Sarahritchie17 2025 has already been a whirlwind of travel and seeing long-distance family and friends. My husband and I are so grateful for the access to cheap flights that living in Miami offers us.
If you ever have family or friends living in Hawaii, don’t pass up an opportunity to visit. This was our first trip to Hawaii, and we fell in love with it. It can be an expensive place to visit, so free lodging was a massive bonus.
At the end of 2024, we wanted to stay home for the holidays and extend the merriment by visiting Hawaii in January. We planned a 9-day visit. The weather was about the same in Hawaii as it was in Miami (mid-70’s) but gave us a break from the humidity. This time we stayed on Oahu the entire trip, but we definitely want to go back to explore the other islands. Even staying on one island for the week, there was no shortage of things to do. Our itinerary was packed with suggestions from someone who has lived on Oahu for about 40 years, along with military friends who have been stationed there for a few years at a time, so you know it’s good.
Our Itinerary:
Day 1: Arrival Day – relax / recover from jet lag
Day 2: Byodo-In Temple, Dinner at Haleiwa Joe’s
Day 3: Sunrise Diamond Head Hike, Dinner at Monkeypod
Day 4: Walking tour of Waikiki, Mai Tai Catamaran, Dinner at Tropics
Day 5: Windward Coast / North Shore Tour
Day 6: Parasailing
Day 7: Sunrise Makapu’u Lighthouse Hike / Lookouts / Punchbowl Cemetery / Chief’s Luau
Day 8: Beach Day
Day 9: Departure Day
Day 1:
Our flight out of Miami was a 6 AM 3-hr flight to Houston on United Airlines. Then we had a 9-hr flight from Houston to Honolulu which got us in at 2:24 PM local with the 6 hr time difference. The flight was okay, but I was expecting something like the international flights to Europe in terms of comfort, and it was definitely subpar in comparison. The plane we were on didn’t have screens, and even sitting in Comfort Plus, we were only able to recline our seats maybe an inch. First world problems for sure, but I just thought it might be a tad nicer for a 9 hour flight. Maybe we just had an old plane, but I wish I’d managed my own expectations better.
We expected to be exhausted when we arrived, but I think we were both just so excited for the trip that we were running on adrenaline. We settled in and had a nice lasagna dinner at home as we took in the view from the balcony.
Day 2:
While my husband, Eddie, is always chipper in the mornings, I’m normally a sleeper. If I don’t have to get up, I don’t. Because of the jet-leg, though, 4 AM local time felt like 10 AM to us. We were both wide awake long before sunrise and decided to take a sunrise walk around the neighborhood.
Once everyone else was up, we made a visit to the Byodo-In Temple. A gorgeous temple modeled after one by the same name in Uji, Japan, the replica was built to scale in commemoration of the first Japanese immigrants in Hawaii. There’s a gong you can ring and a meditation gazebo. It’s worth going to once, but besides admiring the architecture, there’s not much to see. I tried to meditate briefly there but the number of tourists passing through made it difficult to focus inward.
In the afternoon, I met up with a friend who is currently stationed in Oahu, and we went for a beach walk at Castles Beach in Kailua with her dogs. Afterward, we headed to Haleiwa Joe’s for dinner. They don’t take reservations, and they always have a wait, so you have to arrive when they open for dinner to save a place on the waitlist. Luckily they have a beautiful lake and garden for you to walk around and take photos while you wait. The wait is absolutely worth it!
Day 3:
On the third day, we committed to getting up extra early, before 5 AM, for a sunrise hike at Diamondhead. We wanted to arrive before the gates opened so we could beat the crowds and watch the sun rise from the top of the crater. Be sure to make a reservation in advance.
Post-hike malasadas are a must! Leonard’s is a Portuguese donut local chain in Oahu. They have a brick and mortar location as well as food trucks throughout the island. Try the cinnamon sugar and then the custard-filled—actually just try them all.
For lunch, Eddie met up with a friend and mentor stationed in Oahu while I got my nails done with Mom. For dinner, we headed to the Southwest side of the island. I caught up with another friend stationed at Barbers Point while Eddie, Mom, and Andy ate at Monkeypod. I’ll have to go back to try Monkeypod, as I’ve heard they have the best MaiTai’s, and the restaurant received high praises from multiple friends. For dessert, we all met up at Sage Creamery which had flavors unique to Hawaii like Ube Crinkle Cookie, Blue Jasmine Milk Tea, and Horchata to name a few. I tried the Ube Crinkle Cookie and loved it.
Day 4:
Our fourth day kicked off with a birthday celebration. Mom and I decorated the dining room the night before. She made french toast for the occasion, and there were presents and chocolate tuxedo cake. Afterward, we walked around Waikiki while Andy told us about the history of the resort-town. Then we headed to the beach for our Mai Tai Catamaran reservation. Exactly how it sounds, it was a boat-ride with endless pours of Mai-Tai drinks. We had dinner at the Tropics and enjoyed a beautiful view of sunset over the beach. If you go on a Friday, there’s also fireworks.
Day 5:
This was the day I was most looking forward to on the itinerary—the North Shore tour. Having local knowledge and a truck was the best way to do it, but there are also tour busses that run the same route if you don’t have a local connection. Our first stop was the Tropical Farms Macadamia Outlet which was a market of all kinds of things to include a variety of macadamia nuts that you can sample. Stop 2, Kualoa Point Park, would be a nice area to spend a day relaxing or having a picnic. Stop 3 was Waimea Beach where we spent some time watching the mesmerizing surf. Even without surfers out, I could have watched the waves crashing for hours. We proceeded to drive by Ka’a’awa, and Eddie took notes on the pronunciation and fun facts. We stopped for photos at Lā’ie Point Lookout and Sharks Cove.
