Photo: Jkrauska / CC BY-SA 3.0
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Budget
$3,800
Mid-Range
$6,000
Luxury
$10,000
Best Months
Apr, May, Jun
Ready to plan
Book the trip pieces
This is the practical next step: check family-room availability, reserve age-friendly activities, and pack the gear this itinerary assumes you have.
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Getting there & around
From OGG to your Maui stay
Pre-book the airport transfer
A driver meets you at Kahului Airport. Booking.com shows the price before you book and has a child-car-seat request on the booking form.
Rent a car at OGG
Compare rental companies at Kahului Airport side by side. Many of them offer infant and child car seats as an add-on: use the Car seat filter and add one when you book.
Opens Booking.com with sample dates about a month out (or the stay dates saved on your trip board). Change them to your trip there. Tots & Trips may earn a commission.
Make it fit your family
Adjust this Maui, Hawaii itinerary
Slower pace
Treat each morning as the anchor and make the afternoon block optional.
Age-group lens
This plan is tuned for teen travelers, so keep the highest-energy activity early and preserve a low-stakes fallback.
Highlights
Day by day
Day-by-Day Plan
5 days, each paced morning to evening. Gold tags mark the nap and rest windows the plan builds in. Places the plan names are pinned on the Maui map.
Day 1: Arrival & Ka'anapali Surf
Morning
Pick up rental car at Kahului and drive west to Ka'anapali (about 45 min). The coast highway passes Lahaina, still rebuilding after the August 2023 wildfire — it's a community's home, not a photo stop, so keep driving. After check-in, let teens walk the paved Ka'anapali Beach Walk with a camera and no agenda, from Whalers Village to Pu'u Keka'a (Black Rock). Teens get to observe without being guided. Let them photograph what interests them.
Afternoon
Group surf lesson with Ka'anapali Surf Club, which meets at Marriott's Maui Ocean Club on Ka'anapali Beach: ages 13+, 90 minutes (a 20-minute beach briefing, then over an hour in the water), two to five students per instructor, from $119 per person.
Evening
Post-surf fuel at Cool Cat Express in Whalers Village — hand-pattied burgers and hand-spun milkshakes. The café lost its Front Street restaurant in the 2023 fire and now runs this fast-casual counter daily until 9pm. Teens are free to walk the beach path with a meet-back time while you watch the sunset from the sand.
Named today, on the map
Tip: Every Ka'anapali Surf Club class must be reserved ahead, and check-in at their desk is 30 minutes before the lesson. Please don't detour into Lahaina for photos of the burn area; Maui County asks visitors to stay off private property and out of fenced construction areas.
Est. cost: $100-180Find Day 1 ticketsDay 2: Haleakalā Sunrise + Photography Day
Morning
3am wake-up. This is the moment. Book sunrise entry at recreation.gov well in advance. At the summit, give teens 30 minutes to photograph independently — no direction. The alien landscape at dawn produces genuinely remarkable phone images. Then: hike the Sliding Sands Trail 2 miles into the crater. Other-worldly cinder cones.
Afternoon
Drive down to Kula for breakfast/lunch at Kula Bistro — farm-to-table, on the slopes of Haleakalā, genuinely good. Then Surfing Goat Dairy for a farm tour ($20/person) — teens who think they hate goats are proven wrong in approximately 4 minutes.
Evening
Back to west Maui by 4pm. Sunset on Ka'anapali Beach, where the sunset cliff-dive ritual at Pu'u Keka'a (Black Rock) happens every evening. Teens can wander the beach path while you watch from the sand.
Named today, on the map
Tip: It will be 30–40°F at the summit. Teens will insist this doesn't apply to them. Pack the layers anyway and hand them over wordlessly when they're needed.
Est. cost: $80-150Find Day 2 ticketsDay 3: Road to Hana — Independent Exploration
Morning
Road to Hana, departing 6:30am. Give teens the Shaka Guide app and let them navigate for the first half. Stops they control: Twin Falls (rope swing), Ke'anae Arboretum (tropical plants, free, quiet), and the Ke'anae Peninsula lookout.
Afternoon
Wainapanapa State Park black sand beach (parking reservation required). Then Hana town — teens can explore the small town while you get shave ice at Tutu's Snack Shop. The red sand beach at Kaihalulu (15-min hike from Hana) rewards the effort with jaw-dropping crimson sand.
Evening
Drive back. Stop for banana bread from the Halfway to Hana stand at mile marker 17 (cash only, $8 a loaf, worth every cent). Late arrival, hotel room food.
