Maui Itinerary

Taking your family to Hawaii is typically a bucket list item for most families. And if you can only choose one of the Hawaiian islands, we recommend Maui as it has a little bit of everything – city life (like the bigger islands); sandy beaches and rocky beaches; and rustic, tropical, old Hawaii (like you would find on Kauai). What most people don’t realize is just how varied the island of Maui actually is.

There are three very distinct sides of the island where everything from the climates to geology vary greatly. Those areas are West Maui (Lahaina, Kaanapali and Kapalua), Southern Maui (Wailea and Kihei) and Northern Maui (Paia and Hana). And they could not be more different from each other. So if you have saved enough miles or money for the flights over, you might as well experience the entire island and spend some time in each area if you can.

Below are the travel plans we used which included each area for lodging, activities and dining. Under the Destinations tab, we provided more details on each area as well as other options you may want to consider. On this particular trip, we included a self-guided biking trip from the top of the volcano to the beach; the Road to Hana; a boating and snorkeling trip to Lanai; a Luau, etc. However, some families may want to consider some other activities including helicopter rides or zip lining in the rain forests.

DAY 1 – paia – dinner and early bedtime

Fly to Kahului (OGG)

Eat: Flatbread Company ($) – Mopsy’s Kalua Pork Pizza
Stay: The Paia Inn – ($$)

DAY 2 – paia – sunrise and biking down a volcano

Maui Sunriders – Sunrise Tour – See the sun rise above the clouds and a self-paced biking tour to the beach ($$)
Makawao – Snacks and Shopping
Visit Charley’s Restaurant and Saloon (Owned by Willie Nelson)
Shopping in Paia – Clothes, Snacks and Drinks

Eat: Kula Lodge – Breakfast ($) – Loco Moco, Pancakes with Macadamia Nuts and Coconut Syrup
Eat: Komoda Store and Bakery – Snack ($) – Guava Malsadas and Butter Rolls
Eat: Mama’s Fish House ($$$) – Fresh Fish, Ahi Poke, Polynesian Black Pearl Desert and Kuau Chocalate Pie
Stay: The Paia Inn – ($$)

DAY 3 – hana – road to hana

Road to Hana – See Hana under Destinations for full details and an itinerary and tips for the trip

Eat: Aunt Sandy’s – Snacks, Lunch ($) – Banana Bread, Pineapple, Shaved Ice
Eat: Hana Ranch Burger Food Truck – Lunch ($)
Stay: Travaasa Hana – ($$)

DAY 4 – hana – hiking, boogie boarding, body surfing, beach

Hike the Pipiwei Trail ($)
See the Seven Sacred Pools (Ohe’o Gulch) (-)
Spend the afternoon at Hamoa Beach body surfing and boogie boarding

Eat: Leftover banana bread – Breakfast ($)
Eat: Braddah Hutts BBQ Grill – Lunch ($$) – Kalua pork and chicken tacos
Eat: Troy’s Plate Lunch – Dinner ($) or Hana Ranch Restaurant ($$)
Stay: Travaasa Hana – ($$)

DAY 5 – wailea – road to hana, the pool

Waiʻanapanapa State Park – Black Sand Beach and Lava Tubes (-)
Kahanu Garden & Pi’ilanihale Heiau – Polynesian temple and photos ($)

Eat: The Surfin’ Burro – Breakfast tacos and bagels – Breakfast ($)
Eat: Humuhumunukunukuapua’a – Lunch ($)
Stay: Grand Wailea ($$)

DAY 6 – wailea – the pool

Shop at Safeway – Breakfast and Lunches
Water slides, water elevator, rope swings and more

Eat: Volcano Grill – Poolside Dinner ($$)
Stay: Grand Wailea ($$)

DAY 7 – kapalua bay – scenic drive

Morning at the pool
Maui Ocean Center ($$)

Eat: Duke’s Beach House – Fish Tacos, Hula Pie ($$)
Stay: Montage Kapalua Bay ($$$) or any of the hotels in Ka’anapali or Kapalua Bay

DAY 8 – kapalua bay – sailing, snorkeling and Lanai

Trilogy Sunrise Tour – Discover Lanai – Snorkeling, Private Beach, Volleyball, Plantation Tour ($$$)

Eat: On Boat – Breakfast and Lunch (included)
Eat: Merriman’s – Dinner – Steak, Mahi Mahi, Mai Tai, Pineapple Perdu, Chocolate Purse ($$$)
Stay: Montage Kapalua Bay ($$$) or any of the hotels in Ka’anapali or Kapalua Bay

DAY 9 – kapalua bay – hiking, swimming

Hike Kapalua Coastal Trail
Day by the pool and beach

Eat: The Plantation House – Breakfast
Eat: Cane and Canoe – Dinner ($$)
Stay: Montage Kapalua Bay ($$$) or any of the hotels in Ka’anapali or Kapalua Bay

DAY 10 – lahaina – shopping, banyan tree, luau

Shopping
Lunch at Kimo’s – Watching the cruise lines dock and looking over Lanai and Molokai
Lahaina Banyan Court Park – Banyan Tree
Old Lahaina Luau ($$)

Eat: Kimo’s – Kalua Pork Tacos or Sandwich, Calamari
Eat: Ululani’s Shaved Ice ($) or Dole Whips
Eat: Old Lahaina Luau – Dinner ($$)
Stay: Montage Kapalua Bay ($$$) or any of the hotels in Ka’anapali or Kapalua Bay