27 days in Hawaii Itinerary

27 days in Hawaii Itinerary

Created using Inspirock Hawaii Trip Planner

Plan created by another user. Make it yours
1
Honolulu, Oahu
— 3 nights
2
Kapaa, Kauai
— 5 nights
3
Lahaina, Maui
— 6 nights
4
Hilo, Island of Hawaii
— 6 nights
5
Kailua-Kona, Island of Hawaii
— 5 nights

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Honolulu, Oahu

Honolulu ©

Big Pineapple

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 USS Bowfin Submarine Museum & Park. And it doesn't end there: stroll the grounds of USS Arizona Memorial, identify plant and animal life at Hanauma Bay Nature Preserve, see the interesting displays at Pearl Harbor Aviation Museum, and go for a walk through Diamond Head State Monument.

To plan Honolulu vacation without wasting time, ask Inspirock to design an itinerary.

New York City to Honolulu is an approximately 14-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from New York City to Honolulu. In June, Honolulu is a bit warmer than New York City - with highs of 86°F and lows of 74°F. Finish your sightseeing early on the 7th (Tue) to allow enough time to travel to Kapaa.

Things to do in Honolulu

Outdoors · Wildlife · Museums · Parks

Side Trip

Highlights from your trip
©
Water Sport
Rainbow Scuba Hawaii
4.8
©
Scuba / Snorkeling
Kaimana Divers
4.9

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 Fathom Five Divers and Catamaran Kahanu. Step out of the city life by going to Kauai Down Under Dive Team and Hanalei Beach. Explore the numerous day-trip ideas around Kapaa: Kokee Natural History Museum (in Kekaha) and Aloha 'n Paradise Espresso Bar (in Waimea). There's lots more to do: take in the dramatic scenery at Hanakapiai Falls, cast your line with Deep Sea Fishing Kauai, kick back and relax at Tunnels Beach, and examine the collection at Grove Farm Sugar Plantation Museum.

To see reviews, maps, and other tourist information, go to the Kapaa trip itinerary tool.

Traveling by flight from Honolulu to Kapaa takes 3 hours. Expect a daytime high around 83°F in June, and nighttime lows around 73°F. Finish up your sightseeing early on the 12th (Sun) so you can travel to Lahaina.

Things to do in Kapaa

Outdoors · Wildlife · Tours · Parks

Side Trips

Highlights from your trip
©
Scuba / Snorkeling
Fathom Five Divers
4.8
©
Scuba / Snorkeling
Catamaran Kahanu
4.7
©
Scuba / Snorkeling
Kauai Down Under Dive Team
4.7

6
nights
Lahaina, Maui

Lahaina ©

Crown Jewel of Maui

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.
Lahaina United Methodist Church and Kihei Baptist Chapel will appeal to history buffs. Explore hidden gems such as Goofy Foot Surf School, Inc and B&B Scuba. You'll find plenty of places to visit near Lahaina: Hale Ho'ike'ike at the Bailey House (in Wailuku), Hawaiian Paddle Sports (in Kihei) and Kahanu Garden (in Hana). There's lots more to do: see Maui Surfer Girls, make a short side trip with Hawaii Ocean Project, kick back and relax at Honokeana Bay, and get a taste of the local shopping with Reeflections Fine Art Gallery.

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

You can fly from Kapaa to Lahaina in 3.5 hours. Expect a daytime high around 84°F in June, and nighttime lows around 72°F. Finish up your sightseeing early on the 18th (Sat) so you can travel to Hilo.

Things to do in Lahaina

Outdoors · Tours · Adventure · Parks

Side Trips

Highlights from your trip
©
Surfing / Windsurfing / Kitesurfing
Maui Surfer Girls
5.0
©
Surfing / Windsurfing / Kitesurfing
Hawaiian Paddle Sports
5.0
©
River Rafting / Tubing
Hawaii Ocean Rafting
4.6

6
nights
Hilo, Island of Hawaii

Hilo ©

America's Wettest City

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.
Liliuokalani Gardens and Pacific Tsunami Museum are good opportunities to explore the local culture. Step off the beaten path and head to Richardson Beach Park and Rainbow Falls. You'll find plenty of places to visit near Hilo: Hawaii Volcanoes National Park (Kīlauea & Volcano Art Center Gallery), Volcano (Jagger Museum, 2400 Fahrenheit Art Glass, &more) and Waipio Na'alapa Trail (in Waimea). There's much more to do: take in the dramatic scenery at Akaka Falls State Park, see some colorful creatures with Nautilus Dive Center, get up close and personal with brilliant marine life at Mokupapapa Discovery Center, and explore the activities along Wailuku River State Park.

To find ratings, maps, and other tourist information, use the Hilo itinerary site.

Traveling by flight from Lahaina to Hilo takes 3.5 hours. In June in Hilo, expect temperatures between 83°F during the day and 69°F at night. Finish up your sightseeing early on the 24th (Fri) so you can go by car to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Nature · Museums

Side Trips

Highlights from your trip
©
Beach
Onomea Bay
4.5
©
Volcano
Kīlauea
4.4
©
Specialty Museum
Jagger Museum
4.7

5
nights
Kailua-Kona, Island of Hawaii

Kailua-Kona ©

Heart of the Kona Coast

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: Puukohola National Historic Park (in Kawaihae), Honaunau Bay (in Honaunau) and Hapuna Beach State Recreation Area (in Puako). There's lots more to do: discover the deep blue sea with Kona Diving Company, join in the after-dark buzz at Neptune Charlies Ocean Safaris, take a memorable tour with Kona Honu Divers, and kick back and relax at Kahaluu Beach.

To find more things to do, other places to visit, where to stay, 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 · Tours · Wildlife · Parks

Side Trips

Highlights from your trip
©
Beach
Honaunau Bay
4.5
©
Scuba / Snorkeling
Kona Diving Company
4.9
©
Scuba / Snorkeling
Kona Honu Divers
4.7

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