17 days in Hawaii Itinerary

17 days in Hawaii Itinerary

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Route & dates

17 days in Hawaii Itinerary

Start: Boston
Fly:  12​h
1
Honolulu, Oahu
— 6 nights
Fly:  3​h 15​min
2
Lahaina, Maui
— 4 nights
Fly:  4​h
3
Kailua-Kona, Island of Hawaii
— 2 nights
Fly:  2​h 30​min
4
Lihue, Kauai
— 3 nights
Fly:  15​h 15​min
End: Boston

6
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.
USS Arizona Memorial and USS Bowfin Submarine Museum & Park are good opportunities to explore the local culture. Visit Waikiki Beach and Sunset Beach Park for some beach relaxation. Explore the numerous day-trip ideas around Honolulu: North Shore Goodies (in Waialua), Kailua (Kailua Beach Park & Lanikai Beach) and Shark Diving (in Haleiwa). There's still lots to do: take in the pleasant sights at Diamond Head State Monument, appreciate the history behind Pu’u O Mahuka Heiau State Monument, steep yourself in history at Battleship Missouri Memorial, and fulfill a lifelong dream with a swim-with-the-dolphins experience.

To find more things to do, ratings, photos, and other tourist information, go to the Honolulu sightseeing planner .

Boston to Honolulu is an approximately 12-hour flight. You can also do a combination of bus and flight; or do a combination of ferry and flight. Traveling from Boston to Honolulu, you'll gain 5 hours due to the time zone difference. Expect a bit warmer weather when traveling from Boston in May: highs in Honolulu hover around 84°F, while lows dip to 71°F. Cap off your sightseeing on the 17th (Sun) early enough to travel to Lahaina.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Kailua, Haleiwa, Swim with Dolphins, North Shore Goodies, Pu’u O Mahuka Heiau State Monument
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
Kailua Beach Park ©
Kailua Beach Park

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.
We've included these beaches for you: Ka'anapali Beach and Kapalua Beach. Escape the urban bustle at Haleakala Crater and Stand-Up Paddleboarding. Get out of town with these interesting Lahaina side-trips: Kalepolepo Beach Park (in Kihei), Wailea Beach (in Wailea) and Ho'okipa Beach Park (in Paia). There's more to do: cruise along Hana Highway - Road to Hana and make a trip to Lahaina Banyan Court.

To find reviews, other places to visit, ratings, and more tourist information, you can read our Lahaina trip itinerary maker .

Traveling by flight from Honolulu to Lahaina takes 3.5 hours. Alternatively, you can do a combination of flight and ferry; or do a combination of flight and bus. In May, plan for daily highs up to 81°F, and evening lows to 70°F. Finish your sightseeing early on the 21st (Thu) to allow enough time to travel to Kailua-Kona.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

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

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.
On the 22nd (Fri), get engrossed in the history at H.N. Greenwell Store Museum, then explore the striking landscape of Pu'uhonua O Honaunau National Historical Park, then explore the galleries of Kona Coffee Living History Farm, and finally get close to the beloved marine mammals with a swim-with-the-dolphins experience. On the next day, stroll through Mauna Kea Beach and then enjoy the sand and surf at Hapuna Beach State Recreation Area.

To see ratings, where to stay, traveler tips, and other tourist information, you can read our Kailua-Kona journey builder .

Traveling by flight from Lahaina to Kailua-Kona takes 4 hours. Alternatively, you can do a combination of bus, flight, and taxi; or do a combination of bus and flight. Expect a daytime high around 83°F in May, and nighttime lows around 73°F. Wrap up your sightseeing on the 23rd (Sat) early enough to travel to Lihue.

Things to do in Kailua-Kona

Outdoors Parks Beaches

Side Trips

Pu'uhonua O Honaunau National Historical Park, Mauna Kea Beach, Kona Coffee Living History Farm, H.N. Greenwell Store Museum, Hapuna Beach State Recreation Area
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©

3
nights
Lihue, Kauai

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. You'll get in some beach time at Poipu Beach Park and Hanalei Beach. Get outdoors at Waimea Canyon State Park and Spouting Horn. You'll find plenty of places to visit near Lihue: Na Pali Coast State Park (in Wainiha) and Kekaha (Kokee Natural History Museum & Scuba & Snorkeling). The adventure continues: kick back and relax at Tunnels Beach and take in the dramatic scenery at Opaekaa Falls.

To see traveler tips, where to stay, and more tourist information, read our Lihue sightseeing planner.

Traveling by flight from Kailua-Kona to Lihue takes 2.5 hours. In May, daily temperatures in Lihue can reach 82°F, while at night they dip to 71°F. Wrap up your sightseeing on the 26th (Tue) to allow time to travel back home.

Things to do in Lihue

Parks Outdoors Wildlife

Side Trips

Kekaha, Poipu, Kauai, Na Pali Coast State Park, Hanalei Beach
Highlights from your plan
Scuba & Snorkeling
Waimea Canyon State Park ©
Waimea Canyon State Park
Na Pali Coast State Park ©
Na Pali Coast State Park

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