See Painted Hills Travel’s Iconic Cruise Destinations guide and Hawaii cruise guide for more trip ideas.
Norwegian Cruise Line’s Pride of America is the only major ship sailing year-round from Honolulu. Its usual seven-day itinerary visits four islands and five ports, with overnight stays in Maui and Kauai. The ship stays in Hawaii throughout the trip, so guests spend their time exploring islands instead of crossing a long stretch of open ocean.
This is also the only straightforward cruise option for seeing all four main islands in a week without taking inter-island flights or adding a long Pacific crossing. You’ll still need to fly to Honolulu to board, but you can leave the island-hopping flights and hotel changes out of your itinerary.
Route at a glance: Honolulu, Oahu; Kahului, Maui; Hilo and Kona, Hawaii Island; and Nāwiliwili, Kauai. The exact order and port hours may vary by departure, so check the itinerary for your chosen date.
NCL’s Hawaii cruise details include current itineraries and planning information. Confirm 2027 dates, prices and port times before booking.
Honolulu brings together city life, beaches and major historic sites. Visit Pearl Harbor, take in the views from Diamond Head, or spend time on Waikiki Beach. If you arrive a day or two before your cruise, Oahu offers an easy way to settle in and start exploring.
Maui is known for beaches, mountain views and outdoor adventures. Choose a shore excursion to Haleakalā or the Road to Hana, or enjoy the longer visit made possible by the overnight port stay. From December through March, look for humpback whales in Maui’s waters. Sightings are never guaranteed, but this is the best season to plan around them.
Hawaii Island, often called the Big Island, offers a striking mix of landscapes. Hilo is a gateway to waterfalls and Hawaiʻi Volcanoes National Park. Kona is known for coffee, sunny coastlines and historic sites. Since the ship calls at both ports, you can choose between very different sides of the island.
Kauai’s green valleys, dramatic cliffs and rainforests have earned it the name “The Garden Isle.” The ship’s overnight in Nāwiliwili gives you extra time to explore. Some itineraries also include scenic cruising along the Nā Pali Coast. Choose an outing to Waimea Canyon, a boat trip, or a quiet beach day.
NOAA says humpback whales generally visit Hawaiian waters from November through May, with peak numbers from January through March. Follow local wildlife rules and give whales space; NOAA advises people not to approach within 100 yards. Read NOAA’s whale-viewing guidance.
Carnival plans to launch its first dedicated Hawaii cruise program from Long Beach with Carnival Legend. The 14-day sailings, scheduled from October 2027 through March 2028, include Honolulu, Maui, Kauai, Hilo and Kona, plus Ensenada. This option suits travelers who want to sail from Southern California and have time for several sea days. Check Carnival’s 2027–28 Hawaii announcement for program details.
Princess has announced 2027–28 Hawaii sailings aboard Crown Princess, Emerald Princess and Ruby Princess. The 16-day itineraries depart roundtrip from Los Angeles or San Francisco and visit four Hawaiian Islands. Select sailings include late evenings in Honolulu and Kona. See the Princess West Coast season announcement.
Holland America lists 17- and 18-day Circle Hawaii voyages aboard Koningsdam or Zaandam for 2027–28. These itineraries call at Honolulu, Maui, Kauai, Hilo and Kona. Select trips offer an overnight or an extended stay in Honolulu. Browse the Holland America 2027–28 West Coast season.
For 2027, Royal Caribbean lists select repositioning voyages between Honolulu and Vancouver, including an April sailing to Vancouver and a September sailing from Vancouver to Honolulu. These trips pair Hawaii with a longer Pacific voyage rather than a week of island-hopping. Check the April 2027 sailing and September 2027 sailing for their current port details.
Ship deployments and itineraries can change. Confirm the latest route and port schedule with the cruise line when you compare dates.
A one- or two-night stay before your cruise gives you a buffer if a flight runs late and time to explore Oahu before boarding. It also makes Pearl Harbor, Waikiki or a North Shore outing easier to fit into your trip.
A post-cruise stay works well if you want a slower finish, more beach time or another day in Honolulu. If you have a same-day flight home, allow plenty of time between the ship’s arrival and your departure. Flight times, traffic and disembarkation can affect your schedule.
For many travelers, the best plan is one or two nights before the cruise, with extra nights afterward if the budget and vacation days allow. Compare hotel location, transfer costs and cancellation terms alongside your cruise fare.
Contact Painted Hills Travel for personalized help comparing routes, cabins, flights and resort stays. Our team handles the details so you can focus on enjoying the islands. Explore our cruise planning services and all-inclusive vacation options.
