Your complete guide from SJC to the Valley Isle — with kids in tow.
If you’re a Bay Area family dreaming of warm turquoise water, jungle waterfalls, and an escape from the grind — Maui is your island. Better yet, direct flights from San Jose (SJC) mean you can be sipping a mai tai on a Kaanapali beach in under 6 hours. No connections, no chaos, just aloha.
This 7-day itinerary is designed with families in mind: a smart mix of adventure, relaxation, culture, and kid-friendly fun — without trying to cram in everything at once.
Before You Leave the Bay Area
Flights from SJC to Maui
Southwest, United, and Alaska Airlines all offer direct flights from San Jose to Kahului Airport (OGG) on Maui. Flight time is roughly 5.5 to 6 hours. Pro tip: book morning departures so you land with plenty of afternoon daylight to enjoy.
💡 Travel Agent Tip: Families of 4+ should book at least 4–6 months out, especially for summer and holiday travel. Hawaii routes fill fast from the Bay Area.
Best Time to Visit
Maui is gorgeous year-round, but Bay Area families tend to travel during summer (June–August) and the holiday break (December–January). April through early June is our favorite “sweet spot” — whale season overlaps (through May), crowds are thinner, and prices drop slightly after spring break.
What to Pack
Bay Area weather has nothing in common with Maui, so pack accordingly:
- Reef-safe sunscreen (required in Hawaii — chemical sunscreens are banned)
- Light layers for Haleakala sunrise (it gets cold — around 40°F at the summit)
- Water shoes for snorkeling and rocky beaches
- A light rain jacket — Maui’s north and east sides can get showers
- Kids’ snorkel gear (or rent locally — we can arrange)
Your 7-Day Maui Itinerary
Day 1 — Arrival & Settle In (West Maui / Kaanapali)
You’ve landed. Breathe in that warm plumeria-scented air and remind yourself: you’re in Maui.
After picking up your rental car at OGG (I recommend an SUV or minivan for families), head straight to your resort in Kaanapali or Wailea — two of the best family-friendly areas on the island.
- Check in and hit the pool — the kids have been on a plane for 6 hours, they’ve earned it
- Stroll the Kaanapali Beachfront Walk for a casual first sunset
- Dinner at Hula Grill on the beach — open-air seating, fresh fish, great for families
🌅 Don’t Miss: The cliff-diving ceremony at Black Rock (Pu’u Keka’a) at sunset — a nightly Kaanapali tradition that kids absolutely love.
Day 2 — Snorkel, Sea Turtles & Lahaina Town
Start the morning with Maui’s #1 family activity: snorkeling. Head to Kapalua Bay or Napili Bay — both calm, protected, and teeming with sea turtles and tropical fish.
- Morning snorkel at Kapalua Bay (one of the best beginner snorkel spots on the island)
- Lunch in Lahaina — the historic former capital of Hawaii, packed with restaurants, galleries, and shops along Front Street
- Stop by the famous 150-year-old Banyan Tree in Lahaina Court Square — the kids will want to climb it
📸 Photo Op: The Banyan Tree in Lahaina is the largest in the US — a must-see and perfect for a family photo.
Day 3 — Road to Hana (The Full Experience)
No Maui trip is complete without the Road to Hana — one of the most breathtaking drives in the world. Leave early (7 AM or before) and take your time. It’s a 64-mile winding coastal highway with 600 turns and 59 bridges. It’s not about the destination — it’s about the stops.
- Twin Falls — easy 20-minute hike, waterfalls, perfect for kids
- Wai’anapanapa State Park — stunning black sand beach (reserve entry in advance at gostateparks.hawaii.gov)
- Garden of Eden Arboretum — lush botanical gardens and a Jurassic Park filming location
- Keanae Peninsula lookout — dramatic lava coastline and taro fields
- Hana town — grab banana bread from Aunty Sandy’s roadside stand (a Maui institution)
💡 Travel Agent Tip: You do NOT need to drive back the same way. Continue past Hana and loop around the backside of the island (Highway 31) for more stunning views — just note some rental car companies prohibit this, so check your agreement or let me arrange the right rental for you.
