32 days in Hawaii Itinerary

32 days in Hawaii Itinerary

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Route & dates

32 days in Hawaii Itinerary

Start: New York City
+2
Drive + Fly + Drive:  15​h
1
Kipahulu, Maui
— 3 nights
+2
taxi + Fly + taxi:  2​h
2
Wailea, Maui
— 6 nights
bus + Fly:  3​h
3
Volcano, Island of Hawaii
— 5 nights
Drive:  2​h 30​min
4
Kailua-Kona, Island of Hawaii
— 3 nights
Fly + taxi:  3​h 15​min
5
Hanalei, Kauai
— 4 nights
taxi + Fly:  3​h
6
Honolulu, Oahu
— 9 nights
Fly + bus:  14​h
End: New York City

3
nights
Kipahulu, Maui

Kipahulu ©
Visiting Haleakala Crater and Hana Highway - Road to Hana will get you outdoors. Your itinerary includes some good beach time at Wai'anapanapa State Park and Red Sand Beach (Kaihalulu Beach).

For traveler tips, where to stay, maps, and tourist information, read our Kipahulu trip builder tool .

New York City to Kipahulu is an approximately 15-hour flight. Traveling from New York City to Kipahulu, you'll gain 5 hours due to the time zone difference. Expect somewhat warmer temperatures when traveling from New York City in May; daily highs in Kipahulu reach 86°F and lows reach 68°F. Finish your sightseeing early on the 8th (Wed) to allow enough time to drive to Wailea.

Things to do in Kipahulu

Outdoors Parks Nature

Side Trips

Hana, Haleakala Crater, Hana Highway - Road to Hana
Highlights from your plan
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Haleakala Crater ©
Haleakala Crater
Wai'anapanapa State Park ©
Wai'anapanapa State Park

6
nights
Wailea, Maui

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Your itinerary includes some good beach time at Ka'anapali Beach and Kapalua Beach. Take a break from the city and head to Wailea Beach and D.T. Fleming Beach Park. Get out of town with these interesting Wailea side-trips: Lahaina (Lahaina Banyan Court, Glass Mango Designs, & more), Maui Specialty Chocolate (in Kahului) and Iao Valley State Monument (in Wailuku). Next up on the itinerary: kick back and relax at Ulua Beach, see majestic marine mammals with a dolphin and whale watching tour, tour the pleasant surroundings at Ho'okipa Beach Park, and glide peacefully along the water with some of the best stand-up paddleboarding in the area.

To find ratings, maps, photos, and tourist information, read our Wailea itinerary maker site .

Traveling by car from Kipahulu to Wailea takes 2 hours. May in Wailea sees daily highs of 86°F and lows of 68°F at night. Cap off your sightseeing on the 14th (Tue) early enough to travel to Volcano.

Things to do in Wailea

Parks Outdoors Beaches

Side Trips

Lahaina, Kapalua, Kahului, Iao Valley, Ho'okipa Beach Park
Highlights from your plan
Ka'anapali Beach ©
Ka'anapali Beach
Wailea Beach ©
Wailea Beach
Kapalua Beach ©
Kapalua Beach

5
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.
Head to Hilo Farmers Market and Hawaiian Crown Plantation & Chocolate Factoryfor some retail therapy. Satisfy your inner culture vulture at Volcano Art Center and Imiloa Astronomy Center. You'll find plenty of places to visit near Volcano: Hilo (Pacific Tsunami Museum, Akaka Falls State Park, & more) and South Point (Ka Lae) and Green Sand Beach (in Naalehu). And it doesn't end there: hike along Kilauea Iki Trailhead, take in the dramatic natural features at Thurston Lava Tube (Nahuku), stroll through Kipuka Puaulu (Bird Park) Trail, and get impressive views of Kīlauea.

To find more things to do, photos, reviews, and more tourist information, use the Volcano driving holiday tool .

Traveling by combination of taxi, flight, and bus from Wailea to Volcano takes 3 hours. Expect a daytime high around 82°F in May, and nighttime lows around 67°F. Finish your sightseeing early on the 19th (Sun) so you can drive to Kailua-Kona.

