Stunning aerial view of Honolulu's skyline with lush mountains and ocean in foreground.

The Islands

Hawaii

Four islands, one week, and no inter-island flights, the only way to see Hawaii properly without spending half the vacation in airport lines.

Sailings Available

615

Best Time to Go

Year-round; April to May and September to October are quietest

Typical Length

7 nights inter-island, or 14 to 17 round-trip from the mainland

Why sail Hawaii

Island-hopping Hawaii by air means four hotels, four check-ins, four rental cars and a domestic flight every other morning. The ship replaces all of it. You wake up on Maui, and the next day on Kauai, and the bags never move.

The two very different itineraries

Inter-island, round-trip from Honolulu. Seven nights, four islands, almost no sea days, Maui, Hilo and Kona on the Big Island, and Kauai, usually with an overnight so you get a full day and an evening. Because it never leaves US waters, this route is sailed by the one US-flagged ship in the business, Pride of America.

Round-trip from the West Coast. Fourteen to seventeen nights, of which four or five at each end are open Pacific. Far cheaper per night, and a genuinely different vacation: the sea days are the point. Ideal if you want the crossing.

The islands

  • Maui (Kahului): the road to Hāna and the sunrise at Haleakalā, which starts at three in the morning and is worth it.
  • Hawai’i, from Hilo: Volcanoes National Park, rainforest, waterfalls.
  • Hawai’i, from Kona: dry, sunny, the coffee coast, and the best snorkeling and manta dives.
  • Kauai (Nawiliwili): Waimea Canyon and the Nā Pali coast. The prettiest island, and the one most worth an overnight call.

What to know before you book

Hilo and Kona are the same island, two days apart. People book excursions assuming otherwise and end up doing a two-hour drive twice.

Cars sell out. On an inter-island sailing, rental cars at each port are booked by other passengers weeks ahead. Reserve early or take the ship’s tour.

Beautiful view of Waikiki Beach with Diamond Head in the background.
Honolulu, Hawaii
Vibrant port with boats and ships in Ensenada, B.C., Mexico, under a bright summer sky.
Ensenada, Mexico
Aerial photograph of a prominent hotel by the seaside in Apia, Samoa.
Papeete, French Polynesia

Photo: Tony Rios · Re-encoded to WebP.

Stunning aerial shot showcasing the vibrant greenery and suburban layout of a peaceful neighborhood.
Kahului

Photo: Cyrill · Re-encoded to WebP.

Scenic aerial view of a historic church surrounded by urban landscapes in Flores, Costa Rica.
Hilo, Hawaii

Photo: Edgar Arroyo · Re-encoded to WebP.

A sleek red Hyundai Kona SUV parked outdoors on a cobblestone street, near historic buildings.
Kona, Hawaii

Photo: Hyundai Motor Group · Re-encoded to WebP.