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Pineapples, Puka Shells, and Perfect Days: Our Hawaii Journey

  • Writer: CJM
    CJM
  • Aug 21, 2025
  • 7 min read

I know my readers have been dying to know about our recommendations and itinerary for Hawai’i so let’s recap!


Annabel and I went to Oahu, for a sister trip; she flew down a couple days before me for her Plant Science Conference. APS I believe it’s called—but don’t quote me because I don’t know!

The View Flying into Honolulu
The View Flying into Honolulu

Flying in was unlike anything I've ever witnessed. I was nervous for the flight and unsure what to expect, but it truly did not disappoint. It looked like deserted island and felt like I was flying into the unknown. Upon landing, it reminded me of a sunny, tropical Colorado. The mountains, greenery, and sunshine were just beautiful.


Main street in Waikiki
Main street in Waikiki

After driving into to Waikiki, we were greeted with a total city vibe. Designer stores, surf shops, beach bars, hotels, and ABC stores! These had everything from beer, sunscreen, cold medicine, to pool noodles. Everyone is so kind in Hawai'i, which had me wishing to move there. Smiles, greetings, something we're not used to in nasty Boston!


We loved our time in Hawaii. It’s hard to describe it, it’s the most magical, beautiful, blue water dream you could ever imagine. We stayed at the Sheraton Princess in Waikiki which was perfect for us—spacious, clean rooms with a beautiful outdoor area. The staff was so kind—especially the bartenders. We wished there was valet parking--but the garage was easy to manage!

View from our Hotel Balcony
View from our Hotel Balcony


Waikiki, like I said, is kind of like the New York City of Hawai’i. It’s lined with amazing stores, restaurants, and certainly has the hustle and bustle of city life. Parking is limited unless you’re in the garage and the traffic is comparable to Boston I-95. Hate that! Waikiki is perfect for dinners, delicious acai and coffee, and shopping if that’s what you like. 


We rented a Jeep Rubicon, as we wanted a fun island car to off road in. It turns out a car is the key to having the best of both worlds throughout the trip, as you’re able to drive around and witness the different parts of the island. One of our waiters said it best, O’ahu can be split into 4 parts, and all have different feels and environments. The North Shore is the best for surfing—super local and beautiful views. It kind of feels like California but not developed!



The East Side of the island is my favorite part, with deserted beaches, amazing views, and bigger waves. The sand is so white and soft, and the ocean is just perfect. You can drive down the street for a delicious fresh lunch and ice cream and then go back to the beach. We didn’t explore the West Side too much; however, the North Shore and East Shore were definitely our favorites. 


Here’s the in depth recap of what we did:


Best Restaurants: 

Amuse Wine Bar- located on the top floor of a furniture store it sure was hard to find! My friend Maura had recommended it, and it was a perfect place for apps and wine. 


SKY Waikiki- Rooftop bar overlooking the Pacific Ocean and the beautiful city of Waikiki. So many great seafood options including sushi and oyster shooters (a must try.) Great cocktails and photo ops!


Seven Brothers Market- Located on the North Shore of Hawaii, this outdoor restaurant was a perfect spot for ahi tuna and cheeseburgers post horse riding. They have a bunch of locations around Hawaii, and their burger was to die for. They also have the Sugar Mill food truck spot around the corner featuring so many different trucks and cuisines. 


Ali’i Coffee- Uhmm this might’ve been the best coffee I’ve ever had? So many different flavors and delicious breakfast options. Located in the Courtyard Marriott in Waikiki, it’s a must stop for breakfast and coffee.


Kai Coffee- We stumbled upon this coffee shop our first morning and frequented it throughout the trip! Incredible coffee, acai, and breakfast sandwiches. 


View from Hula Grill of the sunset
View from Hula Grill of the sunset

Sunrise Shack- I went here on the last day and had a fantastic acai bowl. Don’t forget to try their Hawaiian original Macadamia Nut coffee!


Hula Grill- This was by far our favorite dinner spot. Located in the Outrigger Hotel, it has the most beautiful views of the ocean and the sunsets. Their homemade focaccia is to die for, and their drinks are delicious. 


Notable Mention: Our hotel the Sheraton Princess had a fantastic pool bar, and restaurant called the Splash Bar. We loved the food and how easy it was to eat there on busy days or nights we were too tired to go out!



Excursions: 

We knew we wanted to have a few main activities in Oahu during our trip. We both wanted to snorkel, horse ride, do a booze cruise, and Annabel requested zip lining (I was terrified). The booze cruise sadly was cancelled due to high winds and surf; however, all our other adventures were trip highlights!!


