36 days in Hawaii Itinerary

36 days in Hawaii Itinerary

Created using Inspirock United States itinerary builder

©
Plan created by another user. Make it yours
Fly
1
Volcano, Island of Hawaii
— 3 nights
+2
Drive to Hilo International Airport, Fly to Lihue Airport, Drive to Wainiha
2
Wainiha, Kauai
— 2 nights
Drive
3
Kalaheo, Kauai
— 2 nights
Drive
4
Kilauea, Kauai
— 2 nights
Drive
5
Poipu, Kauai
— 4 nights
Drive
6
Kapaa, Kauai
— 2 nights
Drive
7
Princeville, Kauai
— 4 nights
Drive
8
Kekaha, Kauai
— 2 nights
Drive
9
Lihue, Kauai
— 2 nights
Fly
10
Wailea
— 5 nights
Drive
11
Kapalua
— 2 nights
Drive
12
Hana
— 3 nights
Fly

S M T W T F S
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30

3
nights
Volcano, Island of Hawaii

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. You'll explore the less-touristy side of things at Kilauea Iki Trailhead and Chain of Craters Rd. There's still lots to do: stroll through Sulphur Banks.

To see traveler tips, reviews, photos, and tourist information, use the Volcano day trip planning tool.

Chicago to Volcano is an approximately 15-hour flight. The time zone changes from Central Standard Time to Hawaii-Aleutian Standard Time, which is usually a -4 hour difference. Traveling from Chicago in April, things will get much warmer in Volcano: highs are around 32°C and lows about 22°C. You will leave for Wainiha on the 28th (Tue).

Things to do in Volcano

Outdoors · Parks · Trails · Scenic Drive

Side Trips

2
nights
Wainiha, Kauai

Your day by day itinerary now includes Hanakapiai Falls as well as Na Pali Coast State Park. Start off your visit on the 29th (Wed): take in the dramatic scenery at Hanakapiai Falls, then make a trip to Kalalau Lookout, then take your sightseeing to a higher altitude at Koke'e Mountains, and finally get great views at Puuo Kila. Here are some ideas for day two: admire the majestic nature at Na Pali Coast State Park.

For more things to do, ratings, photos, and tourist information, read our Wainiha trip planner.

Use the Route module to find suitable travel options from Volcano to Wainiha. In April, daytime highs in Wainiha are 31°C, while nighttime lows are 24°C. Wrap up your sightseeing by early afternoon on the 30th (Thu) to allow time for travel to Kalaheo.

Things to do in Wainiha

Parks · Nature · Wildlife · Historic Sites

Side Trips

2
nights
Kalaheo, Kauai

Kalāheo is an unincorporated census-designated place in Kauai County, island of Kauai, Hawaii, United States. Kick off your visit on the 1st (Fri): tour the pleasant surroundings at Polihale State Park, then explore the stunning scenery at Waimea Canyon State Park, and then steep yourself in history at Lawai International Center. Get ready for a full day of sightseeing on the next day: head outdoors with Tree Tunnel.

For reviews, more things to do, traveler tips, and other tourist information, go to the Kalaheo route planner.

Traveling by car from Wainiha to Kalaheo takes 1.5 hours. In April, daytime highs in Kalaheo are 31°C, while nighttime lows are 24°C. Wrap up your sightseeing by early afternoon on the 2nd (Sat) to allow enough time to drive to Kilauea.

Things to do in Kalaheo

Outdoors · Parks · Nature · Beaches

Side Trip

2
nights
Kilauea, Kauai

Kilauea is a small town on the northeastern shore of Kauai, one of the eight islands that make up the state of Hawaii. Start off your visit on the 3rd (Sun): stroll through North Aliomanu Beach. Get ready for a full day of sightseeing on the 4th (Mon): admire the natural beauty at Princeville Botanical Gardens.

To see ratings, traveler tips, and tourist information, read Kilauea tour planning app.

You can drive from Kalaheo to Kilauea in 1.5 hours. In May, daytime highs in Kilauea are 32°C, while nighttime lows are 25°C. On the 4th (Mon), wrap the sightseeing up by early afternoon so you can drive to Poipu.

Things to do in Kilauea

Parks · Outdoors · Beaches

Side Trips

Highlights from your trip

4
nights
Poipu, Kauai

Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. You've added Ancient Kauai Excursions, Allerton Garden, Shipwreck Beach, and other attractions to your itinerary. Get some historical perspective at Ninini Point Lighthouse Cache Site and Old Koloa Town. You'll discover tucked-away gems like Baby Beach and Lawa'i Beach. Next up on the itinerary: kick back and relax at Poipu Beach Park, take an in-depth tour of Koloa History Center, take in nature's colorful creations at National Tropical Botanical Garden, and take in the dramatic natural features at Spouting Horn.

Start your trip to Poipu by creating a personalized itinerary on Inspirock.

You can drive from Kilauea to Poipu in 1.5 hours. Expect a daytime high around 32°C in May, and nighttime lows around 25°C. Wrap up your sightseeing by early afternoon on the 8th (Fri) to allow time for the car ride to Kapaa.

Things to do in Poipu

Parks · Outdoors · Beaches · Tours

Side Trips

2
nights
Kapaa, Kauai

Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Kick off your visit on the 9th (Sat): hike along Ho'opi'i Falls. Get ready for a full day of sightseeing on the next day: learn about winemaking at Nani Moon Mead LLC and then hike along Kuilau Ridge Trail.

