Hawaii Trip Planner: Which Island, When to Go and a 10-Day Itinerary
Four islands, four different trips. Here is how to pick, how to move between them, what to book before you fly, and a two-island itinerary to start from.
How to plan a Hawaii trip
Hawaiʻi is not one destination. Oʻahu, Maui, the Big Island and Kauaʻi are 30 to 50 minutes apart by air and hours apart in character: a city with a beach, a resort island with a volcano you drive up, an island still being built by lava, and a green one where the road ends at a cliff. The most common planning mistake is treating them as interchangeable, or trying to see all four in a week. The second most common is arriving without the reservations that now control the best-known places. This page fixes both, then hands you off to the four island guides and the planner.
The short version: with seven nights or fewer, stay on one island. With ten nights or more, take two, sleep at least four nights on each, and move once, in the middle of the trip, on a midday flight. Three islands in ten days means three check-ins, three rental cars and three airport mornings, and most people who do it wish they had not.
Which island for which trip
First-timers: Oʻahu, then Maui
Oʻahu has the most direct flights, the only real city, and a first few days that need no car: Waikiki Beach, Diamond Head, the Kūhiō Beach hula show and Pearl Harbor are all a bus or a short taxi from the hotel row. Add a rental car for two days to reach Hanauma Bay and the North Shore. If you would rather have a resort and a beach than a city, start on Maui instead and skip the traffic.
Families: Oʻahu (Waikiki) or Maui (Kīhei)
Waikiki's Canoes break is the gentlest learn-to-surf wave in the state, the beaches are lifeguarded, the Honolulu Zoo and Waikiki Aquarium are at the Diamond Head end of the strip, and hotels with kitchenettes and pools line Kūhiō Avenue. Maui's Kīhei condos with kitchens sit on the lifeguarded Kamaʻole beaches and cost half of Wailea next door; the Molokini boats and a Haleakalā sunset (no reservation needed) suit children who are past the nap years.
Hikers: Kauaʻi
The Kalalau Trail along the Nāpali Coast, Kōkeʻe State Park's 45 miles of ridge and canyon trails above Waimea Canyon, the Sleeping Giant and the Māhāʻulepū coast make Kauaʻi the walking island, with the caveat that Hāʻena State Park needs a reservation 30 days out. The Big Island's Kīlauea Iki crater floor and Maui's Pīpīwai and Sliding Sands trails are the runners-up.
Honeymoon: Maui or Kauaʻi
Maui has the sunset beach walks at Kāʻanapali and Wailea, the sunrise above the clouds on Haleakalā, a night in Hāna and the best-known resorts and restaurants (Mama's Fish House books out weeks ahead). Kauaʻi is the quieter version: Hanalei Bay, a Princeville clifftop, the Nāpali Coast from a boat and beaches that empty by late afternoon.
Volcano: Big Island, and only the Big Island
Kīlauea, in Hawaiʻi Volcanoes National Park, is the volcano that erupts, in episodes since December 2024, with a glow you can watch from the Crater Rim overlooks after dark when it is active. Maunakea's 13,803-foot summit and the 9,200-foot visitor station's stargazing are on the same island. Maui's Haleakalā is a dormant volcano: a spectacular crater to walk into, not lava to see.
Snorkeling: Big Island's Kona coast, then Maui
The Kona and Kohala coast has the calmest, clearest water in the state (Kealakekua Bay, Two Step at Hōnaunau) and the manta ray night snorkel, which exists nowhere else. Maui's Molokini crater and Turtle Town are the classic boat morning, and Oʻahu's Hanauma Bay is the easiest shore snorkel for beginners. Kauaʻi's north shore reefs at Kēʻē and Tunnels are excellent from May to September and dangerous in winter.
