Allison & Keith | Oahu Engagement
One of my favorite destinations to plan romantic getaways to is Hawaii so when Allison and Keith came to me with a romantic trip to Hawaii in mind, I said “Hell yes!!!”
But what made this trip super special? Keith proposed to Allison at the end of the trip and she said YES! But let’s start from the beginning…
Allison and Keith live in Vermont and are super active. When they came to me they had a few ideas in mind for Hawaii: they loved hiking, snorkeling, and being active. They definitely wanted to add some cultural aspects to their itinerary and see nature up close, like whale watching. They were trying to go for a laidback, comfortable vibe where they had some days planned, some days designated for random exploration and wandering, while other days were dedicated to the beautiful beaches.
Oʻahu, affectionately known as “The Gathering Place,” truly lives up to its charming nickname! This delightful third largest Hawaiian island is where most of Hawaiʻi’s wonderfully diverse population calls home. It’s a vibrant mix of East and West cultures, all beautifully intertwined with the rich traditions of the Native Hawaiian people. The magic of Oʻahu lies in its amazing blend of the old and the new, making every moment of exploring — from the lively city streets to the chill vibes of the surf towns, it’s perfect for romance seekers!
One of my favorite excursions for couples who love the outdoors in horseback riding at Kualoa Ranch.
About the Trip
Keith and Allison stayed in Waikiki at the Ohana Waikiki East by Outrigger; this hotel is newly renovated and although not on the beach so close that you’ll get some ocean views and walking distance to all your amenities. Equipped with their rental car, they were ready to explore the entire island from Waikiki. With all my couples, I provided them an easy to use app with all of their reservations, vouchers, and tickets in one accessible location.
One of their first stops was horse back riding in Kualoa Ranch. The ranch offers stunning views of the lush landscapes and has been a backdrop for many movies. Afterwards, I had them hit up a local spot for Hawaiian comfort food where they will pack utensils and napkins on request and you can head right down the street to Waiāhole Beach Park for a little picnic.
Allison and Keith love to be active so I also added a few hiking destinations to their itinerary. Looking for an uphill journey?: Koko Crater is probably the most iconic. Koko Crater Trail, better known as “Koko Head Stairs”, is your StairMaster workout for the day, with a rewarding panoramic view up top. This Oahu hike will test your endurance and strength to continuously take each additional step up the mountain as you stride over 1,000 steps to reach the top! As challenging as it sounds, hiking the Koko Head trail is a fun and very popular hike on Oahu. Hiking uphill doesn’t sound for you but you still want to enjoy the great outdoors? Manoa Falls Trails might be more appropriate for your tastes. Head out on this 1.7-mile out-and-back trail near Honolulu, Oahu. Generally considered a moderately challenging route, it takes an average of 1 h 8 min to complete. This is a very popular area for hiking, so you'll likely encounter other people while exploring. The trail is open year-round and is beautiful to visit anytime of the year!
Snorkeling can be the perfect activity for active couples on their honeymoon in Hawaii. There are so many choices throughout the islands.
Keith had snorkeling high on his list and Hanauma Bay Nature Preserve is a stunning and unique destination located on the southeastern side of Oahu, Hawaii. Formed within a volcanic cone, this pristine marine ecosystem offers visitors an amazing place to snorkel and explore the diverse wildlife that inhabit the area. The bay is protected by vertical crater walls and a peripheral reef which help keep the water calm and tranquil, making it an ideal spot for swimming, snorkeling, and observing marine life. Visitors can expect to see hundreds of species of fish, coral, and other aquatic creatures while exploring Hanauma Bay Nature Preserve. Reservations were required ahead of time and it’s important to check those before heading there.
