36 days in Hawaii Itinerary

36 days in Hawaii Itinerary

Created using Inspirock United States itinerary builder

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Route & dates

36 days in Hawaii Itinerary

Start: Chicago
Fly:  14​h 45​min
1
Volcano, Island of Hawaii
— 2 nights
+2
Drive + Fly + Drive:  6​h
2
Wainiha, Kauai
— 2 nights
Drive:  1​h
3
Kalaheo, Kauai
— 3 nights
Drive:  1​h
4
Kilauea, Kauai
— 2 nights
Drive:  1​h 15​min
5
Poipu, Kauai
— 4 nights
Drive:  45​min
6
Kapaa, Kauai
— 2 nights
Drive:  45​min
7
Princeville, Kauai
— 3 nights
Drive:  1​h 30​min
8
Kekaha, Kauai
— 2 nights
Drive:  45​min
9
Lihue, Kauai
— 3 nights
Fly + taxi:  1​h 15​min
10
Wailea
— 5 nights
Drive:  1​h 15​min
11
Kapalua
— 2 nights
Drive:  3​h
12
Hana
— 3 nights
Drive + Fly:  12​h 45​min
End: Chicago


Learn more about your trip

2
nights
Volcano, Island of Hawaii

Volcano ©
Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
Your day-by-day itinerary now includes Thurston Lava Tube (Nahuku) as well as Jagger Museum. Start off your visit on the 9th (Mon): see the interesting displays at Jagger Museum, explore the striking landscape at Thurston Lava Tube (Nahuku), then stroll through Sulphur Banks, then take a memorable drive along Chain of Craters Rd, and finally trek along Kilauea Iki Trailhead.

To find more things to do, other places to visit, reviews, and more tourist information, read Volcano trip itinerary builder .

Amsterdam, Holland to Volcano is an approximately 26-hour flight. The time zone difference when traveling from Amsterdam to Volcano is minus 11 hours. Traveling from Amsterdam in March, expect Volcano to be warmer, temps between 31°C and 22°C. Wrap up your sightseeing on the 9th (Mon) to allow time to drive to Honaunau.

Things to do in Volcano

Outdoors Parks Trails

Side Trips

Hawaii Volcanoes National Park, Chain of Craters Rd
Highlights from your plan
Jagger Museum ©
Jagger Museum
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Thurston Lava Tube (Nahuku) ©
Thurston Lava Tube (Nahuku)

2
nights
Wainiha, Kauai

Wainiha ©
Your day-by-day itinerary now includes Hanakapiai Falls as well as Na Pali Coast State Park. On the 10th (Tue), admire the sheer force of Hanakapiai Falls, then don't miss a visit to Kalalau Lookout, then take your sightseeing to a higher altitude at Koke'e Mountains, and finally take some stellar pictures from Puuo Kila. Here are some ideas for day two: immerse yourself in nature at Na Pali Coast State Park.

To see maps, traveler tips, and tourist information, read Wainiha trip builder app .

Explore your travel options from Volcano to Wainiha with the Route module. In March, plan for daily highs up to 30°C, and evening lows to 22°C. Wrap up your sightseeing by early afternoon on the 11th (Wed) to allow enough time to travel to Kalaheo.

Things to do in Wainiha

Nature Parks Wildlife

Side Trips

Kauai, Waimea
Highlights from your plan
Hanakapiai Falls ©
Hanakapiai Falls
Na Pali Coast State Park ©
Na Pali Coast State Park
Kalalau Lookout ©
Kalalau Lookout

3
nights
Kalaheo, Kauai

Kalaheo ©
Kalāheo is an unincorporated census-designated place in Kauai County, island of Kauai, Hawaii, United States. On the next day, stroll through Polihale State Park, then explore the stunning scenery at Waimea Canyon State Park, and then contemplate the long history of Lawai International Center.

To find maps, more things to do, other places to visit, and more tourist information, read our Kalaheo road trip planner .

Explore your travel options from Kukuihaele to Kalaheo with the Route module. Traveling from Kukuihaele in April, you will find days in Kalaheo are a bit warmer (31°C), and nights are much hotter (24°C). Wrap up your sightseeing by early afternoon on the 10th (Fri) to allow time for travel to Kahakuloa.

Things to do in Kalaheo

Outdoors Nature Parks

Side Trip

Waimea
Highlights from your plan
Polihale State Park ©
Polihale State Park
Waimea Canyon State Park ©
Waimea Canyon State Park
Tree Tunnel ©
Tree Tunnel

2
nights
Kilauea, Kauai

Kilauea ©
Kilauea is a small town on the northeastern shore of Kauai, one of the eight islands that make up the state of Hawaii. Your day-by-day itinerary now includes Kilauea Lighthouse as well as Kilauea Point National Wildlife Refuge. Kick off your visit on the 28th (Sat): enjoy the sea views from Kilauea Point National Wildlife Refuge, head outdoors with Kilauea Lighthouse, then take a memorable drive along Hanalei Valley Lookout, and finally kick back and relax at Anini Beach. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at North Aliomanu Beach.

