27 days in Hawaii Itinerary

27 days in Hawaii Itinerary

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Route & dates

27 days in Hawaii Itinerary

Start: New York City
bus + Fly:  9​h 30​min
1
Honolulu, Oahu
— 3 nights
Fly:  2​h 30​min
2
Kapaa, Kauai
— 5 nights
Fly + bus:  3​h 30​min
3
Lahaina, Maui
— 6 nights
bus + Fly:  3​h 15​min
4
Hilo, Island of Hawaii
— 6 nights
Drive:  1​h 45​min
5
Kailua-Kona, Island of Hawaii
— 5 nights
Fly + foot:  16​h 15​min
End: New York City

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 Rainbow Scuba Hawaii and Banzai Pipeline. You'll explore the less-touristy side of things at Kaimana Divers and US Army Museum of Hawaii. There's still lots to do: explore the different monuments and memorials at USS Arizona Memorial, identify plant and animal life at Hanauma Bay Nature Preserve, take in the pleasant sights at Diamond Head State Monument, and take a tour of Battleship Missouri Memorial.

For maps, other places to visit, and more tourist information, use the Honolulu trip app .

New York City to Honolulu is an approximately 14-hour combination of bus and flight. You can also fly. The time zone difference moving from Eastern Standard Time (EST) to Hawaii Standard Time (HST) is minus 5 hours. Traveling from New York City in June, things will get somewhat warmer in Honolulu: highs are around 86°F and lows about 74°F. Cap off your sightseeing on the 7th (Tue) early enough to travel to Kapaa.

Things to do in Honolulu

Outdoors Wildlife Museums

Side Trip

Banzai Pipeline
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Rainbow Scuba Hawaii ©
Rainbow Scuba Hawaii
Kaimana Divers ©
Kaimana Divers

5
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.
Explore hidden gems such as Catamaran Kahanu and Hanakapiai Falls. Step out of the city life by going to Fathom Five Divers and Opaekaa Falls. Explore the numerous day-trip ideas around Kapaa: Kokee Natural History Museum (in Kekaha), Aloha 'n Paradise Espresso Bar (in Waimea) and Hanalei Beach (in Hanalei). The adventure continues: see some colorful creatures with Kauai Down Under Dive Team, see what you can catch with Island Fishing Kauai, stroll through Tunnels Beach, and see the interesting displays at Grove Farm Sugar Plantation Museum.

For traveler tips, ratings, maps, and tourist information, read our Kapaa online trip maker .

Fly from Honolulu to Kapaa in 2.5 hours. June in Kapaa sees daily highs of 83°F and lows of 73°F at night. Finish your sightseeing early on the 12th (Sun) so you can travel to Lahaina.

Things to do in Kapaa

Outdoors Tours Wildlife

Side Trips

Kauai, Koloa, Lihue, Kokee Natural History Museum, Aloha 'n Paradise Espresso Bar
Highlights from your plan
Fathom Five Divers ©
Fathom Five Divers
Catamaran Kahanu ©
Catamaran Kahanu
Hanakapiai Falls ©
Hanakapiai Falls

6
nights
Lahaina, Maui

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.
Kihei Baptist Chapel and Kahanu Garden will appeal to history buffs. Explore hidden gems such as Goofy Foot Surf School, Inc and Maui Surfer Girls. You'll find plenty of places to visit near Lahaina: Hale Ho'ike'ike at the Bailey House (in Wailuku), Hui No‘eau Visual Arts Center (in Makawao) and Kihei (B&B Scuba & Hawaiian Paddle Sports). The adventure continues: relax and float downstream with Hawaii Ocean Rafting, kick back and relax at Honokeana Bay, make a short side trip with Hawaii Ocean Project, and see the interesting displays at Whalers Village Museum.

To see other places to visit, reviews, traveler tips, and tourist information, you can read our Lahaina trip planner .

You can do a combination of flight and bus from Kapaa to Lahaina in 3.5 hours. In June, daytime highs in Lahaina are 84°F, while nighttime lows are 72°F. Finish your sightseeing early on the 18th (Sat) so you can travel to Hilo.

Things to do in Lahaina

Outdoors Tours Adventure

Side Trips

Kihei, Hale Ho'ike'ike at the Bailey House, Kahanu Garden, Honokeana Bay, Hui No‘eau Visual Arts Center
Highlights from your plan
Hawaii Ocean Rafting ©
Hawaii Ocean Rafting
B&B Scuba ©
B&B Scuba
Ka'anapali Beach ©
Ka'anapali Beach

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.
Jagger Museum and 2400 Fahrenheit Art Glass are good opportunities to explore the local culture. Step off the beaten path and head to Kīlauea and Richardson Beach Park. You'll find plenty of places to visit near Hilo: Volcano Art Center Gallery (in Hawaii Volcanoes National Park), Volcano Garden Arts (in Volcano) and Waipio Na'alapa Trail (in Waimea). And it doesn't end there: take in nature's colorful creations at Liliuokalani Gardens, see some colorful creatures with Nautilus Dive Center, examine the collection at Pacific Tsunami Museum, and pause for some serene contemplation at St. Joseph Catholic Church,.

For more things to do, where to stay, reviews, and more tourist information, read Hilo route maker site .

You can do a combination of bus and flight from Lahaina to Hilo in 3.5 hours. Other options are to fly; or do a combination of bus and flight. In June, daily temperatures in Hilo can reach 83°F, while at night they dip to 69°F. Cap off your sightseeing on the 24th (Fri) early enough to go by car to Kailua-Kona.

Things to do in Hilo

Parks Outdoors Nature

Side Trips

Volcano, Hawaii Volcanoes National Park, Onomea Bay, Waipio Na'alapa Trail
Highlights from your plan
Kīlauea ©
Kīlauea
Jagger Museum ©
Jagger Museum
Richardson Beach Park ©
Richardson Beach Park

5
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.
Get some historical perspective at Kealakekua Bay and Puukohola Heiau. Museum-lovers will get to explore Kona Historical Society and Parker Ranch. Change things up with these side-trips from Kailua-Kona: Honaunau Bay (in Honaunau), Hapuna Beach State Recreation Area (in Puako) and Puukohola National Historic Park (in Kawaihae). There's lots more to do: get a taste of local nightlife at Neptune Charlies Ocean Safaris, see some colorful creatures with Kona Diving Company, take a memorable tour with Kona Honu Divers, and kick back and relax at Kahaluu Beach.

To find maps, ratings, more things to do, and tourist information, refer to the Kailua-Kona day trip app .

Drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. In June, daytime highs in Kailua-Kona are 85°F, while nighttime lows are 74°F. Wrap up your sightseeing on the 29th (Wed) early enough to travel back home.

Things to do in Kailua-Kona

Outdoors Wildlife Tours

Side Trips

Kawaihae, Honaunau Bay, Kona Historical Society, Kahaluu Beach, Kealakekua Bay
Highlights from your plan
Hapuna Beach State Recreation Area ©
Kona Diving Company ©
Kona Diving Company
Kona Honu Divers ©
Kona Honu Divers

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