60 days in Hawaii Itinerary

60 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary builder

This plan was created by another user. Make it your plan

Route & dates

Start: New York City
Bus + Fly:  14 h 45 min
1
Hilo, Island of Hawaii
— 6 nights
Drive:  2 h
2
Captain Cook, Island of Hawaii
— 6 nights
Drive:  30 min
3
Kailua-Kona, Island of Hawaii
— 7 nights
Drive:  45 min
4
Waikoloa, Island of Hawaii
— 7 nights
Fly:  2 h 30 min
5
Kahului, Maui
— 7 nights
Drive:  15 min
6
Wailuku, Maui
— 7 nights
Bus + Fly:  3 h 15 min
7
Honolulu, Oahu
— 12 nights
Drive:  1 h
8
Waianae, Oahu
— 4 nights
Drive:  1 h
9
Haleiwa, Oahu
— 2 nights
+2
Bus + Foot + Fly:  3 h 30 min
10
Kapaa, Kauai
— Few hours
Fly:  15 h 15 min
End: New York City

6
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.
Step off the beaten path and head to Holei Sea Arch and Kilauea Iki Trailhead. Explore Hilo's surroundings by going to Jagger Museum (in Volcano), Pahoa (Kapoho Tide Pools & Kehena Black Sand Beach) and Hawaii Volcanoes National Park (Sulphur Banks, Kīlauea, &more). And it doesn't end there: head off the coast to Coconut Island, Head underground at Kaumana Caves Park, admire the sheer force of Akaka Falls State Park, and enjoy the sand and surf at Richardson Beach Park.

To see where to stay, maps, photos, and tourist information, go to the Hilo day trip planning tool.

New York City to Hilo is an approximately 15- hour combination of bus and flight. You can also fly; or do a combination of bus and flight. The time zone difference when traveling from New York City to Hilo is minus 5 hours. In June, plan for daily highs up to 83°F, and evening lows to 69°F. Wrap up your sightseeing on the 14th (Sun) early enough to drive to Captain Cook.

Things to do in Hilo

Parks Nature Outdoors

Side Trips

Hawaii Volcanoes National Park, Pahoa, Jagger Museum, Hilo Coffee Mill
Highlights from your plan
Akaka Falls State Park ©
Akaka Falls State Park
Holei Sea Arch ©
Holei Sea Arch
Coconut Island ©
Coconut Island

6
nights
Captain Cook, Island of Hawaii

Captain Cook ©
A small town with big ocean views, Captain Cook lies on top of an ancient fault line that was responsible for creating the nearby Kealakekua Bay thousands of years ago.
You'll discover tucked-away gems like Pu'uhonua O Honaunau National Historical Park and Two Step. You'll find plenty of places to visit near Captain Cook: Mauna Loa (in Volcano) and Naalehu (Hawai'i Volcanoes National Park Kahuku Unit, Paradise Meadows Orchard & Bee Farm Home of Hawaii's Local Buzz, &more). There's much more to do: experience rural life at Kona Pacific Farmers Cooperative, paddle through the water with a kayaking and canoeing tour, contemplate the waterfront views at Kealakekua Bay, and admire the natural beauty at Paleaku Gardens Peace Sanctuary.

For reviews, photos, ratings, and other tourist information, you can read our Captain Cook road trip planning site.

You can drive from Hilo to Captain Cook in 2 hours. Alternatively, you can take a bus. June in Captain Cook sees daily highs of 85°F and lows of 74°F at night. Finish up your sightseeing early on the 20th (Sat) so you can go by car to Kailua-Kona.

Things to do in Captain Cook

Outdoors Parks Tours

Side Trips

Kealakekua, Naalehu, Mauna Loa, Pu'uhonua O Honaunau National Historical Park, Hawaii Offshore
Highlights from your plan
Papakōlea Green Sand Beach ©
Papakōlea Green Sand Beach
Pu'uhonua O Honaunau National Historical Park ©
Pu'uhonua O Honaunau National Historical Park
Kona Pacific Farmers Cooperative ©
Kona Pacific Farmers Cooperative

7
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 explore the less-touristy side of things at Mauna Kea and Ocean Rider Inc. Next up on the itinerary: cast your line with a fishing tour, experience rural life at Hula Daddy Kona Coffee, identify plant and animal life at Kanaloa Octopus Farm, and fulfill a lifelong dream with a swim-with-the-dolphins experience.

