IN THIS GUIDE
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Hawaii holiday with a toddler? Sounded ambitious when we first booked it, two islands, fifteen days, and a two-year-old who’d never been on a flight longer than three hours. We travelled in March 2025, and it’s taken us a while to get this write-up live, but the trip itself ended up exceeding every expectation we had going in. This is the full day-by-day Hawaii itinerary, real costs included, from the ESTA application right through to the flight home.
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Before You Go: Getting Ready for Hawaii Holiday
ESTA Application
As Australians, Murray and our daughter needed an ESTA to enter the US. The process was straightforward, applied online at esta.cbp.dhs.gov, approval came through in under 24 hours, and it’s valid for two years. Cost was $21 USD each. I travelled on my Philippine passport with an existing 10-year US tourist visa, so no ESTA was needed on that side, worth checking your own passport’s specific entry requirements before you book.
Flights
We flew Brisbane to Sydney return with Virgin Australia ($683.88 AUD for the three of us), then Sydney to Honolulu return with Hawaiian Airlines ($2,603.68 AUD for two adults and a toddler). Inter-island flights between Oahu and Maui with Hawaiian Airlines came to $865.20 USD for the three of us. The international leg was a 9-hour flight, and having an empty seat next to us made a real difference for stretching out with a toddler.
Travel Insurance
We booked through Covermore, $669 AUD for the full trip.
Currency: How We Saved on USD
We signed up for Wise about six months before the trip and started buying USD gradually whenever the AUD/USD exchange rate was in our favour, rather than converting everything at once closer to departure. It meant we weren’t at the mercy of a single exchange rate on the day, and by the time we left, most of our spending money was already sitting in USD at a better rate than we’d have gotten converting last-minute.
Money Tip:
Sign up for Wise a few months before you travel and buy USD gradually whenever the exchange rate favours you, rather than converting everything right before departure. Order the physical card too, it’s handy for withdrawing cash at ATMs once you’re in Hawaii.
Airport-Night Accommodation
Our Honolulu to Sydney flight arrived back late, so we booked one night at Travelodge Sydney Airport before the final short flight home to Brisbane, $244.04 AUD. If your family wants more time in the city rather than just an airport stopover, our Sydney with kids guide covers how to make the most of it.
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Hawaii Holiday Cost Overview
Here’s what we spent on the fixed, bookable parts of the trip, flights, insurance, ESTA, all four Hawaii accommodation stays, and the tours below. This doesn’t include daily food and general spending, which we cover separately. All figures reflect what we paid during our March 2025 trip, prices change, so check the linked booking pages for current rates before you plan your own budget.
Brisbane–Sydney return flights (Virgin, 3 people)
$683.88 AUD
Sydney–Honolulu return (2 adults + toddler)
$2,603.68 AUD
Inter-island flights, Hawaiian Airlines (3 people)
$865.20 USD
Travel insurance, Covermore
$669 AUD
ESTA applications (2 people)
$42 USD
Car rental, 1 day, Oahu (via Turo)
$200 USD
Travelodge Sydney Airport (1 night)
$244 AUD
Waikiki Airbnb, Waikiki Grand Hotel (3 nights)
$1,115.52 AUD
Kihei Kai Nani Rentals, Maui (4 nights)
$1,942.59 AUD
Westin Maui Resort and Spa (1 paid night, 1 gifted by family)
$600 USD
Alohilani Resort Waikiki Beach (4 nights)
$1,677.41 AUD
Old Lahaina Luau (2 adults, toddler free)
$460.74 USD
Pearl Harbor Aviation Museum (2 adults)
$55.98 USD
Molokini snorkel & whale watching (2 adults)
$367.56 USD
Kualoa Ranch full-day tour (2 adults)
$252.04 USD
Oahu Family Itinerary (Days 1–4)
Staying: Waikiki, Honolulu (Airbnb), 3 nights
Day 1, March 15: Arrival in Honolulu
We flew Brisbane to Sydney in the morning, then Sydney to Honolulu overnight, arriving into a bright, sunny Honolulu at 10:35am. We booked an airport transfer from Honolulu Airport to our hotel in Waikiki in advance for a stress-free start, one less thing to think about with a jet-lagged toddler in tow.
