Getting There and Around
Kahului Airport (OGG) has nonstop flights from many West Coast cities, taking about five to six hours, with some direct service from farther away. From the East Coast, plan on a connection, often through the West Coast or Honolulu.
A rental car is close to essential on this route. Book it as soon as you have flights, since Maui's fleet can sell out in peak season. Traffic around Kahului and on the main highways is slow at rush hour, so plan airport runs with extra time.
Within Wailea, resort shuttles and the beach path make car-free days easy. For the Haleakalā sunrise and the Road to Hana, consider a guided tour if neither of you wants to drive in the dark or on narrow curves. Tours also let both of you look out of the window.
Where to Stay
Wailea is the best base for this route, with calm beaches and quick access to Molokini boats and Haleakalā. Hotel Wailea is the kid-free choice, a 72-suite Relais & Châteaux retreat on a hillside with big views and a private Treehouse dinner. Four Seasons Resort Maui at Wailea is the classic full-service resort on Wailea Beach, with Forbes Five-Star service, a kid-free infinity pool, open-air spa hale and restaurants including Spago.
If you prefer West Maui, Montage Kapalua Bay has one- to four-bedroom residences on the bluff between two bays and a large spa. It is quieter and greener, but adds about an hour of driving to Haleakalā and the Road to Hana.
Couples on a tighter budget can rent a condo in Kīhei, just north of Wailea. Spend the savings on the splurge dinner.
When to Go
Maui is warm year-round, with coastal highs usually in the upper 70s to upper 80s Fahrenheit. The south and west shores are the sunniest. Hana and the windward coast are wetter and greener.
April to May and September to October are the best months for this trip. The weather is good, crowds are lighter and rates are lower than in winter.
December to April is humpback whale season, with peak sightings usually January to March. You can often see spouts from the beach in Wailea. It is also the busiest and priciest period, especially over the holidays.
June to August brings families on school holidays, but the south shore sea is generally calm and good for snorkeling. Winter swells can make north-facing beaches dangerous, so check conditions before swimming anywhere on the north shore.
Budget and Booking
Maui is expensive, especially in Wailea. As an approximate guide, the top resorts often run about $800 to well over $1,500 a night for two in high season. Good condos in Kīhei can cost a third of that. Resort fees and parking add up, so check them when comparing.
Book in this order: hotel, flights, rental car, Haleakalā sunrise reservation, Waiʻānapanapa reservation and Mama's Fish House. Sunrise slots open in advance and go quickly. Book Molokini and any luau a few weeks ahead.
Tell your hotel you are on your honeymoon. Many add a small gift or an upgrade if one is free. Save on lunches by picking up poke and plate lunches from local shops, then spend on the dinners that matter.
Staying Comfortable and Safe
On the Haleakalā summit, the cold and the altitude catch people out. Dress in layers, move slowly and drink water. If either of you has heart or breathing problems, check with your doctor before a sunrise visit.
On the Road to Hana, drive slowly, pull over to let locals pass and never stop on a one-lane bridge. Respect private property and closed trails. Flash floods can hit waterfall pools after rain, so stay out of streams when the water is brown or rising.
Snorkel in the morning, when the water is calmest. Swim with a buddy, watch lifeguard flags and give turtles plenty of room. Use reef-safe mineral sunscreen, since Hawaii bans sunscreens with oxybenzone and octinoxate. If you're pregnant or hoping to be soon, check CDC travel health notices before you book.
Make It Shorter or Longer
For a five-day trip, keep Haleakalā, Molokini and one slow day, then skip the Road to Hana. You can see a taste of it by driving to Twin Falls and back in a morning.
For nine or ten days, add three nights on Lānaʻi, a short ferry ride from Māʻalaea Harbor, for a quiet luxury finale. Or fly to Kauaʻi for three nights of Nā Pali cliffs and Waimea Canyon before Maui.
Couples who want two moods on Maui itself can split the six nights: three in Kapalua or Kāʻanapali in the west, then three in Wailea. The drive between them takes about an hour. You gain different beaches and sunsets. Keep the Road to Hana for the Wailea half, since it starts closer.
