For a Maui family reunion, choose your base first: Kaanapali for one long, swimmable resort beach, Wailea for polished resorts in South Maui, or Kihei for condos and beach parks at a lower cost. Then plan two anchor days that need advance work: Haleakala, where every car needs its own sunrise reservation, and the Road to Hana, where key stops need timed bookings.
This guide compares the three bases for a group and walks through both big days, with the rules that catch large families out.
Kaanapali, Wailea or Kihei: choosing a base
| Base | Best for | Trade-offs |
|---|---|---|
| Kaanapali (West Maui) | Families who want one beach, a beach path and everything within walking distance | Busy in high season; furthest from Haleakala and Hana |
| Wailea (South Maui) | Groups wanting full-service resorts, pools and calm mornings on the beach | Higher rates; most dining is in the resorts |
| Kihei (South Maui) | Budget-minded families who want condos with kitchens and several beach parks | Less of a resort feel; more driving between condos |
Kaanapali. The beach runs about three miles, with a walking path behind it linking hotels, restaurants and shops. Hawaii.com notes the sandy ocean floor gives a gentle entry for children and elders, with Pu'u Keka'a (Black Rock) dividing a livelier south end from a quieter north end. Lahaina, just south, was hit hard by the August 2023 wildfire; follow local guidance and be respectful of the community.
Wailea. A planned resort area with large hotels and condo villages along a string of beaches. It works well when the grandparents want room service, pools and shade, and the group wants a single meeting place.
Kihei. A long stretch of condos facing the Kamaole beach parks. Renting two or three neighbouring condos gives each household a kitchen and keeps costs down.
If you are booking condos for future years, check the unit's status carefully. Maui County has moved to phase out vacation-rental use in apartment-zoned buildings in areas including West and South Maui.
Haleakala: sunrise rules for a group
Watching sunrise from the summit is the moment many families come for, but the rules matter when you are travelling in several cars. Per the National Park Service:
- Every vehicle entering between 3:00 and 7:00 a.m. needs a sunrise reservation, booked on recreation.gov for a small per-vehicle fee.
- Reservations open up to 60 days ahead at 7:00 a.m. Hawaii time, with some held back and released 2 days ahead.
- A visitor can only buy one sunrise reservation per three-day period, so with four cars, four different adults need to book.
- The reservation is separate from park entry. The entrance fee is charged per private vehicle and valid for three days, covering vehicles with up to 14 seats. That three-day pass also covers the Kipahulu District near Hana.
Also from the NPS: there is no gas in the park (the last stop is Pukalani), no food for sale, no EV charging, and summit temperatures can drop near freezing. Driving time to the summit is about 2.5 hours from Kahului, 3 hours from Wailea and 3.5 hours from Lahaina.
Sunrise means waking small children around 2 a.m. and a cold wait. Many families split it: adults and teens go for sunrise, while grandparents and young children visit in late morning, which needs no reservation, then everyone meets for lunch upcountry.
The Road to Hana with a family group
The Hana Highway is a slow, winding drive with narrow bridges and blind curves. Plan it as a full day with three or four stops, not a checklist.
- Book Wai'anapanapa early. The black-sand beach and coastal trail need advance reservations for non-residents: an entry ticket for every person and a parking reservation for each car, per the Hawaii State Parks FAQ. Bookings open 30 days ahead, must be made at least a day in advance, are sold in time slots, and cannot be changed or refunded.
- Kipahulu District. Past Hana, this part of Haleakala National Park has the Pipiwai trail through a bamboo forest. The NPS puts it about four hours from Kahului, advises against entering or wading in the streams because of flash floods, and notes rangers at the visitor centre.
- Consider a guided van. For a big family, one guide driving a single van means no one is stuck behind the wheel, everyone sees the views, and the group stays together. Our group transportation tips cover vans and transfers.
- Motion sickness. Seat sensitive travellers up front, pack snacks and water, and plan regular stops.
Staying overnight in Hana turns the drive into two relaxed halves and is easier on grandparents.
Other days that work for all ages
- Beach mornings. Calm-water mornings at your base beach are the backbone of the week. Rent a cabana or umbrella for shade.
- A snorkel cruise. Many boats leave from Maalaea or Kaanapali. Choose a larger, stable boat with steps and shade if grandparents are joining.
- An upcountry afternoon. Farms, gardens and small towns on the slopes of Haleakala make an easy, cooler outing.
- A family luau or celebration dinner. Book a private section or a group table well ahead for 20 or more.
Getting the group around the island
Maui is a driving island, and a reunion needs a transport plan before anyone lands. Pick up rental cars at Kahului airport, and size the fleet around your big days rather than beach days: each car going to Haleakala at sunrise needs its own reservation, and each car going to Wai'anapanapa needs its own parking booking. Minivans keep families together and hold car seats, strollers and beach gear.
Ask your resort or condo whether parking is charged per car per night, since that adds up with four vehicles. On days when everyone heads to the same place, carpool and name a meeting point in advance. For the Road to Hana, a single guided van often costs less in stress than three cars trying to stay in convoy.
A sample seven-day plan
- Day 1. Arrive, check in, beach and early dinner.
- Day 2. Beach morning; group welcome dinner.
- Day 3. Haleakala: sunrise for those who want it, a late-morning visit for everyone else, lunch upcountry.
- Day 4. Rest day at the pool or beach.
- Day 5. Snorkel cruise or a split day of activities by age.
- Day 6. Road to Hana with a guide, or drive to Hana and stay overnight.
- Day 7. Family photo session and farewell dinner.
Avoid putting Haleakala and Hana on back-to-back days; both start early and involve long drives.
Bottom line
Pick your base, then set calendar reminders for the Haleakala sunrise window 60 days out and Wai'anapanapa 30 days out, with one adult assigned per car. For flights, lodging styles and island comparisons, see our Hawaii family reunion trips page and our guide to planning a family reunion trip to Hawaii; Far & Away Adventures can coordinate the resorts, cars and tours for your group.
Frequently asked questions
How many rental cars does a reunion of 20 need on Maui?
Usually three or four mid-size vehicles or minivans, or fewer if you book group transfers and guided tours for the big days. Remember that each car needs its own Haleakala sunrise reservation.
Is Haleakala safe for young children and older relatives?
Many families visit, but the summit is high, cold and windy. Bring warm layers and food, and check with a doctor if anyone has heart or breathing concerns about altitude.
Which Maui base is closest to the airport?
Kihei and Wailea in South Maui are generally a shorter drive from Kahului airport than Kaanapali in West Maui.