Five days is enough to see Maui properly if you stop trying to see all of it every day. The island is bigger than it looks, the drive from the west side to the Hana road is two hours, and the single most common first-timer mistake is booking a dawn Molokini boat, a Haleakala sunrise and a luau in the same 48 hours.
This itinerary does one region a day. Each day has one headline adventure, one easy thing, and a built-in gap for the pool, a nap or a long lunch. It assumes you are staying in Kaanapali, which is the simplest base for a first trip. Swaps for a Wailea or Kihei base are at the end, and so are the winter and summer versions of each day.
Before you go: the three bookings that need lead time
- Haleakala sunrise, if you want it, needs a recreation.gov reservation that opens 60 days out and sells out. This plan uses the downhill bike tour instead, which does not require one.
- A luau sells out two to four weeks ahead in winter and summer. Our Maui luau guide explains the options.
- Waianapanapa State Park on the Hana road needs an advance reservation. A guided Hana tour handles it for you.
Everything else on this list can usually be booked a week out, except in late December, February, March and June through mid August, when the morning slots go first.
Day 1: Arrive, West Maui, easy
Most flights land at Kahului between late morning and mid afternoon, and the drive to Kaanapali is 45 to 60 minutes. Do not book anything with a check-in time today. Jet lag from the mainland is real, and a 5 pm body clock that thinks it is 11 pm is not the one you want on a boat.
Afternoon. Stop at the big-box stores in Kahului for water, sunscreen, snacks and a cheap cooler before you leave town. Check in, put on a swimsuit and walk Kaanapali Beach. Black Rock, at the north end, has turtles most afternoons, and the beach walk gets you oriented.
Evening. If you have energy, the sunset cocktail cruise boards off the sand at Whalers Village, lasts two hours, and is the gentlest possible first-night activity. Open bar, pupus, live music on Tuesday and Thursday, and you are back on the beach by 8. If you do not have energy, dinner at Whalers Village and bed. Either is correct.
Rest built in. All of it. This is the day you let the trip start.
Day 2: West Maui on the water
Today is the day Kaanapali exists for. Everything leaves from the beach, so there is no driving.
Morning. Book the first available parasailing slot, usually 8 or 9 am, when the water is flattest and the light is best. Check-in is on the sand under yellow umbrellas three minutes north of Whalers Village. The outing is about an hour, with 8 to 14 minutes at up to 1,200 feet, and takeoff and landing are dry from the boat deck. From $75 a flyer, kids from 5.
If you would rather drive something, the jet ski rental meets at a red and white umbrella outside Whalers Village and runs 45 minutes on a Sea-Doo from a floating platform offshore. Drivers 16 and up, or 15 with an adult. Early slots cost less.
Both run May 16 to December 14. For the winter version of this day, see below.
Midday. Lunch at Whalers Village, then the pool or the beach. This gap matters. Two tours in one day is fine on paper and tiring in practice.
Late afternoon and evening. The sunset dinner cruise boards off the same beach, runs about two and a half hours, and covers dinner with a buffet, open bar and a champagne toast at sunset. Wednesday and Saturday have live music. If you did the cocktail cruise last night, make tonight a dinner in Kaanapali instead and save the dinner cruise for Day 5.
Rest built in. Noon to 4 pm.
Day 3: South Maui and Molokini
Today involves a drive. Kaanapali to the Kihei Boat Ramp is 40 to 50 minutes, so leave by 9:00 for a 10:00 check-in. Pack the cooler, because you are going to be on the south side until mid afternoon.
Late morning. The Molokini snorkeling raft departs the Kihei Boat Ramp at 10:30 am sharp, reaches the crater in 15 to 20 minutes, and spends more than an hour in the water. Two hours total, 19 guests maximum, from $129. The late start is the reason this day works from Kaanapali: no 5 am alarm, no drive in the dark. It runs April 1 to December 14. If turtles matter, the 3-hour version adds Turtle Town.
For the rest of the Molokini fleet, including the big catamarans with breakfast, see our Molokini tours comparison.
Afternoon. You are back on land at 12:30 with wet hair and an appetite. Kihei has plenty of casual lunch spots along South Kihei Road. Then drive 10 minutes south to Wailea and walk the coastal path from Wailea Beach to Polo Beach, or swim at Ulua, the best snorkel beach on the strip. If the family is done with water, Kamaole III beach park next to the ramp has grass, shade and a playground.
Evening. Drive back before 3:30 to beat the pali traffic, or stay south for dinner and drive back after 7 when it clears. If tonight is luau night, this is a good one for it: the West Maui luaus start around 5 pm, which lines up with a 4 pm return.
Rest built in. The whole afternoon is unstructured.
Day 4: Upcountry and Haleakala
Haleakala is the 10,023-foot volcano that makes up the eastern two thirds of the island. Sunrise at the summit is famous, cold, and requires a reservation and a 3 am alarm from Kaanapali. The Haleakala bike tour is the way to experience the mountain without any of that.
Morning. Check-in is 8:20 am at the bike shop in Paia, an hour from Kaanapali, so leave by 7:15. A van takes you up to 6,500 feet, where it is often in the 40s with wind, and you coast roughly 20 miles of paved road down through Kula ranch land and the cowboy town of Makawao to Paia at sea level. A guide leads, sets the pace and stops for photos. Five hours total, from $169, riders 15 and up. Bring layers.
