Maui is home to spectacular beaches, scenic drives, waterfalls, national and state parks, resorts, vacation rentals, and water activities. So this guide for planning a trip to Maui will help you have an epic vacation.

How To Plan a Multi-Island Hawaii Trip

Know Before You Go: driving the “backside” of Hāna, on Highway 31, past ʻOheʻo Gulch, is rough, narrow, unpaved, and prone to landslides. Most car rental companies specify certain roads as “unauthorized,” and this is one of those roads.

Here’s everything you need to know for planning a trip to Maui!

When To Go

Maui’s peak travel season is December – March when prices and tourist numbers will be at their highest everywhere on the island. So book your accommodation, rental cars, and tours in advance to ensure availability. These months have the best surfing conditions, and this is the prime whale-watching season.

June – August is only slightly less crowded and expensive than December – March. The weather is perfect during these months – sunny and dry. Summer also has calmer currents, giving you ideal swimming conditions.

The year-round warm weather means Maui doesn’t have an off-season. But April – May and September – November are shoulder seasons when you can score some excellent (by Hawaii standards) accommodation and airfare deals.

Driving the Road to Hana is especially pleasant in these shoulder months since there are fewer tourists, and traffic won’t be as much of an issue along the route.

Getting Around

A car is essential on Maui. Many tour companies provide transportation to and from guided tours, and taxis and rideshares can be arranged by your hotel. But these can be expensive.

So if you’re going to leave your hotel more than a couple of times (which I highly recommend!), then a rental car can save you money. Plus, a rental car gives you flexibility over your itinerary and room to store and transport your belongings.

I spent three days on Maui with a rental car, and I drove all over the island. But because the island is so small, I only had to fill up my tank once.

What To Do

Drive The Road To Hāna – my favorite stops are Ho’okipa Beach Park, Wailua Valley State Wayside overlook (take the stairs to the right), Hanawi Falls (bring your swimsuit), Hāna Harvest, and Wai’anapanapa State Park.

Go on a boat tour to snorkel at the Molokini Crater.

See a luau.

Spend some time relaxing at a beach and the pool at your hotel or rental home.

Hike the Pīpīwai Trail (moderate-difficult) in Haleakalā National Park. 

Drive to the summit of Haleakalā volcano. You’ll need to dress warmly, and reservations are required to see the sunrise from the summit.

Go outrigger canoe surfing.

Do a helicopter tour (my favorite is a no-doors helicopter).

Take a surf lesson.

Where To Stay

Most people who visit Maui stay in the Wailea area and visit Hāna as a day trip. I recommend splitting your trip to spend a couple of nights in Wailea (my favorite hotel is the Andaz Maui), then drive the road to Hāna and stay in Hāna at the Hana-Maui Resort for two nights.

So I’ve rounded up the best hotels on Maui for every budget and preference, and the island also has some incredible vacation homes.

Suggested Itinerary

Day 1: Arrive on the island, pick up your rental car, and check into your hotel or vacation home in the Wailea area. Then see a luau.

Day 2: Go on a boat tour to snorkel at the Molokini Crater in the morning. In the afternoon, go outrigger canoe surfing or take a surf lesson.

Day 3: Do a helicopter tour (my favorite is a no-doors helicopter) in the morning. Then spend the afternoon enjoying a beach or the pool at your hotel or vacation home.

Day 4: Drive The Road To Hāna – make sure you stop at Ho’okipa Beach Park, Wailua Valley State Wayside overlook (take the stairs to the right), Hanawi Falls (bring your swimsuit), Hāna Harvest, and Wai’anapanapa State Park.

Day 5: Hike the Pīpīwai Trail (moderate-difficult) in Haleakalā National Park in the morning. Then spend the afternoon relaxing at a beach and the pool at your hotel or rental home.

Day 6: Fly home or to another Hawaiian Island.

Where To Eat

Wailea: Morimotos (Japanese, $$$$), Whale’s Tale (Coffee Shop, $$), Ka’Ana Kitchen (Hawaiian, $$$$), Matteo’s Osteria (Italian, $$).

Lahaina/Kaanapali: Monkeypod (Hawaiian, American, $$-$$$), Frida’s (Mexican, $$), Merriman’s (Farm-To-Table, $$$$), Duke’s Beach House (Seafood, $$).

Road To Hāna: Hāna Harvest (Coffee Shop, $), Coconut Glen’s (Ice Cream, $), Halfway To Hāna (Burgers, $$), Huelo Lookout (Fruit Stand, $), Peacocks Cafe Maui (Food Truck, $$), Mama’s Fish House (Seafood, $$$$).

Hāna: Hāna Ranch Restaurant (American, $$$-$$$$), I Lava Tacos (Mexican, $$), The Preserve Kitchen + Bar (Hawaiian, American, $$$$), The Broken Mouth (Food Truck, $$).

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This guide for planning a trip to Maui is not a sponsored post, and the thoughts and opinions expressed in this post are entirely my own. Some of the links in this guide for planning a trip to Maui are affiliate links, and, at no cost to you, I may earn a small commission from this guide for planning a trip to Maui.