Inter-island flights
There is no ferry between the four main islands (the only passenger ferry links Maui and Lānaʻi), so every island change is a flight, and they are short. Hawaiian Airlines, now part of Alaska Air Group but still flying under its own name, runs the densest schedule, with Boeing 717 jets out of Honolulu every 30 to 60 minutes through the day to Kahului (Maui), Kona and Hilo (Big Island) and Līhuʻe (Kauaʻi), plus nonstops between the neighbor islands. Southwest flies 737s on the Honolulu routes and a few neighbor-island nonstops, and its fares are what keep the market honest. Mokulele Airlines flies nine-seat Cessna Grand Caravans from small terminals with no security lines to the airports the jets skip: Kapalua on West Maui, Hāna, Molokaʻi, Lānaʻi and Waimea-Kohala on the Big Island; you and your bags are weighed at check-in.
Typical flight times: Honolulu to Kahului 35 to 40 minutes, Honolulu to Līhuʻe 35 to 40, Honolulu to Kona 45 to 50, Honolulu to Hilo about 50, and Kahului to Kona 30 to 35. Fares run about $60 to $150 one way, more over the holidays, and the cheapest seats go weeks ahead. Book the morning after you fix your dates, choose a late-morning or midday flight so the moving day still has a beach at each end, allow 90 minutes at the airport (Honolulu's interisland terminal is a walk from the mainland gates), and fly open-jaw from the mainland when you can: into one island, home from the other, with no backtrack to Honolulu.
Rental cars
Rent a car on every island except for the Waikiki days of an Oʻahu stay, and reserve it with the flights: Maui and Kauaʻi run out of cars at Christmas and in summer, and walk-up rates double. Expect $60 to $120 a day for a standard car, resort parking of $25 to $50 a night in Wailea, Kāʻanapali and Waikiki, and free parking at most condos. A standard car handles every paved road in the four guides, including the Road to Hāna. Four-wheel drive matters for exactly two places, the Maunakea summit road and the dirt road to Polihale on Kauaʻi, and most rental contracts forbid both, so treat those as tour or shuttle trips. Fill the tank before the Saddle Road on the Big Island and before Hāna; neither has fuel in the middle.
The reservations that decide the trip
Haleakalā sunrise (Maui)
Vehicles entering Haleakalā National Park between 3am and 7am need a sunrise reservation from recreation.gov, released 60 days ahead at 7am Hawaiʻi time with a smaller batch two days before, $1 per car and one per person per three-day period. The $30 park pass is separate. Sunset and daytime need nothing.
Hanauma Bay (Oʻahu)
Non-resident entry is $25 (12 and under free), and the timed slots open on the City and County of Honolulu's reservation site at 7am Hawaiʻi time two days ahead and go within minutes. Closed Mondays and Tuesdays; first entry 6:45am, when the water is clearest.
Diamond Head (Oʻahu)
Out-of-state visitors need a timed entry from gostateparks.hawaii.gov, $5 a person plus $10 to park, bookable up to 30 days ahead. Gates open at 6am and the last entry is 4pm; the early slots are cool and the parking lot is not yet full.
Waiʻānapanapa State Park (Maui)
The black-sand beach on the Road to Hāna admits non-residents only with a timed window booked on gostateparks.hawaii.gov, $5 a person plus $10 a vehicle, no walk-ups. Book it the day you fix your Hāna date; holiday slots go first.
Hāʻena State Park and the Kalalau Trail (Kauaʻi)
Everyone entering Hāʻena, including day hikers, needs a parking reservation or a seat on the North Shore Shuttle from Waipā, released 30 days ahead on the state's Hāʻena site and gone in minutes for summer. Hiking beyond Hanakāpīʻai needs a Kalalau camping permit, issued per person per night by the Division of State Parks and sold out months ahead.
Also worth booking early (All islands)
Pearl Harbor's USS Arizona Memorial boat program (recreation.gov, free with a $1 fee, released eight weeks out), ʻĪao Valley on Maui (state parks site), Kīlauea Point lighthouse on Kauaʻi (recreation.gov), the Big Island's manta night snorkel and Maui's Molokini boats, and any Mama's Fish House table.
10 days, two islands: Maui and the Big Island
Five nights on Maui and four on the Big Island, one flight in the middle, and every reservation above that applies. Fly into Kahului (OGG) and home from Kona (KOA) or Hilo (ITO). Each line links to the full day in the island guides; the Plan-this-trip buttons open the planner prefilled with the island, so you can shift the dates, pace and budget without retyping any of it.
- Day 1, Maui: Land at Kahului, collect the car, check into Kīhei or Wailea, and end the day on the Wailea Beach Path at sunset with poke from the Foodland counter.
- Day 2, Maui: Haleakalā sunrise with the recreation.gov reservation (leave by 3:30am), a walk down the Sliding Sands trail, then Upcountry: Kula farms, Komoda Store cream puffs in Makawao, Maui Wine.
- Day 3, Maui: The Road to Hāna from Pāʻia at 7am: Twin Falls, Keʻanae banana bread, your Waiʻānapanapa window, lunch in Hāna, the Pīpīwai Trail at Kīpahulu, and a night in Hāna or the drive back by dark.
- Day 4, Maui: The earliest Molokini snorkel boat from Māʻalaea with the Turtle Town stop, ʻĪao Valley in the afternoon, then Route 30 to Kāʻanapali for the sunset torch-lighting at Puʻu Kekaʻa.
- Day 5, Maui to Big Island: A slow beach morning at Kamaʻole or Kāʻanapali, the 30-minute Kahului to Kona flight after lunch, a new car at KOA, and the seawall in Kailua-Kona at sunset.
- Day 6, Big Island: A Kona coffee farm in Hōlualoa at 9am, Puʻuhonua o Hōnaunau and the Two Step snorkel, poke from Da Poke Shack, then the manta ray night snorkel from Keauhou Bay.
- Day 7, Big Island: Cross to the Hāmākua coast: Tex Drive-In malasadas in Honokaʻa, the Waipiʻo Valley Lookout by 10am, ʻAkaka Falls, Hilo's Farmers Market and a loco moco at Café 100, then stars at the Maunakea visitor station until 9pm. Sleep in Hilo or Volcano Village.
- Day 8, Big Island: Hawaiʻi Volcanoes National Park: check the webcams, the Crater Rim overlooks, the Kīlauea Iki loop, Chain of Craters Road to the sea arch, then Punaluʻu black sand beach for the resting turtles and, if Kīlauea is active, the glow after dark.
- Day 9, Big Island: Back across the Saddle Road to the Kohala Coast: Hāpuna Beach for a swim, lunch in Waimea's farm restaurants, the Pololū Valley Lookout, and a last sunset from the Waikoloa petroglyph fields.
- Day 10, Big Island: Fly home from Kona, or from Hilo if you ended in the east: an open-jaw ticket saves the drive back across the island.
When to go: whales, surf and rain
Whale season (December to April, peak January to March)
Around 10,000 North Pacific humpbacks winter in the shallow channels between Maui, Lānaʻi and Molokaʻi and along every island's leeward coast. Maui's Māʻalaea boats are the classic trip, but from January you will see breaches from the Wailea and Kāʻanapali beach paths, Kauaʻi's Kīlauea Point and the Big Island's Kohala shore. Federal law keeps boats and swimmers 100 yards away.
Surf season (North shores November to February; south shores May to September)
Winter swells turn Oʻahu's North Shore (Pipeline, Waimea Bay, Sunset Beach), Kauaʻi's Hanalei and Maui's Hoʻokipa into spectator sports and close those beaches to swimming; the pro contests run November and December. Summer flips the pattern: the north shores go flat and clear for snorkeling while gentle south swells reach Waikiki and Poʻipū, which is why beginners learn there.
Rainy months (November to March, mostly on the windward sides)
Rain falls on the east and north (windward) coasts that face the trade winds: Hilo averages more than 120 inches a year, Hanalei and Hāna are lush for the same reason, and heavy winter storms occasionally close the Kūhiō Highway beyond Hanalei or the Hāna road for a day. The leeward coasts, Kona, Wailea, Kāʻanapali, Poʻipū and Waikiki, stay dry and about 80°F in every month. Hurricane season is June to November and landfalls are rare; Haleakalā and Maunakea are near freezing before dawn all year.
