Can one destination feel like three completely different vacations? After visiting Hawaii three times over four decades, I can answer with an enthusiastic yes.
Some destinations are worth visiting once. Hawaii, in my experience, is worth rediscovering over a lifetime.
The first time I visited Hawaii was in the 1980s with my fiancé. Like many first-time visitors, we checked off the classics. We rose before dawn on our very first morning—still operating on East Coast time—and drove to the summit of Haleakalā wrapped in hotel blankets to watch the sunrise above the clouds. We navigated the winding Road to Hāna, snorkeled in the crystal-clear waters of Molokini Crater, and stood quietly at Pearl Harbor, deeply moved by memories of World War II that had been part of both my studies and my family’s stories.
But one day still ranks among the ten best of my life.
After taking a helicopter flight over Kauaʻi’s spectacular Nā Pali Coast, we returned the following day aboard a motorized raft. Towering emerald cliffs plunged into impossibly blue water. Our captain maneuvered into sea caves carved from ancient lava flows, where we shouted just to hear our voices echo off the stone walls. It was exhilarating, breathtaking, and unlike anything I had ever experienced.
The second time, Hawaii challenged me.
A girlfriend and I joined a Backroads bicycle tour around the Big Island. One memorable day we slowly climbed the flank of a volcano using the old “paper boy” technique—zigzagging back and forth because riding straight uphill simply wasn’t an option. Progress was measured in feet rather than miles.
Another day, I found myself alone during a torrential tropical downpour. While the rest of the group wisely accepted a ride in the support van, I stubbornly kept pedaling through sheets of rain toward our destination—a macadamia nut farm. Just as I rolled into the driveway, the sun emerged. I wrung out my soaking clothes, enjoyed a warm cup of macadamia nut coffee and a fresh cookie while learning about Hawaii’s nut industry, then climbed back on my bike. Naturally, the skies opened again the moment I left. By the time I reached the hotel, everyone else was warm, dry, and comfortably settled. I was drenched—but I wouldn’t trade that adventure for anything.
The third visit revealed the Hawaii I never knew existed.
This February, a longtime friend and I experienced the islands from an entirely different perspective aboard a small expedition ship. Don’t expect luxury accommodations—they’re comfortable, clean, and about what I’d call three-star. But everything else is unquestionably five-star: the cuisine, expedition leaders, naturalists, crew, and unforgettable experiences. One company in particular, UnCruise Adventures, has perfected this style of travel. It’s an outstanding choice for active adults and families with older children, teens, and twenty-somethings who prefer adventures over pool chairs.
We arrived in Maui during humpback whale birthing season, watching mothers patiently teach their calves how to breach while escort whales remained nearby to protect them. During one kayaking excursion, an escort whale surfaced directly in front of us, almost seeming to politely suggest we’d come close enough. It felt like a gift.
One evening we slipped into the ocean wearing wetsuits and snorkel gear, each of us holding onto a surfboard while our feet rested on pool noodles beneath the water. Lights from nearby resorts attracted plankton, which in turn attracted giant manta rays. One after another, these graceful creatures glided inches beneath us, their enormous mouths open as they fed. We could clearly see their bellies and cavernous mouths as they passed directly below us. Then, as if on cue, schools of brilliantly colored tropical fish surrounded us, creating one of the most magical underwater experiences I’ve ever had.
Yet the greatest surprise of all was Molokaʻi. Often overlooked by visitors, the island offered one of the trip’s most meaningful experiences. Beyond its breathtaking landscapes, we were introduced to Hawaiian history, traditions, and storytelling. We visited local residents who shared their customs, learned about King Kamehameha’s remarkable legacy in unifying the Hawaiian Islands, and gained a much deeper appreciation for the culture that continues to shape Hawaii today. Our evening at the Kalaupapa Museum brought that history to an even more personal level. We learned the heartbreaking story of Hansen’s disease (formerly called leprosy) and how, for decades, patients from across America were exiled there. Even after an effective treatment was discovered, many remained because the community had become their family. A candlelit dinner featuring traditional Hawaiian food and music, surrounded by powerful historic photographs, made for an evening none of us will ever forget.
If you’re planning your own Hawaiian adventure, spring offers pleasant temperatures, blooming landscapes, and the tail end of humpback whale season. Summer brings warm water, excellent snorkeling, and wonderful family beach vacations. Trade winds keep temperatures comfortable, although they can occasionally become breezy. Hurricane season officially runs from June through November, but direct hurricane strikes on Hawaii are rare. Winter offers lush green landscapes, spectacular surf on the north shores, and, from December through March, some of the world’s best humpback whale watching. And if Maui has been on your wish list, this is an especially meaningful time to visit. Following the devastating Lahaina wildfires, the island continues its recovery and warmly welcomes visitors whose tourism dollars are helping local families and businesses rebuild.
Looking back, I’m struck by how one destination has given me three completely different vacations: romance in my twenties, adventure in my thirties, and discovery later in life. Perhaps that’s Hawaii’s greatest gift—there are countless ways to experience these remarkable islands, and no two visits ever have to be the same. Whether you’re dreaming of a honeymoon, a multigenerational family vacation, an active adventure, or simply the trip you’ve promised yourself for years, I’d love to help you discover the Hawaii that’s perfect for you. As both a lifelong traveler and a travel advisor with Cruise Planners, there’s nothing I enjoy more than helping others create memories they’ll still be talking about forty years from now.
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