This is 41! My Solo Birthday Adventure in Hawaii

My first official solo birthday trip was for my 34th birthday. I ventured to Iceland and had the time of my life. The freedom to explore at my own pace, journal, and listen to my inner thoughts was a game changer for me.

Since then, I’ve traveled solo quite a bit. Ten days in Morocco, a long weekend in Antigua, a week in Napa Valley, two days in Panama, etc.

My birthdays since, however, were different. The following year I hosted a group trip to Bali for 22 people to celebrate my 35th birthday. I continued to host birthday group trips for a couple years after that. Guatemala (38), Dubai (39), Mozambique (40)…

For my 41st birthday, I decided I wanted to do something different. I wanted to return to that initial feeling of self-liberation that I experienced at 34. So, I took a solo trip to a place I’ve had on my bucket list since I was a kid.

Hawaii.

Itinerary Snapshot

Day 1: Arrived in Honolulu, explored the area, watched the sunset on Waikiki Beach.
Day 2: Beach day, sunset catamaran cruise, dinner at Maui Brewing Company.
Day 3: Circle tour of Oahu, Dinner @ Mai Tai Bar
Day 4: Surfing lessons with Big Wave Dave Surf, Beach photoshoot with Henry Li.
Day 5 (Birthday): Helicopter tour of Oahu, Mauka Warrior Luau, live music at Secret Spot.
Day 6: Checked out, relaxed until flight departure.

Day 1: Vibe Check

As soon as I checked into my hotel, I did what I always do when I travel solo—I took to the streets to explore. I never plan activities on my arrival day. I usually use this day to settle in, familiarize myself with my surroundings, and intentionally explore the the sights, sounds, and smells of the area.

This is how I feel out the vibe of where I am. I specifically watch how people move, how they interact, assess my safety, etc.

After walking and stopping to eat at Paia Fish Market (so good), I found a spot on the beach to watch the sunset. Watching the sun sink into the Pacific while waves gently roll onto the shore was such a peaceful and calming experience. That first night, I felt a deep sense of peace and excitement for the week ahead.

I ended the night chatting with strangers and enjoying a Mai Tai flight at The Rumfire Bar in the Sheraton Waikiki Beach Resort.

Day 2: Beach Day and Sunset Cruise

My second day was dedicated to relaxing on the sandy shores of Waikiki. I slept in and then spent the day laying around on the beach, reading, people watching, and taking a dip in the ocean every so often.

My Beach Must Haves:

Waterproof Fanny Pack

Backup Battery Charger

After a relaxing day, I booked a catamaran cruise to take in the sunset from the water. Listen, golden hour in Hawaii hits differently when you’re out on the sea, watching the sky light up with shades of pink, orange, and lavender. It was gorgeous.

When the catamaran brought us back, the sun was still setting and I was still in awe. I walked off the boat and found a spot on the beach to finish watching the sunset. I COMPLETELY forgot to get my flip-flops out of the container that we were required to place them in before boarding and of course the boat was long gone when I realized this. I ended up crossing the street barefoot and buying a new pair across the street!!

Day 3: My Super Touristy Day

When I was researching things to do for solo travelers in Hawaii, I heard a lot about the famous circle tours of Oahu, so I decided to give it a try. The tour took me to some breathtaking spots around the island, but honestly? I confirmed something about myself—I’m just not a fan of big tourist groups. If I could do it over, I would’ve rented a car and explored at my own pace. But hey, it’s all part of the experience, right? You live, you learn.

The day wasn’t a total loss, though. I still enjoyed the tour overall. I just found myself uncomfortable around a group of older, white tourists who seemed to question my presence as a Black, solo traveling woman. Their questions felt loaded, and I realized that I was an anomaly to them. The vibes were just weird, and I found myself keeping more to myself than I usually would in this kind of setting.

Nonetheless, I ended my day back on beach at the Mai Tai Bar, located in the Royal Hawaiian. This time I relaxed under the stars long enough to watch the moon fade into the water with live music and great drinks.

Day 4: Surf Lesson and Beach Photoshoot

Surfing has always been on my bucket list, so I figured why not learn in a place known for surfing!!! I signed up for a lesson with Big Wave Dave Surf and Coffeeshop on Airbnb Experiences. My instructor Lloyd was super patient with me. He helped tow me when my arms got tired of paddling, and he was my biggest cheerleader when I struggled to stand still on the board. After a few tries, I actually managed to catch a small wave for the coolest .375 seconds of my life! It was such a rush!!

Later that evening, I treated myself to a photoshoot on the beach to capture all the birthday glow and good vibes. An experience that I also found on Airbnb excursions with Henry Li Photography. And I must say… the photos came out really nice!

Day 5: The Ultimate Birthday—Helicopter Tour & Luau

My actual birthday was packed with excitement. I started the day with a helicopter tour of Oahu, and it was seriously like something out of a movie. Flying over the lush mountains, the sparkling coastline, and even seeing Pearl Harbor from above was an unforgettable experience. It was one of those “pinch me” moments where I couldn’t believe I was living this life.

After the ride, I spent some time chillin’ by the pool in my Airbnb before heading out to my evening Luau. That evening I attended the Mauka Warrior Luau. From flower-making to a kava tasting, and of course, the traditional dances, it was such a vibrant, joyful way to end my birthday.

After the luau, I ventured out for some live music at a bar called Secret Spot located in The Laylow Autograph Collection Hotel. It was the perfect vibe to wrap up the day. I was grateful for every moment.

Day 6: The Last Day…

The next morning, I woke up with that conflicting feeling of being ready to get back home yet wanting to stay a few more days. After packing up and checking out of my hotel, I spent the day people-watching and soaking up the last bit of Hawaiian sunshine. My flight wasn’t until later in the evening, so I had some time to just relax and reflect on the week. I was able to store my bags at a nearby facility and returned to the Secret Spot for brunch to get some work done before my journey home.

Overall, this solo trip to Honolulu was the perfect way to celebrate my birthday. I got to relax, try new things (like surfing!!), and experience the rich culture of Hawaii. Whether you’re thinking of a solo adventure or group trip, Hawaii is a vibe for sure.

Book that flight, secure the accommodations, build the itinerary, and have fun!