For lunch, we had to taste test two different shrimp trucks recommended to us. Giovanni’s is the more famous one and the one we tried first. They have two locations on the North Shore, one in Kahuku and one in Haleiwa. We tried the shrimp scampi plate, and it was very tasty. Big Wave Shrimp Truck was recommended by friends who knew the previous owners. There we tried the Garlic and Butter Shrimp plate which was also delicious! We couldn’t decide on the better of the two if our lives depended on it. The latter was definitely more garlic-y though, so you have to love that flavor to enjoy it.
Hale’iwa Town was our next stop. Besides shrimp trucks, the North Shore of Oahu is known for shave ice. Matsumoto Shave Ice is famous, but we decided to skip it since the line was long and we’re not the biggest fans of shave ice anyways. Bellies still full from all the shrimp, we headed to Dole Plantation. We watched a pineapple demonstration where we learned how to select the perfect pineapple and how to chop and serve the fruit. The store had all kinds of pineapple flavored, scented, shaped, and themed things. And even though we were still full, you can’t go to Dole Plantation and not try the Dole Whip. It’s a pineapple-flavored dairy-free soft serve. They had all kinds of toppings to make it your own. Outside, we walked around the gardens and took advantage of the photo ops. The last stop on our tour was Green World Coffee. You can sample various coffees and teas there and walk through the farm where they grow their own coffee.
Day 6:
We had a reservation to go parasailing on Day 6, but it was cancelled for weather. Instead, we enjoyed a slow morning and then went to Mid Pacific Country Club for lunch with a mentor of mine. Apparently the Obamas are also members there!
After lunch, we went shopping at Ala Moana Shopping Center and had dinner there at an Italian restaurant called Assagio. Depending on what time you go to Ala Moana, you can enjoy a Luau performance and music from local artists.
Day 7:
We kicked off Day 7 with another early morning hike—this time Makapu’u Lighthouse. This hike was less crowded and the path was paved the whole way up. Post-hike malasadas are a must! Afterwards, we did a driving tour to see some iconic lookouts on the Southeast side of the island including Hanauma Bay, Koko Crater, and Blowhole Lookout. In the afternoon, we walked around Punchbowl Cemetery, an impressive memorial honoring veterans who served in wars on the Pacific front.
On the way home, we picked up a poke bowl from Foodland, the grocery store. I’d heard people rave about Foodland poke, and I had to try it. I stole my friend’s order which is the Ahi Cali poke bowl with furikake, unagi sauce, and onions. When I got home, I added fresh avocado and pineapple on top. It was worth the hype!
To end the day, we had a reservation for Chief’s Luau. We had an authentic Hawaiian feast including kalua pork, taro rolls, purple Okinawan sweet potatoes, lomi lomi salmon, and poi. The night also included learning to start a fire the traditional Hawaiian way and how to weave palm fronds. The show was incredible with traditional dances representing different Pacific islands and award-winning fire dancers.
Day 8:
We had breakfast at Kaneohe Pancake House, and I got the special, Ube Pancakes. I was hooked on the Ube flavor, and having purple pancakes (that were naturally colored) made me feel like a kid in the best way. This place felt like a locals spot, and it was difficult to get a parking spot with how popular it is. I also got a hot chocolate, and the whipped cream on top was piled a mile high. We got coffee after breakfast at Tradition Coffee in Kailua and then went to Kailua Beach to enjoy a lazy beach day.
Day 9:
On our last day, we wrote postcards and packed up. Our departure was at 3:50 PM which got us back to Miami the next day at 1:50 PM with a 4 hour layover in Newark. Luckily, we have lounge access, but it was still a lonnnnng day of travel.
I think we crammed as many things into the trip as we could while still making it relaxing and delightful. We’ve found that choosing one or two excursions a day is a good travel pace for us, but everyone is different with what they like for vacations and travel. Still, we didn’t hit everything that was recommended to us by friends and colleagues. We can’t wait for our next trip!
Here’s a list of Oahu things that remain on our list to try:
-Snorkeling at Hanauma Bay
-Aulani Disney Resort
-Dukes Restaurant in Waikiki
-Marine Corps Beach – cross a runway to get there; must have base access
-Waimea Falls – botanical garden and waterfall that you can swim in
-Paradise Cove – beach with sea turtles
-Electric Beach – snorkel spot with sea turtles, limited parking, wear fins
-Kō Hana Distillers
-Bishop Museum
-Helenas Hawaiian Food
-Maiko Matcha Stand
-Ko’olau Distillery
-La Mariana Sailing Club – restaurant
-Side Street Inn – restaurant
-Rise and Grind – coffee shop in Kailua
What else did I miss? I’d love to hear from you in the comments!
Bonus: Steal My Closet! Most of my outfits in this post are actually rented from the clothing rental brand Nuuly. They offer a monthly subscription that gets you 6 items per month. As of May 2025, the rate is $98 a month, you can freeze at any time, and you can add additional items to your rental for $20 per item. I love this for vacations and when I have multiple events to dress up for in a month. It is so fun to rent unique pieces that I don’t necessarily want permanently but just for an occasion. You can use this link to get $30 off. (Disclaimer, it’ll give me $10 off too.)
Cheers!
Sarah