After checking in and a short rest, we headed to Ala Moana Shopping Centre by bus (cash only, $3 USD per adult, and note that prams need to be folded before boarding). We grabbed lunch at the food court, stocked up on essentials at Target, which stocks far more than its Australian counterpart, everything from groceries to nappies to luggage, and let our daughter loose on the one playground we found near the mall entrance. Play spaces here are much thinner on the ground than what we’re used to at home.
Getting back with a toddler, a pram, and a trolley of groceries, the bus driver asked us to fold the pram with our hands full. First logistics lesson of our Hawaii holiday. So we walked instead, a 50-minute stroll along Waikiki Beach as the afternoon crowds settled in and surfers caught the sunset waves. A beautiful way to see the beach for the first time. On the way back we caught the free Kuhio Beach Hula Show, held Tuesday and Saturday evenings from 6:30-7:30pm near the Duke Kahanamoku Statue. A low-key introduction to Hawaiian culture on day one.
Money and Bus Tips:
You can withdraw US dollars at Daniel K. Inouye International Airport (HNL) using a physical Wise card, though fees apply. ATMs are scattered across the check-in and baggage claim levels in Terminals 1 and 2. We withdrew $200 USD on arrival, handy for tipping, bus fares, and getting smaller change from ABC Store purchases. For the bus itself, a HOLO card is worth grabbing, $3 USD per journey compared to $3.25 USD paying cash on board, and you can buy one at any ABC Store in Waikiki.
Airport Transfer Tip:
If you are traveling with small kids, always request a car seat when booking airport transfer from Honolulu Airport to your hotel. Tipping shuttle drivers is customary in Hawaii, around 15% of the fare is standard.
Sunset over Diamond Head, then free hula show at Kuhio Beach.
Day 2, March 16: Farmer's Market and a Sunset Swim
A slower morning, coffee at Knots Coffee Roasters, then a small Sunday farmer’s market (Aloha Market at Waikiki, 8am-1pm) right near our accommodation. After church and a nap, we headed to Kuhio Beach for an afternoon swim with a boogie board, swimming alongside locals. A quick warning worth passing on: theft is a known issue at this beach, so bring only what you need. Dinner was casual, Mexican food at International Market Place’s food court.
Day 3, March 17: A Scenic Drive Around Oahu
We hired a car for the day through Turo ($200 USD) and did a loop covering the North Shore and windward coast. Stops included Green World Coffee Farm (a quick coffee tasting, though we’re admittedly spoiled by Australian coffee), the Dole Plantation, and Haleiwa Store Lots for shave ice at Matsumoto’s. Lunch was garlic butter shrimp at Giovanni’s Shrimp Truck, arrive before 11am to beat the crowds. Best lunch of our Hawaii holiday, hands down.
If self-driving isn’t your thing, the Oahu: Full or Half Day Grand Circle Island Tour is worth a look, especially for first-time visitors. It covers Oahu’s most iconic landmarks, from Diamond Head to the North Shore, includes hassle-free pickup from select Honolulu hotels, and comes with a guide sharing Hawaiian history and culture along the way, a stress-free option if you’d rather sit back and take it all in.
The afternoon took us to Byodo-In Temple (we paid $5 USD per adult, our daughter entered free), a stunning, historical stop with koi ponds that our daughter loved, modeled after a 950-year-old temple in Uji, Japan. We rounded out the day with Hoʻomaluhia Botanical Gardens and a stop at Halona Blowhole on the southeastern coast. The weather turned drizzly and windy, so we skipped any beach stops for the day, not every day on a Hawaii holiday is a swim day, and that’s okay. Wild roosters, by the way, are everywhere on Oahu, worth mentioning before it catches you off guard.
A quiet detour to Byodo-In Temple, then wandering Hoʻomaluhia Botanical Garden on our Oahu road trip.
Day 4, March 18: Flying to Maui
A quick last-minute Target run for a car seat and a replacement suitcase (one wheel had already given up). Then a coffee stop at Kona Coffee Purveyors. Off to the airport next for our Hawaiian Airlines flight to Maui, arriving into Kahului at 5pm to a warm welcome from family with fresh orchid leis. We used my cousin’s car to get around Maui for the rest of our stay, a huge help given how spread out the island is. If you don’t have that option, a Kahului OGG Airport and Kihei Wailea Hotels Private Transfer is a straightforward way to get from the airport to your accommodation without needing to rent a car straight away.