To see traveler tips, other places to visit, and more tourist information, go to the Kilauea visit planner .

Drive from Poipu to Kilauea in 1.5 hours. Expect a daytime high around 30°C in March, and nighttime lows around 22°C. Cap off your sightseeing on the 30th (Mon) early enough to travel to Haleakala National Park.

Things to do in Kilauea

Parks Outdoors Beaches

Side Trips

North Aliomanu Beach, Hanalei Valley Lookout, Anini Beach, Princeville Botanical Gardens
Highlights from your plan
Princeville Botanical Gardens ©
Princeville Botanical Gardens
Anini Beach ©
Anini Beach
Hanalei Valley Lookout ©
Hanalei Valley Lookout

4
nights
Poipu, Kauai

Poipu ©
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. Your day-by-day itinerary now includes Ancient Kauai Excursions, Allerton Garden, Shipwreck Beach, and other attractions you added. Start off your visit on the 25th (Wed): kick back and relax at Shipwreck Beach, then take in nature's colorful creations at Allerton Garden, and then look for all kinds of wild species at Ancient Kauai Excursions. On your second day here, take in nature's colorful creations at National Tropical Botanical Garden, explore the striking landscape at Spouting Horn, then take an in-depth tour of Koloa History Center, then appreciate the extensive heritage of Old Koloa Town, and finally hike along Maha'ulepu Heritage Trail.

To find where to stay, ratings, reviews, and tourist information, read Poipu online sightseeing planner .

Traveling by combination of bus and flight from Lahaina to Poipu takes 4 hours. Alternatively, you can fly. In March, plan for daily highs up to 30°C, and evening lows to 22°C. Wrap up your sightseeing by early afternoon on the 28th (Sat) to allow time for the car ride to Kilauea.

Things to do in Poipu

Parks Outdoors Beaches

Side Trips

Koloa, Ninini Point Lighthouse Cache Site
Highlights from your plan
Shipwreck Beach ©
Shipwreck Beach
Poipu Beach Park ©
Poipu Beach Park
Baby Beach ©
Baby Beach

2
nights
Kapaa, Kauai

Kapaa ©
Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
On the 20th (Fri), you'll have a packed day of sightseeing: walk around Haena Beach Park, then learn about winemaking at Nani Moon Mead LLC, and then hike along Kuilau Ridge Trail.

To find photos, traveler tips, more things to do, and more tourist information, read our Kapaa travel planning site .

Getting from Poipu to Kapaa by car takes about an hour. March in Kapaa sees daily highs of 30°C and lows of 22°C at night. Finish up your sightseeing early on the 21st (Sat) so you can go by car to Princeville.

Things to do in Kapaa

Outdoors Trails Parks

Side Trip

Ho'opi'i Falls
Highlights from your plan
Ho'opi'i Falls ©
Ho'opi'i Falls

3
nights
Princeville, Kauai

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. Queen's Bath has been added to your itinerary. Start off your visit on the 18th (Sat): admire all the interesting features of Hanalei Valley Lookout, then stroll through Pali Ke Kua Beach (Hideaway s Beach), and then take in the dramatic natural features at Queen's Bath. Keep things going the next day: stop by Hanalei Farmer’s Market, then examine the collection at Waioli Mission House, and then kick back and relax at Puu Poa Beach.

Plan trip to Princeville with our itinerary maker to find out where to go and what to do.

Traveling by car from Kapaa to Princeville takes an hour. Expect a daytime high around 31°C in April, and nighttime lows around 24°C. You'll have a few hours on the 20th (Mon) to wrap things up before traveling to Kekaha.

Things to do in Princeville

Parks Outdoors Beaches

Side Trips

Hanalei, Waioli Mission House
Highlights from your plan
Pali Ke Kua Beach (Hideaway s Beach) ©
Queen's Bath ©
Queen's Bath
Hanalei Valley Lookout ©
Hanalei Valley Lookout

2
nights
Kekaha, Kauai

Kekaha ©
Kekaha is a census-designated place in Kauai County, Hawaii, United States. Na Pali Experience has been added to your itinerary. Get ready for a full day of sightseeing on the 24th (Tue): get a new perspective on things with Na Pali Experience.

Planning Kekaha trip won't be overwheling when you use's Insprock itinerary maker.

Traveling by car from Princeville to Kekaha takes 2 hours. March in Kekaha sees daily highs of 30°C and lows of 22°C at night. Finish up your sightseeing early on the 25th (Wed) so you can go by car to Lihue.

