59 days in Maui Itinerary

59 days in Maui Itinerary

Created using Inspirock Maui Trip Planner

Make it your trip
Fly
1
Kihei
— 20 nights
Drive
2
Napili-Honokowai
— 22 nights
Drive
3
Kipahulu
— 13 nights
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Kihei

— 20 nights
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Appreciate the collections at Alexander & Baldwin Sugar Museum and Makai Glass Maui. Deepen your sense of the past at sights like Saint Theresa Roman Catholic Church and Hui No‘eau Visual Arts Center. You'll find plenty of places to visit near Kihei: Ho'okipa Beach Park (in Paia) and Maui Wine, Ulupalakua Vineyards (in Kula). Next up on the itinerary: tour the pleasant surroundings at Kamaole Beach Park III, enjoy the sand and surf at Maluaka Beach, learn and have fun at Island Art Party, and immerse yourself in nature at Iao Valley.

For maps, other places to visit, photos, and tourist information, read Kihei trip planner.

New York City to Kihei is an approximately 12.5-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from New York City to Kihei. Traveling from New York City in October, expect Kihei to be a bit warmer, temps between 88°F and 70°F. Finish your sightseeing early on the 12th (Sat) to allow enough time to travel to Napili-Honokowai.

Things to do in Kihei

Outdoors · Parks · Beaches · Tours

Side Trips

Napili-Honokowai

— 22 nights
You'll enjoy a bit of beach vacationing at Ka'anapali Beach and D.T. Fleming Park. Get a sense of the local culture at Lahaina Front Street and Maria Lanakila Catholic Church. Explore Napili-Honokowai's surroundings by going to Lahaina (Papawai Scenic Lookout & Lahaina Pali Trail) and Waihee Ridge Trail (in Waihee).

Start your trip to Napili-Honokowai by creating a personalized itinerary on Inspirock.

Traveling by car from Kihei to Napili-Honokowai takes an hour. In November, daily temperatures in Napili-Honokowai can reach 81°F, while at night they dip to 71°F. Cap off your sightseeing on the 4th (Sun) early enough to travel to Kipahulu.

Things to do in Napili-Honokowai

Outdoors · Parks · Beaches · Tours

Side Trips

Kipahulu

— 13 nights
Hana Coast Gallery and Hana Cultural Center are good opportunities to explore the local culture. Get in touch with nature at Haleakala Crater and Hamoa Beach. Explore Kipahulu's surroundings by going to Hana (Wai'anapanapa State Park, Hana Fresh, &more).

To find ratings and other tourist information, use the Kipahulu trip itinerary builder tool.

Traveling by car from Napili-Honokowai to Kipahulu takes 3 hours. In December, daytime highs in Kipahulu are 82°F, while nighttime lows are 66°F. You will leave for home on the 17th (Sat).

Things to do in Kipahulu

Parks · Outdoors · Nature · Beaches

Side Trips

Maui travel guide

4.5
Scuba & Snorkeling · Beaches · Luaus
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.