Maui Family Itinerary (Days 5–10)
Staying: Kihei and Lahaina, Maui (Airbnb + Resort), 6 nights
Day 5, March 19: Family Time in Kihei
This day was set aside for a family reunion, my relatives are mostly based in Maui, and it was the first time Murray and our daughter had met that side of my family. A relaxed, no-itinerary day, exactly what you want in the middle of a longer trip.
Day 6, March 20: Molokini Crater Snorkel and Whale Watching
An early start from Ma’alaea Harbor for a snorkel and whale-watching tour, we spotted a whale waving its tail on the way out, a lucky moment we managed to photograph. Keep in mind the whale-watching portion only runs during whale season, roughly December to May, so if you’re visiting outside that window you’ll get the snorkel without the whales.
The water at Molokini Crater itself is bracingly cold, and while our daughter enjoyed watching the fish from the glass-bottom section of the boat, Murray went in for the full swim. Lunch was included, fresh fish tacos, and it’s worth knowing that SNUBA gear is an additional cost if you want to try it.
Whale watching at sunrise, then Murray in the blue waters of Molokini Crater.
That evening we had dinner booked at The Plantation House, valet parking, ocean views, and colouring pages for kids at the table. It was the most expensive meal of the whole trip, though we had a lovely experience.
Day 7, March 21: Turtles at Ho'okipa Beach Park and Local Town Paia
Coffee at Akamai Coffee and Co (a genuine contender against Australian coffee), then Ho’okipa Beach Park to watch dozens of turtles resting on the sand and a sea lion nearby, while our daughter splashed in a calm rock pool. Lunch in Paia, a lovely little town for browsing galleries and shops, at Flatbread Company for wood-fired pizza. Dinner was a home-cooked Filipino feast with relatives in Kahului.
Day 8, March 22: Checking Into the Westin
A morning swim at Kamaole Beach Park II, close enough to walk to from our accommodation, with turtles bumping gently against our feet in the shallows. After checkout, we stopped at Maui Ku’ia Estate Chocolate in Lahaina for hot chocolate and a few bars to bring home, then checked into the Westin Maui Resort and Spa for a two-night stay, one night gifted by family, since my cousin works there.
Lahaina Beach with Molokai on the horizon, and a food van pit stop in front of the Westin.
Day 9, March 23: Old Lahaina Luau
Morning coffee and acai at Vintage Coffee in Whalers Village, then a swim at the resort’s kids’ pool, complete with a slide our daughter didn’t want to leave. In the afternoon we did a family photoshoot on Lahaina Beach right in front of the resort.
The evening’s Old Lahaina Luau was one of the highlights of the whole trip, greeted with fresh leis on arrival, a beautiful setting, sunset timing, and a story-driven performance that held our daughter’s attention the whole way through, at one point dancing along beside our table. The food was excellent, taro rolls, kalua pork, poke, and grilled fish among the highlights, and the staff were warm and attentive throughout.
Day 10, March 24: Back to Oahu
A last morning coffee at Whalers Village and pool swim at the resort, then checkout, returning the car to family and heading to the airport for our flight back to Honolulu. We arrived at Alohilani Resort Waikiki Beach just after sunset, a comfortable stay right in the heart of Waikiki with a partial ocean view, an infinity pool, and easy access to nearby restaurants.
Two things we’d planned for Maui but let go of as the trip took shape: the Road to Hana and a sunrise tour of Haleakalā. If your kids can manage a long day out, this Road to Hana tour covers the full route including stops at Ho’okipa and Paia, without you needing to drive the winding road yourself. For sunrise, this Haleakalā sunrise tour is stroller-friendly and includes breakfast, though it’s worth noting the summit sits at around 9,740 feet, so it’s worth checking with your doctor first if you’re travelling with young children.
Back to Oahu Family Itinerary (Days 10-13)
Staying: Waikiki, Honolulu (Airbnb), 4 nights
Day 11, March 25: Pearl Harbor
A buffet breakfast at Duke’s Waikiki ($29 USD per adult, $17 USD for kids under 10, no bookings needed but expect a queue), then off to Pearl Harbor. We took an Uber rather than public transport, our earlier experience with folding the pram on the bus made that decision easy, roughly 30-45 minutes depending on traffic.