With my travelers, I love to balance the itinerary with high and low intensity activities. Located in Oʻahu’s northeast corner in the town of Lāʻie, the Polynesian Cultural Center is one of the island’s top cultural attractions. It is an intriguing place for anyone interested in Polynesian Culture, but it is especially popular with families, who are drawn to its array of kid-friendly activities and fun, educational opportunities. The cultural presentations of the island nations are usually informative and full of crowd-pleasing jokes. The Polynesian Football Hall of Fame is very small, but interesting for NFL fans. The evening show, Hā Breath of Life, is an entertaining Hawaiian musical [& honestly a 10/10, a highlight of my own trip], although it doesn’t end until 9 p.m., and the one-hour drive back to the south shore afterwards is a drag. That didn’t stop Keith and Allison who were so moved by the show, driving back to Waikiki wasn’t all that bad.
She said YES! How gorgeous is this ring. They found in locally in Oahu.
The best part of the trip? Keith planned an engagement after their whale watching tour. Armed with coffee from Green World Coffee Farm in the botanical gardens, Keith asked Allison to marry him and she of course said YES!!! ::squeals:: How romantic is it to get proposed to in literal paradise. Together they picked out a beautiful ring from a local jeweler in Kailua, the perfect souvenir for a memorable trip! I’ll leave it to the couple to tell their story in the next section
Q&A With The Couple
How did you meet? Tell me a little about your love story.
Okay soooo, we actually met as roommates when we both moved to VT for the first time. Keith is from NJ and I am from MD. I found an apartment and knew I needed a roommate and he happened to be one of the people who reached out about my ad on Craigslist (we always joke that we met on Craigslist). We clicked instantly and did so much together all over Vermont. We were hiking and camping and kayaking every weekend and I immediately knew he was my soulmate. We have been pretty much inseparable since meeting for the first time 8 years ago.
Did this vacation incorporate any special history, hobbies, or passions that are special to you as a couple?
Hawaii has always been on the top of our list to visit together and Keith had been stationed there while in the Marine Corps and has always wanted to go back.
Describe the feeling of this vacation (season, weather, atmosphere, vibe, emotion)
This vacation was very special to us. It was our first real solo vacation together and our first time flying together. We tried to hit something that incorporated each of our passions. Trying local food like Waiahole poi factory and getting cut fruit from a fruit stand on the side on the road, hiking up Diamond Head, seeing local plants at the Wahiawa Botanical Gardens, and a boat tour to see whales, dolphins and sea turtles!!
We went at the end of March which felt like a great time to be there. Not too rainy, mid to high 70s or even low 80s during the day and cool 60-70s at night. Busy in Waikiki but there were moments in the mornings at certain beaches where we were the only people there!
This vacation felt magical. I felt so happy and excited for each day, each excursion/activity felt better than the last. We felt more connected and closer to each other.
What was a unique touch, location, or activity that stood out on your vacation?
If I had to choose highlights, which is tough, I would choose the Polynesian cultural center and the whale watching tour. The polynesian cultural center was so cool, very well put together and engaging. We did the package of the tour, the luau and the breath of life show and it was awesome. The breath of life show was unbelievable and so moving, we were both tearing up at certain points. The whale watching tour was super cool. It was a small semi private group with three crew members and up to 6 passengers. The crew member leading the tour was a marine biologist and took incredible photos as well. He was really knowledgeable and told us tons of information about the animals we were seeing. We saw spinner dolphins, a humpback whale and pilot whales! Since dolphins and humpbacks are protected, you can’t get in the water while they are around but we got an opportunity to snorkel while the pilot whales were around and at one point they swam below us and you could hear them making noises. It was so amazing. The last hour or so they took us over to a coral reef and let us snorkel around there to see the fish and the sea turtles. Amazing!
What was a special moment of this vacation that stood out in your memory?
The day we did the whale watching tour, it was early so after that we went to the Green World Coffee farm and got coffees to walk around the botanical gardens. While we were there Keith asked me to marry him!!! It was such a surprise! He didn’t have a ring picked out so we went to some local jewelers in Kailua and Waikiki and found a ring towards the end of the trip.
Honestly a trip of a lifetime. And we are 100% going back to get married there
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