Some places stay with you long after you’ve left. For me, Hawaii is one of them.
Over the years, I’ve visited during very different stages of my life – as a young woman travelling on my own, on our honeymoon and later with my family. Looking back, each trip has given me a completely different reason to love the islands.
Hawaii isn’t just somewhere I’ve visited. It’s somewhere that’s quietly woven itself through different chapters of my life.
Why I Keep Returning
One of the things I’ve always loved about Hawaii is how familiar and unique it feels at the same time.
If you’re visiting from outside the United States, there’s something exciting about experiencing iconic American hotels, shopping and diners while being surrounded by swaying palms, warm ocean breezes and the sound of Hawaiian music drifting through the streets.
Waikiki, in particular, has a timeless quality. The beachfront hotels, surfers carrying boards down Kalākaua Avenue and sunset drinks overlooking the ocean give it a nostalgic charm that never seems to fade. No matter how many times I return, it still feels unmistakably like Hawaii.
Staying in Waikiki
On our honeymoon, we stayed at the Sheraton Waikiki, which remains one of my favourite hotels on the island. Its adults-only infinity pool overlooking Waikiki Beach is reason enough to stay there. We spent our mornings swimming in the ocean before wandering along Kalākaua Avenue and relaxing by the pool in the afternoons.
On other visits, we’ve also stayed at Hilton Hawaiian Village Waikiki Beach Resort and Alohilani Resort Waikiki Beach, both of which are excellent options depending on the type of trip you’re planning.
Waikiki is special to me for another reason too. Many years ago, after a difficult breakup, I travelled there on my own. I found myself spending evenings at the iconic Duke’s Waikiki, listening to live music and chatting with fellow travellers, pilots, footballers and locals sitting nearby.
There was something about being somewhere completely different, surrounded by people I’d never met before, that was exactly what I needed at the time. Duke’s somehow managed to feel lively without ever feeling overwhelming, and it’s still one of the first places I visit whenever I’m back in Waikiki.
Exploring Oahu
For our honeymoon, we combined Oahu with several days in Maui. We stayed at Aston at The Whaler on Kāʻanapali Beach, rented a convertible Mustang and spent our days driving along the coastline with the roof down, stopping whenever we found another beautiful beach or lookout.
Kāʻanapali Beach was fantastic for snorkelling, with clear water and plenty of marine life just offshore. Our holiday had actually started with a 24-hour flight delay leaving Sydney, meaning we lost an entire day in Maui, but thankfully Hawaii has a way of making you forget travel delays remarkably quickly.
One of my favourite memories from Maui still makes me laugh. We stopped at a Hawaiian food truck, and my husband confidently tried to walk straight inside, assuming it worked like a café.
A very amused local gently explained that the truck was actually someone’s home and that ordering happened through the serving window instead.
It’s those unexpected little moments that often become the stories you remember most.
Maui
For our honeymoon, we combined Oahu with several days in Maui. We stayed at Aston at The Whaler on Kāʻanapali Beach, rented a convertible Mustang and spent our days driving along the coastline with the roof down, stopping whenever we found another beautiful beach or lookout.
Kāʻanapali Beach was fantastic for snorkelling, with clear water and plenty of marine life just offshore. Our holiday had actually started with a 24-hour flight delay leaving Sydney, meaning we lost an entire day in Maui, but thankfully Hawaii has a way of making you forget travel delays remarkably quickly.
One of my favourite memories from Maui still makes me laugh. We stopped at a Hawaiian food truck, and my husband confidently tried to walk straight inside, assuming it worked like a café.
A very amused local gently explained that the truck was actually someone’s home and that ordering happened through the serving window instead.
It’s those unexpected little moments that often become the stories you remember most.
Final Thoughts
What keeps bringing me back to Hawaii isn’t just the scenery. It’s how easy it is to settle into island life. The beaches, warm evenings, live music and relaxed atmosphere make it somewhere I find myself slowing down almost without thinking about it.
Whether it’s watching surfers in Waikiki, driving the coastline of Maui or listening to ukulele music as the sun goes down, Hawaii has a way of becoming more than simply another holiday destination.
For me, Hawaii will always represent different stages of my life – travelling independently when I needed a new beginning, celebrating our honeymoon, returning with family and creating completely different memories each time.
Perhaps that’s why I keep going back. The islands haven’t really changed, but each time I visit, I have.
Mrs Globetrotter Tips
Best for: Couples, honeymooners, families and first-time visitors to Hawaii.
How long to stay: Seven to ten days if combining Oahu and Maui. If you have the time, I’d rather spend a few nights on each island than try to squeeze both into a very short trip.
Where to stay: In Waikiki, Sheraton Waikiki is my pick for couples and honeymooners, particularly for its incredible oceanfront infinity pool. For families, Hilton Hawaiian Village Waikiki Beach Resort has extensive resort facilities and plenty to keep everyone entertained. Alohilani Resort Waikiki Beach is another great option if you prefer a more contemporary Waikiki stay. On Maui, we loved Aston at The Whaler on Kāʻanapali Beach for its beachfront location and apartment-style accommodation.
Don’t miss: Duke’s Waikiki, a drive to the North Shore, snorkelling at Kāʻanapali Beach in Maui and sunset walks along Waikiki.
Worth splurging on: An oceanfront room for at least a few nights. Waking up to the Pacific and watching the sunset from your hotel completely changes the experience.
Would I return? Absolutely. Every visit has been different, and I still find new reasons to love Hawaii.
