57 days in Maui Itinerary

57 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
Drive to Kahului Airport, Fly to La Guardia Airport

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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 Keawala'i Congregational Church. You'll find plenty of places to visit near Kihei: Maui Wine, Ulupalakua Vineyards (in Kula), Ho'okipa Beach Park (in Paia) and Hui No‘eau Visual Arts Center (in Makawao). 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 15.5-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 The Spa at Black Rock. Get a sense of the local culture at Lahaina Front Street and Old Lahaina Courthouse. 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 Kahanu Garden are good opportunities to explore the local culture. Museum-lovers will appreciate Hana Cultural Center and Laura Mango Art Gallery. Explore the numerous day-trip ideas around Kipahulu: Haleakala Crater (in Haleakala National Park) and Hana (Wai'anapanapa State Park, Hana Fresh, &more).

For other places to visit and tourist information, use the Kipahulu trip planner.

You can drive from Napili-Honokowai to Kipahulu in 3 hours. In December, daily temperatures in Kipahulu can reach 82°F, while at night they dip to 66°F. On the 17th (Sat), you'll travel back home.

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.