| Evening | Resort relaxing | Off the Hook | |
| Day 9 | Morning | North Shore – surf lessons | Haleiwa Bowls |
| Afternoon | North 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 | |
| Evening | Resort relaxing | Monkeypod Kitchen | |
| Day 10 | Morning | Resort relaxing | Island Vintage Coffee |
| Afternoon | Flight 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.
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