18 days in Hawaii Itinerary

18 days in Hawaii Itinerary

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Route & dates

18 days in Hawaii Itinerary

Start: Chicago
Fly:  11 h 30 min
1
Honolulu, Oahu
— 6 nights
Fly:  2 h 15 min
2
Lihue, Kauai
— 2 nights
Fly + Bus:  3 h 15 min
3
Lahaina, Maui
— 5 nights
Bus + Fly:  3 h 15 min
4
Hilo, Island of Hawaii
— 4 nights
Fly:  13 h
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.
Kids will enjoy Diamond Head State Monument and Waimea Valley. Your itinerary includes some good beach time at Waikiki Beach and Sunset Beach Park. Change things up with these side-trips from Honolulu: Waimanalo Beach (in Waimanalo), Kailua (Lanikai Beach & Kailua Beach Park) and Swim with Dolphins (in Waianae). And it doesn't end there: trek along Lanikai Pillboxes, stroll around Kapiolani Regional Park, capture your vacation like a pro with an inspiring photography tour, and explore the different monuments and memorials at USS Arizona Memorial.

To find traveler tips, more things to do, maps, and tourist information, use the Honolulu trip itinerary planner.

Chicago to Honolulu is an approximately 11.5-hour flight. The time zone difference moving from Central Standard Time (CST) to Hawaii Standard Time (HST) is minus 4 hours. Traveling from Chicago in June, Honolulu is somewhat warmer at night with lows of 74°F. Wrap up your sightseeing on the 28th (Sun) to allow time to travel to Lihue.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Kailua, Haleiwa, Pupukea, Ko Olina Lagoons, Swim with Dolphins
Find places to stay Jun 22 — 28:
Highlights from your plan
Lanikai Pillboxes ©
Lanikai Pillboxes
Swim with Dolphins
Kailua Beach Park ©
Kailua Beach Park

2
nights
Lihue, Kauai

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Start off your visit on the 29th (Mon): whizz through the canopy at categoryPhrases.alias.some_of_the_top_local_zipline_courses_and_adventure_parks, then discover the deep blue sea with a scuba or snorkeling tour, then kick back and relax at Shipwreck Beach, and finally tour the pleasant surroundings at Maha'ulepu Heritage Trail. On the 30th (Tue), you'll have a packed day of sightseeing: admire the sheer force of Wailua Falls, then enjoy the sand and surf at Tunnels Beach, then tour the pleasant surroundings at Hanalei Beach, and finally enjoy the sand and surf at Hanalei Bay.

To see ratings, other places to visit, traveler tips, and more tourist information, use the Lihue day trip planning site.

You can fly from Honolulu to Lihue in 2.5 hours. June in Lihue sees daily highs of 83°F and lows of 73°F at night. Wrap up your sightseeing on the 30th (Tue) to allow time to travel to Lahaina.

Things to do in Lihue

Outdoors Parks Beaches

Side Trips

Poipu, Kauai, Hanalei Beach, Scuba & Snorkeling
Find places to stay Jun 28 — 30:
Highlights from your plan
Zipline
Scuba & Snorkeling
Maha'ulepu Heritage Trail
Maha'ulepu Heritage Trail

5
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.
Get outdoors at Napili Beach and Wailea Beach. You'll explore the less-touristy side of things at Ho'okipa Beach Park and Parasailing & Paragliding. Explore the numerous day-trip ideas around Lahaina: Zipline (in Haiku), Hot Island Glass (in Makawao) and Nisei Veterans Memorial Center (in Kahului). There's still lots to do: look for all kinds of wild species at Honolua Bay, enjoy the sand and surf at Kamaole Beach Park III, get some jogging in at Wailea Beach Path, and tour the pleasant surroundings at Kapalua Beach.

For ratings, reviews, more things to do, and tourist information, go to the Lahaina journey maker website.

Traveling by combination of flight and bus from Lihue to Lahaina takes 3.5 hours. Expect a daytime high around 84°F in June, and nighttime lows around 72°F. Cap off your sightseeing on the 5th (Sun) early enough to travel to Hilo.

Things to do in Lahaina

Parks Outdoors Beaches

Side Trips

Wailea, Kihei, Kapalua, Wailuku, Ho'okipa Beach Park
Find places to stay Jun 30 — Jul 5:
Highlights from your plan
Napili Beach ©
Napili Beach
Keawakapu Beach ©
Keawakapu Beach
Wailea Beach Path ©
Wailea Beach Path

4
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.
You'll visit kid-friendly attractions like Punalu‘U Beach and Liliuokalani Gardens. Visit 49 Black Sand Beach and Richardson Beach Park for some beach relaxation. Venture out of the city with trips to Puukohola National Historic Park (in Kawaihae), Puako (Puako Bay & Swim with Dolphins) and Saddle Road (in Kailua-Kona). Next up on the itinerary: take in nature's colorful creations at Hawaii Tropical Botanical Garden, get impressive views of Kīlauea, take in the dramatic natural features at Thurston Lava Tube (Nahuku), and see the interesting displays at Jagger Museum.

For other places to visit, where to stay, more things to do, and more tourist information, read our Hilo journey planner.

You can do a combination of bus and flight from Lahaina to Hilo in 3.5 hours. Alternatively, you can fly; or do a combination of bus and flight. In July, daily temperatures in Hilo can reach 85°F, while at night they dip to 71°F. Finish up your sightseeing early on the 9th (Thu) so you can travel back home.

Things to do in Hilo

Parks Nature Outdoors

Side Trips

Hawaii Volcanoes National Park, Puako, Saddle Road, Jagger Museum, Puukohola National Historic Park
Find places to stay Jul 5 — 9:
Highlights from your plan
Hawaii Tropical Botanical Garden ©
Hawaii Tropical Botanical Garden
Punalu‘U Beach ©
Punalu‘U Beach
Swim with Dolphins

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