At a glanceThree nights on Oʻahu, then four each on Kauaʻi, Maui and the Big Island, linked by short interisland flights. It suits couples with two weeks or more who want to see how different the islands feel, with a slow day built into every stop. April to June and September to October are the best months.
This 16-day route covers the four main Hawaiian islands in one honeymoon, with three nights on Oʻahu and four on each of Kauaʻi, Maui and the Big Island. Each interisland flight is under an hour in the air, so moving day costs you a morning, not a whole day.
The order is built around how a honeymoon feels. Oʻahu comes first because Honolulu has the most flights from the mainland and Waikiki is an easy place to shake off jet lag. Kauaʻi follows with its green cliffs and slow pace. Maui brings the big set pieces, from the Haleakalā sunrise to a snorkel at Molokini. The Big Island closes the trip with manta rays, stars over Mauna Kea and the volcano, then a nonstop flight home from Kona.
Four stops is the most we recommend, so each island gets one day with nothing on the schedule. Go April to June or September to October for the best weather and rates. From December to April you add whales and higher prices.
The route
- OʻahuUnited States · 3 nights
- KauaʻiUnited States · 4 nights
- MauiUnited States · 4 nights
- Hawaiʻi Island (Big Island)United States · 4 nights
- Best months
- April to June and September to October
- Trip length
- 16 days
- Budget
- About $500–1,500 a night for two in upscale hotels, more at the top resorts in winter (approximate)
Day by day
Days 1–3: Oʻahu
Fly into Honolulu (HNL) and settle into Waikiki without a car. Halekulani is the quiet classic and its House Without a Key terrace, with hula and mai tais at sunset, is the romantic moment of Oʻahu.
On day two, hike the Lanikai pillboxes at sunrise, then swim at Lanikai or Kailua beach. Rent a car for the day to continue up the windward coast to the North Shore, with shave ice in Haleʻiwa and a look at Waimea Bay. In winter, watch the surf from the sand. In summer, snorkel Shark's Cove.
Keep day three light. Reserve timed tickets for the USS Arizona Memorial at Pearl Harbor, or simply take a catamaran sail off Waikiki and an early dinner. Return the car the night before your flight, or keep it for the airport run in the morning.
Days 4–7: Kauaʻi
Fly to Līhuʻe (LIH). From May to September, base yourselves on the North Shore. 1 Hotel Hanalei Bay, on the Princeville bluff, has one of the best views in Hawaii. From October to April, choose the sunnier south shore around Poʻipū.
On day five, take a Nā Pali Coast catamaran tour in the morning for sea caves, cliffs and spinner dolphins. On day six, drive west to Waimea Canyon and the Kalalau Lookout early, before the clouds settle in. Looking straight down into the Nā Pali valleys from the lookout is the romantic moment of Kauaʻi.
Day seven is your slow day: a beach, a book and sunset at Hanalei Pier. If you want one more adventure, paddle the Wailua River to Secret Falls with a guide or book a doors-off helicopter flight.
Days 8–11: Maui
Fly to Kahului (OGG), well under an hour in the air. Drive on to Wailea. Hotel Wailea, small and kid-free, or Four Seasons Resort Maui at Wailea make a fine splurge stop for the middle of the trip.
On day nine, rise around 3 a.m. for Haleakalā sunrise, with a reservation from the National Park Service and every warm layer you own. The summit is above 10,000 feet and often near freezing at dawn. Watching the light fill the crater is the romantic moment of Maui. Spend the afternoon by the pool.
On day ten, snorkel Molokini Crater on a morning boat and take a sunset sail in the evening, which doubles as whale watching from December to April. Keep day eleven slow with a spa treatment and a long lunch, or drive the Road to Hana if you still have energy. Book Hotel Wailea's private Treehouse dinner for one of these nights.
Days 12–16: The Big Island
Fly to Kona (KOA) and drive to the Kohala Coast. Mauna Kea Beach Hotel, Four Seasons Resort Hualalai and Mauna Lani are the top choices.
On day thirteen, rest, then take a manta ray night snorkel off Kona. On day fourteen, join a permitted Mauna Kea sunset and stargazing tour. The summit stands near 14,000 feet, so skip it within 24 hours of scuba diving and talk to a doctor first if either of you has heart or breathing problems.
On day fifteen, make the long day trip to Hawaiʻi Volcanoes National Park, about three hours each way, stopping at Punaluʻu black sand beach to see the turtles. Stay for the crater glow if Kīlauea is active, or book a final night at Volcano House on the rim and adjust the schedule. On day sixteen, fly home from Kona, which has nonstops to several West Coast cities.
Getting Between Stops
Book an open-jaw ticket into Honolulu (HNL) and home from Kona (KOA). Interisland flights connect Honolulu to Līhuʻe, Līhuʻe to Kahului and Kahului to Kona, mostly on Hawaiian Airlines. Each runs under an hour in the air, but allow half a day with the car return, security and pickup.
Book interisland flights for mid-morning, so you can enjoy a last breakfast and still arrive for an afternoon swim. Pack light. Checked bag fees add up over three hops and small carry-on bags fit more easily in rental cars.
