60 days in Hawaii Itinerary

60 days in Hawaii Itinerary

Created using Inspirock Hawaii trip itinerary builder

Plan created by another user. Make it yours

Route & dates

1
Hilo, Island of Hawaii
— 6 nights
2
Captain Cook, Island of Hawaii
— 6 nights
3
Kailua-Kona, Island of Hawaii
— 7 nights
4
Waikoloa, Island of Hawaii
— 7 nights
5
Kahului, Maui
— 7 nights
6
Wailuku, Maui
— 7 nights
7
Honolulu, Oahu
— 12 nights
8
Waianae, Oahu
— 4 nights
9
Haleiwa, Oahu
— 2 nights
10
Kapaa, Kauai
— Few hours

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 Kilauea Iki Trailhead and Holei Sea Arch. Explore Hilo's surroundings by going to Jagger Museum (in Volcano), Hawaii Volcanoes National Park (Sulphur Banks, Kīlauea, &more) and Pahoa (Kapoho Tide Pools & Kehena Black Sand Beach). There's still lots to do: stroll through Richardson Beach Park, enjoy the sand and surf at Carlsmith Beach Park, step off the mainland to explore Coconut Island, and don't miss a visit to Pepeekeo Scenic Drive.

To see where to stay, maps, photos, and tourist information, go to the Hilo tour planner.

New York City to Hilo is an approximately 15-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from New York City to Hilo. June in Hilo sees daily highs of 83°F and lows of 69°F at night. Finish your sightseeing early on the 14th (Sun) to allow enough time 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
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Richardson Beach Park ©
Richardson Beach Park

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 Scuba & Snorkeling and Kayaking & Canoeing. 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 lots more to do: explore the activities along Kealakekua Bay, explore the wealth of natural beauty at Pu'uhonua O Honaunau National Historical Park, experience rural life at Kona Pacific Farmers Cooperative, and take in nature's colorful creations at Paleaku Gardens Peace Sanctuary.

For photos, where to stay, more things to do, and other tourist information, use the Captain Cook sightseeing planner.

You can drive from Hilo to Captain Cook in 2 hours. Alternatively, you can take a bus. Expect a daytime high around 85°F in June, and nighttime lows around 74°F. Wrap up your sightseeing on the 20th (Sat) to allow time to drive to Kailua-Kona.

Things to do in Captain Cook

Outdoors · Parks · Tours

Side Trips

Kealakekua, Naalehu, Mauna Loa, Hawaii Offshore, Pu'uhonua O Honaunau National Historical Park
Highlights from your plan
Papakōlea Green Sand Beach ©
Papakōlea Green Sand Beach
Kayaking & Canoeing
Kealakekua Bay ©
Kealakekua Bay

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. There's still lots to do: see what you can catch with a fishing tour, enjoy the sand and surf at Manini'owali Beach (Kua Bay), fulfill a lifelong dream with a swim-with-the-dolphins experience, and tour the pleasant surroundings at Magic Sands.

For ratings, other places to visit, where to stay, and tourist information, read our Kailua-Kona trip itinerary builder.

Kailua-Kona is just a short distance from Captain Cook. In June, plan for daily highs up to 85°F, and evening lows to 74°F. On the 27th (Sat), wrap the sightseeing up by early afternoon so you can drive 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 Scuba & Snorkeling. Change things up with these side-trips from Waikoloa: Hawi (Kohala Mountain Road, Hawaii Cigar & Ukulele, &more), Ackerman Galleries (in Kapaau) and Honokaa (Waipiʻo Valley Lookout & Mauna Kea Tea). There's still lots to do: appreciate the views at Waipio Valley, see the sky in a new way at Mauna Kea Observatories, identify plant and animal life at Waikoloa Petroglyph Preserve, and contemplate in the serene atmosphere at Puukohola Heiau.

To find more things to do, traveler tips, where to stay, and tourist information, refer to the Waikoloa online holiday builder.

Traveling by car from Kailua-Kona to Waikoloa takes an hour. Alternatively, you can take a bus. In June, daytime highs in Waikoloa are 85°F, while nighttime lows are 74°F. Cap off your sightseeing on the 4th (Sat) early enough to travel to Kahului.

Things to do in Waikoloa

Parks · Outdoors · Nature

Side Trips

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

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 Pipiwai Trail and Photography Tours. You'll find plenty of places to visit near Kahului: The Awakening Church (in Kihei), Haleakala Crater (in Haleakala National Park) and Zipline (in Haiku). Next up on the itinerary: tour the pleasant surroundings at Keawakapu Beach, kick back and relax at Kamaole Beach Park II, indulge your thirst for a good beer at Maui Brewing Company, and see some colorful creatures with a scuba or snorkeling tour.

To find ratings, reviews, maps, and more tourist information, read Kahului trip builder website.

Traveling by flight from Waikoloa to Kahului takes 2.5 hours. 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, Makawao, Wailea, Maui, Haleakala National Park
Highlights from your plan
Photography Tours
Keawakapu Beach ©
Keawakapu Beach
Zipline

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 Old Lahaina Courthouse and Adrenaline & Extreme Tours. Explore Wailuku's surroundings by going to Lahaina (The Ocean Project On Maui, Lahaina Harbor, &more). The adventure continues: identify plant and animal life at Honolua Bay, whizz through the canopy at some of the top local zipline courses and adventure parks, get up close and personal with brilliant marine life at Maui Ocean Center, and admire the majestic nature at Iao Valley.

To find where to stay, ratings, traveler tips, 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 ©
Punakea Palms
Old Lahaina Courthouse ©
Old Lahaina Courthouse
Zipline

12
nights
Honolulu, Oahu

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 Stand-Up Paddleboarding and Helicopter Tours. You'll find plenty of places to visit near Honolulu: Waimanalo Beach (in Waimanalo), Kailua (Kailua Beach Park & Lanikai Beach) and Byodo-In Temple (in Kaneohe). Next up on the itinerary: take in the pleasant sights at Diamond Head State Monument, capture your vacation like a pro with an inspiring photography tour, indulge your taste buds at Food & Drink, and take a memorable tour with Tours.

To see other places to visit, where to stay, more things to do, and tourist information, you can read our Honolulu trip app.

Fly from Wailuku to Honolulu in 3.5 hours. 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
Stand-Up Paddleboarding
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach

4
nights
Waianae, Oahu

Waianae is a census-designated place (CDP) in Honolulu County, Hawaii, United States. Eschew the tourist crowds and head to Swim with Dolphins and Ko Olina Lagoons. Venture out of the city with trips to Kapolei (Ko Olina Golf Club & Naval Air Museum Barbers Point). And it doesn't end there: get outside with Stars Above Hawaii, hike along Pu’U’Ohulu Kai, explore the striking landscape at Ka'ena Point State Park, and Head underground at Mermaid Caves.

To see more things to do, maps, photos, and tourist information, go to the Waianae trip planner.

Traveling by car from Honolulu to Waianae takes an hour. Alternatively, you can take a bus. Traveling from Honolulu in July, expect Waianae to be little chillier, temps between 83°F and 69°F. Cap off your sightseeing on the 3rd (Mon) early enough to go by car 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.

For photos, more things to do, 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 see photos, reviews, traveler tips, and more tourist information, use the Kapaa route planner.

Fly 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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