To see ratings, other places to visit, where to stay, and other tourist information, go to the Kailua-Kona attractions planner.

Kailua-Kona is just a stone's throw from Captain Cook. In June, daily temperatures in Kailua-Kona can reach 85°F, while at night they dip to 74°F. Wrap up your sightseeing by early afternoon on the 27th (Sat) to allow time for the car ride to Waikoloa.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Holualoa, Kekaha Kai State Park
Highlights from your plan
Kona Cloud Forest ©
Kona Cloud Forest
Mauna Kea ©
Mauna Kea
Fishing Charters & Tours

7
nights
Waikoloa, Island of Hawaii

Waikoloa ©
Waikoloa Village is a census-designated place (CDP) in Hawaii County, Hawaii, United States. Step off the beaten path and head to Hapuna Beach State Recreation Area and Waipiʻo Valley Lookout. Change things up with these side-trips from Waikoloa: Ackerman Galleries (in Kapaau), Hawi (Kohala Mountain Road, Hawaii Cigar & Ukulele, &more) and Waipio Na'alapa Trail (in Waimea). The adventure continues: admire the verdant scenery at Waipio Valley, take in the awesome beauty at Kohala Mountain Range, relax in the rural setting at Mauna Kea Tea, and see the sky in a new way at W. M. Keck Observatory.

To find where to stay, ratings, other places to visit, and other tourist information, read our Waikoloa tour itinerary maker.

You can drive from Kailua-Kona to Waikoloa in an hour. Another option is to take a bus. In June, daytime highs in Waikoloa are 85°F, while nighttime lows are 74°F. Finish your sightseeing early on the 4th (Sat) to allow enough time to travel to Kahului.

Things to do in Waikoloa

Parks Outdoors Nature

Side Trips

Island of Hawaii, Waimea, Hawi, Kawaihae, Puako
Highlights from your plan
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Waipio Valley ©
Waipio Valley
Waipiʻo Valley Lookout ©
Waipiʻo Valley Lookout

7
nights
Kahului, Maui

Kahului is a census-designated place (CDP) in Maui County, on the island of Maui, in the U.S. Discover out-of-the-way places like Keawakapu Beach and Ho'okipa Beach Park. You'll find plenty of places to visit near Kahului: Zipline (in Haiku), The Awakening Church (in Kihei) and Haleakala National Park (Pipiwai Trail & Haleakala Crater). Next up on the itinerary: explore and take pictures at Hana Highway - Road to Hana, stroll through Polo Beach, experience rural life at Leilani Farm Sanctuary, and see some colorful creatures with a scuba or snorkeling tour.

To see traveler tips, maps, other places to visit, and more tourist information, read Kahului trip builder website.

Traveling by flight from Waikoloa to Kahului takes 2.5 hours. Alternatively, you can do a combination of bus and flight. Expect a daytime high around 89°F in July, and nighttime lows around 72°F. Wrap up your sightseeing on the 11th (Sat) early enough to drive to Wailuku.

Things to do in Kahului

Outdoors Parks Beaches

Side Trips

Kihei, Maui, Wailea, Makawao, Haiku
Highlights from your plan
Photography Tours
Keawakapu Beach ©
Keawakapu Beach
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana

7
nights
Wailuku, Maui

Wailuku ©
Wailuku is a census-designated place (CDP) in Maui County, Hawaii, United States. You'll discover tucked-away gems like Honolua Bay and Lahaina Harbor. Explore Wailuku's surroundings by going to Lahaina (Old Lahaina Courthouse, The Ocean Project On Maui, &more). The adventure continues: admire the majestic nature at Iao Valley, get a taste of life in the country at Mendes Ranch, get interesting insight from Tours, and experience rural life at Punakea Palms Coconut Farm.

To see where to stay, reviews, photos, and more tourist information, read Wailuku tour planning site.

Wailuku is just a short distance from Kahului. July in Wailuku sees daily highs of 89°F and lows of 72°F at night. Wrap up your sightseeing on the 18th (Sat) early enough to travel to Honolulu.

