55 days in Hawaii Itinerary

55 days in Hawaii Itinerary

Created using Inspirock Hawaii travel route planner

Make it your trip
Fly
1
Honolulu, Oahu
— 13 nights
Fly
2
Lihue, Kauai
— 9 nights
Fly
3
Kailua-Kona, Island of Hawaii
— 10 nights
Drive
4
Volcano, Island of Hawaii
— 6 nights
Fly
5
Lahaina, Maui
— 12 nights
Drive
6
Kipahulu, Maui
— 4 nights
Drive to Kahului Airport, Fly to New York City

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Honolulu, Oahu

— 13 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 find plenty of places to visit near Honolulu: Haleiwa (Waimea Bay, Sunset Beach Park, &more), Pu’u O Mahuka Heiau State Monument (in Pupukea) and Laie (Malaekahana State Recreation Area & Polynesian Cultural Center). There's much more to do: go for a walk through Diamond Head State Monument, see some colorful creatures with a scuba or snorkeling tour, contemplate the waterfront views at Hanauma Bay Nature Preserve, and explore the world behind art at Honolulu Museum of Art.

To see reviews, traveler tips, where to stay, and tourist information, use the Honolulu online trip itinerary maker.

New York City to Honolulu is an approximately 12.5-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from New York City to Honolulu. Expect somewhat warmer temperatures when traveling from New York City in June; daily highs in Honolulu reach 86°F and lows reach 74°F. Finish your sightseeing early on the 25th (Fri) so you can fly to Lihue.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trips

Lihue, Kauai

— 9 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Explore the numerous day-trip ideas around Lihue: Hanalei (Hanalei National Wildlife Refuge, Hanalei Beach, &more), Waimea Canyon State Park (in Waimea) and Kekaha (Boat Tours & Water Sports & Na Pali Makai). The adventure continues: take an unforgettable tour with a helicopter tour, hit the best photo ops around with an inspiring photography tour, contemplate the long history of Kilohana, and kick back and relax at Poipu Beach Park.

To find where to stay, maps, other places to visit, and other tourist information, read our Lihue route planner.

Fly from Honolulu to Lihue in 2.5 hours. Expect a daytime high around 83°F in June, and nighttime lows around 73°F. Wrap up your sightseeing on the 4th (Sun) early enough to fly to Kailua-Kona.

Things to do in Lihue

Parks · Outdoors · Beaches · Nature

Side Trips

Kailua-Kona, Island of Hawaii

— 10 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.
Explore the numerous day-trip ideas around Kailua-Kona: Puukohola National Historic Park (in Kawaihae), Hapuna Beach State Recreation Area (in Puako) and Parker Ranch (in Waimea). There's still lots to do: get close to the beloved marine mammals with a swim-with-the-dolphins experience, contemplate in the serene atmosphere at Kohala Historical Sites State Monument, look for all kinds of wild species at Kona Cloud Forest, and head outdoors with Aloha Rail Company.

To see traveler tips, photos, more things to do, and tourist information, refer to the Kailua-Kona attractions planning app.

Traveling by flight from Lihue to Kailua-Kona takes 2.5 hours. In July in Kailua-Kona, expect temperatures between 86°F during the day and 76°F at night. Wrap up your sightseeing on the 14th (Wed) early enough to drive to Volcano.

Things to do in Kailua-Kona

Parks · Outdoors · Nature · Wildlife

Side Trips

Volcano, Island of Hawaii

— 6 nights
Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
Get out of town with these interesting Volcano side-trips: Hilo (Rainbow Falls, Mokupapapa Discovery Center, &more), Hawaii Volcanoes National Park (Kalapana & Holei Sea Arch) and Laupahoehoe Beach Park (in Laupahoehoe). There's lots more to do: trek along Kilauea Iki Trailhead, tour the pleasant surroundings at Kipuka Puaulu (Bird Park) Trail, explore and take pictures at Chain of Craters Rd, and contemplate the geological forces at Kīlauea.

To find traveler tips, where to stay, ratings, and tourist information, use the Volcano travel route planner.

Traveling by car from Kailua-Kona to Volcano takes 2.5 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in July, Volcano is slightly colder at night with lows of 71°F. Wrap up your sightseeing on the 20th (Tue) early enough to fly to Lahaina.

Things to do in Volcano

Parks · Outdoors · Nature · Trails

Side Trips

Lahaina, Maui

— 12 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.
You'll find plenty of places to visit near Lahaina: Wailea (Wailea Beach, Keawakapu Beach, &more), Wailuku (Hale Ho'ike'ike at the Bailey House, Iao Valley, &more) and Helicopter Tours (in Kahului). And it doesn't end there: discover the deep blue sea with a scuba or snorkeling tour, whizz through the canopy at some of the top local zipline courses and adventure parks, kick back and relax at Napili Beach, and relax and rejuvenate at Ho'omana Spa Maui.

For photos, more things to do, other places to visit, and more tourist information, refer to the Lahaina planner.

Fly from Volcano to Lahaina in 2.5 hours. In July in Lahaina, expect temperatures between 86°F during the day and 73°F at night. Wrap up your sightseeing on the 1st (Sun) to allow time to drive to Kipahulu.

Things to do in Lahaina

Parks · Outdoors · Beaches · Tours

Side Trips

Kipahulu, Maui

— 4 nights
Take a break from Kipahulu with a short trip to Haleakala Crater in Haleakala National Park, about 40 minutes away. Spend the 3rd (Tue) exploring the striking scenery along Hana Highway - Road to Hana.

To see where to stay, traveler tips, ratings, and other tourist information, go to the Kipahulu trip planner.

You can drive from Lahaina to Kipahulu in 2.5 hours. August in Kipahulu sees daily highs of 90°F and lows of 73°F at night. Finish up your sightseeing early on the 5th (Thu) so you can travel back home.

Things to do in Kipahulu

Outdoors · Parks · Scenic Drive · Nature

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.