21 days in Hawaii Itinerary

21 days in Hawaii Itinerary

Created using Inspirock United States trip planner

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Route & dates

Start: Philadelphia
Train + Fly:  13 h 30 min
1
Honolulu, Oahu
— 3 nights
Fly + Taxi:  3 h
2
Hanalei, Kauai
— 3 nights
Taxi + Fly:  3 h 30 min
3
Kailua-Kona, Island of Hawaii
— 3 nights
Bus + Fly:  4 h
4
Lahaina
— 3 nights
+3
Bus + Fly + Foot + Bus:  4 h 30 min
5
Haleiwa, Oahu
— 2 nights
+2
Drive + Fly + Drive:  6 h 30 min
6
Keauhou, Island of Hawaii
— 2 nights
Drive:  2 h 15 min
7
Hawaii Volcanoes National Park, Island of Hawaii
— 3 nights
Taxi + Fly:  16 h
End: Philadelphia


Learn more about your trip

3
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.
Step out of the city life by going to Diamond Head State Monument and Makapuu Lighthouse Trail. You'll explore the less-touristy side of things at Waimea Valley and Sharks Cove. Get out of town with these interesting Honolulu side-trips: Haleiwa (Laniakea Beach, Scuba & Snorkeling, &more) and Kailua (Kayaking & Canoeing & Lanikai Beach). There's more to do: contemplate the waterfront views at Hanauma Bay Nature Preserve.

To find where to stay, other places to visit, ratings, and more tourist information, you can read our Honolulu trip maker site.

Philadelphia to Honolulu is an approximately 13.5- hour combination of train and flight. You can also do a combination of train and flight; or fly. The time zone changes from Eastern Standard Time (EST) to Hawaii Standard Time (HST), which is usually a -5 hour difference. In July, daily temperatures in Honolulu can reach 88°F, while at night they dip to 75°F. Cap off your sightseeing on the 15th (Thu) early enough to travel to Hanalei.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Haleiwa, Kailua, Sharks Cove
Highlights from your plan
Waimea Valley ©
Waimea Valley
Makapuu Lighthouse Trail ©
Makapuu Lighthouse Trail
Lanikai Beach ©
Lanikai Beach

3
nights
Hanalei, Kauai

Hanalei ©
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Bring the kids along to Hanalei Beach and Kilauea Point National Wildlife Refuge. Discover out-of-the-way places like Maha'ulepu Heritage Trail and Hanalei National Wildlife Refuge. Take a break from Hanalei with a short trip to Shipwreck Beach in Poipu, about 1h 20 min away. There's lots more to do: kick back and relax at Tunnels Beach, putt your heart out at Kauai Mini Golf & Botanical Gardens, cruise along Hanalei Valley Lookout, and shop like a local with 7 Artists Gallery.

To find maps, traveler tips, where to stay, and other tourist information, use the Hanalei trip planner.

You can do a combination of flight and taxi from Honolulu to Hanalei in 3 hours. In July in Hanalei, expect temperatures between 84°F during the day and 74°F at night. Finish your sightseeing early on the 18th (Sun) to allow enough time to travel to Kailua-Kona.

Things to do in Hanalei

Parks Outdoors Beaches

Side Trips

Poipu, Kilauea, Tunnels Beach
Highlights from your plan
Hanalei Beach ©
Hanalei Beach
Maha'ulepu Heritage Trail
Maha'ulepu Heritage Trail
Kilauea Point National Wildlife Refuge ©
Kilauea Point National Wildlife Refuge

3
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.
Attractions like Pololu Valley Lookout and Liliuokalani Gardens make great kid-friendly stops. Get in touch with nature at Kanaloa Octopus Farm and Kealakekua Bay. Explore the numerous day-trip ideas around Kailua-Kona: Waialea Beach (in Waimea) and Hilo (Carlsmith Beach Park & Akaka Falls State Park). There's lots more to do: kick back and relax at Magic Sands, Head underground at Lava Tube Cave, and explore the striking landscape of Lapakahi State Historical Park.

To find traveler tips, other places to visit, maps, and more tourist information, use the Kailua-Kona route planner.

You can do a combination of taxi and flight from Hanalei to Kailua-Kona in 3.5 hours. July in Kailua-Kona sees daily highs of 86°F and lows of 76°F at night. Finish up your sightseeing early on the 21st (Wed) so you can travel to Lahaina.

Things to do in Kailua-Kona

Parks Beaches Outdoors

Side Trips

Hilo, Island of Hawaii, Kealakekua Bay, Waialea Beach
Highlights from your plan
Kanaloa Octopus Farm ©
Kanaloa Octopus Farm
Kealakekua Bay ©
Kealakekua Bay
Liliuokalani Gardens ©
Liliuokalani Gardens

3
nights
Lahaina

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.
You've now added Kapalua Ziplines to your itinerary. Kick off your visit on the 22nd (Thu): get interesting insight from Kapalua Ziplines, stroll through Baby Beach, then kick back and relax at Wailea Beach Path, and finally enjoy the sand and surf at Kalepolepo Beach Park. Here are some ideas for day two: walk around Lahaina Banyan Court, contemplate the waterfront views at Lahaina Harbor, then relax in the rural setting at Maui Tropical Plantation, then enjoy the sand and surf at Polo Beach, and finally enjoy the sand and surf at Ho'okipa Beach Park.

