16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

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Route & dates

16 days in Hawaii Itinerary

Start: Washington DC
+2
Train + Bus + Fly:  14 h 30 min
1
Princeville, Kauai
— 4 nights
Taxi + Fly:  2 h
2
Wailea, Maui
— 3 nights
Taxi + Bus:  45 min
3
Lahaina, Maui
— 2 nights
Fly + Bus:  3 h 30 min
4
Kailua-Kona, Island of Hawaii
— 4 nights
Drive:  1 h 45 min
5
Volcano, Island of Hawaii
— 1 night
+4
Bus + Taxi + Fly + Bus + Subway:  15 h 45 min
End: Washington DC

4
nights
Princeville, Kauai

Princeville ©
Princeville is a 9,000acre, upscale, unincorporated, master-planned community of vacation homes and condos on the north shore of the island of Kauai in Kauai County, Hawaii. Step out of the city life by going to Anini Beach and Hanalei Bay. Explore hidden gems such as Ke'e Beach and Hanakapiai Falls. Go for a jaunt from Princeville to Poipu to see Zipline about 1:10 hours away. And it doesn't end there: look for all kinds of wild species at Kilauea Point National Wildlife Refuge, kick back and relax at Pali Ke Kua Beach (Hideaway s Beach), get great views at Hanalei Valley Lookout, and pause for some serene contemplation at Wai'oli Hui'ia Church.

To find other places to visit, where to stay, photos, and more tourist information, you can read our Princeville itinerary planner.

Washington DC to Princeville is an approximately 14.5-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Washington DC to Princeville. In October, Princeville is a bit warmer than Washington DC - with highs of 84°F and lows of 73°F. Finish up your sightseeing early on the 22nd (Sun) so you can travel to Wailea.

Things to do in Princeville

Parks Outdoors Beaches

Side Trips

Kauai, Hanalei, Kilauea Point National Wildlife Refuge, Ke'e Beach, Zipline
Highlights from your plan
Hanakapiai Falls ©
Hanakapiai Falls
Ke'e Beach ©
Ke'e Beach
Zipline

3
nights
Wailea, Maui

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. We've included these beaches for you: Keawakapu Beach and Makena Beach. Take a break from the city and head to Ulua Beach and Polo Beach. Step out of Wailea with an excursion to Maui Wine, Ulupalakua Vineyards in Kula--about 1:05 hours away. There's lots more to do: kick back and relax at Maluaka Beach, glide peacefully along the water with some of the best stand-up paddleboarding in the area, take in the architecture and atmosphere at St. Theresa Church, and stroll through Wailea Beach Path.

For reviews, more things to do, other places to visit, and more tourist information, read Wailea travel itinerary creator.

You can do a combination of taxi and flight from Princeville to Wailea in 2 hours. Expect a daytime high around 88°F in October, and nighttime lows around 69°F. Wrap up your sightseeing on the 25th (Wed) to allow time to drive to Lahaina.

Things to do in Wailea

Outdoors Parks Beaches

Side Trips

Saint Theresa Roman Catholic Church, Maui Wine, Ulupalakua Vineyards
Highlights from your plan
Wailea Beach Path ©
Wailea Beach Path
Keawakapu Beach ©
Keawakapu Beach
Ulua Beach ©
Ulua Beach

2
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.
Kick off your visit on the 25th (Wed): contemplate the long history of Old Lahaina Courthouse. On the 26th (Thu), you'll have a packed day of sightseeing: stroll through D.T. Fleming Beach Park, enjoy the sand and surf at Kahekili Beach Park, and then pause for some serene contemplation at Lahaina United Methodist Church.

To find more things to do, maps, and other tourist information, use the Lahaina tour planner.

Drive from Wailea to Lahaina in an hour. Alternatively, you can drive; or do a combination of taxi and bus. In October, daytime highs in Lahaina are 84°F, while nighttime lows are 72°F. Wrap up your sightseeing on the 27th (Fri) early enough to travel to Kailua-Kona.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Parasailing & Paragliding, The Spa at Black Rock, D.T. Fleming Park
Highlights from your plan
Parasailing & Paragliding
D.T. Fleming Park ©
D.T. Fleming Park
Old Lahaina Courthouse ©
Old Lahaina Courthouse

4
nights
Kailua-Kona, Island of Hawaii

Kailua-Kona ©
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 hidden gems such as Kahaluu Beach and 49 Black Sand Beach. Get some cultural insight at Kailua Pier and Holualoa Village. The adventure continues: admire the majestic nature at Kahalu'u Beach Park, paddle through the water with a kayaking and canoeing tour, contemplate the waterfront views at Kiholo Bay, and contemplate in the serene atmosphere at Mokuaikaua Church.

To see maps, traveler tips, reviews, and other tourist information, you can read our Kailua-Kona trip itinerary maker.

Getting from Lahaina to Kailua-Kona by combination of flight and bus takes about 3.5 hours. October in Kailua-Kona sees daily highs of 85°F and lows of 74°F at night. Cap off your sightseeing on the 31st (Tue) early enough to travel to Volcano.

Things to do in Kailua-Kona

Parks Nature Outdoors

Side Trips

Keauhou, 49 Black Sand Beach
Highlights from your plan
Kiholo Bay ©
Kiholo Bay
Mokuaikaua Church ©
Mokuaikaua Church
Kahalu'u Beach Park ©
Kahalu'u Beach Park

1
night
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.
Start off your visit on the 31st (Tue): view the masterpieces at Volcano Art Center, then appreciate the extensive heritage of Pu'u Loa Petroglyphs, and then take a stroll through Kalapana. Keep things going the next day: stroll through Kehena Black Sand Beach, stroll through Kipuka Puaulu (Bird Park) Trail, and then take a memorable drive along Devastation Trail.

To find more things to do, traveler tips, where to stay, and other tourist information, you can read our Volcano custom trip planner.

You can drive from Kailua-Kona to Volcano in 2.5 hours. Expect slightly colder evenings in Volcano when traveling from Kailua-Kona in October, with lows around 69°F. Wrap up your sightseeing on the 1st (Wed) to allow time to travel back home.

Things to do in Volcano

Parks Outdoors Trails

Side Trips

Hawaii Volcanoes National Park, Kehena Black Sand Beach
Highlights from your plan
Pu'u Loa Petroglyphs ©
Pu'u Loa Petroglyphs
Kipuka Puaulu (Bird Park) Trail ©
Kipuka Puaulu (Bird Park) Trail
Kehena Black Sand Beach ©
Kehena Black Sand Beach

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