59 days in Hawaii Itinerary

59 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

Make it your trip
Fly
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Honolulu, Oahu
— 13 nights
Fly
2
Kihei, Maui
— 12 nights
Fly
3
Hilo, Island of Hawaii
— 9 nights
Drive
4
Kailua-Kona, Island of Hawaii
— 12 nights
Fly
5
Kapaa, Kauai
— 12 nights
Fly

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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: Laie (Malaekahana State Recreation Area & Polynesian Cultural Center), Pupukea (Pu’u O Mahuka Heiau State Monument & Banzai Pipeline) and Haleiwa (Pupukea Beach Park, Sunset Beach Park, &more). The adventure continues: explore the different monuments and memorials at USS Arizona Memorial, see the interesting displays at Bishop Museum, enjoy the sand and surf at Kailua Beach Park, and take in the dramatic scenery at Manoa Falls.

To see where to stay, traveler tips, reviews, and other tourist information, you can read our Honolulu trip planner.

Washington DC to Honolulu is an approximately 13-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Washington DC to Honolulu. Traveling from Washington DC in February, things will get much hotter in Honolulu: highs are around 81°F and lows about 69°F. Finish your sightseeing early on the 14th (Sun) so you can travel to Kihei.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trips

Kihei, Maui

— 12 nights
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Explore the numerous day-trip ideas around Kihei: Zipline (in Kula), Lahaina (Maui Hands, Lahaina Banyan Court, &more) and Haleakala Crater (in Haleakala National Park). Spend the 16th (Tue) exploring the striking scenery along Hana Highway - Road to Hana. The adventure continues: observe the fascinating underwater world at Maui Ocean Center, enjoy the sand and surf at Makena Beach, tour the pleasant surroundings at Wailea Beach, and take in the architecture and atmosphere at Saint Theresa Roman Catholic Church.

To find ratings, where to stay, maps, and other tourist information, read Kihei trip itinerary maker.

Fly from Honolulu to Kihei in 4.5 hours. Expect a daytime high around 81°F in February, and nighttime lows around 65°F. Cap off your sightseeing on the 26th (Fri) early enough to travel to Hilo.

Things to do in Kihei

Parks · Outdoors · Beaches · Nature

Side Trips

Hilo, Island of Hawaii

— 9 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.
Explore Hilo's surroundings by going to Hawaii Volcanoes National Park (Nature & Wildlife Tours, Napau-Makaopuhi Crater Trail, &more), Laupahoehoe Beach Park (in Laupahoehoe) and Jagger Museum (in Volcano). There's still lots to do: take in the dramatic scenery at Akaka Falls State Park, see the world from above with a helicopter tour, see the interesting displays at Pacific Tsunami Museum, and see the sky in a new way at Imiloa Astronomy Center.

For other places to visit, ratings, maps, and other tourist information, you can read our Hilo driving holiday planning website.

You can fly from Kihei to Hilo in 3 hours. In February, daytime highs in Hilo are 81°F, while nighttime lows are 65°F. Wrap up your sightseeing on the 7th (Sun) to allow time to drive to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Museums · Trails

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 Puukohola National Historic Park (in Kawaihae), Captain Cook (Kealakekua Bay, Big Island Bees, &more) and Puako (Puako Bay & Hapuna Beach State Recreation Area). There's still lots to do: fulfill a lifelong dream with a swim-with-the-dolphins experience, explore the wealth of natural beauty at Pu'uhonua O Honaunau National Historical Park, experience rural life at Heavenly Hawaiian Kona Coffee Farm, and take a memorable drive along Mauna Loa Scenic Drive.

To see photos, where to stay, reviews, and more tourist information, use the Kailua-Kona vacation maker site.

Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. In March, daytime highs in Kailua-Kona are 81°F, while nighttime lows are 70°F. Wrap up your sightseeing on the 19th (Fri) to allow time to travel to Kapaa.

Things to do in Kailua-Kona

Parks · Outdoors · Beaches · Nature

Side Trips

Kapaa, Kauai

— 12 nights
Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Change things up with these side-trips from Kapaa: Poipu Bay Resort Golf Course (in Koloa), Waimea Canyon State Park (in Waimea) and Poipu (Shipwreck Beach, Maha'ulepu Heritage Trail, &more). The adventure continues: trek along Kauai Path, contemplate the long history of Kilohana, experience rural life at Lydgate Farms Kauai Chocolate, and admire the majestic nature at Na Pali Coast State Park.

To see reviews and tourist information, go to the Kapaa trip itinerary maker website.

Getting from Kailua-Kona to Kapaa by flight takes about 3 hours. In March, plan for daily highs up to 78°F, and evening lows to 66°F. Wrap up your sightseeing on the 31st (Wed) early enough to travel back home.

Things to do in Kapaa

Parks · Outdoors · Beaches · Trails

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.