5 days in Maui Itinerary

Created using Inspirock Maui trip builder
Make it your trip
Fly
1
Wailea
— 1 day
Drive
2
Haleakala National Park
— 1 day
Drive
3
Lahaina
— 1 day
Taxi
4
Ka'anapali
— 1 day
Drive
5
Kahului
— 1 night
Fly

S M T W T F S
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3
4
5
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Wailea — 1 day

Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. For maps, more things to do, traveler tips, and other tourist information, use the Wailea trip itinerary planning website.

San Jose to Wailea is an approximately 6.5-hour flight. You'll gain 2 hours traveling from San Jose to Wailea due to the time zone difference. In October, Wailea is a bit warmer than San Jose - with highs of 88°F and lows of 70°F. You'll set off for Haleakala National Park on the 4th (Tue).
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Outdoors · Parks · Tours · Wildlife
Find places to stay Oct 3 — 4:

Haleakala National Park — 1 day

A Rare and Sacred Landscape

Haleakala National Park offers visitors the rare opportunity to walk down into the intact crater of a volcano.
Start off your visit on the 4th (Tue): admire all the interesting features of Haleakala Highway (Crater Road), get impressive views of Haleakala Crater, and then see the sky in a new way at Haleakala Observatories.

Start your trip to Haleakala National Park by creating a personalized itinerary on Inspirock.

Explore your travel options from Wailea to Haleakala National Park with the Route module. In October, daily temperatures in Haleakala National Park can reach 88°F, while at night they dip to 70°F. Finish your sightseeing early on the 4th (Tue) to allow enough time to travel to Lahaina.
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Nature · Parks · Scenic Drive · Outdoors
Side Trip
Find places to stay Oct 4 — 5:
Highlights from your trip

Lahaina — 1 day

Crown Jewel of Maui

Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
Kick off your visit on the 5th (Wed): kick back and relax at Ka'anapali Beach, stroll around Lahaina Banyan Court, then stop by Vintage European Posters, and finally get a taste of the local shopping with Lahaina Printsellers.

To find more things to do, photos, where to stay, and more tourist information, refer to the Lahaina trip itinerary builder app.

Explore your travel options from Haleakala National Park to Lahaina with the Route module. In October, plan for daily highs up to 84°F, and evening lows to 73°F. Finish up your sightseeing early on the 5th (Wed) so you can go by car to Ka'anapali.
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Parks · Beaches · Outdoors · Shopping
Find places to stay Oct 4 — 5:

Ka'anapali — 1 day

Perched at the western tip of Maui, the tourist hub of Ka'anapali offers a range of resorts and activities revolving around the beach.
To see other places to visit, traveler tips, photos, and more tourist information, you can read our Ka'anapali holiday planner.

Ka'anapali is just a short distance from Lahaina. Expect a daytime high around 84°F in October, and nighttime lows around 73°F. You will leave for Kahului on the 6th (Thu).
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Outdoors · Parks · Tours · Wildlife
Find places to stay Oct 5 — 6:

Kahului — 1 night

Kahului is a census-designated place (CDP) in Maui County, on the island of Maui, in the U.S. state of Hawaii. On the 6th (Thu), cruise along West Maui Circle Drive, experience rural life at Surfing Goat Dairy, and then cast your line with Maui Fun Charters. On the 7th (Fri), you'll have a packed day of sightseeing: look for gifts at Maui Specialty Chocolate and then take an unforgettable tour with a helicopter tour.

To see where to stay, reviews, maps, and tourist information, read our Kahului day trip app.

You can drive from Ka'anapali to Kahului in an hour. Alternatively, you can take a bus. In October in Kahului, expect temperatures between 88°F during the day and 70°F at night. Wrap up your sightseeing by early afternoon on the 7th (Fri) to allow time for the flight back home.
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Tours · Outdoors · Wildlife · Scenic Drive
Side Trips
Find places to stay Oct 6 — 7:

Maui travel guide

4.5
Scuba & Snorkeling · Beaches · Zipline
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.
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