Following the Wind and Waves: The World of Hawaii Cruising

There are countless ways to experience Hawaii, but few compare with waking up each morning to a completely different island beyond your cabin window or balcony. Instead of repeating airport check-ins and repacking your luggage, you spend the day exploring an island and return to the ship in the evening to relax.

Set in the middle of the Pacific, Hawaii is visited by a variety of cruise routes. The best-known island-hopping option is a seven-night itinerary from Honolulu connecting Maui, Hawaii Island and Kauai. Other cruises cross the Pacific from the U.S. West Coast, call in Hawaii on seasonal routes from Canada, or continue toward Tahiti, Australia and other South Pacific destinations.

We chose Pride of America, a cruise designed around exploring Hawaii’s major islands. In 2024, three of us traveled together on the seven-night itinerary. This story is based on that firsthand experience, with key information updated for December 2025.

The Journey Begins

Pride of America alongside the pier at golden hour, with balconies and lifeboats above the quay
Wine and champagne raised on the deck rail as the sun sets over the harbour before sailing
Sunset from the open promenade deck of Pride of America, with the NCL funnel above

A cruise vacation begins well before you step aboard. As the sailing date approaches, the cruise line sends check-in instructions, baggage tags, travel-document information and other pre-departure details by email and through your online account. Completing online check-in and reviewing the instructions in advance makes embarkation much easier.

Unlike a hotel stay, cruise passengers can usually select a cabin category, and often a specific cabin, when booking. At the terminal, the process is primarily about confirming the reservation, verifying identification and completing embarkation. International travelers should carry the passport and travel documents required for their nationality and itinerary, and should always check the cruise line’s final instructions before departure.

We arrived at Honolulu’s Pier 2 a little early and completed check-in without rushing. If possible, arriving early enough to enjoy the first hours onboard is worthwhile. Once aboard, complimentary dining and snacks are available, while alcoholic beverages and certain drinks depend on the package booked.

As departure approaches, the atmosphere becomes festive, almost like a small party. We took wine and champagne out to the deck and watched Honolulu Harbor and the Pacific while waiting to sail. By evening, the ship’s horn sounded and Pride of America slowly pulled away from the harbor. Our week of island hopping had begun.

Four Islands in Seven Nights

Pride of America sails roundtrip from Honolulu, visiting Oahu, Maui, Hawaii Island and Kauai. The ship overnights in Maui and Kauai and visits both Hilo and Kona on Hawaii Island. With no full sea days on the standard itinerary, much of the week can be devoted to exploring the islands.

At each port, travelers can choose among the cruise line’s shore excursions, locally operated guided tours and independent sightseeing, including rental cars where practical. We used a combination of these options depending on what we wanted to see.

Typical 7-Night Itinerary

Pride of America normally departs Honolulu every Saturday and returns to Honolulu the following Saturday morning.

Day Port and plan
Saturday Depart Honolulu
Sunday Maui, Kahului ; arrive and overnight
Monday Maui ; sightseeing and departure
Tuesday Hawaii Island, Hilo
Wednesday Hawaii Island, Kona
Thursday Kauai, Nawiliwili ; arrive and overnight
Friday Kauai ; sightseeing, afternoon departure and Napali Coast cruising
Saturday Return to Honolulu in the morning

Maui | Haleakala and a Helicopter Flight

Visitors at the Haleakala crater rim on Maui, looking out over a sea of cloud
A Stay on Trail sign on the cinder slope inside the Haleakala crater

The next morning, the ship was already docked in Kahului. After breakfast, we headed to Haleakala, where we looked across the enormous volcanic crater, saw silversword plants and spent about 90 minutes hiking into the crater landscape. It felt completely different from the beaches and palm trees usually associated with Maui.

Because the ship stays overnight in Maui, the schedule offers more flexibility than a single-day port call. On our second day, we took a roughly 50-minute helicopter tour over Haleakala and the Hana area, viewing rainforest, valleys and coastline from above. Seeing the same island first by land and then from the air was one of the highlights of the trip.

Life Onboard

The pool deck of Pride of America by day, with loungers, bar and open ocean beyond
The pool deck of Pride of America lit in blue and pink after sunset

Pride of America suited our style of traveling: active island sightseeing during the day and a comfortable place to relax in the evening. During our cruise, onboard activities included hula lessons, lei making, Hawaiian music, dance programs, wine tasting, yoga and other activities.

There is no need to join every program. After a day ashore, we were just as happy relaxing by the pool or hot tub, browsing the gallery or simply spending time on deck watching the ocean.

Dining at Sea

The Skyline main dining room on Pride of America, with its mirrored ceiling and chandeliers
Breakfast, fruit and pizza on a table by the window as the ship sits in port

The cruise fare includes a selection of complimentary dining venues. We often had breakfast at the Aloha Cafe buffet and also enjoyed more leisurely meals at Skyline. For dinner, we tried Liberty and Skyline as well as specialty restaurants.

Specialty dining, alcoholic beverages and certain drinks may cost extra depending on the package booked. Restaurant lineups and package conditions can change, so it is best to check the current details when making a reservation.