Midday. You finish in Paia, which is the right place to be hungry. It is a small surf town with good fish tacos, a natural foods store and a few shops. Hookipa Beach Park, five minutes east, has a lookout where turtles haul out on the sand in the late afternoon and windsurfers work the break when the trades are up.
Afternoon. Drive back through Kahului, about an hour to Kaanapali. If you have the energy, Iao Valley State Monument in Wailuku is 15 minutes off the route and takes an hour. Non-residents need a reservation.
Evening. An easy dinner near the hotel. Tomorrow is the long day.
Rest built in. The afternoon drive is the rest. Keep the evening open.
If nobody in your group is 15. Swap the bike ride for a self-drive Upcountry morning: Kula Lavender Farm, lunch in Makawao, the Hookipa turtle lookout. Or drive to the summit mid morning, after sunrise, when no reservation is needed and the crater view is just as good.
Day 5: The Road to Hana
The Hana Highway runs 52 miles along the wet, green north and east coast of Haleakala, with around 600 curves and more than 50 one-lane bridges. Waterfalls, bamboo, black-sand beaches, banana bread. It is the best day on the island and the most tiring one, which is why it is last.
The guided version. The private Road to Hana tour picks you up at your hotel in a luxury SUV, which from Kaanapali means a departure around 6:30 to 7 am. The guide drives, handles the Waianapanapa reservation, knows which stops are open and which waterfall pools are safe that day, and takes you as far as you want to go. Eight to ten hours, from $1,300 per vehicle for up to six people, which works out to about $325 each for a family of four. All ages.
The self-drive version. Leave Kaanapali by 6 am, fill the tank in Paia, and pick five or six stops rather than trying to hit all thirty. Twin Falls, the Keanae Peninsula, Aunty Sandy’s banana bread, Waianapanapa with your reservation, and Hamoa Beach in Hana is a good day. Turn around in Hana and come back the same way; the back road past Kaupo is rough and most rental agreements do not cover it. You will be home after dark. Pack food, water and a rain jacket.
Rest built in. None, honestly. This is why Day 4 ends early and why the trip ends with it. If you are flying home on a red-eye tonight, the guided tour can drop you at the airport.
If you have a sixth day. Add a slow West Maui morning with the afternoon snorkel tour at 12:30, which was built for people who want to sleep in, and a last sunset on the beach.
The winter version (December through April)
Whale season runs December 1 to April 30, and the state pauses parasailing and jet skis from December 15 to May 15. The Molokini raft pauses December 15 to March 31. Here is how the days change.
Day 2 becomes a whale day. The whale watching raft loads behind Whalers Village, with a 7 am first trip, a naturalist, a hydrophone that plays whale song through the speakers and a sighting guarantee. Two hours, from $79, kids from 2. Then the West Maui snorkel sail or the ATV tour above Lahaina, which runs year round, rain or shine, and is a good swap for the thrill rides. Riders from 7.
Day 3 keeps Wailea and Kihei but swaps the raft for a big Molokini catamaran from Maalaea, which runs year round and doubles as a whale watch on the crossing. Or skip the south side entirely and do the West Maui snorkel sail instead, which spots whales from December 15 to April 14.
Days 1, 4 and 5 stay the same. The sunset cruises spot whales December 15 to April 15, and the bike ride and Hana road are year round. Pack a real jacket for the mountain; winter mornings at 6,500 feet can be near freezing.
The summer version (May 16 through December 14)
The plan above is the summer plan. Everything runs. The only adjustment is to book earlier in June, July and the first half of August, when the morning parasail, jet ski and Molokini slots fill a week or more out. Honolua Bay is calm in summer, so the West Maui snorkel sail is at its best.
If you are staying in Wailea or Kihei
Flip the order so the driving days bracket the trip. Day 1 stays easy, on your own beach. Day 2 becomes the Molokini day, with the raft a 10-minute drive away. Day 3 is the Upcountry day, since Paia is only 35 to 40 minutes from Wailea. Day 4 is the West Maui day: drive over by 8 for parasailing or the whale raft, do the afternoon snorkel at 12:30 or the ATV, and stay for the dinner cruise, driving home after 8 when the traffic has cleared. Day 5 is Hana, with hotel pickup. Our Kaanapali vs Wailea guide covers the trade-offs of each base.
A few rules that keep the trip pleasant
- One check-in time per day. Everything else should be flexible.
- Mornings for the water. The wind rises after noon on every coast. Boats, parasails and jet skis are smoother before 11.
- Avoid the pali road from 3 to 6 pm. The highway between Maalaea and Lahaina backs up every afternoon. Be on the side you want to be on, or wait it out over dinner.
- Book Molokini and whales early in the trip. Both are weather dependent, and an early slot leaves room to reschedule.
- Reef-safe sunscreen and a rash guard. The sun here is stronger than it feels in the trade wind.
- Leave a day unplanned if you have one. The best Maui afternoons are usually the ones with nothing on the calendar.
For the full list of what else is out there, including the things we did not fit into five days, see our best things to do in Maui guide, and the island map for how the regions connect.
Written by West Maui locals with 25 years in Maui water sports. How we make money.