Use Inspirock's suggestions to plan your Kapaa trip and find the best activities and attractions for your vacation.

Traveling by car from Poipu to Kapaa takes an hour. May in Kapaa sees daily highs of 32°C and lows of 25°C at night. Wrap up your sightseeing on the 10th (Sun) to allow time to drive to Princeville.

Things to do in Kapaa

Parks · Outdoors · Trails · Wineries

Side Trip

4
nights
Princeville, Kauai

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. Visiting Pali Ke Kua Beach (Hideaway s Beach) and Hanalei National Wildlife Refuge will get you outdoors. Eschew the tourist crowds and head to Hanalei Valley Lookout and Puu Poa Beach. There's more to do: stop by Hanalei Farmer’s Market and examine the collection at Waioli Mission House.

For more things to do, traveler tips, ratings, and other tourist information, use the Princeville online journey planner.

You can drive from Kapaa to Princeville in an hour. In May, daily temperatures in Princeville can reach 32°C, while at night they dip to 25°C. On the 14th (Thu), you'll travel to Kekaha.

Things to do in Princeville

Parks · Outdoors · Beaches · Nature

Side Trips

2
nights
Kekaha, Kauai

Kekaha is a census-designated place in Kauai County, Hawaii, United States. You've now added Na Pali Experience to your itinerary. On the 15th (Fri), you'll have a packed day of sightseeing: take a tour by water with Na Pali Experience.

To see ratings, photos, other places to visit, and other tourist information, you can read our Kekaha road trip planning app.

Drive from Princeville to Kekaha in 1.5 hours. In May in Kekaha, expect temperatures between 34°C during the day and 26°C at night. Finish your sightseeing early on the 16th (Sat) to allow enough time to drive to Lihue.

Things to do in Kekaha

Outdoors · Parks · Tours · Beaches

Side Trip

2
nights
Lihue, Kauai

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. On the 17th (Sun), brush up on your knowledge of spirits at Koloa Rum Company, then steep yourself in history at Kilohana, and then kick back and relax at Kalapaki Beach. Here are some ideas for day two: immerse yourself in nature at Wailua River State Park.

To see other places to visit, more things to do, reviews, and more tourist information, go to the Lihue trip builder tool.

Traveling by car from Kekaha to Lihue takes an hour. In May in Lihue, expect temperatures between 32°C during the day and 25°C at night. Wrap up your sightseeing by early afternoon on the 18th (Mon) to allow enough time to travel to Wailea.

Things to do in Lihue

Parks · Historic Sites · Outdoors · Beaches

Side Trip

5
nights
Wailea

Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. You'll enjoy a bit of beach vacationing at Maluaka Beach and Mokapu Beach Park. Take a break from the city and head to Palauea Beach and Makena State Park. Step out of Wailea with an excursion to Sliding Sands Trail in Haleakala National Park--about 38 minutes away. Next up on the itinerary: stroll through Oneuli Beach, pause for some serene contemplation at Keawala'i Congregational Church, do a tasting at Maui Wine, Ulupalakua Vineyards, and get impressive views of Molokini Crater.

To find ratings, other places to visit, more things to do, and tourist information, read Wailea tour itinerary builder.

Traveling by flight from Lihue to Wailea takes 3 hours. Expect a daytime high around 35°C in May, and nighttime lows around 23°C. Finish your sightseeing early on the 23rd (Sat) so you can drive to Kapalua.

Things to do in Wailea

Parks · Outdoors · Beaches · Trails

Side Trips

2
nights
Kapalua

Kapalua is a census-designated place (CDP) in Maui County, Hawaii, United States. On the 24th (Sun), stroll through Napili Beach, then kick back and relax at Honokeana Bay, and then hike along Acid War Zone Trail. On your second day here, kick back and relax at Kapalua Beach, head outdoors with The Ocean Project On Maui, then relax and rejuvenate at some of the top local wellness centers, and finally trek along Village Walking Trails.

For reviews, maps, more things to do, and tourist information, go to the Kapalua trip itinerary planner.

Traveling by car from Wailea to Kapalua takes 1.5 hours. Alternatively, you can take a bus. Traveling from Wailea in May, you will find days in Kapalua are little chillier (32°C), and nights are about the same (24°C). Wrap up your sightseeing on the 25th (Mon) early enough to drive to Hana.

Things to do in Kapalua

Outdoors · Parks · Beaches · Trails

Side Trips

3
nights
Hana

Hana is one of the most isolated communities in Hawaii, with a permanent population of just over 1,000 people.
On the 26th (Tue), take in the dramatic scenery at Wailua Falls, then take in the architecture and atmosphere at Palapala Ho'omau Church, then get impressive views of Haleakala Crater, and finally view the masterpieces at Laura Mango Art Gallery. Get ready for a full day of sightseeing on the 27th (Wed): explore the striking landscape at Ke‘anae Point, then take in the dramatic scenery at Hanawi Falls, then take in the dramatic scenery at Waimoku Falls, and finally explore by horseback at Pipiwai Trail.

To see where to stay, ratings, traveler tips, and more tourist information, you can read our Hana trip itinerary builder website.

You can drive from Kapalua to Hana in 3 hours. Another option is to do a combination of bus and taxi. In May in Hana, expect temperatures between 35°C during the day and 23°C at night. On the 28th (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Hana

Parks · Nature · Outdoors · Beaches

Side Trips

Hawaii travel guide

4.3
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.

Maui travel guide

4.4
Scuba & Snorkeling · Beaches · Luaus
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.