Rent a car on Kauaʻi, Maui and the Big Island. On Oʻahu, rent one for a single day, since Waikiki hotel parking is expensive. Book every car early, as island fleets sell out in peak season. Some routes connect via Honolulu rather than nonstop, so check before you book.
Where to Stay
On Oʻahu, Halekulani is the classic Waikiki honeymoon hotel. On Kauaʻi, 1 Hotel Hanalei Bay is the North Shore splurge for summer, while Poʻipū's resorts suit winter. On Maui, Hotel Wailea is the small, kid-free choice and Four Seasons Resort Maui at Wailea is the full-service classic on the beach. On the Big Island, Mauna Kea Beach Hotel sits on one of the island's finest beaches, with Four Seasons Resort Hualalai and Mauna Lani as alternatives.
Mixing price levels helps on a long trip. Spend big on two islands and choose a condo or smaller hotel on the others. Poʻipū condos and Volcano village cottages often cost far less than the big resorts. Top resorts on every island often run well over $1,000 a night in high season (approximate).
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When to Go
April to June and September to October are the best months for a four-island trip. Weather is warm and dry on the leeward coasts, rates are lower and you avoid the school holidays.
Winter, from December to April, brings humpback whales and the highest prices of the year. It also brings big surf to north-facing shores, including Oʻahu's North Shore and Kauaʻi's Hanalei, where swimming can be off for days. Nā Pali boat tours may sail only from the south side.
Summer is the best season for Kauaʻi's North Shore and calm snorkeling everywhere, though families fill the resorts in July and August. Kīlauea's activity is not seasonal, so check the USGS Hawaiian Volcano Observatory the week before you reach the Big Island.
Budget and Booking
A four-island trip has many moving parts, so book early and in this order: flights, hotels, interisland flights, the Haleakalā sunrise slot and rental cars. Then add tours, keeping them early in each stay in case weather forces a change.
Several sights need advance reservations for visitors: Haleakalā sunrise, Hāʻena State Park on Kauaʻi, Diamond Head and the USS Arizona Memorial on Oʻahu and Waiʻānapanapa on the Road to Hana.
As an approximate guide, plan on $500 to $1,500 a night for upscale hotels, plus resort fees, parking and about $100 to $200 per person for each interisland flight with bags. Boat tours run a few hundred dollars for two. Mention your honeymoon to each hotel. Small touches add up over four stops.
Staying Comfortable and Safe
The ocean is the main hazard on every island. Swim at lifeguarded beaches, check the flags and stay out of rough water, especially on north shores in winter. Never swim at Hanakāpīʻai Beach on Kauaʻi.
Haleakalā and Mauna Kea are both high. Dress warmly, move slowly and skip Mauna Kea within 24 hours of scuba diving. Volcanic haze, called vog, can bother people with asthma on the Big Island.
Use reef-safe mineral sunscreen; Hawaii bans sunscreens with oxybenzone and octinoxate. Bring insect repellent for evenings on Kauaʻi and near the volcano. If you're pregnant or hoping to be soon, check CDC travel health notices. Never leave valuables in rental cars at trailheads or beaches. Resort casual works at dinner for both of you, with a light jacket for the mountains.
Make It Shorter or Longer
For 12 to 13 days, drop Oʻahu and fly straight into Līhuʻe from the West Coast. Spend four nights each on Kauaʻi, Maui and the Big Island.
For 10 days, choose two islands. Maui and Kauaʻi is the classic pair. Oʻahu and the Big Island gives more contrast.
For 18 to 21 days, add three nights on Lānaʻi after Maui, reached by a passenger ferry of about 75 minutes, or add two nights at Volcano House so you can stay near the crater instead of making a long day trip. Longer trips also give you room for a second slow day on Kauaʻi, which most couples end up wanting.
FAQPlanning this trip
Is it too much to visit four Hawaiian islands on a honeymoon?
It works with at least 15 or 16 days. Each island gets three or four nights and one slow day. Interisland flights are short. With fewer than two weeks, two islands is better. Three hotel changes is the most we suggest for a relaxing trip.
Which order should we visit the Hawaiian islands?
Start on Oʻahu, since Honolulu has the most flights, then go to Kauaʻi, Maui and the Big Island. Ending in Kona gives you nonstop flights home to the West Coast. The order also saves the Big Island's night snorkel and stargazing for the finale.
How do you travel between the Hawaiian islands?
By plane. Interisland flights link Honolulu, Līhuʻe, Kahului and Kona, each under an hour in the air. The only regular passenger ferry among the main islands connects Maui and Lānaʻi. Allow half a day for each hop with car returns and pickups.
Which island is best for the splurge night?
Maui, for most couples. Wailea's resorts sit in the middle of the trip, when you need a reset. Hotel Wailea's Treehouse dinner is one of the most romantic tables in Hawaii. On Kauaʻi in summer, 1 Hotel Hanalei Bay's views are a close second.
What should we pack for four islands?
Pack light: swimwear, reef shoes, a rain jacket for Kauaʻi and warm layers for Haleakalā and Mauna Kea, where dawn and night can be near freezing. Bring reef-safe mineral sunscreen, insect repellent and one smart outfit each for resort dinners.
