Everything you need to plan a great trip from Oahu to Maui — from deciding whether Maui is right for you to booking flights, rental cars, and knowing what to pack.
Start Here: Are You New to Maui?
If this is your first trip to Maui, the planning process can feel overwhelming. There are decisions to make in a specific order — and making them out of sequence (booking a hotel before knowing which area suits you, or booking tours before sorting out transportation) leads to stress and wasted money.
Here’s the order we recommend:
Step 1: Decide if Maui is the right island for your trip Step 2: Figure out how many days you need Step 3: Book your flights Step 4: Book your rental car immediately after Step 5: Choose your area and book accommodation Step 6: Plan your activities and book tours in advance Step 7: Read the pre-trip essentials so nothing surprises you
The guides below walk you through every step.
The Planning Guides
Is Maui Right for You? Maui vs Oahu
Not sure whether to spend your time on Maui or Oahu — or how to split your time between them? This guide compares both islands honestly across beaches, cost, activities, food, nightlife, families, and couples so you can make the right call for your trip.
👉 Maui vs Oahu: Which Island Should You Visit? →
How Many Days Do You Need? Maui Itineraries
Three days, five days, or a full week — the right trip length changes everything about how you plan. This section has day-by-day itineraries for each, so you know exactly what you can fit in and what to prioritize.
👉 Maui Itinerary: 3, 5 & 7 Days →
Flights from Oahu to Maui
The flight is only 35–40 minutes, but knowing which airline to book, when to buy, and how to find the best fares makes a real difference. Five airlines fly this route — here’s how they compare.
👉 Flights from Oahu to Maui: Airlines, Prices & Tips →
Maui Car Rental Guide
A rental car is non-negotiable on Maui. The island has almost no public transportation, and the best experiences — Road to Hana, Haleakala, the beaches of West and South Maui — all require one. Maui also has a well-documented car shortage. Book early.
How Much Does a Maui Trip Cost?
Maui is one of the most expensive destinations in the United States — but the range is wide. This guide breaks down every cost category with real 2026 prices: flights, car rental, accommodation, food, tours, and the hidden fees most visitors don’t see coming.
👉 How Much Does a Trip to Maui Cost? →
Where to Stay in Maui
West Maui or South Maui? Kaanapali or Wailea? Hotel or vacation rental? This guide covers every area with honest pros, cons, and specific hotel recommendations at every price point.
Travel Tips: What to Know Before You Go
The practical stuff that doesn’t fit anywhere else — what to pack, what to book before you leave Oahu, how the HNL inter-island terminal works, cultural etiquette, ocean safety, driving tips, and a complete pre-trip checklist.
Key Things to Book Before You Arrive
A few things on Maui sell out weeks or months in advance. Don’t leave these until you land:
- Rental car — Book immediately. Prices rise and availability disappears fast.
- Haleakala Sunrise Permit — Free but extremely limited. Book at recreation.gov the moment your dates are set.
- Waianapanapa State Park — Black sand beach on Road to Hana. Reservations required at gostateparks.hawaii.gov.
- Molokini Snorkel Tour — Morning departures fill up fast in peak season.
- Luau — Popular shows sell out weeks ahead, especially December–April.
Ready to Explore Maui?
Once you’ve got the planning sorted, here’s where to go next: