Passengers on a cruise ship's top deck watching the Na Pali Coast of Kauai during scenic cruising

A Hawaii cruise gives you two kinds of proposal settings: quiet days at sea on the long roundtrips from the West Coast, and volcanoes, canyons and sea cliffs once you reach the islands. These seven ideas cover both, from a helicopter over Kauai's Na Pali Coast to a sunrise above the clouds on Maui, with the reservations and timing each one needs.

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Total Votes: 37
Votes

Heather and I put Hawaii on the same short list as Alaska and Mexico for planning a proposal, because the islands give you settings no ship can match.

That's probably one of the reasons that Hawaii weddings and marriage proposals tend to consistently rank among the top romantic destinations around. While flying to Hawaii and booking a suite at a beach-front resort is probably easier ... being able to travel from island to island without having to unpack is an amazing adventure that we did a few years ago sailing on Pride of America and I can't wait to go back and do it again sometime soon.

Hawaii cruises come in two shapes. Princess, Holland America Line and others sail long roundtrips from west coast ports including: Los Angeles, San Francisco, San Diego, and Vancouver, with several days at sea in each direction, while Norwegian's Pride of America and UnCruise's small ships sail between the islands from Honolulu and Kona. Our guide to the ways to cruise Hawaii compares them and our guide on how to plan a marriage proposal on a cruise covers the cruise line packages and how to plan around everything from bad weather to an unexpected "no" to your proposal.

Hawaii Proposal Ideas At Sea and On Land

Two of the best settings on a Hawaii cruise come with the ship, no excursion needed.

Propose On A Sea Day Crossing The Pacific

A roundtrip from the West Coast spends several days at sea each way, with nothing but open ocean at sunset. Princess runs 16-day Hawaii roundtrips from Los Angeles and San Francisco, and with no port to rush back from, the crossing is an easy time for a proposal package, a private balcony dinner, or a quiet table on deck. Our cruise proposal guide compares the packages.

Sail Past The Na Pali Coast At Sunset

Pride of America's evening sail-by of the Na Pali Coast passes 17 miles of sea cliffs rising as high as 4,000 feet, and the low sun lights the cliffs up. The line dropped the sail-by from its itinerary for several years and scheduled it to resume in October 2026, so confirm it is on your sailing if you are looking to book it in 2027 or 2028. Don't worry about what side of the ship to book your balcony though - just like when sailing into the Alaska fjords to see glaciers, the ship will pause and rotate slowly so everyone gets a fantasic viewing experience no matter where they are on the ship.

Visitors at a Waimea Canyon lookout on Kauai, the canyon known as the Grand Canyon of the Pacific

Hawaii Proposal Ideas In Port, From Kauai's Canyon To Kilauea's Crater

Port calls on Kauai, Maui, Oahu and the Big Island each put a different landscape within reach, and the sunrise ideas need an early start or an overnight.

Fly Over Na Pali By Helicopter From Kauai

Helicopter tours leave from Lihue, about three miles from the cruise port at Nawiliwili on Kauai, and fly over the Na Pali Coast, Waimea Canyon and waterfalls you can't reach by road. At least one operator offers a landing at Manawaiopuna Falls, the waterfall from the original Jurassic Park, which gives you a few minutes on the ground beside the falls. Confirm the landing is included when you book, and take the earliest departure you can in case weather pushes the flight.

Look Into Waimea Canyon On Kauai

Waimea Canyon on Kauai's west side has drive-up lookouts over the red and green canyon walls, so you get the view without a hike, and no reservation is needed for day use. The drive from Nawiliwili takes much of a port day, so check your all aboard time and pick either the canyon or the helicopter for one Kauai call, not both.

Watch Sunrise From Haleakala On Maui

Sunrise from the summit of Haleakala on Maui, often above a layer of clouds, draws visitors up the mountain in the dark every morning. It only works on a sailing with an overnight in Kahului, which some Pride of America itineraries have included, because you have to be on the road in the middle of the night, and you need a vehicle reservation for the summit district on top of the park entrance fee.

Hike Diamond Head Before Your Cruise From Honolulu

Diamond Head State Monument in Honolulu has a moderate 1.6-mile round trip trail to the crater rim, with Waikiki and the Pacific below. It fits best on a pre-cruise day before a Pride of America sailing. Non-residents need an advance reservation for entry and parking.

See Hawaii Volcanoes National Park From Hilo

From the cruise port in Hilo, Hawaii Volcanoes National Park is about 30 miles away, roughly 45 minutes each way by ship excursion or private driver, with crater overlooks at Kilauea's summit. Kilauea's activity comes and goes, so the scenery ranges from a steaming crater to a glowing one depending on the week, and the glow shows best after dark, which a day call rarely allows.

Plan Your Hawaii Proposal Around The Overnights And Reservations

The excursion desk books group tours, but an experienced travel advisor can help you choose the right sailing with the overnight you need for Haleakala, book the reservations the day they open, and confirm whether Pride of America is running its Na Pali sail-by on your dates.

If sunrise on Haleakala is the dream, ask your advisor to find a sailing with an overnight in Kahului first and build everything else around it. Heather Hills at Flow Voyages can plan a Hawaii proposal cruise this way when you book your Hawaii cruise with her.