A 7 Day Itinerary for Oahu, Hawaii

Over the course of the last year, I’ve written a bunch of posts about the week that I spent in Hawai’i (Oahu, to be specific), and since it’s approaching summer and you may be planning your vacations, I figured I’d share my Hawai’i itinerary with you in its entirety!

A 7 Day Itinerary for Oahu, Hawaii

One year ago, I flew from Oakland to Honolulu as a present to myself for graduating from medical school. The round-trip plane ticket was $518 (sigh), but I managed to keep costs down pretty well, considering all the things I managed to pack into the 7 days I spent there!

I stayed at an Airbnb ($242 for 7 nights) in downtown Waikiki! H(ere’s some tips on how to travel on the cheap in Oahu!) I definitely allowed myself to splurge on eats because…once again, celebrations for finishing med school in one piece, and also because…it’s Hawai’i! Poke bowls were my jam.

Day 1

I landed at the Honolulu airport in the morning and took a bus over to Waikiki where my Airbnb was. First order of business was of course…food! I got a delicious Strawberry Lychee Shave Ice from Hau Nani Shave Ice (they’ve unfortunately since closed but it’s located in food truck paradise so you’ll definitely find something you like there)!

The first hike I did was Diamond Head Summit Trail (I took the bus for $2.50 bus and admission is $1 if you walk in! $5 if you’re in a car).

I also hung around Bryan Clay Exercise Park (located super close to Diamond Head) and went window-shopping at Crazy Shirts Outlet, found a delicious Shichimi-Crusted Seared Ahi Tuna Bowl at Pa’ina Cafe, and got a bunch of hair flowers + kukui nut leis/bracelets at Crafts Way.

Day 2

The next morning, I started my day off with an acai bowl at Tropical Tribe and wandered my way over to the Royal Hawaiian Center, where I took two lessons (Lomilomi Massage + Beginning Ukulele) for free! I grabbed a ground sirloin steak curry bowl over at HI Steaks and decided to pop into a grocery store (Food Pantry Express) to pick up some provisions. “Some” ended up being: strawberry guava pancake mix, passionfruit pancake mix (I took these back to CA and made em’ on my Tahoe trip!, 1 futomaki roll, 1 california roll, 2 spam musubi, 1 egg salad wrap, 1 tuna wrap, and donburi!

I did a lot of window-shopping and happened upon an actual physical store location for flip flops I’ve been wanting to get since 2012-2013–Sanuk!!! I may or may not have ended up getting two pairs over the course of two days. I also stopped by at King’s Village Farmer’s Market and discovered a delicious tapioca/coconut milk dessert topped with fresh fruit for $2!

I wandered along Waikiki Beach and Kaimana Beach in the evening and headed back to where I was staying. Along the way, I found Pineapple Country and got a backpack and a beach tote for $8! :D

Day 3+4

I’d come across a Lululemon during my walk the day before and they apparently had a free yoga class in the morning on Saturday, so I popped in for that before meeting up with one of my college friends, Liz, to have a lazy beach day with her and some of her friends at Sherwoods Beach! There was a lot of tasty food involved! :D

On Sunday, she and her boyfriend took me touristing over the island! We stopped at…

• Macadamia nut farm and tried a bunch of samples + some of their kona coffee
• Kualoa Ranch (they filmed Jurassic Park here!)
• La’ie Point to jump off the cliff (they filmed part of Forgetting Sarah Marshall here!)
• Food truck hopping (I got to try this super tasty “Oasis” drink that was sugarcane juice + coconut milk), banana lumpia, shaved ice, fish + chips…and we also stopped at Romy’s Shrimp Place! (I can’t have shrimp though so I just got corn :P )
• Shark’s Cove
• Chinaman’s Hat
• My friend had a performance at the Turtle Bay Resort that evening so that was our last stop of the day!

Day 5

The next morning, I woke up bright and early to take a couple buses (there wasn’t a direct line over that early in the morning) to Haunama Bay for a snorkeling adventure with Pure Aloha Adventures! Afterward, my tour guide dropped me off at the trailhead of the Makapu’u Lighthouse Trail, where I managed to squeeze in two hikes:

• Kaiwi Shoreline Trail + Pele’s Chair
• Makapu’u Lighthouse Trail

I walked/bused my way back to Waikiki and went to Ahi Poke and Bowl for dinner (..as well as Musubi Cafe Iyasume for snacks and Hawaiian Crown Plantation for dessert…)!

Day 6

I woke up super early (willingly!) for pretty much every day that I was in Hawai’i–this day was for my very first surfing lesson with Kimo, the Hawaiian Surf Guru! I’d found great reviews about him on Yelp and they definitely weren’t wrong! I had a ton of fun and actually managed to catch a bunch of waves (+ my back pain miraculously disappeared)! I enjoyed talking with him about life. I really hope I can take more surfing lessons someday!!

Surfing on an empty stomach may not have been the best of ideas, but I treated myself to another acai bowl at Tropical Tribe afterward and hung out at Ala Moana Beach Park for a bit. Originally, I was going to try to head to Manoa Falls for another hike but…I missed about 3 consecutive buses and took it as a sign from above not to go since it was getting late in the day (sigh). Instead, I got some shaved ice from Waiola Shave Ice and did a little shopping (yay for swimsuits and more hair flowers?!) and had a poke bowl for dinner!

Day 7

I found a great deal for an SUP lesson over in Kailua where they picked me up from Waikiki! It included equipment rentals and since I was the only one who’d signed up for SUP, they offered to move my lesson to later on in the day so I could bike over to hike the Lanikai Pill Boxes and hang out on Lanikai Beach!

My Stand Up Paddleboarding (SUP) lesson was super fun! :] We went from Kailua Beach Park to Flat Island and my guide packed us snacks and water so we could have a picnic when we made it out to the island! I got back to Waikiki in the late afternoon and did a little more window-shopping (hehh…) before meeting up with friends (yay for our college Hawai’i Club family!) for a sushi buffet at Kats Sushi!

“Day 8”

I was only here for the morning on my 8th day, so I decided to finish it off with guava pancakes, a macadamia nut cinnamon roll + pineapple juice at Cinnamon’s before taking a bus back to the airport.

• Have you ever been to Hawai’i? (Which island?!)
• Are you the type to stuff everything you possibly can into a vacation?