29 days in Hawaii Itinerary

29 days in Hawaii Itinerary

Created using Inspirock Hawaii trip builder

This plan was created by another user.  Make it your plan

Route & dates

29 days in Hawaii Itinerary

Start: Dubai
Fly:  23​h 30​min
1
Poipu, Kauai
— 4 nights
Fly:  2​h 45​min
2
Kailua-Kona, Island of Hawaii
— 5 nights
Drive:  1​h 45​min
3
Hilo, Island of Hawaii
— 5 nights
Fly + taxi:  1​h 15​min
4
Kihei, Maui
— 4 nights
Fly:  2​h 30​min
5
Honolulu, Oahu
— 9 nights
Fly:  22​h
End: Dubai

4
nights
Poipu, Kauai

Poipu ©
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. You'll find plenty of places to visit near Poipu: Na Pali Coast State Park (in Wainiha), Kapaa (Kayaking & Canoeing & Photography Tours) and Waimea Canyon State Park (in Waimea). There's still lots to do: kick back and relax at Poipu Beach Park, take an unforgettable tour with a helicopter tour, take in nature's colorful creations at Na Aina Kai Botanical Gardens, and take in the dramatic natural features at Spouting Horn.

For maps, ratings, other places to visit, and other tourist information, refer to the Poipu route tool .

Dubai, United Arab Emirates to Poipu is an approximately 23.5-hour flight. Due to the time zone difference, you'll gain 14 hours traveling from Dubai to Poipu. When traveling from Dubai in November, plan for slightly colder days and about the same nights in Poipu: temperatures range from 32°C by day to 25°C at night. Wrap up your sightseeing on the 27th (Wed) to allow time to travel to Kailua-Kona.

Things to do in Poipu

Parks Tours Outdoors

Side Trips

Hanalei, Kapaa, Kauai, Waimea Canyon State Park, Helicopter Tours
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

5
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.
Explore the numerous day-trip ideas around Kailua-Kona: Pu'uhonua O Honaunau National Historical Park (in Honaunau), Hapuna Beach State Recreation Area (in Puako) and Puukohola National Historic Park (in Kawaihae). And it doesn't end there: fulfill a lifelong dream with a swim-with-the-dolphins experience, explore the fascinating underground world of Kula Kai Caverns, explore the wealth of natural beauty at Lapakahi State Historical Park, and admire the verdant scenery at Pololu Valley Lookout.

For where to stay, reviews, and tourist information, refer to the Kailua-Kona trip planner .

Fly from Poipu to Kailua-Kona in 3 hours. Expect a daytime high around 34°C in November, and nighttime lows around 26°C. Cap off your sightseeing on the 2nd (Mon) early enough to go by car to Hilo.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Island of Hawaii, Pu'uhonua O Honaunau National Historical Park, Papakōlea Green Sand Beach, Kona Coffee Living History Farm, Hapuna Beach State Recreation Area
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©
Mauna Kea ©
Mauna Kea

5
nights
Hilo, Island of Hawaii

Hilo ©
One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
Explore the numerous day-trip ideas around Hilo: Hawaii Volcanoes National Park (Kilauea Iki Trailhead, Sulphur Banks, & more) and Jagger Museum (in Volcano). The adventure continues: admire the sheer force of Akaka Falls State Park, pick up some local products at Hilo Farmers Market, and admire the natural beauty at Liliuokalani Gardens.

For more things to do, ratings, and tourist information, go to the Hilo trip planner .

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in December, Hilo is little chillier at night with lows of 21°C. Finish your sightseeing early on the 7th (Sat) so you can travel to Kihei.

Things to do in Hilo

Parks Outdoors Trails

Side Trips

Hawaii Volcanoes National Park, Jagger Museum
Highlights from your plan
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Liliuokalani Gardens ©
Liliuokalani Gardens
Kipuka Puaulu (Bird Park) Trail ©
Kipuka Puaulu (Bird Park) Trail

4
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 find plenty of places to visit near Kihei: Haleakala Crater (in Haleakala National Park) and Lahaina (Lahaina Jodo Mission, Lahaina Banyan Court, & more). There's lots more to do: cruise along Hana Highway - Road to Hana, enjoy the sand and surf at Ho'okipa Beach Park, observe the fascinating underwater world at Maui Ocean Center, and stop by Maui Specialty Chocolate.

For more things to do, reviews, maps, and tourist information, you can read our Kihei travel route planning site .

Getting from Hilo to Kihei by combination of flight and taxi takes about 1.5 hours. Other options: do a combination of bus and flight. Expect a daytime high around 32°C in December, and nighttime lows around 22°C. Wrap up your sightseeing on the 11th (Wed) early enough to travel to Honolulu.

Things to do in Kihei

Parks Outdoors Beaches

Side Trips

Wailuku, Lahaina, Hana Highway - Road to Hana, Haleakala Crater, Maui Specialty Chocolate
Highlights from your plan
Haleakala Crater ©
Haleakala Crater
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Ka'anapali Beach ©
Ka'anapali Beach

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.
Explore Honolulu's surroundings by going to Haleiwa (Sunset Beach Park & Waimea Bay), Pu’u O Mahuka Heiau State Monument (in Pupukea) and Kailua Beach Park (in Kailua). There's lots more to do: explore the different monuments and memorials at USS Arizona Memorial, contemplate the waterfront views at Hanauma Bay Nature Preserve, see the interesting displays at Bishop Museum, and take in the pleasant sights at Diamond Head State Monument.

To see other places to visit, where to stay, photos, and more tourist information, use the Honolulu trip itinerary website .

Getting from Kihei to Honolulu by flight takes about 2.5 hours. Other options: do a combination of taxi and flight; or do a combination of car and flight. December in Honolulu sees daily highs of 32°C and lows of 24°C at night. On the 20th (Fri), you'll have the morning to explore before heading back home.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

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

Similar Plans

9 days in Hawaii BY A USER FROM UNITED STATES December, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: December, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 7 days in Hawaii BY A USER FROM UNITED STATES August, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: August, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 12 days in Hawaii BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Hawaii BY A USER FROM AUSTRALIA April, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular sights PREFERENCES: April, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 13 days in Hawaii BY A USER FROM AUSTRALIA January, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, hidden gems PREFERENCES: January, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 12 days in Hawaii BY A USER FROM UNITED STATES January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: January, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Hawaii BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 10 days in Hawaii BY A USER FROM CANADA September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, hidden gems PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Hidden gems PACE: Medium
View more plans