For photos, more things to do, reviews, and more tourist information, read Lahaina trip itinerary planner.

Traveling by combination of bus and flight from Kailua-Kona to Lahaina takes 4 hours. Alternatively, you can do a combination of taxi, flight, and bus; or do a combination of bus and flight. Expect a daytime high around 86°F in July, and nighttime lows around 73°F. Finish your sightseeing early on the 24th (Sat) to allow enough time to travel to Haleiwa.

Things to do in Lahaina

Parks Outdoors Beaches

Side Trips

Wailea, Maui Tropical Plantation, Kalepolepo Beach Park, Ho'okipa Beach Park
Highlights from your plan
Wailea Beach Path ©
Wailea Beach Path
Ho'okipa Beach Park ©
Ho'okipa Beach Park
Lahaina Harbor ©
Lahaina Harbor

2
nights
Haleiwa, Oahu

Haleiwa ©
Haleiwa is a North Shore community and census-designated place (CDP) in the Waialua District of the island of Oahu, City and County of Honolulu. Hang Gliding Hawaii has been added to your itinerary. Start off your visit on the 24th (Sat): identify plant and animal life at Wildlife Areas and then kick back and relax at Mokuleia Beach Park. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Laniakea Beach, contemplate the waterfront views at Waimea Bay, then kick back and relax at Sunset Beach Park, and finally hike along Ehukai Pillbox Hike.

For ratings, other places to visit, reviews, and tourist information, use the Haleiwa trip itinerary maker app.

Traveling by combination of flight and bus from Lahaina to Haleiwa takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of ferry, flight, and bus. July in Haleiwa sees daily highs of 83°F and lows of 69°F at night. On the 26th (Mon), wrap the sightseeing up by early afternoon so you can travel to Keauhou.

Things to do in Haleiwa

Outdoors Parks Beaches

Side Trip

Mokuleia Beach Park
Highlights from your plan
Sunset Beach Park ©
Sunset Beach Park
Laniakea Beach ©
Laniakea Beach
Waimea Bay ©
Waimea Bay

2
nights
Keauhou, Island of Hawaii

Keauhou ©
Keauhou is an unincorporated community on the island of Hawaii in Hawaii County, Hawaii, United States. Your day-by-day itinerary now includes Eka Canoe Adventures. On the 27th (Tue), admire the majestic nature at Kahalu'u Beach Park, then kick back and relax at Kahaluu Beach, and then see some colorful creatures with Eka Canoe Adventures.

For other places to visit, where to stay, more things to do, and more tourist information, read Keauhou trip maker tool.

Explore your travel options from Haleiwa to Keauhou with the Route module. Traveling from Haleiwa in July, Keauhou is a bit warmer at night with lows of 76°F. On the 28th (Wed), you're off to Hawaii Volcanoes National Park.

Things to do in Keauhou

Outdoors Parks Wildlife
Highlights from your plan
Kahaluu Beach ©
Kahaluu Beach
Eka Canoe Adventures ©
Eka Canoe Adventures
Kahalu'u Beach Park ©
Kahalu'u Beach Park

3
nights
Hawaii Volcanoes National Park, Island of Hawaii

Hawaii Volcanoes National Park ©
Volcanoes have played an important role in shaping the Earth, and Hawaii Volcanoes National Park shows visitors the process in action.
Eschew the tourist crowds and head to Kīlauea and Sulphur Banks. Kids will enjoy Rainbow Falls and Laupahoehoe Beach Park. Change things up with these side-trips from Hawaii Volcanoes National Park: Hilo (Akaka Falls State Park, Carlsmith Beach Park, &more). Next up on the itinerary: stroll through Holei Sea Arch and take in the natural beauty of Steam Vents.

Plan a trip to Hawaii Volcanoes National Park easily and quickly by telling Inspirock to suggest an itinerary.

Getting from Keauhou to Hawaii Volcanoes National Park by car takes about 2.5 hours. Traveling from Keauhou in July, Hawaii Volcanoes National Park is a bit cooler at night with lows of 71°F. Wrap up your sightseeing on the 31st (Sat) early enough to travel back home.

Things to do in Hawaii Volcanoes National Park

Parks Outdoors Nature

Side Trips

Hilo, Laupahoehoe Beach Park, Steam Vents
Highlights from your plan
Kīlauea ©
Kīlauea
Holei Sea Arch ©
Holei Sea Arch
Rainbow Falls ©
Rainbow Falls

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