43 days in Hawaii Itinerary

43 days in Hawaii Itinerary

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Route & dates

43 days in Hawaii Itinerary

Start: Cape Girardeau
Drive + Fly:  22​h
1
Honolulu, Oahu
— 11 nights
Fly + taxi:  3​h
2
Hanalei, Kauai
— 7 nights
taxi + Fly:  3​h 15​min
3
Kailua-Kona, Island of Hawaii
— 12 nights
Fly:  4​h
4
Lahaina, Maui
— 10 nights
+2
Drive + Fly + Drive:  21​h 45​min
End: Cape Girardeau

11
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.
You'll visit kid-friendly attractions like Sharks Cove and Makapuu Lighthouse Trail. Step off the beaten path and head to Skydiving and Kapiolani Regional Park. Venture out of the city with trips to Waimanalo Beach (in Waimanalo), Byodo-In Temple (in Kaneohe) and Kailua (Lanikai Pillboxes, Kailua Beach Park, & more). There's lots more to do: glide peacefully along the water with some of the best stand-up paddleboarding in the area, take a memorable tour with Tours, see majestic marine mammals with a dolphin and whale watching tour, and see the interesting displays at Bishop Museum.

To see maps, photos, traveler tips, and more tourist information, use the Honolulu route maker tool .

Cape Girardeau to Honolulu is an approximately 22-hour flight. The time zone changes from Central Standard Time to Hawaii Standard Time, which is usually a -4 hour difference. Traveling from Cape Girardeau in June, Honolulu is somewhat warmer at night with lows of 74°F. Wrap up your sightseeing on the 16th (Sun) early enough to travel to Hanalei.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Haleiwa, Kailua, Kapolei, Oahu, Sharks Cove
Highlights from your plan
Makapuu Lighthouse Trail ©
Makapuu Lighthouse Trail
Photography Tours
Scuba & Snorkeling

7
nights
Hanalei, Kauai

Hanalei ©
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Attractions like Hanalei Beach and Tunnels Beach make great kid-friendly stops. Step off the beaten path and head to Kauai Path and Dolphin & Whale Watching. Get out of town with these interesting Hanalei side-trips: Polihale State Park (in Waimea), Poipu (Maha'ulepu Heritage Trail & Shipwreck Beach) and Kauai Coffee Company (in Kalaheo). Next up on the itinerary: look for all kinds of wild species at Na Pali Coast State Park, kick back and relax at Kalapaki Beach, hike along Kalalau Trail, and stroll through Ke'e Beach.

To see other places to visit, ratings, and tourist information, you can read our Hanalei trip planner .

Do a combination of flight and taxi from Honolulu to Hanalei in 3 hours. In June in Hanalei, expect temperatures between 83°F during the day and 73°F at night. Finish your sightseeing early on the 23rd (Sun) to allow enough time to travel to Kailua-Kona.

Things to do in Hanalei

Parks Outdoors Beaches

Side Trips

Kauai, Poipu, Kilauea, Na Pali Coast State Park, Polihale State Park
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Dolphin & Whale Watching
Hanakapiai Falls ©
Hanakapiai Falls

12
nights
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.
You'll visit kid-friendly attractions like Manini'owali Beach (Kua Bay) and Honaunau Bay. You'll discover tucked-away gems like Kanaloa Octopus Farm and Kayaking & Canoeing. Get out of town with these interesting Kailua-Kona side-trips: Puako (Stand-Up Paddleboarding & Hapuna Beach State Recreation Area), Volcano (Jagger Museum & Akatsuka Orchid Gardens) and Hawaii Volcanoes National Park (Kilauea Iki Trailhead, Thurston Lava Tube (Nahuku), & more). And it doesn't end there: explore the wealth of natural beauty at Kaloko-Honokohau National Historical Park, admire all the interesting features of Mountain Thunder Coffee Plantation, take a tour by water with Boat Tours & Water Sports, and kick back and relax at 49 Black Sand Beach.

To find traveler tips, where to stay, ratings, and more tourist information, use the Kailua-Kona travel planner .

You can do a combination of taxi and flight from Hanalei to Kailua-Kona in 3.5 hours. In June in Kailua-Kona, expect temperatures between 85°F during the day and 74°F at night. Wrap up your sightseeing on the 5th (Fri) early enough to travel to Lahaina.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Holualoa, Island of Hawaii, Hawaii Volcanoes National Park, Hilo, Volcano
Highlights from your plan
Hapuna Beach State Recreation Area ©
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Punalu‘U Beach ©
Punalu‘U Beach

10
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.
Eschew the tourist crowds and head to Baby Beach and Kayaking & Canoeing. Family-friendly places like Keawakapu Beach and Napili Beach will thrill your kids. Venture out of the city with trips to Wailea (Wailea Beach, Makena Beach, & more), Zipline (in Haiku) and Ho'okipa Beach Park (in Paia). There's lots more to do: fly like a bird with a parasailing or paragliding tour, find your balance on the water with some of the best stand-up paddleboarding in the area, let the river carry you with a rafting and tubing tour, and stroll through Kapalua Coastal Trail.

Take the guesswork out of planning a Lahaina vacation by using our trip itinerary maker.

Fly from Kailua-Kona to Lahaina in 4 hours. Alternatively, you can do a combination of taxi, flight, and bus; or do a combination of flight and bus. In July, plan for daily highs up to 86°F, and evening lows to 73°F. Finish your sightseeing early on the 15th (Mon) so you can travel back home.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Wailea, Kihei, Wailuku, Maui, Kapalua
Highlights from your plan
Napili Beach ©
Napili Beach
Stand-Up Paddleboarding
Zipline

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