Things to do in Volcano

Parks Outdoors Museums

Side Trips

Hilo, Hawaii Volcanoes National Park, Papakōlea Green Sand Beach
Highlights from your plan
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Papakōlea Green Sand Beach ©
Papakōlea Green Sand Beach
Akaka Falls State Park ©
Akaka Falls State Park

3
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.
Get outdoors at Swim with Dolphins and Pu'uhonua O Honaunau National Historical Park. Do your shopping at Waikoloa Beach Resort and Big Island Bees. Explore Kailua-Kona's surroundings by going to Puukohola National Historic Park (in Kawaihae) and Hapuna Beach State Recreation Area (in Puako). Next up on the itinerary: enjoy the sand and surf at Mauna Kea Beach, see majestic marine mammals with a dolphin and whale watching tour, and get engrossed in the history at H.N. Greenwell Store Museum.

For ratings, maps, other places to visit, and more tourist information, read Kailua-Kona trip maker .

Drive from Volcano to Kailua-Kona in 2.5 hours. Alternatively, you can take a bus. Traveling from Volcano in May, you can expect nighttime temperatures to be a bit warmer in Kailua-Kona, with lows of 73°F. Finish up your sightseeing early on the 22nd (Wed) so you can travel to Hanalei.

Things to do in Kailua-Kona

Outdoors Parks Tours

Side Trips

H.N. Greenwell Store Museum, Hapuna Beach State Recreation Area, Puukohola National Historic Park, Big Island Bees, Pu'uhonua O Honaunau National Historical Park
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©

4
nights
Hanalei, Kauai

Hanalei ©
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Relax by the water at Poipu Beach Park and Hanalei Beach. Visiting Waimea Canyon State Park and Na Pali Coast State Park will get you outdoors. You'll find plenty of places to visit near Hanalei: Shipwreck Beach (in Poipu) and Lihue (Kauai Museum, Kalapaki Beach, & more). There's still lots to do: enjoy the sand and surf at Tunnels Beach and take some stellar pictures from Hanalei Valley Lookout.

For maps, ratings, photos, and other tourist information, read Hanalei driving holiday site .

You can do a combination of flight and taxi from Kailua-Kona to Hanalei in 3.5 hours. In May, daytime highs in Hanalei are 82°F, while nighttime lows are 71°F. Finish your sightseeing early on the 26th (Sun) to allow enough time to travel to Honolulu.

Things to do in Hanalei

Parks Outdoors Beaches

Side Trips

Lihue, Poipu, Tunnels Beach, Waimea Canyon State Park, Na Pali Coast State Park
Highlights from your plan
Na Pali Coast State Park ©
Na Pali Coast State Park
Waimea Canyon State Park ©
Waimea Canyon State Park
Poipu Beach Park ©
Poipu Beach Park

9
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.
Head to Polynesian Cultural Center and Ala Moana Centerfor plenty of shopping. Step out of the city life by going to Hanauma Bay Nature Preserve and Waikiki Beach. You'll find plenty of places to visit near Honolulu: Kailua (Kailua Beach Park & Lanikai Beach), Haleiwa (Waimea Bay & Sunset Beach Park) and Pu’u O Mahuka Heiau State Monument (in Pupukea). The adventure continues: contemplate the long history of Iolani Palace, admire the masterpieces at Honolulu Museum of Art, appreciate the history behind USS Arizona Memorial, and examine the collection at Bishop Museum.

To see maps, ratings, other places to visit, and more tourist information, read our Honolulu trip itinerary planner .

You can do a combination of taxi and flight from Hanalei to Honolulu in 3 hours. In May, daily temperatures in Honolulu can reach 84°F, while at night they dip to 71°F. Wrap up your sightseeing on the 4th (Tue) to allow time to travel back home.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Oahu, Haleiwa, Kailua, Polynesian Cultural Center, Pu’u O Mahuka Heiau State Monument
Highlights from your plan
Polynesian Cultural Center ©
Polynesian Cultural Center
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach

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