16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

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Route & dates

16 days in Hawaii Itinerary

Start: Miami, Florida
Fly:  16​h 30​min
1
Ka'anapali, Maui
— 4 nights
Fly:  3​h
2
Honolulu, Oahu
— 4 nights
Fly:  2​h 15​min
3
Lihue, Kauai
— 2 nights
Fly:  3​h 45​min
4
Kailua-Kona, Island of Hawaii
— 2 nights
Fly + Bus:  2​h 15​min
5
Kihei, Maui
— 2 nights
Fly:  14​h
End: Miami, Florida

4
nights
Ka'anapali, Maui

Ka'anapali ©
Perched at the western tip of Maui, the tourist hub of Ka'anapali offers a range of resorts and activities revolving around the beach.
Relax by the water at Kapalua Beach and Black Rock. For shopping fun, head to Kush Fine Art or Pakaloha Bikinis.

For photos, other places to visit, where to stay, and other tourist information, you can read our Ka'anapali vacation planner.

Miami to Ka'anapali is an approximately 16.5-hour combination of train, flight, and bus. Traveling from Miami to Ka'anapali, you'll gain 5 hours due to the time zone difference. In July, Ka'anapali is little chillier than Miami - with highs of 85°F and lows of 72°F. Wrap up your sightseeing on the 12th (Wed) to allow time to travel to Honolulu.

Things to do in Ka'anapali

Outdoors Parks Beaches

Side Trips

Lahaina, The Spa at Black Rock, Kapalua Beach
Highlights from your plan
Kapalua Beach ©
Kapalua Beach
Parasailing & Paragliding
Kapalua Coastal Trail ©
Kapalua Coastal Trail

4
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.
Get a sense of the local culture at Makapuu Lighthouse Trail and Bishop Museum. We've included these beaches for you: Sharks Cove and Ko Olina Lagoons. Get out of town with these interesting Honolulu side-trips: Haleiwa (Waimea Bay & Sunset Beach Park). There's much more to do: browse the different shops at Ala Moana Center, see the world from above with a helicopter tour, hike along Koko Crater Trail, and make a trip to The Byodo-In Temple.

For other places to visit, reviews, maps, and tourist information, you can read our Honolulu trip generator.

You can do a combination of bus and flight from Ka'anapali to Honolulu in 3 hours. Expect a daytime high around 87°F in July, and nighttime lows around 75°F. Wrap up your sightseeing on the 16th (Sun) early enough to travel to Lihue.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Byodo-In Temple, Sharks Cove, Nu’uanu Pali, Ko Olina Lagoons
Highlights from your plan
Makapuu Lighthouse Trail ©
Makapuu Lighthouse Trail
Ko Olina Lagoons ©
Ko Olina Lagoons
Koko Crater Railway Trail ©
Koko Crater Railway Trail

2
nights
Lihue, Kauai

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. On the 16th (Sun), view the masterpieces at Seductions of Kauai Gallery, kick back and relax at Kalapaki Beach, and then get great views at Sleeping Giant Trail. Get ready for a full day of sightseeing on the next day: look for gifts at Kapaia Stitchery, then get engrossed in the history at Kauai Museum, and then steep yourself in history at Kauai Plantation Railway at Kilohana.

For more things to do, traveler tips, and tourist information, refer to the Lihue trip generator.

You can fly from Honolulu to Lihue in 2.5 hours. In July in Lihue, expect temperatures between 84°F during the day and 74°F at night. Finish your sightseeing early on the 18th (Tue) to allow enough time to travel to Kailua-Kona.

Things to do in Lihue

Parks Outdoors Museums

Side Trip

Sleeping Giant Trail
Highlights from your plan
Kalapaki Beach ©
Kalapaki Beach
Kauai Museum ©
Kauai Museum
Kilohana ©
Kilohana

2
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.
On the 18th (Tue), kick back and relax at Makalawena/Pu'u Ali'i and then contemplate the waterfront views at Kiholo Bay. Get ready for a full day of sightseeing on the next day: contemplate in the serene atmosphere at Mokuaikaua Church, immerse yourself in nature at Kahalu'u Beach Park, stroll through Kahaluu Beach, then glide through the air with a parasailing or paragliding tour, and finally wander the streets of Kailua Pier.

For traveler tips, ratings, other places to visit, and other tourist information, refer to the Kailua-Kona travel itinerary planner.

Fly from Lihue to Kailua-Kona in 4 hours. In July, daytime highs in Kailua-Kona are 85°F, while nighttime lows are 75°F. Wrap up your sightseeing on the 20th (Thu) early enough to travel to Kihei.

Things to do in Kailua-Kona

Parks Nature Beaches

Side Trip

Keauhou
Highlights from your plan
Kiholo Bay ©
Kiholo Bay
Kahalu'u Beach Park ©
Kahalu'u Beach Park
Mokuaikaua Church ©
Mokuaikaua Church

2
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.
Start off your visit on the 20th (Thu): stroll through Kamaole Beach Park III and then kick back and relax at Kamaole Beach Park II. Get ready for a full day of sightseeing on the next day: find your balance on the water with some of the best stand-up paddleboarding in the area, do a tasting at Maui Wine, Ulupalakua Vineyards, and then enjoy the sand and surf at Polo Beach.

To find photos, traveler tips, more things to do, and more tourist information, read our Kihei itinerary planner.

Fly from Kailua-Kona to Kihei in 2.5 hours. Expect a daytime high around 87°F in July, and nighttime lows around 71°F. You will leave for home on the 22nd (Sat).

Things to do in Kihei

Beaches Parks Outdoors

Side Trips

Polo Beach, Maui Wine, Ulupalakua Vineyards
Highlights from your plan
Kamaole Beach Park II ©
Kamaole Beach Park II
Kamaole Beach Park III ©
Kamaole Beach Park III
Polo Beach ©
Polo Beach

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