Hawaii Island | Hilo and Kona

Hilo Harbour on the Big Island seen from the ship, with tugs at the quay and Mauna Kea beyond
The Kilauea caldera from the air through a helicopter window, steam rising through cloud
A Pride of America tender boat approaching Kailua-Kona on the Big Island
The seawall path along Alii Drive in Kailua-Kona, with palms and turquoise water

In Hilo, we joined a locally guided tour to Hawaii Volcanoes National Park and other sights around the Hilo area. The lush tropical landscape and immense volcanic terrain gave this side of Hawaii Island a character very different from Maui.

The following day in Kona, we explored Kailua-Kona at our own pace, visiting historic sites, the waterfront and local shops. Although Hilo and Kona are on the same island, the contrast between Hilo’s greener landscape and Kona’s brighter, drier coast was striking.

Kauai | Waimea Canyon and the Napali Coast

NCL Pride of America cruising past the green cliffs of the Napali Coast on Kauai

On Kauai, we explored Waimea Canyon and the Princeville area. Deep valleys and green mountain scenery revealed yet another side of Hawaii after the volcanic landscapes we had seen earlier in the week. Kauai is also an overnight port, allowing more flexibility when planning sightseeing than a short daytime call.

The second day in Kauai ends with the part of the itinerary you cannot reach by car. After leaving Nawiliwili in the afternoon, the ship runs along the Napali Coast, where the cliffs drop straight into the ocean and the valleys between them open up one after another. There is no road to this stretch of coastline, so passing it slowly from the deck is one of the strongest arguments for seeing Hawaii by ship. We stayed outside until the light went.

How Should You Explore Each Port?

There is no single best way to explore every island. A guided tour can be convenient for first-time visitors or those who prefer not to drive long distances, while independent sightseeing works well for travelers with specific places they want to visit. Helicopter flights, snorkeling, hiking, golf and many other activities can also be incorporated depending on the island.

We mixed the two. In Hilo we booked a guided tour, because we wanted someone who knew the national park and could judge the weather. In Kona we walked, since everything we wanted to see sat near the pier. Both days worked, for different reasons.

When exploring independently, always check the ship’s final boarding time before leaving the port. On days when the ship sails that evening, allow a generous margin for traffic and travel time back to the terminal.

Cabins and Approximate Cruise Fares

Arriving into Kahului Harbour on Maui from the ship rail, with Haleakala in the distance

Pride of America fares vary considerably by month, sailing date, season, booking time, promotion and cabin category. The following figures are only a general planning range for one person based on double occupancy, including taxes and basic mandatory charges.

An Inside cabin, with no ocean view, can generally be budgeted at around $1,500 to $2,000 per person. An Oceanview cabin, which has a window but no private balcony, is roughly $2,000 to $3,000 per person. A Balcony cabin, with its own outdoor space, is roughly $3,000 to $4,000 per person. Suites and higher categories can vary much more widely.

The cruise fare covers the cabin and standard complimentary dining, but specialty dining, alcoholic beverages and some other drinks, Wi-Fi, spa services, shore excursions and service charges may be additional depending on the booking and package. A realistic trip budget should therefore include both the cruise fare and the activities or services you plan to use.

Cabin choice also depends on how you intend to spend the week. If most daylight hours will be spent exploring the islands, an Inside cabin can be practical. For travelers who want to watch arrivals and departures from their own room, a Balcony can add considerably to the experience. We took a Balcony, and on the mornings the ship came into Kahului and Nawiliwili it earned the difference ; we watched both arrivals from the room before breakfast.

One practical detail worth settling before you sail. A balcony cabin is laid out with two single beds, which suited us as two friends traveling together. Couples can ask for them to be made up as one bed instead, and that request is far easier to arrange with the cruise line in advance than on the day you board.

A balcony cabin on Pride of America made up with two single beds, balcony door open to the ocean
The same balcony cabin made up as one bed, with the balcony and ocean beyond

Pride of America, Refreshed in 2025

The Capitol Atrium on Pride of America, with its domed ceiling and glass lifts
A refreshed sun deck on Pride of America, with cabanas, day beds and a bar

Our cruise took place in 2024, but Pride of America underwent a refurbishment in 2025. New Club Balcony Suites and Inside Staterooms were added, Starbucks was introduced in the Capitol Atrium, pickleball was added to the sports court, and spaces for children and teens were updated.

The ship may have changed, but the basic idea remains the same: a Honolulu-based cruise connecting several of Hawaii’s major islands in one week.

Looking Back on Seven Days in Hawaii

Over seven nights, we experienced Haleakala and the Hana region on Maui, Hawaii Volcanoes National Park from Hilo, the Kona waterfront, and Waimea Canyon and the Napali Coast on Kauai. Days were spent exploring the islands, while evenings brought us back to the restaurants, pool and open decks of the ship.

Travelers who prefer to settle into one island and explore slowly may be happier with a traditional land vacation. But for those who want to experience the different landscapes and personalities of several Hawaiian islands in a single trip, Pride of America offers a distinctive way to travel.

Seven nights, with the blue Pacific connecting one island to the next. For us, this Hawaii cruise felt less like a conventional voyage at sea and more like an island-hopping journey with a floating hotel carrying us along the way.

Before You Book

Itineraries, port times, onboard venues, activity schedules and package conditions are all subject to change, and fares move with the season and sailing date. Check the cruise line’s current itinerary and pricing for your specific departure before booking.