Prices and crowds (Cheapest April to May and September to October)
Mid-December to early January and June to August are peak, with holiday hotel rates that double. Late April brings Japan's Golden Week to Waikiki, Merrie Monarch hula week fills Hilo the week after Easter, and the Ironman fills Kailua-Kona in October. Spring and fall shoulder months have the lowest fares, calm seas on most coasts and, in April, the last of the whales.
Reef-safe and respectful
Reef-safe sunscreen is the law
Since January 1, 2021, Hawaiʻi has banned the sale of sunscreens containing oxybenzone and octinoxate, and Maui County and Hawaiʻi County (the Big Island) went further in late 2022, allowing only mineral sunscreens with zinc oxide or titanium dioxide to be sold. Pack a mineral sunscreen from home and a rash guard for snorkeling; the reef and your shoulders both do better.
Wildlife has a distance
Stay 10 feet from green sea turtles (honu), 50 feet from Hawaiian monk seals and more from a mother with a pup, 50 yards from spinner dolphins and 100 yards from whales. Touching or feeding a turtle or seal is a state and federal offense with real fines, and the volunteers who rope them off on Poʻipū and Laniākea beaches are not being fussy.
Sacred sites and closed places
Heiau (temples), burial dunes, Maunakea's summit and the Haleakalā and Kīlauea craters are sacred to Native Hawaiians. Do not climb on stone walls, stack rocks, take lava, sand or coral home (illegal in the national parks), or move a stone that someone has placed. A kapu or no-trespassing sign means exactly that, including the closed Haʻikū Stairs and the private waterfalls social media keeps recommending. In Lahaina, stay out of the burn zone while residents rebuild.
Hawaii trip planning FAQ
Which Hawaiian island is best for a first visit?
Oʻahu for the easiest trip: the most direct flights, a first few days in Waikiki that need no car, Diamond Head, Pearl Harbor, Hanauma Bay and the North Shore. Maui if you want a resort beach, the Haleakalā sunrise and the Road to Hāna more than a city. The Big Island is for volcanoes and snorkeling, Kauaʻi for hiking and scenery.
How many islands should I visit in 7 or 10 days?
One island for seven nights or fewer, two islands for ten nights or more, with at least four nights on each and a single midday flight in the middle. Every island change costs most of a day (check-out, airport, flight, new car, check-in), so three islands in ten days leaves little time for the islands.
How do you get between the Hawaiian islands?
By air. Hawaiian Airlines and Southwest fly jets between Honolulu, Kahului, Kona, Hilo and Līhuʻe in 35 to 50 minutes for about $60 to $150 one way, and Mokulele flies small turboprops to the little airports such as Kapalua, Hāna, Molokaʻi and Lānaʻi. There is no ferry between the four main islands; the only passenger ferry links Maui and Lānaʻi.
Do I need a rental car in Hawaii?
Yes on Maui, the Big Island and Kauaʻi, where the sights are 45 to 90 minutes apart and the buses do not reach the parks. On Oʻahu you can skip the car for the Waikiki days and rent for one or two days to reach Hanauma Bay and the North Shore. Book cars with the flights, since the islands sell out at Christmas and in summer.
When is the best time to visit Hawaii?
April to May and September to October have the lowest prices, the fewest people and calm water on most coasts. December to April adds humpback whales (peak January to March) and big North Shore surf, with holiday rates from mid-December to early January. Summer is the flattest, clearest water on the north shores and the busiest family season. The leeward coasts are dry and about 80°F in every month.
The four island guides
Waikiki
World-Famous Beach, Perfect Waves, and the Spirit of Aloha
Maui
Sunrise Above the Clouds, the Road to Hāna and a Beach for Every Mood
Big Island
Live Volcanoes, a Snow-Capped Summit and the Pacific's Wildest Coastline
Kauai
The Garden Isle — Nāpali Cliffs, Waimea Canyon and Beaches Without the Crowds
