Three Girls, One Bucket List: Hawaiʻi on Pride of America

Hurricane Lala had other plans for our sailing before we ever set foot on the ship—a shortened itinerary, a lost day, a canceled Maui port. But if there's one thing I want every client to know, it's this: Even when Hawaiʻi throws you a curveball, it still finds a way to leave you speechless. For most people, Hawaiʻi sits at the very top of the bucket list—and for good reason. Few places on earth blend adventure, culture, and romance quite like this.

This coastline. These cliffs. This ocean. Maui, you're stunning!

We opened in Oahu, standing inside Iolani Palace, imagining what it must have felt like to be Hawaiian royalty within those walls—then closed our loop on the same island weeks later at Pearl Harbor, where the ship still rests beneath the water and the silence around the memorial says more than words could. In between, there was a rooftop dinner with live music drifting over Waikiki, and a plate of poke eaten with Diamond Head glowing pink in the distance. Maui handed us a curveball of its own—mudslides shut down the Road to Hana—so we grabbed a Jeep and carved our own path along the coast instead, chasing waterfalls and blowholes with the windows down, ending the day with a chocolate tasting in a Lahaina still writing its comeback story.

Can't beat this view: Waikiki Beach with Diamond Head watching over us!

Iolani Palace: stunning architecture and a reminder of Hawaii's rich royal past.

On the Big Island, Kona wrapped us in the smell of fresh-roasted coffee grown on volcanic soil, while a centuries-old painted church sat quietly on a hilltop above the coastline—proof that this island rewards those who go beyond the ship's shadow. And Kauai, the Garden Isle, saved its magic for last: torchlight and drumbeats at a traditional luau, then standing at the edge of Waimea Canyon the next morning, watching the colors shift across a landscape that earns every bit of its "Grand Canyon of the Pacific" nickname. It's easy to see why so many couples choose Kauai—and Hawaiʻi as a whole—for honeymoons and milestone celebrations; the scenery alone does half the romancing for you.

One of my favorite shots of the whole trip—palms framing this hidden, sacred cove in Kona!

Small church, huge impact. The Painted Church near Kona is a hidden gem.

Lost in the view at Waimea Canyon—pure, jaw-dropping beauty.

I didn't just read about these islands—I stood in them, tasted them, and let the unexpected moments shape the trip just as much as the planned ones. That's the kind of firsthand insight I bring to every itinerary I build. Whether Hawaiʻi has been on your bucket list for years, or you're dreaming of it as your honeymoon destination, let's talk—I'll help you write your own version of this story.

Big Kahuna, big flavor. This poke bowl was everything.

Honoring the past at Pearl Harbor—a moment we won't forget.

Before you go

• Book excursions independently when possible—ship excursions are convenient but often pricier than booking directly with local operators for the same activity.

• Pack reef-safe sunscreen—some islands restrict traditional sunscreens due to coral reef protection laws.

• Bring layers—mornings, evenings, and higher elevations (like Haleakalā or coffee farms) can be noticeably cooler than the coast.

Getting around

• Tender ports (like Kona) require taking a small boat from ship to shore—budget extra time, especially during peak disembarkation.

• Rideshares (Lyft/Uber) are convenient but pricey, particularly airport-to-resort routes—renting a car for a day is often more cost-effective if you want to explore beyond the port area.

• If road conditions or weather affect a planned route (like Road to Hana), have a backup plan—a rental car gives you flexibility ship excursions don't.

Weather & timing

• Hurricane season runs roughly June to November—itineraries can shift with little notice, so it's worth booking cruise or travel insurance.

• Whale watching season (roughly December to April) is a great add-on if visiting during those months

Culture & etiquette

• A little Hawaiian language goes a long way—learning words like "mahalo" (thank you) and "aloha" shows respect for the culture.

• Many historical and cultural sites (like Iolani Palace or Puʻuhonua o Hōnaunau) are deeply meaningful to Hawaiians—treat them with the same respect you would any sacred site.

Food

• Try poi at least once—it's a cultural staple, though it pairs best with other dishes if it's your first time.

• Don't skip local, non-resort restaurants—some of the best meals (chocolate tastings, coffee farms, poke bowls) came from small, local spots near the ports.

For more inspiration and insider recommendations, visit our Hawai'i page.