We booked general admission to the Pearl Harbor Aviation Museum ($27.99 USD per adult at the time, our March 2025 ticket price, free for our under-3 daughter), which suited her love of planes, she headed straight for the aircraft displays. Prices have gone up since our visit, so check current rates and book ahead through the link. A free shuttle connects the Visitor Center to Ford Island, worth noting that photography is restricted on the shuttle and around parts of the active military base.
Bag and Pram Tip:
Bags must be deposited before entry ($7-$10), so pack light, a transparent bag skips the fee if you’re travelling with a toddler. Prams are fine in outdoor areas and museums, but not on the shuttle boats or USS Arizona Memorial, park yours before boarding.
Day 12, March 26: Kualoa Ranch
Kualoa Ranch’s mountains, straight out of Jurassic Park.
An early malasada run to Leonard’s Bakery (get there early, the line grows fast), then a scenic drive across the island to Kualoa Ranch, arriving around 9am. We booked two tours back to back: the Ocean Voyage Tour, lunch in between, then the Movie Sites and Ranch Tour in the afternoon.
The Ocean Voyage Tour covers an ancient Hawaiian fishpond and a catamaran cruise across Kāneʻohe Bay, sea turtles and manta rays included. The Movie Sites and Ranch Tour takes in several well-known filming locations, our daughter slept through most of it, which gave us a relaxed hour to enjoy the scenery ourselves. We finished the day with a swim at Kaaawa Beach, shallow water for kids and a gorgeous mountain backdrop, it quickly became our favourite spot for a swim.
Day 13, March 27: Last Day in Waikiki
A deliberately relaxed final day, a sleep-in, a swim at Waikiki Beach, and packing. In the afternoon we caught a free cultural performance at the Royal Hawaiian Center’s courtyard, where our daughter made a new friend among the other kids watching. Dinner was hotpot at Ala Moana.
Heading Home: Days 13-15
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An early transfer to the airport on Day 13, then the long flight back to Sydney, arriving into Sydney International on Day 14. We stayed overnight at Travelodge Sydney Airport before the final short flight home to Brisbane on Day 15, arriving early afternoon. Jet lag took about a week to fully shake off.
What We'd Skip Next Time
The Plantation House dinner on Maui is the one we’d cut. Valet parking, ocean views, colouring pages for kids at the table, it was the most expensive meal we’ve had on the trip, and lovely as it was, it didn’t feel essential compared to everything else the day already gave us. We had a lovely experience, but next time we’d probably put that budget toward touring Hana and other parts of Maui instead.
Where We Stayed
Four different stays across two islands, a mix of Airbnb and hotel bookings depending on the leg of the trip.
OAHU
Waikiki (Airbnb) →
Kapahulu Avenue, Honolulu, in the Waikiki Grand Hotel
March 15-18, 3 nights, $1,115.52 AUD
Rooftop views of Diamond Head and Kuhio Beach, an easy walk to the beach and public transport.
MAUI
Kihei Kai Nani Rentals (Airbnb)→
South Kihei Road #228, Kihei
March 18-22, 4 nights, $1,942.59 AUD
A one-bedroom vacation home with a full kitchen and living room, plus a shared pool and self-serve laundry on site.
MAUI
Westin Maui Resort and Spa→
Kaanapali
March 22-24, 2 nights, $600 USD
A smooth check-in and a kids’ pool with a slide our daughter didn’t want to leave, right on Lahaina Beach. One night was gifted by family in Maui.
OAHU
Alohilani Resort Waikiki Beach (Airbnb)→
2490 Kalākaua Avenue, Honolulu
March 24-28, 4 nights, $1,677.41 AUD
A partial ocean view balcony, an infinity pool, on-site laundry, and easy walking access to Waikiki’s restaurants.
Where We Ate
A running list of the spots that stood out, from quick bites to the occasional splurge.
Breakfast buffet, $29 USD per adult, $17 USD for kids under 10, walk-ins welcome but expect a queue.
Malasadas, get there early, the line grows fast.
Garlic butter shrimp with rice, North Shore. Arrive before 11am to beat the lunch crowd.
The closest we found to Australian-strength coffee.
FAQs: Planning a Hawaii Holiday With Kids
Entry Requirements: ESTA for Australians
Do Australians need an ESTA for Hawaii?