Things to do in Kekaha

Outdoors Parks Nature

Side Trip

Polihale State Park
Highlights from your plan
Polihale State Park ©
Polihale State Park
Na Pali Experience ©
Na Pali Experience
Awa'awapuhi Trail Parking ©
Awa'awapuhi Trail Parking

3
nights
Lihue, Kauai

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Your day-by-day itinerary now includes Koloa Rum Company as well as Kilohana. Start off your visit on the 2nd (Sat): sample the fine beverages at Koloa Rum Company, then contemplate the long history of Kilohana, and then enjoy the sand and surf at Kalapaki Beach. Get ready for a full day of sightseeing on the 3rd (Sun): admire the majestic nature at Wailua River State Park.

For other places to visit, ratings, traveler tips, and more tourist information, use the Lihue trip itinerary planner .

Explore your travel options from Hawi to Lihue with the Route module. While traveling from Hawi, expect a bit warmer days and warmer nights in Lihue, ranging from highs of 32°C to lows of 25°C. You will leave for home on the 4th (Mon).

Things to do in Lihue

Parks Historic Sites Outdoors

Side Trip

Wailua River State Park
Highlights from your plan
Koloa Rum Company ©
Koloa Rum Company
Kalapaki Beach ©
Kalapaki Beach
Kilohana ©
Kilohana

5
nights
Wailea

Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Step off the beaten path and head to Scuba & Snorkeling and Palauea Beach. Keawala'i Congregational Church and Maui Wine, Ulupalakua Vineyards are good opportunities to explore the local culture. Take a break from Wailea with a short trip to Sliding Sands Trail in Haleakala National Park, about 38 minutes away. There's much more to do: kick back and relax at Maluaka Beach, trek along Hoapili Trail, stroll through Mokapu Beach Park, and take in the dramatic natural features at Lava Fields.

To see other places to visit, more things to do, reviews, and other tourist information, use the Wailea travel route planner.

Traveling by combination of flight and taxi from Lihue to Wailea takes 1.5 hours. In May, plan for daily highs up to 35°C, and evening lows to 23°C. Finish your sightseeing early on the 30th (Sat) to allow enough time to drive to Kapalua.

Things to do in Wailea

Parks Outdoors Beaches

Side Trips

Maui, Sliding Sands Trail, Maui Wine, Ulupalakua Vineyards
Highlights from your plan
Scuba & Snorkeling
Mokapu Beach Park ©
Mokapu Beach Park
Palauea Beach ©
Palauea Beach

2
nights
Kapalua

Kapalua ©
Kapalua is a census-designated place (CDP) in Maui County, Hawaii, United States. Start off your visit on the 31st (Sun): trek along Acid War Zone Trail, stroll through Ohai Loop Trail and Overlook, and then kick back and relax at Napili Beach. Get ready for a full day of sightseeing on the next day: hike along Village Walking Trails, then relax and rejuvenate at some of the top local wellness centers, then get outside with The Ocean Project On Maui, and finally enjoy the sand and surf at Kapalua Beach.

To find reviews, where to stay, ratings, and other tourist information, you can read our Kapalua holiday planner .

Traveling by car from Wailea to Kapalua takes 1.5 hours. Alternatively, you can take a bus. When traveling from Wailea in May, plan for slightly colder days in Kapalua, with highs around 32°C, while nights are about the same with lows around 24°C. Finish your sightseeing early on the 1st (Mon) to allow enough time to drive to Hana.

Things to do in Kapalua

Outdoors Parks Trails

Side Trip

Lahaina
Highlights from your plan
Napili Beach ©
Napili Beach
Kapalua Beach ©
Kapalua Beach
Acid War Zone Trail ©
Acid War Zone Trail

3
nights
Hana

Hana
Hana is one of the most isolated communities in Hawaii, with a permanent population of just over 1,000 people.
On the 2nd (Tue), take in the dramatic scenery at Wailua Falls, take in the spiritual surroundings of Palapala Ho'omau Church, then explore the striking landscape at Haleakala Crater, and finally view the masterpieces at Laura Mango Art Gallery. Get ready for a full day of sightseeing on the 3rd (Wed): take some stellar pictures from Ke‘anae Point, admire the sheer force of Hanawi Falls, then take in the dramatic scenery at Waimoku Falls, and finally explore by horseback at Pipiwai Trail.

For reviews, more things to do, where to stay, and more tourist information, read Hana travel route builder site .

Traveling by car from Kapalua to Hana takes 3 hours. Alternatively, you can do a combination of bus and taxi. In June in Hana, expect temperatures between 36°C during the day and 25°C at night. On the 4th (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Hana

Parks Nature Outdoors

Side Trips

Maui, Haleakala National Park, Palapala Ho'omau Church
Highlights from your plan
Red Sand Beach (Kaihalulu Beach)
Red Sand Beach (Kaihalulu Beach)
Haleakala Crater ©
Haleakala Crater
Ke‘anae Point ©
Ke‘anae Point

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