Day 4 — Haleakala Sunrise & Upcountry Maui
This is the day that will make your whole trip unforgettable. Rising at 2:30 AM might sound brutal, but watching the sunrise from 10,023 feet above the clouds at Haleakala summit is one of those once-in-a-lifetime moments.
- Book your Haleakala sunrise reservation in advance at recreation.gov (they sell out weeks ahead)
- Dress in layers — it’s cold at the summit, even in summer
- After sunrise, explore Upcountry Maui — the cool, green farming community above Kula
- Stop at Surfing Goat Dairy for a farm tour the kids will love
- Lunch at Kula Lodge for gorgeous views over the valley
⚠️ Important: The drive from Kaanapali to the Haleakala summit takes about 1.5–2 hours. Set multiple alarms. It’s worth every groggy minute.
Day 5 — Molokini Crater Snorkel & Afternoon at the Beach
Today is all about the water. A snorkel boat trip to Molokini Crater — a partially submerged volcanic crater just off the coast — is one of the best snorkeling experiences in all of Hawaii.
- Book a morning Molokini snorkel tour (we can arrange this through our preferred vendors)
- Water visibility frequently exceeds 100 feet — expect sharks, rays, and hundreds of fish species
- Most tours also stop at Turtle Town on the way back
- Spend the afternoon at Wailea Beach or Big Beach (Makena) — one of Maui’s most beautiful white sand stretches
💡 Travel Agent Tip: Morning tours leave around 6:30–7 AM when the water is calmest. Afternoon winds can make for rough seas — especially for kids prone to seasickness.
Day 6 — West Maui Mountains & Kaanapali Beach Day
Take a slower pace today. West Maui is stunning and often overlooked — but the waterfalls, valleys, and viewpoints here are spectacular.
- Drive through Iao Valley State Monument — home of the iconic Iao Needle, a 1,200-foot green rock pinnacle
- Stop in Wailuku town — charming, non-touristy, with great local plate lunch spots
- Afternoon beach day at Kaanapali — paddleboards, snorkel gear, or just relax
- Dinner at Monkeypod Kitchen — a Bay Area family favorite every time we send clients
🍽️ Eat Like a Local: Don’t leave Maui without trying a plate lunch. Two scoop rice, mac salad, and kalua pork — that’s Hawaii comfort food.
Day 7 — Last Morning Magic & Fly Home
Your last morning is precious. Don’t waste it in a hotel room.
- Early sunrise walk on the beach — quiet, peaceful, and a perfect goodbye to the island
- Grab shave ice at Ululani’s (the best on the island — multiple locations)
- Last swim or snorkel if time permits
- Return your rental car and head to OGG — give yourself 2 hours before departure
Most afternoon flights from OGG land back in SJC by early evening, getting you home in time for the Bay Area fog — and about a week of post-vacation blues.
Practical Family Travel Info
Getting Around
A rental car is essential. Maui has no real public transit, and you’ll want the freedom to explore on your own schedule. Book early — cars sell out fast in summer and over the holidays.
Where to Stay
- Kaanapali (West Maui) — iconic resort strip, walking distance to Lahaina, great beach, calm water
- Wailea (South Maui) — more upscale, beautiful beaches, excellent restaurants, more consistent weather
- Kihei (South Maui) — best value for budget-conscious families; vacation rentals with full kitchens are a great option
Budgeting for Your Trip
Here’s a rough daily guide for a family of four:
- Budget: $300–$450/day (vacation rental, grocery shopping, mix of free and paid activities)
- Mid-range: $500–$750/day (resort hotel, mix of dining out and groceries, 1–2 paid activities)
- Luxury: $1,000+/day (beachfront resort, fine dining, private tours and charters)
💡 Travel Agent Tip: I can package flights, hotels, and car rental together to save you money — and we have preferred rates with top Maui resorts. Reach out before you book anything on your own.
Ready to Book Your Maui Family Vacation?
This itinerary barely scratches the surface of what Maui has to offer — and every family trip is different. Whether you want more beach days, a helicopter tour over the volcanoes, or a private sunset sail, we can customize this trip to fit your family perfectly.
As a Bay Area travel specialist, I know Maui well — and we know the specific needs of families flying out of SJC. Let me handle the details so you can focus on making memories.
📞 Contact me today to start planning your Maui getaway.
Your Bay Area travel agency — proudly serving San Jose and the greater Bay Area.