Yes, Australian citizens need an approved ESTA to enter the US, including Hawaii. Apply online at esta.cbp.dhs.gov well before you travel, approval usually comes through within 24 hours, and it’s valid for two years.
What do I need to apply for an ESTA?
You’ll need a valid passport from a Visa Waiver Program country, a recent selfie-style photo, your email address, home address and phone number, and an emergency contact’s phone and email. Payment is required at the time of application, most major cards and PayPal are accepted. A small number of applicants may also be asked for extra details like aliases, a national ID number, or Global Entry information, though this isn’t required for most travellers.
How long does it take for an ESTA to be approved?
Ours came through in about 24 hours, though many applications are approved much faster, sometimes within minutes. You can apply as early as 3 months before you travel, and we’d recommend doing so well ahead of your trip rather than leaving it until the last minute.
How much does an ESTA cost?
Planning Your Hawaii Holiday
How much does a 15-day Hawaii holiday cost for a family?
Our fixed costs, flights, insurance, ESTA, all four Hawaii accommodation stays, and tours, came to several thousand dollars across AUD and USD. Daily food and general spending are on top of that. See our full cost breakdown above for the exact figures.
Should we split our time between Oahu and Maui?
For a longer trip, yes. Oahu and Maui offer different experiences, Oahu leans more urban, while Maui has plenty of history of its own too, just with a slower, more relaxed pace. Splitting time let us see both without feeling rushed on either island.
Getting Around on Your Hawaii Holiday
Is public transport in Hawaii pram-friendly?
Not particularly. Buses require prams to be folded before boarding, which is difficult with a toddler and shopping in hand. We found Uber a far easier option once we had a pram involved, especially for longer trips like Pearl Harbor. If you do plan to use the bus, a HOLO card is cheaper than paying cash on board, $3 USD per journey versus $3.25 USD cash, and it’s available at any ABC Store in Waikiki.
How many days do you need for a Hawaii holiday with kids?
A week is enough to settle into one island without rushing, but if you want to see both Oahu and Maui properly, budget at least ten to fifteen days. Our own itinerary ran fifteen days across two islands and still felt unhurried rather than packed, which is the pace we always aim for with a young child in tow.
What's the best time of year to visit Hawaii with kids?
Hawaii’s climate stays mild year-round, so there’s no bad time to go. Shoulder seasons, spring and autumn, bring fewer crowds and better prices than the summer and Christmas peaks. We travelled in March and caught the tail end of whale watching season, which runs roughly December to April.
Do you need a rental car in Hawaii with kids?
On Oahu, Uber and the bus network cover Waikiki well enough that a car is optional unless you’re doing a full island loop like we did. On Maui, a car is close to essential, distances between towns are longer and public transport is limited, so factor that into your Hawaii holiday budget.
Do you need a car seat for self-driving in Hawaii?
Yes, a car seat is essential if you’re self-driving with young kids in Hawaii, it’s a legal requirement, not just good practice. We bought ours at Target in Ala Moana rather than relying on a rental company’s option, and it turned out to be one of our better purchases, it folds down small enough to pack in our luggage, and we still use it on trips now.
What is the tipping culture like in Hawaii?
Yes, tipping is part of everyday life in Hawaii, more so than in Australia, so we always kept cash on hand for tours, shuttles, and meals out. Most hospitality services expect a tip, restaurants, hotel staff, transfers, and tour guides among them. Standard tips usually run 15-20%, though it’s worth using your own judgement, even takeaway coffee orders often prompt for a tip, and we didn’t feel obliged to tip on those. For sit-down service or anything where someone’s gone out of their way, we tipped generously.
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Murray & Jomana
Really Traveling, Slow Family Travel. We’re a Brisbane-based family writing about slow travel with young kids across Australia and beyond, and winners of the South Bank Local Guides competition, taking home the Key to South Bank prize worth more than $14,000 (see the official announcement, also on LinkedIn and Instagram). Everything on this site comes from trips we actually took with our own daughter. Read our story here.
Jomana is the heart behind Really Traveling — the one making sure every itinerary actually works when you’ve got a tired toddler and a delayed flight. She’s the family’s chief researcher, packing list perfectionist, and the reason our trips run smoother than they have any right to. If the advice on this site is practical and honest, that’s Jomana’s doing.
