14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary builder

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

Route & dates

Start: Chicago
Fly:  11 h 30 min
1
Honolulu, Oahu
— 6 nights
Fly:  2 h 30 min
2
Hilo, Island of Hawaii
— 2 nights
Drive:  1 h 45 min
3
Kailua-Kona, Island of Hawaii
— 1 night
Bus + Fly:  4 h
4
Lahaina, Maui
— 3 nights
Fly:  13 h 45 min
End: Chicago

6
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Explore Honolulu's surroundings by going to Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua Beach Park (in Kailua) and Haleiwa (Sunset Beach Park & Waimea Bay). The adventure continues: take in the pleasant sights at Diamond Head State Monument, take in the dramatic scenery at Manoa Falls, see the interesting displays at USS Bowfin Submarine Museum & Park, and contemplate the waterfront views at Hanauma Bay Nature Preserve.

To see reviews and tourist information, read Honolulu trip itinerary maker website.

Chicago to Honolulu is an approximately 11.5- hour flight. Traveling from Chicago to Honolulu, you'll gain 4 hours due to the time zone difference. In May, Honolulu is somewhat warmer than Chicago - with highs of 84°F and lows of 71°F. Finish your sightseeing early on the 19th (Tue) so you can travel to Hilo.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Pu’u O Mahuka Heiau State Monument, Kailua Beach Park
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
USS Arizona Memorial ©
USS Arizona Memorial

2
nights
Hilo, Island of Hawaii

Hilo ©
One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
Change things up with these side-trips from Hilo: Hawaii Volcanoes National Park (Thurston Lava Tube (Nahuku), Kilauea Iki Trailhead, &more) and Jagger Museum (in Volcano). There's lots more to do: take in the dramatic scenery at Akaka Falls State Park, take in nature's colorful creations at Liliuokalani Gardens, pick up some local products at Hilo Farmers Market, and take in the exciting artwork at Banyan Gallery.

To see photos, reviews, where to stay, and tourist information, go to the Hilo online itinerary maker.

Traveling by flight from Honolulu to Hilo takes 2.5 hours. Expect a daytime high around 82°F in May, and nighttime lows around 67°F. Finish your sightseeing early on the 21st (Thu) so you can drive to Kailua-Kona.

Things to do in Hilo

Parks Nature Shopping

Side Trips

Hawaii Volcanoes National Park, Jagger Museum
Highlights from your plan
Akaka Falls State Park ©
Akaka Falls State Park
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Liliuokalani Gardens ©
Liliuokalani Gardens

1
night
Kailua-Kona, Island of Hawaii

Kailua-Kona ©
Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Start off your visit on the 22nd (Fri): relax in the rural setting at Heavenly Hawaiian Kona Coffee Farm, then relax in the rural setting at Greenwell Farms, then take in the spiritual surroundings of Mokuaikaua Church, and finally take a tour by water with Boat Tours & Water Sports.

Start your trip to Kailua-Kona by creating a personalized itinerary on Inspirock.

Getting from Hilo to Kailua-Kona by car takes about 2 hours. Other options: take a bus. Traveling from Hilo in May, you can expect nighttime temperatures to be somewhat warmer in Kailua-Kona, with lows of 73°F. Wrap up your sightseeing on the 22nd (Fri) to allow time to travel to Lahaina.

Things to do in Kailua-Kona

Wildlife Outdoors Tours

Side Trips

Greenwell Farms, Heavenly Hawaiian Kona Coffee Farm
Highlights from your plan
Heavenly Hawaiian Kona Coffee Farm ©
Heavenly Hawaiian Kona Coffee Farm
Swim with Dolphins
Mokuaikaua Church ©
Mokuaikaua Church

3
nights
Lahaina, Maui

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.
Go for a jaunt from Lahaina to Paia to see Ho'okipa Beach Park about 52 minutes away. There's much more to do: admire all the interesting features of Hana Highway - Road to Hana, tour the pleasant surroundings at Ka'anapali Beach, whizz through the canopy at categoryPhrases.alias.some_of_the_top_local_zipline_courses_and_adventure_parks, and walk around Lahaina Banyan Court.

For photos, where to stay, and more tourist information, you can read our Lahaina tour itinerary site.

Getting from Kailua-Kona to Lahaina by combination of bus and flight takes about 4 hours. Other options: do a combination of taxi, flight, and bus; or do a combination of bus and flight. In May, daily temperatures in Lahaina can reach 81°F, while at night they dip to 70°F. Cap off your sightseeing on the 25th (Mon) early enough to travel back home.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Hana Highway - Road to Hana, Ho'okipa Beach Park
Highlights from your plan
Ka'anapali Beach ©
Ka'anapali Beach
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Scuba & Snorkeling

Similar Plans

15 days in Hawaii BY A USER FROM UNITED STATES July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular & hidden gems Preferences: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 15 days in Hawaii BY A USER FROM UNITED STATES June, kids, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular & hidden gems Preferences: June, kids, culture, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 15 days in Hawaii BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, popular & hidden gems Preferences: May, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Medium 15 days in Hawaii BY A USER FROM NEW ZEALAND June, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, popular sights Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife Attraction style: Popular sights Pace: Medium 12 days in Hawaii BY A USER FROM UNITED STATES April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, slow & easy, popular & hidden gems Preferences: April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 17 days in Hawaii BY A USER FROM CANADA July, teens, outdoors, relaxing, beaches, shopping, wildlife, popular sights Preferences: July, teens, outdoors, relaxing, beaches, shopping, wildlife Attraction style: Popular sights Pace: Medium 15 days in Hawaii BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular sights Preferences: June, culture, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular sights Pace: Medium 16 days in Hawaii BY A USER FROM UNITED STATES May, outdoors, relaxing, romantic, beaches, extra slow, popular & hidden gems Preferences: May, outdoors, relaxing, romantic, beaches Attraction style: Popular & hidden gems Pace: Extra slow 16 days in Hawaii BY A USER FROM AUSTRALIA April, outdoors, relaxing, beaches, shopping, hidden gems Preferences: April, outdoors, relaxing, beaches, shopping Attraction style: Hidden gems Pace: Medium 15 days in San Francisco & Hawaii BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, popular & hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches Attraction style: Popular & hidden gems Pace: Medium 12 days in Hawaii BY A USER FROM UNITED STATES April, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife, popular & hidden gems Preferences: April, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 15 days in Hawaii BY A USER FROM MEXICO September, outdoors, relaxing, romantic, beaches, popular sights Preferences: September, outdoors, relaxing, romantic, beaches Attraction style: Popular sights Pace: Medium
See more plans