Snorkeling- We snorkeled for sea turtles through a company called Charter Oahu. It left the pier at 9:00 am and took a little under two hours. They boat you out to the middle of the ocean to see turtles, fish, and a coral reef in different spots. We had fantastic weather and saw about 15 sea turtles! They were so amazing. I highly recommend this company for all things snorkeling. 


Hike- We did a hike our first morning at Diamond Head State Park. It was definitely a tourist hike and overly crowded up the narrow walkways. The views were fantastic despite this! Remember to reserve a spot and pay $10 to enter—which we didn’t know until we got there…thankfully the staff was so kind. 


Horseback Riding- Another morning we ventured out to the North Shore to Gunstock Ranch for a horse trail ride! As a horse girl for almost 30 years, I wanted to do the advanced ride, but we decided on the scenic trail ride. The wranglers were amazing, and the horses were very sweet. It was about two hours, and while hot out, it was so worth it! Go earlier in the day and make a North Shore day of it!


Ziplining- Annabel loves ziplining and anything with an adrenaline rush. I originally was goi ng to let her do it and hang back, and then I decided to say screw it and go. I’m working on not letting fear control me! We ziplined through Coral Crater Adventures—the instructors were knowledgeable, fun, and make it a safe experience. We did the 3 Lines Excursion that lasts an hour; however, there’s all different options.


Botanical Garden- Annabel is our little plant lover, and she requested a botanical trip! I wasn’t sure how fun seeing the botanical garden would be for myself, but boy was I wrong! It is hands down one of the most beautiful places I have ever seen. The lush side of the mountains, the beautiful greenery, and views make you feel like you’re right on the set of Jurassic Park. As we should know, Jurassic Park was filmed there! Definitely a must see and check out the little town around it.



Beaches:

The interesting part about Oahu is that unless you’re staying at a resort with a beach, they’re hard to figure out. The beaches around Waikiki are very crowded and often feel like you’re swimming in Times Square—sorry! So, we ventured out to find our favorite beaches on the island. The East Shore beaches are truly beautiful and fantastic…they feel deserted, and the water is so blue. 


The North Shore beaches are calmer in the summer months, meaning they’re perfect for surfing lessons or for Charty to swim. That blue Hawai’i water is truly the most beautiful, magical waters I have ever swam in. The North Shore is notorious for having large waves and sharks in the winter months, but summer is such a dream there.  



Both the North and East shore beaches have pure white sand, and feel like something out of a movie. The Waikiki beaches are a little more city feel, with pebble rock sandy beaches that are small, and numerous people floating around. It's hard to find a spot!


Charty's Extra Notables:

  1. We are so glad we rented a car. Like I said before, it gave us the best of both worlds being in Waikiki, the city, as well as the locals part of the island with beautiful beaches and food. 

  2. Mai tais suck! Seriously. They're a dark rum drink mixed with orange curaçao, and other sugar water. They’re lowkey gross—get a pineapple infused drink or ranch water.

  3. Make sure you’re in a hotel with a bar…it’s truly the best to be at a pool and get a cocktail or two during the swim! 

  4. Leave the first night or morning open and free when you arrive due to time change. I was much more overwhelmed and tired than I thought.

  5. The 11-hour flight is WORTH IT. I promise. The ocean, the views, the food, everything makes the long trip so worth it. 

  6. Leave extra time for travel! Even in the mornings if you’re driving 10 minutes away, give yourself time. O’ahu traffic is no joke and sometimes takes us 35 minutes to go 3 miles.


Thoughts for our Future Trip:

When I come back to Hawai'i either with Annabel or my future husband, I already know exactly what we'll be doing! Thanks Type A personality!


I wish we had time to see Pearl Harbor, but we just ran out of time. People always rave about how it is a must see and really impactful to witness. Next time!


I think I'd want to go to Maui and The Big Island next time as well. People say that the North Shore of Oah'u is like all of Maui and the other islands. I feel it'd be so beautiful!


Kualoa Ranch is supposed to be so amazing. They are a massive ranch on the way to the North Shore and have ziplining, horse riding, ATV tours, and movie set tours. Their ranch is where Jurassic Park 1 and 2 and Lost World were filmed as well as 50 First Dates.


We had such an amazing time on this island and are so grateful for the experiences! The best was coming home in the HI airport, and having to be checked for not firearms--but pineapple! You're legally not allowed to take home any produce from Hawai'i.


Hawai'i is truly such a dream and I will be missing it forever ❤️


-Charty


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