20 days in Oahu, Maui & Kauai Itinerary

20 days in Oahu, Maui & Kauai Itinerary

Created using Inspirock Hawaii trip planner

This plan was created by another user. Make it your plan

Route & dates

Start: Chicago
Fly:  11 h 30 min
1
Honolulu
— 4 nights
Fly:  3 h 15 min
2
Lahaina
— 6 nights
Bus + Fly:  4 h
3
Princeville
— 6 nights
Fly + Bus:  4 h 45 min
4
Laie
— 2 nights
Bus + Fly:  14 h
End: Chicago

4
nights
Honolulu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Your day-by-day itinerary now includes Pearl Harbor Tours as well as Queen's Beach. You'll enjoy a bit of beach vacationing at Waikiki Beach and Lanikai Beach. Escape the urban bustle at Diamond Head State Monument and Scuba & Snorkeling.

For photos, ratings, more things to do, and more tourist information, read our Honolulu day trip tool.

Chicago to Honolulu is an approximately 11.5- hour flight. The time zone changes from Central Standard Time (CST) to Hawaii Standard Time (HST), which is usually a -4 hour difference. Expect much hotter temperatures when traveling from Chicago in March; daily highs in Honolulu reach 81°F and lows reach 68°F. Finish your sightseeing early on the 22nd (Sun) so you can travel to Lahaina.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trip

Lanikai Beach
Find places to stay Mar 18 — 22:
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
Scuba & Snorkeling

6
nights
Lahaina

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.
Get outdoors at Scuba & Snorkeling and Ka'anapali Beach. You'll enjoy a bit of beach vacationing at Wailea Beach and Kalepolepo Beach Park. Get out of town with these interesting Lahaina side-trips: Maui Veterans Cemetery (in Makawao), Haleakala Crater (in Haleakala National Park) and The Awakening Church (in Kihei). Next up on the itinerary: cruise along Hana Highway - Road to Hana, walk around Lahaina Banyan Court, kick your exploration up a notch at categoryPhrases.alias.some_of_the_top_local_zipline_courses_and_adventure_parks, and steep yourself in history at Lahaina Jodo Mission.

For more things to do, where to stay, other places to visit, and more tourist information, refer to the Lahaina trip builder tool.

Fly from Honolulu to Lahaina in 3.5 hours. Alternatively, you can do a combination of flight and ferry; or do a combination of flight and bus. In March, daytime highs in Lahaina are 78°F, while nighttime lows are 67°F. Wrap up your sightseeing on the 28th (Sat) early enough to travel to Princeville.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Kihei, Hana Highway - Road to Hana, Maui Veterans Cemetery, Ho'okipa Beach Park, Haleakala Crater
Find places to stay Mar 22 — 28:
Highlights from your plan
Scuba & Snorkeling
Haleakala Crater ©
Haleakala Crater
Ka'anapali Beach ©
Ka'anapali Beach

6
nights
Princeville

Princeville ©
Princeville is a 9,000acre, upscale, unincorporated, master-planned community of vacation homes and condos on the north shore of the island of Kauai in Kauai County, Hawaii. Get outdoors at Scuba & Snorkeling and Na Pali Coast State Park. You'll get in some beach time at Poipu Beach Park and Pali Ke Kua Beach (Hideaway s Beach). You'll find plenty of places to visit near Princeville: Spouting Horn (in Poipu), Helicopter Tours (in Lihue) and Kayaking & Canoeing (in Kapaa). There's much more to do: enjoy the sand and surf at Hanalei Beach, contemplate the waterfront views at Menehune Fishpond, look for all kinds of wild species at Hanalei National Wildlife Refuge, and tee off at Princeville Golf Club - Prince Course.

To see maps, traveler tips, photos, and other tourist information, read our Princeville travel planner.

You can do a combination of bus and flight from Lahaina to Princeville in 4 hours. Another option is to fly. Expect a daytime high around 78°F in March, and nighttime lows around 66°F. Cap off your sightseeing on the 3rd (Fri) early enough to travel to Laie.

Things to do in Princeville

Parks Outdoors Beaches

Side Trips

Hanalei, Kauai, Poipu, Na Pali Coast State Park, Helicopter Tours
Find places to stay Mar 28 — Apr 3:
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Poipu Beach Park ©
Poipu Beach Park
Hanalei Beach ©
Hanalei Beach

2
nights
Laie

Laie ©
Laie is a census-designated place (CDP) located in the Koolauloa District on the island of Oahu in Honolulu County, Hawaii, United States. Take a break from the city and head to Sunset Beach Park and Kualoa Regional Park. You'll enjoy a bit of beach vacationing at Turtle Bay Beach and Laniakea Beach. Change things up with these side-trips from Laie: Haleiwa (North Shore Macadamia Nut Company & Shark Diving). And it doesn't end there: make a trip to Polynesian Cultural Center, appreciate the history behind Pu’u O Mahuka Heiau State Monument, and explore the activities along Waimea Bay.

To see photos, maps, reviews, and more tourist information, read Laie trip itinerary planner.

Getting from Princeville to Laie by combination of flight and bus takes about 5 hours. Traveling from Princeville in April, expect little chillier with lows of 65°F in Laie. Finish your sightseeing early on the 5th (Sun) so you can travel back home.

Things to do in Laie

Outdoors Parks Beaches

Side Trips

Haleiwa, Kualoa Regional Park, Pu’u O Mahuka Heiau State Monument, Turtle Bay Beach
Find places to stay Apr 3 — 5:
Highlights from your plan
Sunset Beach Park ©
Sunset Beach Park
Shark Diving
Turtle Bay Beach ©
Turtle Bay Beach

Similar Plans

22 days in Oahu BY A USER FROM BRAZIL January, culture, historic sites, museums, wildlife, hidden gems Preferences: January, culture, historic sites, museums, wildlife Attraction style: Hidden gems Pace: Medium 21 days in Maui, Oahu & Kailua-Kona BY A USER FROM BOTSWANA December, outdoors, relaxing, romantic, shopping, slow & easy, hidden gems Preferences: December, outdoors, relaxing, romantic, shopping Attraction style: Hidden gems Pace: Slow & easy 18 days in United States BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, popular & hidden gems Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 8 days in Oahu BY A USER FROM UNITED STATES January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, hidden gems Preferences: January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Hidden gems Pace: Medium 8 days in Oahu BY A USER FROM UNITED STATES January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 8 days in Kauai BY A USER FROM UNITED STATES December, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: December, teens, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 33 days in United States BY A USER FROM AUSTRALIA May, relaxing, beaches, shopping, popular sights Preferences: May, relaxing, beaches, shopping Attraction style: Popular sights Pace: Medium 12 days in Oahu BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular sights Preferences: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular sights Pace: Medium 14 days in Kauai BY A USER FROM UNITED STATES January, culture, outdoors, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: January, culture, outdoors, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 8 days in Oahu BY A USER FROM UNITED STATES February, culture, relaxing, romantic, beaches, museums, wildlife, popular sights Preferences: February, culture, relaxing, romantic, beaches, museums, wildlife Attraction style: Popular sights Pace: Medium 4 days in Oahu BY A USER FROM UNITED STATES December, culture, relaxing, beaches, historic sites, shopping, hidden gems Preferences: December, culture, relaxing, beaches, historic sites, shopping Attraction style: Hidden gems Pace: Medium 15 days in Kauai BY A USER FROM UNITED STATES January, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: January, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium
See more plans