60 days in Hawaii Itinerary

60 days in Hawaii Itinerary

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Route & dates

60 days in Hawaii Itinerary

Start: Orlando
Fly:  15​h
1
Kailua-Kona, Island of Hawaii
— 13 nights
Drive:  2​h 15​min
2
Volcano, Island of Hawaii
— 7 nights
Fly + bus:  5​h
3
Lahaina, Maui
— 14 nights
Fly:  3​h 15​min
4
Honolulu, Oahu
— 15 nights
Fly:  2​h 30​min
5
Kapaa, Kauai
— 9 nights
Fly:  14​h 45​min
End: Orlando

13
nights
Kailua-Kona, Island of Hawaii

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.
You'll discover tucked-away gems like Manini'owali Beach (Kua Bay) and Hapuna Beach State Recreation Area. Explore the numerous day-trip ideas around Kailua-Kona: Kawaihae (Pua Mau Place Arboretum & Botanical Garden & Puukohola National Historic Park), Captain Cook (Kealakekua Bay, The Captain Cook Monument, & more) and Waipio Valley Lookout (in Honokaa). Next up on the itinerary: explore the striking landscape of Kaloko-Honokohau National Historical Park, get a new perspective on things with Boat Tours & Water Sports, enjoy the sand and surf at Makalawena/Pu'u Ali'i, and stroll through Honaunau Bay.

To see photos, traveler tips, maps, and other tourist information, go to the Kailua-Kona trip itinerary builder .

Orlando to Kailua-Kona is an approximately 15-hour flight. You can also do a combination of flight and bus. The time zone changes from Eastern Standard Time to Hawaii Standard Time, which is usually a -5 hour difference. When traveling from Orlando in May, plan for little chillier days and about the same nights in Kailua-Kona: temperatures range from 83°F by day to 73°F at night. Finish your sightseeing early on the 10th (Mon) so you can drive to Volcano.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Island of Hawaii, Captain Cook, Waikoloa, Kealakekua, Kawaihae
Highlights from your plan
Swim with Dolphins
Manini'owali Beach (Kua Bay) ©
Manini'owali Beach (Kua Bay)

7
nights
Volcano, Island of Hawaii

Volcano ©
Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
Step off the beaten path and head to Kilauea Iki Trailhead and Hawaii Tropical Botanical Garden. Venture out of the city with trips to Naalehu (Paradise Meadows Orchard & Bee Farm Home of Hawaii's Local Buzz & Papakōlea Green Sand Beach), Hilo (Rainbow Falls, Hilo Farmers Market, & more) and Punalu‘U Beach (in Pahala). The adventure continues: take in the dramatic natural features at Thurston Lava Tube (Nahuku), take some stellar pictures from Holei Sea Arch, take in nature's colorful creations at Hawaiian Vanilla Company, and get outside with Keanakakoi Crater Overlook.

To see traveler tips, reviews, maps, and other tourist information, read our Volcano trip planner .

Traveling by car from Kailua-Kona to Volcano takes 2.5 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in June, plan for little chillier nights in Volcano, with lows around 69°F. Finish your sightseeing early on the 17th (Mon) to allow enough time to travel to Lahaina.

Things to do in Volcano

Parks Outdoors Nature

Side Trips

Hilo, Hawaii Volcanoes National Park, Pahoa, Island of Hawaii, Naalehu
Highlights from your plan
Hawaii Tropical Botanical Garden ©
Hawaii Tropical Botanical Garden
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Thurston Lava Tube (Nahuku) ©
Thurston Lava Tube (Nahuku)

14
nights
Lahaina, 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.
Step off the beaten path and head to Stand-Up Paddleboarding and Keawakapu Beach. Change things up with these side-trips from Lahaina: Kula (Ali'i Kula Lavender Farm, O'o Farm, & more), Wailea (Makena Beach, Wailea Beach, & more) and Haleakala Crater (in Haleakala National Park). Spend the 18th (Tue) exploring the striking scenery along Hana Highway - Road to Hana. There's lots more to do: hike along Kapalua Coastal Trail, stroll through Kamaole Beach Park II, explore the activities along Lahaina Harbor, and kick back and relax at Napili Beach.

To see traveler tips, other places to visit, where to stay, and tourist information, use the Lahaina trip builder .

You can do a combination of flight and bus from Volcano to Lahaina in 5 hours. Another option is to fly. In June in Lahaina, expect temperatures between 84°F during the day and 72°F at night. Wrap up your sightseeing on the 1st (Mon) early enough to travel to Honolulu.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Maui, Kihei, Wailuku, Kula, Wailea
Highlights from your plan
Stand-Up Paddleboarding
Kayaking & Canoeing
Napili Beach ©
Napili Beach

15
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Step off the beaten path and head to Photography Tours and Food Tours. Venture out of the city with trips to Haleiwa (Laniakea Beach, Sunset Beach Park, & more), Pupukea (Sharks Cove & Pu’u O Mahuka Heiau State Monument) and Byodo-In Temple (in Kaneohe). And it doesn't end there: browse the exhibits of USS Arizona Memorial, stroll through Waikiki Beach, hike along Koko Crater Railway Trail, and admire all the interesting features of Diamond Head State Monument.

To find where to stay, ratings, photos, and other tourist information, use the Honolulu online travel planner .

Traveling by flight from Lahaina to Honolulu takes 3.5 hours. Alternatively, you can do a combination of ferry and flight; or do a combination of bus and flight. In July, plan for daily highs up to 88°F, and evening lows to 75°F. Finish your sightseeing early on the 16th (Tue) to allow enough time to travel to Kapaa.

Things to do in Honolulu

Outdoors Parks Tours

Side Trips

Haleiwa, Kailua, Oahu, Wahiawa, Kapolei
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Stand-Up Paddleboarding
Photography Tours

9
nights
Kapaa, Kauai

Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Step off the beaten path and head to Photography Tours and Dolphin & Whale Watching. Change things up with these side-trips from Kapaa: Waimea (Waimea Canyon State Park & Polihale State Park), Kauai Coffee Company (in Kalaheo) and Na Pali Coast State Park (in Wainiha). There's much more to do: stroll through Kauai Path, hike along Kalalau Trail, kick back and relax at Hanalei Beach, and admire the natural beauty at Princeville Botanical Gardens.

For maps, where to stay, traveler tips, and other tourist information, read Kapaa online trip itinerary builder .

Fly from Honolulu to Kapaa in 2.5 hours. July in Kapaa sees daily highs of 84°F and lows of 74°F at night. On the 25th (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Kapaa

Parks Outdoors Beaches

Side Trips

Kauai, Poipu, Hanalei, Lihue, Waimea
Highlights from your plan
Photography Tours
Dolphin & Whale Watching
Na Pali Coast State Park ©
Na Pali Coast State Park

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