Things to do in Wailuku

Outdoors Parks Tours

Side Trips

Lahaina, Off-Road Tours, Waihee Ridge Trail, Honolua Bay
Highlights from your plan
Punakea Palms Coconut Farm ©
Punakea Palms Coconut Farm
Iao Valley ©
Iao Valley
Maui Tropical Plantation ©
Maui Tropical Plantation

12
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 discover tucked-away gems like Helicopter Tours and National Memorial Cemetery of the Pacific. You'll find plenty of places to visit near Honolulu: Byodo-In Temple (in Kaneohe), Waimanalo Beach (in Waimanalo) and Kailua (Kailua Beach Park & Lanikai Beach). Next up on the itinerary: explore the different monuments and memorials at USS Arizona Memorial, hike along Lanikai Pillboxes, identify plant and animal life at Hanauma Bay Nature Preserve, and tour the pleasant surroundings at Waikiki Beach.

To find reviews, more things to do, traveler tips, and tourist information, you can read our Honolulu trip app.

Do a combination of bus and flight from Wailuku to Honolulu in 3.5 hours. Alternatively, you can do a combination of bus, ferry, and flight; or do a combination of bus, taxi, and flight. In July in Honolulu, expect temperatures between 88°F during the day and 75°F at night. Finish your sightseeing early on the 30th (Thu) so you can drive to Waianae.

Things to do in Honolulu

Outdoors Parks Tours

Side Trips

Kailua, Oahu, Kaneohe, Waimanalo Beach
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Helicopter Tours
Diamond Head State Monument ©
Diamond Head State Monument

4
nights
Waianae, Oahu

Waianae is a census-designated place (CDP) in Honolulu County, Hawaii, United States. Eschew the tourist crowds and head to Ko Olina Lagoons and Waianae Mountain Range. The adventure continues: head outdoors with Stars Above Hawaii, explore the striking landscape at Ka'ena Point State Park, explore the fascinating underground world of Mermaid Caves, and tee off at Ko Olina Golf Club.

For photos, reviews, more things to do, and tourist information, go to the Waianae online travel route planner.

Traveling by car from Honolulu to Waianae takes an hour. Alternatively, you can take a bus. Traveling from Honolulu in July, things will get little chillier in Waianae: highs are around 83°F and lows about 69°F. Wrap up your sightseeing on the 3rd (Mon) early enough to drive to Haleiwa.

Things to do in Waianae

Outdoors Parks Beaches

Side Trip

Kapolei
Highlights from your plan
Swim with Dolphins
Ko Olina Lagoons ©
Ko Olina Lagoons
Stars Above Hawaii ©
Stars Above Hawaii

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. On the 3rd (Mon), kick back and relax at Pupukea Beach Park, contemplate the waterfront views at Waimea Bay, then add some adventure to your tour with a kayaking and canoeing tour, and finally look for gifts at Pakaloha Bikinis - Oahu. Get ready for a full day of sightseeing on the 4th (Tue): kick back and relax at Shark's Cove, contemplate the waterfront views at Kawela Bay, then enjoy the sand and surf at Sunset Beach Park, and finally buy something for everyone on your list at Haleiwa Town Center.

To find other places to visit, traveler tips, ratings, and tourist information, refer to the Haleiwa trip itinerary planner.

Drive from Waianae to Haleiwa in an hour. Alternatively, you can take a bus. In August, daily temperatures in Haleiwa can reach 83°F, while at night they dip to 70°F. Finish your sightseeing early on the 5th (Wed) so you can travel to Kapaa.

Things to do in Haleiwa

Parks Outdoors Beaches

Side Trip

Kawela Bay
Highlights from your plan
Waimea Bay ©
Waimea Bay
Sunset Beach Park ©
Sunset Beach Park
Shark's Cove ©
Shark's Cove

few
hours
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 5th (Wed), look for gifts at Garden Isle Bath & Body LLC.

To find where to stay, traveler tips, and more tourist information, use the Kapaa route planner.

Do a combination of bus and flight from Haleiwa to Kapaa in 3.5 hours. Traveling from Haleiwa in August, you can expect nighttime temperatures to be somewhat warmer in Kapaa, with lows of 76°F. On the 5th (Wed), you'll have the morning to explore before heading back home.

Things to do in Kapaa

Shopping
Highlights from your plan
Garden Isle Bath & Body LLC ©
Garden Isle Bath & Body LLC

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