60 days in Hawaii Itinerary

60 days in Hawaii Itinerary

Created using Inspirock Hawaii travel route planner

Make it your trip
Fly
1
Hilo, Island of Hawaii
— 8 nights
Drive
2
Kailua-Kona, Island of Hawaii
— 12 nights
Fly
3
Kapaa, Kauai
— 11 nights
Fly
4
Lahaina, Maui
— 13 nights
Fly
5
Honolulu, Oahu
— 15 nights
Fly to New York JFK, Train to Philadelphia

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Hilo, Island of Hawaii

— 8 nights

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.
You'll find plenty of places to visit near Hilo: Waipiʻo Valley Lookout (in Honokaa), Hawaii Volcanoes National Park (Kilauea Iki Trailhead, Thurston Lava Tube (Nahuku), &more) and Laupahoehoe Beach Park (in Laupahoehoe). The adventure continues: take in the dramatic scenery at Akaka Falls State Park, see the interesting displays at Lyman Museum, take in nature's colorful creations at Liliuokalani Gardens, and pick up some local products at Hilo Farmers Market.

To find photos, ratings, where to stay, and more tourist information, read our Hilo day trip planning site.

Philadelphia to Hilo is an approximately 14.5-hour flight. Traveling from Philadelphia to Hilo, you'll gain 5 hours due to the time zone difference. Prepare for warmer weather when traveling from Philadelphia in March: high temperatures in Hilo hover around 80°F and lows are around 66°F. Finish up your sightseeing early on the 26th (Fri) so you can go by car to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Nature · Museums

Side Trips

Kailua-Kona, Island of Hawaii

— 12 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 Kailua-Kona's surroundings by going to Captain Cook (Big Island Bees, Kealakekua Bay, &more), Hapuna Beach State Recreation Area (in Puako) and Waikoloa (Anaehoomalu & 49 Black Sand Beach). And it doesn't end there: get close to the beloved marine mammals with a swim-with-the-dolphins experience, admire the verdant scenery at Pololu Valley Lookout, tour the pleasant surroundings at Puukohola National Historic Park, and play a few rounds at Mauna Lani Resort .

To find ratings, photos, where to stay, and more tourist information, read our Kailua-Kona trip builder app.

Drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. March in Kailua-Kona sees daily highs of 81°F and lows of 70°F at night. Wrap up your sightseeing on the 7th (Wed) to allow time to fly to Kapaa.

Things to do in Kailua-Kona

Parks · Outdoors · Beaches · Nature

Side Trips

Kapaa, Kauai

— 11 nights
Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Explore the numerous day-trip ideas around Kapaa: Poipu (Prince Kuhio Park, Spouting Horn, &more), Zipline (in Lihue) and Waimea (Puu Hinahina Lookout, Waimea Canyon State Park, &more). There's much more to do: hit the best photo ops around with an inspiring photography tour, see the world from above with a helicopter tour, admire the majestic nature at Na Pali Coast State Park, and admire the natural beauty at Na Aina Kai Botanical Gardens.

To see reviews, other places to visit, where to stay, and other tourist information, use the Kapaa online trip itinerary planner.

Traveling by flight from Kailua-Kona to Kapaa takes 2.5 hours. In April, plan for daily highs up to 80°F, and evening lows to 70°F. Finish your sightseeing early on the 18th (Sun) to allow enough time to fly to Lahaina.

Things to do in Kapaa

Parks · Outdoors · Beaches · 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 (Hale Ho'ike'ike at the Bailey House & Iao Valley), Haleakala Crater (in Haleakala National Park) and Makawao (Maui Veterans Cemetery, Bike Park Maui, &more). Spend the 20th (Tue) exploring the striking scenery along Hana Highway - Road to Hana. The adventure continues: discover the deep blue sea with a scuba or snorkeling tour, walk around Lahaina Banyan Court, tour the pleasant surroundings at Napili Beach, and observe the fascinating underwater world at Maui Ocean Center.

To find traveler tips, ratings, reviews, and more tourist information, go to the Lahaina trip itinerary app.

Traveling by flight from Kapaa to Lahaina takes 2.5 hours. In April, daily temperatures in Lahaina can reach 80°F, while at night they dip to 69°F. Wrap up your sightseeing on the 1st (Sat) early enough to fly to Honolulu.

Things to do in Lahaina

Outdoors · Parks · Beaches · Nature

Side Trips

Honolulu, Oahu

— 15 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.
Explore the numerous day-trip ideas around Honolulu: Kailua (Lanikai Beach & Kailua Beach Park), Pupukea (Pu’u O Mahuka Heiau State Monument & Ehukai Beach Park) and Ko Olina Golf Club (in Kapolei). There's lots more to do: explore the different monuments and memorials at USS Arizona Memorial, stroll through Waikiki Beach, trek along Diamond Head State Monument, and take a memorable tour with Tours.

For traveler tips, reviews, maps, and other tourist information, refer to the Honolulu trip planner.

Getting from Lahaina to Honolulu by flight takes about 2.5 hours. In May in Honolulu, expect temperatures between 84°F during the day and 71°F at night. Wrap up your sightseeing on the 16th (Sun) to allow time to travel back home.

Things to do in Honolulu

Parks · Outdoors · 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.