37 days in Hawaii Itinerary

37 days in Hawaii Itinerary

Created using Inspirock Hawaii travel planner
Make it your trip
Fly
1
Kailua-Kona, Island of Hawaii
— 4 nights
Drive
2
Hilo, Island of Hawaii
— 5 nights
Fly
3
Lahaina, Maui
— 10 nights
Fly
4
Koloa, Kauai
— 5 nights
Fly
5
Honolulu, Oahu
— 12 nights
Fly

S M T W T F S
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23

Kailua-Kona, Island of Hawaii — 4 nights

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.
Kids will enjoy Swim with Dolphins and Pololu Valley Lookout. Explore the numerous day-trip ideas around Kailua-Kona: Pu'uhonua O Honaunau National Historical Park (in Honaunau), Hapuna Beach State Recreation Area (in Puako) and Kula Kai Caverns (in Ocean View). There's still lots to do: look for all kinds of wild species at Kona Cloud Forest, head outdoors with Hawaii Offshore, play a few rounds at Mauna Lani Resort , and explore the striking landscape of Lapakahi State Historical Park.

To see ratings, reviews, where to stay, and more tourist information, read our Kailua-Kona trip maker.

Dallas to Kailua-Kona is an approximately 9-hour flight. You can also fly. You'll gain 4 hours traveling from Dallas to Kailua-Kona due to the time zone difference. When traveling from Dallas in June, plan for little chillier days and about the same nights in Kailua-Kona: temperatures range from 85°F by day to 74°F at night. Finish your sightseeing early on the 21st (Tue) to allow enough time to drive to Hilo.
more
Parks · Outdoors · Nature · Beaches
Side Trips

Hilo, Island of Hawaii — 5 nights

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.
You'll visit kid-friendly attractions like Akaka Falls State Park and Liliuokalani Gardens. You'll find plenty of places to visit near Hilo: Hawaii Volcanoes National Park (Volcano Art Center Gallery, Kilauea Iki Trailhead, &more). There's much more to do: engage your brain at Mokupapapa Discovery Center, take in nature's colorful creations at Hawaii Tropical Bioreserve and Garden, take an unforgettable tour with a helicopter tour, and see the interesting displays at Lyman Museum.

Plan my day in Hilo using traveler tips and tourist information provided by Inspirock.

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. Plan for little chillier nights when traveling from Kailua-Kona in June since evenings lows in Hilo dip to 69°F. Finish your sightseeing early on the 26th (Sun) to allow enough time to fly to Lahaina.
more
Parks · Outdoors · Museums · Tours
Side Trips

Lahaina, Maui — 10 nights

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.
Kids will appreciate attractions like Scuba & Snorkeling and Maui Ocean Center. Change things up with these side-trips from Lahaina: Haleakala National Park (Haleakala Observatories & Haleakala Crater), Wailuku (Iao Valley, Mendes Ranch, &more) and Wailea (Uplift Maui, Keawakapu Beach, &more). Spend the 6th (Wed) exploring the striking scenery along Hana Highway - Road to Hana. There's much more to do: kick back and relax at Ka'anapali Beach, stroll through Kapalua Beach, get impressive views of Molokini Crater, and walk around D.T. Fleming Park.

To see where to stay, reviews, more things to do, and tourist information, you can read our Lahaina online trip planner.

Traveling by flight from Hilo to Lahaina takes 2.5 hours. In June, plan for daily highs up to 84°F, and evening lows to 72°F. Wrap up your sightseeing on the 6th (Wed) to allow time to fly to Koloa.
more
Parks · Outdoors · Beaches · Nature
Side Trips

Koloa, Kauai — 5 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Kids will appreciate attractions like Waimea Canyon State Park and Koke'e Mountains. Get out of town with these interesting Koloa side-trips: Kauai Path (in Kapaa), Na Pali Coast State Park (in Wainiha) and Kekaha (Na Pali Makai & Boat Tours & Water Sports). And it doesn't end there: tour the pleasant surroundings at Poipu Beach Park, admire the sheer force of Opaekaa Falls, head outdoors with Kauai Safaris, and kick back and relax at Anini Beach.

To see maps, photos, traveler tips, and other tourist information, read our Koloa online trip builder.

Traveling by flight from Lahaina to Koloa takes 2.5 hours. In July, daytime highs in Koloa are 84°F, while nighttime lows are 74°F. Finish up your sightseeing early on the 11th (Mon) so you can catch the flight to Honolulu.
more
Parks · Outdoors · Beaches · Nature
Side Trips

Honolulu, Oahu — 12 nights

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Kids will appreciate attractions like Waikiki Beach and Diamond Head State Monument. Venture out of the city with trips to Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua (Lanikai Beach & Kailua Beach Park) and Haleiwa (Pupukea Beach Park, Sunset Beach Park, &more). The adventure continues: stroll the grounds of USS Arizona Memorial, buy something for everyone on your list at Ala Moana Center, identify plant and animal life at Hanauma Bay Nature Preserve, and see the interesting displays at Iolani Palace.

To see ratings, maps, photos, and more tourist information, read our Honolulu driving holiday planner.

Getting from Koloa to Honolulu by flight takes about 2.5 hours. July in Honolulu sees daily highs of 88°F and lows of 75°F at night. Wrap up your sightseeing on the 23rd (Sat) to allow time to fly back home.
more
Outdoors · Parks · Beaches · Historic Sites
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.
more