27 days in New York City & Hawaii Itinerary

27 days in New York City & Hawaii Itinerary

Created using Inspirock United States trip itinerary maker

Make it your trip
Fly
1
New York City
— 5 nights
Fly
2
Honolulu, Oahu
— 4 nights
Fly
3
Hanalei, Kauai
— 4 nights
Drive
4
Kekaha, Kauai
— 1 night
Fly
5
Kailua-Kona, Island of Hawaii
— 3 nights
Drive
6
Volcano, Island of Hawaii
— 4 nights
Fly
7
Wailea, Maui
— 3 nights
Fly

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New York City

— 5 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Visiting Narwhal Yacht Charters and Tribeca Sailing will get you outdoors. There's much more to do: go for a walk through Central Park, walk around The High Line, admire the masterpieces at The Metropolitan Museum of Art, and admire the striking features of Grand Central Terminal.

Plan my New York City trip by asking Inspirock to come up with tips and suggestions.

London, UK to New York City is an approximately 11-hour flight. The time zone difference when traveling from London to New York City is minus 5 hours. Traveling from London in July, expect New York City to be somewhat warmer, temps between 35°C and 26°C. Cap off your sightseeing on the 10th (Wed) early enough to catch the flight to Honolulu.

Things to do in New York City

Parks · Outdoors · Tours · Transportation
Find places to stay Jul 5 — 10:
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Honolulu, Oahu

— 4 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 enjoy a bit of beach vacationing at Waikiki Beach and Kailua Beach Park. Escape the urban bustle at Swim with Dolphins and Waimea Bay. You'll find plenty of places to visit near Honolulu: Lanikai Beach (in Kailua), Pu’u O Mahuka Heiau State Monument (in Pupukea) and Sunset Beach Park (in Haleiwa). There's lots more to do: trek along Diamond Head State Monument, admire the sheer force of Manoa Falls, explore the different monuments and memorials at USS Arizona Memorial, and explore the gorgeous colors at Pele's Chair.

To find where to stay, ratings, traveler tips, and more tourist information, you can read our Honolulu trip itinerary planner.

Traveling by flight from New York City to Honolulu takes 12.5 hours. The time zone difference moving from Eastern Standard Time to Hawaii-Aleutian Standard Time is minus 5 hours. In July, plan for daily highs up to 36°C, and evening lows to 28°C. Cap off your sightseeing on the 15th (Mon) early enough to catch the flight to Hanalei.

Things to do in Honolulu

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay Jul 10 — 15:
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Hanalei, Kauai

— 4 nights
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. You'll enjoy a bit of beach vacationing at Tunnels Beach and Hanalei Beach. Step out of the city life by going to Na Pali Coast State Park and Kalalau Trail. Next up on the itinerary: enjoy the sand and surf at Anini Beach, admire all the interesting features of Hanalei Valley Lookout, pause for some serene contemplation at Wai`oli Hui`ia Church, and stroll through Hanalei Bay.

For traveler tips, other places to visit, maps, and other tourist information, use the Hanalei online trip itinerary planner.

Fly from Honolulu to Hanalei in 2.5 hours. July in Hanalei sees daily highs of 34°C and lows of 27°C at night. Wrap up your sightseeing on the 19th (Fri) early enough to drive to Kekaha.

Things to do in Hanalei

Parks · Outdoors · Beaches · Wildlife

Side Trips

Find places to stay Jul 15 — 19:
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Kekaha, Kauai

— 1 night
Kekaha is a census-designated place in Kauai County, Hawaii, United States. Kick off your visit on the 20th (Sat): take some stellar pictures from Waimea Canyon State Park and then take a tour by water with Boat Tours & Water Sports.

To see more things to do, other places to visit, photos, and tourist information, use the Kekaha road trip planning tool.

Getting from Hanalei to Kekaha by car takes about 2 hours. Other options: take a bus. Expect a daytime high around 34°C in July, and nighttime lows around 26°C. Finish up your sightseeing early on the 20th (Sat) so you can catch the flight to Kailua-Kona.

Things to do in Kekaha

Wildlife · Outdoors · Tours · Parks

Side Trip

Find places to stay Jul 19 — 20:
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Kailua-Kona, Island of Hawaii

— 3 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.
Get outdoors at Swim with Dolphins and Pu'uhonua O Honaunau National Historical Park. Relax by the water at Hapuna Beach State Recreation Area and Mauna Kea Beach. There's lots more to do: choose your vessel at Kona Boat Rentals, enjoy the sand and surf at Kahaluu Beach, and see majestic marine mammals with a dolphin and whale watching tour.

To see other places to visit, traveler tips, where to stay, and tourist information, use the Kailua-Kona online travel planner.

Traveling by flight from Kekaha to Kailua-Kona takes 2.5 hours. Expect a daytime high around 35°C in July, and nighttime lows around 28°C. Wrap up your sightseeing on the 23rd (Tue) to allow time to drive to Volcano.

Things to do in Kailua-Kona

Outdoors · Tours · Parks · Beaches

Side Trips

Find places to stay Jul 20 — 23:
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Volcano, Island of Hawaii

— 4 nights
Those who named Volcano opted for simplicity in choosing a title, taking the nearby fire-spewing Kilauea as a source of inspiration.
Take a break from the city and head to Devastation Trail and Akaka Falls State Park. Explore the numerous day-trip ideas around Volcano: Holei Sea Arch (in Hawaii Volcanoes National Park), Laupahoehoe Beach Park (in Laupahoehoe) and Liliuokalani Gardens (in Hilo). There's much more to do: hike along Sulphur Banks, tour the pleasant surroundings at Kipuka Puaulu (Bird Park) Trail, get outside with Keanakakoi Crater Overlook, and view the masterpieces at Volcano Art Center Gallery.

Use Inspirock's suggestions to plan your Volcano trip and find the best activities and attractions for your vacation.

Traveling by car from Kailua-Kona to Volcano takes 2.5 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in July, expect a bit cooler with lows of 25°C in Volcano. Wrap up your sightseeing on the 27th (Sat) to allow time to fly to Wailea.

Things to do in Volcano

Outdoors · Parks · Trails · Nature

Side Trips

Find places to stay Jul 23 — 27:
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Wailea, Maui

— 3 nights
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Your itinerary includes some good beach time at Wailea Beach and Oneloa Beach. Step out of the city life by going to Makena Beach and Ulua Beach. There's lots more to do: enjoy the sand and surf at Maluaka Beach, work some fitness into your day at Wailea Beach Path, and stroll through Po'olenalena Beach.

To find traveler tips, more things to do, and tourist information, use the Wailea trip planning app.

Fly from Volcano to Wailea in 2.5 hours. In July, daytime highs in Wailea are 37°C, while nighttime lows are 26°C. Finish your sightseeing early on the 30th (Tue) so you can fly back home.

Things to do in Wailea

Outdoors · Parks · Beaches
Find places to stay Jul 27 — 30:
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Hawaii travel guide

4.4
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.