60 days in Hawaii Itinerary

60 days in Hawaii Itinerary

Created using Inspirock Hawaii travel route maker

Make it your trip
Fly to Kahului Airport, Drive to Kipahulu
1
Kipahulu, Maui
— 3 nights
Drive
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Lahaina, Maui
— 13 nights
Fly
3
Volcano, Island of Hawaii
— 6 nights
Drive
4
Kailua-Kona, Island of Hawaii
— 11 nights
Fly
5
Lihue, Kauai
— 10 nights
Fly
6
Honolulu, Oahu
— 16 nights
Fly to New York JFK, Train to Philadelphia

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Kipahulu, Maui

— 3 nights
Take a break from Kipahulu with a short trip to Haleakala Crater in Haleakala National Park, about 40 minutes away. Spend the 14th (Wed) exploring the striking scenery along Hana Highway - Road to Hana.

Planning Kipahulu trip won't be overwhelming when you use Inspirock's itinerary maker.

Philadelphia to Kipahulu is an approximately 15.5-hour combination of flight and car. You can also travel. The time zone difference when traveling from Philadelphia to Kipahulu is minus 5 hours. While traveling from Philadelphia, expect somewhat warmer days and much hotter nights in Kipahulu, ranging from highs of 85°F to lows of 68°F. Wrap up your sightseeing on the 16th (Fri) to allow time to drive to Lahaina.

Things to do in Kipahulu

Outdoors · Parks · Scenic Drive · Nature

Side Trips

Lahaina, Maui

— 13 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.
Explore Lahaina's surroundings by going to Wailuku (Iao Valley & Maui Tropical Plantation), Kahului (Photography Tours & Helicopter Tours) and Makawao (Bike Park Maui, Hui No‘eau Visual Arts Center, &more). There's still lots to do: look for all kinds of wild species at Wildlife Areas, stroll around Lahaina Banyan Court, take in the architecture and atmosphere at Maria Lanakila Catholic Church, and kick your exploration up a notch at some of the top local zipline courses and adventure parks.

For reviews, maps, other places to visit, and more tourist information, read Lahaina trip itinerary planning site.

You can drive from Kipahulu to Lahaina in 2.5 hours. Expect a bit cooler weather when traveling from Kipahulu in April: highs in Lahaina hover around 80°F, while lows dip to 69°F. Finish your sightseeing early on the 29th (Thu) so you can fly to Volcano.

Things to do in Lahaina

Outdoors · Parks · Beaches · Tours

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: Hawaii Volcanoes National Park (Kalapana, Holei Sea Arch, &more) and Hilo (Reeds Bay Beach Park, Liliuokalani Gardens, &more). The adventure continues: stroll through Kilauea Iki Trailhead, admire all the interesting features of Devastation Trail, contemplate the geological forces at Kīlauea, and take in the dramatic natural features at Thurston Lava Tube (Nahuku).

For where to stay, ratings, maps, and tourist information, you can read our Volcano road trip site.

Getting from Lahaina to Volcano by flight takes about 2.5 hours. In April in Volcano, expect temperatures between 81°F during the day and 67°F at night. Finish your sightseeing early on the 5th (Wed) so you can drive to Kailua-Kona.

Things to do in Volcano

Parks · Outdoors · Trails · Museums

Side Trips

Kailua-Kona, Island of Hawaii

— 11 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 Waikoloa (Anaehoomalu & Waikoloa Kings' Course). And it doesn't end there: get close to the beloved marine mammals with a swim-with-the-dolphins experience, experience rural life at Heavenly Hawaiian Kona Coffee Farm, take in the spiritual surroundings of Kohala Historical Sites State Monument, and admire the verdant scenery at Pololu Valley Lookout.

For traveler tips, other places to visit, photos, and tourist information, read our Kailua-Kona road trip planning website.

You can drive from Volcano to Kailua-Kona in 2.5 hours. Alternatively, you can take a bus. Expect somewhat warmer evenings in Kailua-Kona when traveling from Volcano in May, with lows around 73°F. Finish your sightseeing early on the 16th (Sun) so you can fly to Lihue.

Things to do in Kailua-Kona

Parks · Outdoors · Beaches · Nature

Side Trips

Lihue, Kauai

— 10 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Change things up with these side-trips from Lihue: Allerton Garden (in Poipu), Waimea (Puu Hinahina Lookout, Waimea Canyon State Park, &more) and Princeville Golf Club - Prince Course (in Princeville). Next up on the itinerary: kick your exploration up a notch at some of the top local zipline courses and adventure parks, capture your vacation like a pro with an inspiring photography tour, look for all kinds of wild species at Na Pali Coast State Park, and enjoy the sand and surf at Hanalei Beach.

To see where to stay, reviews, ratings, and tourist information, refer to the Lihue itinerary planning tool.

You can fly from Kailua-Kona to Lihue in 2.5 hours. In May, plan for daily highs up to 82°F, and evening lows to 71°F. Finish your sightseeing early on the 26th (Wed) to allow enough time to fly to Honolulu.

Things to do in Lihue

Parks · Outdoors · Beaches · Nature

Side Trips

Honolulu, Oahu

— 16 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.
Change things up with these side-trips from Honolulu: Laie (Malaekahana State Recreation Area & Polynesian Cultural Center), Haleiwa (Waimea Valley, Wys Galleries, &more) and Byodo-In Temple (in Kaneohe). There's much more to do: explore the different monuments and memorials at USS Arizona Memorial, enjoy the sand and surf at Waikiki Beach, examine the collection at Bishop Museum, and tour the pleasant surroundings at Diamond Head State Monument.

To see traveler tips, more things to do, and tourist information, read Honolulu tour itinerary planning app.

You can fly from Lihue to Honolulu in 2.5 hours. In May, plan for daily highs up to 84°F, and evening lows to 71°F. Finish up your sightseeing early on the 11th (Fri) so you can travel back home.

Things to do in Honolulu

Parks · Outdoors · Museums · Beaches

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.