14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

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Route & dates

14 days in Hawaii Itinerary

Start: Rochester
Fly:  13​h 45​min
1
Honolulu, Oahu
— 5 nights
Fly:  3​h
2
Waimea, Kauai
— 1 night
Fly:  3​h
3
Kailua-Kona, Island of Hawaii
— 2 nights
Fly:  4​h
4
Lahaina, Maui
— 4 nights
bus + Fly:  14​h 45​min
End: Rochester

5
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.
Your itinerary includes some good beach time at Waikiki Beach and USS Arizona Memorial. Get some historical perspective at Diamond Head State Monument and Hanauma Bay Nature Preserve. Explore the numerous day-trip ideas around Honolulu: Lanikai Beach (in Kailua) and Haleiwa (Sunset Beach Park & Waimea Bay). Next up on the itinerary: steep yourself in history at Battleship Missouri Memorial, hit the best photo ops around with an inspiring photography tour, appreciate the history behind King Kamehameha Statue, and examine the collection at Iolani Palace.

To see more things to do, other places to visit, reviews, and tourist information, read our Honolulu route planner .

Rochester to Honolulu is an approximately 14-hour flight. You can also do a combination of bus and flight; or do a combination of train and flight. The time zone difference moving from Eastern Standard Time (EST) to Hawaii Standard Time (HST) is minus 5 hours. In June, Honolulu is somewhat warmer than Rochester - with highs of 86°F and lows of 74°F. Finish your sightseeing early on the 5th (Fri) so you can travel to Waimea.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Haleiwa, Halona Blowhole, Lanikai Beach
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach
Diamond Head State Monument ©
Diamond Head State Monument

1
night
Waimea, Kauai

Waimea ©
On the 6th (Sat), get up close to creatures of the deep with a dolphin and whale watching tour, take in the views from Swinging Bridge, and then admire all the interesting features of Waimea Canyon State Park.

To find reviews, where to stay, photos, and other tourist information, read Waimea vacation builder .

Getting from Honolulu to Waimea by flight takes about 3 hours. In July in Waimea, expect temperatures between 85°F during the day and 73°F at night. Wrap up your sightseeing on the 6th (Sat) early enough to travel to Kailua-Kona.

Things to do in Waimea

Parks Nature

Side Trip

Swinging Bridge
Highlights from your plan
Waimea Canyon State Park ©
Waimea Canyon State Park
Swinging Bridge ©
Swinging Bridge

2
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.
Kick off your visit on the 7th (Sun): explore the striking landscape of Pu'uhonua O Honaunau National Historical Park, then contemplate in the serene atmosphere at Mokuaikaua Church, and then fulfill a lifelong dream with a swim-with-the-dolphins experience. Get ready for a full day of sightseeing on the next day: get engrossed in the history at Kona Coffee Living History Farm, explore and take pictures at Hula Daddy Kona Coffee, then immerse yourself in nature at Hapuna Beach State Recreation Area, and finally contemplate the long history of Puako Petroglyph Archaeological Preserve.

For reviews, photos, ratings, and more tourist information, refer to the Kailua-Kona trip itinerary planning website .

You can fly from Waimea to Kailua-Kona in 3 hours. In July, daytime highs in Kailua-Kona are 86°F, while nighttime lows are 76°F. Cap off your sightseeing on the 8th (Mon) early enough to travel to Lahaina.

Things to do in Kailua-Kona

Outdoors Parks Nature

Side Trips

Hula Daddy Kona Coffee, Hapuna Beach State Recreation Area, Pu'uhonua O Honaunau National Historical Park, Kona Coffee Living History Farm, Puako Petroglyph Archaeological Preserve
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©

4
nights
Lahaina, Maui

Lahaina ©
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.
Visit Haleakala Crater and Stand-Up Paddleboarding for some beach relaxation. Step out of the city life by going to Ka'anapali Beach and Wailea Beach. Take a break from Lahaina with a short trip to Kalepolepo Beach Park in Kihei, about 50 minutes away. Spend the 9th (Tue) exploring the striking scenery along Hana Highway - Road to Hana. The adventure continues: kick back and relax at Kapalua Beach and don't miss a visit to Lahaina Banyan Court.

To see reviews, where to stay, more things to do, and other tourist information, refer to the Lahaina trip planning website .

You can fly from Kailua-Kona to Lahaina in 4 hours. Other options are to do a combination of taxi, flight, and bus; or do a combination of flight and bus. In July, plan for daily highs up to 86°F, and evening lows to 73°F. Finish your sightseeing early on the 12th (Fri) so you can travel back home.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Hana Highway - Road to Hana, Kapalua Beach, Wailea Beach, Haleakala Crater, Kalepolepo Beach Park
Highlights from your plan
Ka'anapali Beach ©
Ka'anapali Beach
Haleakala Crater ©
Haleakala Crater
Wailea Beach ©
Wailea Beach

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