14 days in Hawaii Itinerary

14 days in Hawaii Itinerary

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Route & dates

14 days in Hawaii Itinerary

Start: Boston
Fly:  12​h
1
Honolulu, Oahu
— 6 nights
Fly:  2​h 15​min
2
Lihue, Kauai
— 1 night
Fly + taxi:  1​h 15​min
3
Kihei, Maui
— 5 nights
Fly:  15​h
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.
Take a break from the city and head to Sharks Cove and Ko Olina Lagoons. Explore hidden gems such as Scuba & Snorkeling and Dolphin & Whale Watching. Change things up with these side-trips from Honolulu: Kailua Beach Park (in Kailua), Haleiwa (Waimea Valley & Sunset Beach Park) and Pu’u O Mahuka Heiau State Monument (in Pupukea). The adventure continues: trek along Koko Crater Railway Trail, explore the gorgeous colors at Pele's Chair, explore the activities along Hanauma Bay Nature Preserve, and tour the pleasant surroundings at Waikiki Beach.

To find more things to do, photos, reviews, and more tourist information, use the Honolulu holiday 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. The time zone difference moving from Eastern Standard Time (EST) to Hawaii Standard Time (HST) is minus 5 hours. Traveling from Boston in August, expect Honolulu to be a bit warmer, temps between 88°F and 75°F. Finish your sightseeing early on the 20th (Tue) so you can travel to Lihue.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Haleiwa, Pupukea, Ko Olina Lagoons, Kailua Beach Park, Pele's Chair
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Kailua Beach Park ©
Kailua Beach Park
Scuba & Snorkeling

1
night
Lihue, Kauai

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Start off your visit on the 21st (Wed): explore and take pictures at Kauai Coffee Company, see some colorful creatures with a scuba or snorkeling tour, and then enjoy the sand and surf at Shipwreck Beach.

To see where to stay, other places to visit, photos, and other tourist information, you can read our Lihue day trip planning tool .

Getting from Honolulu to Lihue by flight takes about 2.5 hours. Expect a daytime high around 86°F in August, and nighttime lows around 76°F. Wrap up your sightseeing on the 21st (Wed) early enough to travel to Kihei.

Things to do in Lihue

Outdoors Tours Wildlife

Side Trips

Kauai Coffee Company, Shipwreck Beach, Scuba & Snorkeling
Highlights from your plan
Scuba & Snorkeling
Shipwreck Beach ©
Shipwreck Beach
Kauai Coffee Company ©
Kauai Coffee Company

5
nights
Kihei, Maui

Kihei ©
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
You'll get in some beach time at Ulua Beach and Kamaole Beach Park II. Step out of the city life by going to Parasailing & Paragliding and Kamaole Beach Park III. You'll find plenty of places to visit near Kihei: Kapalua Beach (in Kapalua) and Lahaina (Napili Beach, Surf Ripper Shave Ice Co, & more). Next up on the itinerary: get interesting insight from Tours, identify plant and animal life at Honolua Bay, stroll through Wailea Beach, and enjoy the sand and surf at Ho'okipa Beach Park.

Ask Inspirock to suggest an itinerary and make planning a trip to Kihei fast, fun, and easy.

Do a combination of flight and taxi from Lihue to Kihei in 1.5 hours. Alternatively, you can fly. In August, plan for daily highs up to 90°F, and evening lows to 73°F. Finish up your sightseeing early on the 26th (Mon) so you can travel back home.

Things to do in Kihei

Outdoors Parks Beaches

Side Trips

Wailea, Lahaina, Zipline, Ho'okipa Beach Park, Honolua Bay
Highlights from your plan
Kapalua Beach ©
Kapalua Beach
Wailea Beach ©
Wailea Beach
Kamaole Beach Park II ©
Kamaole Beach Park II

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