Named today, on the map
Tip: The red sand beach hike is on a narrow cliff trail. Not dangerous but requires careful footing. Worth it for teens who want the shot no one else has.
Est. cost: $70-120Find Day 3 ticketsDay 4: Kapalua Bay & a Sunset Sail
Morning
Daytime beach day at Kapalua Bay — calm, clear, protected by headlands. Best snorkeling you can do without a boat. The sea turtles here are habituated to humans and come close. Teens can free-dive down 5–8 feet for the angles.
Afternoon
Nap / rest built inNap and recharge. Night snorkel requires alertness.
Evening
Sunset sail off Ka'anapali Beach — several catamaran operators board right from the sand in front of the resorts, so there's no harbor drive. Teens get the trampoline nets at the bow; in winter (roughly December to April) humpback whales are often visible from the boat. Book a family-friendly departure and check the operator's minimum age.
Named today, on the map
Tip: Manta ray night snorkels are a Big Island (Kona) experience, not a Maui one — if your teens want that, it's a reason to add Kona. On Maui, keep turtle viewing at a respectful distance at Kapalua Bay and choose calm morning water for free-diving.
Est. cost: $100-200Find Day 4 ticketsDay 5: Cliff Jumping + Departure
Morning
Kapalua Coastal Trail — 1.76 miles along lava cliffs with sea arches. Teens who research will find the jump spots (10–15 ft into deep water through natural rock arches). Parents: scout first, ensure deep water. The trail itself is dramatic for photography even if no jumping happens.
Afternoon
Ululani's shave ice in Kahului (near airport location). Buy a bag of Maui Gold pineapple from the airport shops — the best pineapple in the world, genuinely. Departure.
Evening
Flight home. Teens will be quiet in a good way — the rare kind of tired that comes from actually doing things.
Tip: Maui Brewing Company has an airport-adjacent taproom near Kahului — good for a last meal if you have a 2pm+ flight.
Est. cost: $80-130Find Day 5 tickets
Day 1 on the map
Numbered pins are places this plan names; H is a hotel it mentions. Pins are approximate, from our Maui map.
Packing List
- Surf rash guard — long sleeve for sun during lessons
- Reef-safe mineral sunscreen (Hawaii state law, not optional)
- Winter layers for Haleakalā (puffy, gloves, beanie)
- Waterproof hiking sandals for Road to Hana swimming
- GoPro with chest mount for surf and night snorkel
- Dry bag for valuables on boat and hike days
- Cash for roadside vendors (banana bread, food stands are cash-only)
- Downloaded Shaka Guide app for Road to Hana
- Portable battery pack — long days drain phones
- Journal or sketchbook — Maui inspires more than expected
Recommended Gear for This Trip
The travel-with-kids essentials we'd pack for a trip like this — with current prices and ratings.
Monobeach Baby Beach Tent (Pop-Up, UPF 50+)
Amazon's ChoiceA pop-up shade base for naps, snacks and diaper changes on beaches with little natural shade.
Thinkbaby SPF 50+ Baby Sunscreen, 3 oz
Best SellerMineral SPF 50+ without oxybenzone or octinoxate, the two filters Hawaii bans.
LeIsfIt Toddler Barefoot Quick-Dry Non-Slip Water Shoes
Best SellerProtects little feet on hot sand, rocky shorelines, and slippery pool decks.
Sawyer 20% Picaridin Insect Repellent Pump Spray, 4 oz
DEET-free picaridin bug protection for tropical evenings, jungle trails, and dusk strolls.
AMACOOL Battery-Operated Clip-On Stroller Fan
Best SellerHeat melts kids faster than parents realize — clips to the stroller, car seat, or carrier.
Welly First Aid Kit (70 Count)
Fabric and waterproof bandages plus single-use antibiotic, hydrocortisone and cleansing packets, in a tin.
Prices and ratings are approximate and may vary — check the latest on Amazon. As an Amazon Associate we earn from qualifying purchases at no extra cost to you.
Safety Notes
Maui beaches require genuine ocean literacy — many have no lifeguards, shore breaks are powerful, and rip currents form on north and west shores in winter. Check conditions daily at Surf News Network. For cliff jumping: adults must scout for submerged rocks before teens jump, every time, regardless of 'it's always been fine.' The night manta snorkel is from a boat in the open ocean — confirm teen comfort with open-water swimming before booking. Haleakalā at 10,000 ft: some people experience altitude-related headaches — ibuprofen and water help.
Full Destination Guide
Maui offers the quintessential Hawaiian family vacation: stunning beaches, whale watching, and a relaxed pace that lets families slow down and enjoy the island life.