30 days in Hawaii Itinerary

30 days in Hawaii Itinerary

Created using Inspirock Hawaii holiday planner

Make it your trip
Fly to Daniel K Inouye International Airport, Drive to Hawaii Kai
1
Hawaii Kai, Oahu
— 1 day
Drive
2
Waimanalo, Oahu
— 2 nights
Drive
3
Honolulu, Oahu
— 6 nights
Fly
4
Hanalei, Kauai
— 2 nights
Fly
5
Kailua-Kona, Island of Hawaii
— 3 nights
Fly
6
Lahaina, Maui
— 15 nights
Fly to Knoxville, Drive to Chattanooga

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Hawaii Kai, Oahu

— 1 day
Start off your visit on the 1st (Tue): get close to the beloved marine mammals with Dolphin Quest, head outdoors with Dead Man's Catwalk, take a memorable drive along Makapu'u Point, then explore the gorgeous colors at Pele's Chair, and finally take in the dramatic natural features at Halona Blowhole.

To see other places to visit, more things to do, ratings, and other tourist information, use the Hawaii Kai tour itinerary planning site.

Chattanooga to Hawaii Kai is an approximately 14.5-hour combination of flight and car. You can also do a combination of flight and car. Due to the time zone difference, you'll gain 5 hours traveling from Chattanooga to Hawaii Kai. Traveling from Chattanooga in June, you will find days in Hawaii Kai are a bit cooler (83°F), and nights are somewhat warmer (74°F). Finish your sightseeing early on the 1st (Tue) so you can travel to Waimanalo.

Things to do in Hawaii Kai

Outdoors · Wildlife · Tours · Parks

Side Trip

Waimanalo, Oahu

— 2 nights
Waimānalo is a census-designated place (CDP) in the City & County of Honolulu, in the District of Koolaupoko on the island of Oahu, Hawaii, United States. You've now added Waimanalo Beach to your itinerary. On the 2nd (Wed), kick back and relax at Waimanalo Beach, take in the dramatic natural features at Makapu'u Point, identify plant and animal life at Pele's Chair, explore the striking landscape at Halona Blowhole, then head outdoors with Dead Man's Catwalk, and finally tour the pleasant surroundings at Lanikai Pillbox Hike. Keep things going the next day: get in on the family fun at Sea Life Park Hawaii, stroll through Kaiona Beach Park, and then enjoy the sand and surf at Waimanalo Beach.

Take the guesswork out of planning a Waimanalo vacation by using our trip itinerary maker.

Waimanalo is just a short distance from Hawaii Kai. In June, plan for daily highs up to 83°F, and evening lows to 74°F. Finish your sightseeing early on the 3rd (Thu) to allow enough time to drive to Honolulu.

Things to do in Waimanalo

Parks · Outdoors · Beaches · Wildlife

Side Trips

Honolulu, Oahu

— 6 nights

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.
You'll enjoy a bit of beach vacationing at Waikiki Beach and Kuhio Beach. Get outdoors at Diamond Head State Monument and Koko Crater Railway Trail. You'll find plenty of places to visit near Honolulu: Pupukea (Banzai Pipeline & Sharks Cove) and Sunset Beach Park (in Haleiwa). And it doesn't end there: fulfill a lifelong dream with a swim-with-the-dolphins experience, get a dose of the wild on a nature and wildlife tour, pause for some photo ops at Makua and Kila statue, and hit the best photo ops around with an inspiring photography tour.

To find ratings and other tourist information, use the Honolulu road trip planning app.

Getting from Waimanalo to Honolulu by car takes about an hour. Other options: take a bus. Expect a daytime high around 86°F in June, and nighttime lows around 74°F. Wrap up your sightseeing on the 9th (Wed) early enough to fly to Hanalei.

Things to do in Honolulu

Outdoors · Parks · Wildlife · Beaches

Side Trips

Hanalei, Kauai

— 2 nights
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Start off your visit on the 10th (Thu): kick back and relax at Puu Poa Beach, enjoy the sand and surf at Secret Beach, then get interesting insight from Tours, and finally identify plant and animal life at Hanalei National Wildlife Refuge. On the next day, trek along Hanakapi`ai Trail, take some stellar pictures from Hanalei Day Spa, then kick back and relax at Hanalei Beach, and finally take in the architecture and atmosphere at Wai`oli Hui`ia Church.

For photos, where to stay, more things to do, and more tourist information, go to the Hanalei online visit planner.

You can fly from Honolulu to Hanalei in 2.5 hours. In June in Hanalei, expect temperatures between 83°F during the day and 73°F at night. Finish up your sightseeing early on the 11th (Fri) so you can catch the flight to Kailua-Kona.

Things to do in Hanalei

Outdoors · Parks · Beaches · Trails

Side Trips

Kailua-Kona, Island of Hawaii

— 3 nights

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.
Relax by the water at Honaunau Bay and Mahai'ula Beach. Get some cultural insight at H.N. Greenwell Store Museum and Mokuaikaua Church. Next up on the itinerary: get close to the beloved marine mammals with a swim-with-the-dolphins experience, kick back and relax at Makalawena/Pu'u Ali'i, look for all kinds of wild species at Kanaloa Octopus Farm, and surround yourself with nature on a nature and wildlife tour.

To see traveler tips, where to stay, photos, and more tourist information, refer to the Kailua-Kona online road trip planner.

Traveling by flight from Hanalei to Kailua-Kona takes 2.5 hours. Expect a daytime high around 85°F in June, and nighttime lows around 74°F. Wrap up your sightseeing on the 14th (Mon) to allow time to fly to Lahaina.

Things to do in Kailua-Kona

Outdoors · Parks · Wildlife · Beaches

Side Trips

Lahaina, Maui

— 15 nights

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.
Step out of the city life by going to Napili Beach and Honolua Bay. Step off the beaten path and head to Parasailing & Paragliding and Ulua Beach. Explore Lahaina's surroundings by going to Paia (Mantokuji Temple Mission of Paia, Ho'okipa Beach Park, &more), Haleakala Crater (in Haleakala National Park) and Wailea (Keawakapu Beach, Wailea Beach, &more). There's much more to do: tour the pleasant surroundings at Kapalua Coastal Trail, explore the striking landscape at Nakalele Blowhole, get a dose of the wild on a nature and wildlife tour, and enjoy the sand and surf at D.T. Fleming Park.

To find reviews, where to stay, other places to visit, and other tourist information, go to the Lahaina trip planner.

Getting from Kailua-Kona to Lahaina by flight takes about 2.5 hours. June in Lahaina sees daily highs of 84°F and lows of 72°F at night. Wrap up your sightseeing on the 29th (Tue) early enough to travel back home.

Things to do in Lahaina

Outdoors · Parks · Beaches · Wildlife

Side Trips

Hawaii travel guide

4.4
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.