49 days in Hawaii Itinerary

49 days in Hawaii Itinerary

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Route & dates

49 days in Hawaii Itinerary

Start: Buenos Aires
Fly:  26​h
1
Kailua-Kona, Island of Hawaii
— 9 nights
Drive:  1​h 45​min
2
Hilo, Island of Hawaii
— 9 nights
Fly:  1​h 15​min
3
Kihei, Maui
— 9 nights
Fly:  1​h 30​min
4
Kapaa, Kauai
— 8 nights
Fly:  2​h 30​min
5
Honolulu, Oahu
— 11 nights
Fly:  25​h
End: Buenos Aires

9
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 the numerous day-trip ideas around Kailua-Kona: Hapuna Beach State Recreation Area (in Puako), Kula Kai Caverns (in Ocean View) and Papakōlea Green Sand Beach (in Naalehu). The adventure continues: get close to the beloved marine mammals with a swim-with-the-dolphins experience, tee off at Mauna Lani Resort , get up close to creatures of the deep with a dolphin and whale watching tour, and take some stellar pictures from Waipio Valley Lookout.

To find reviews, other places to visit, maps, and tourist information, read Kailua-Kona trip builder website .

Buenos Aires, Argentina to Kailua-Kona is an approximately 26-hour flight. You can also do a combination of flight and bus. Due to the time zone difference, you'll gain 7 hours traveling from Buenos Aires to Kailua-Kona. Prepare for a bit warmer weather when traveling from Buenos Aires in May: high temperatures in Kailua-Kona hover around 33°C and lows are around 26°C. Wrap up your sightseeing on the 25th (Mon) to allow time to drive to Hilo.

Things to do in Kailua-Kona

Outdoors Parks Nature

Side Trips

Island of Hawaii, Holualoa, Waikoloa, Kula Kai Caverns, Mauna Loa Scenic Drive
Highlights from your plan
Kula Kai Caverns ©
Kula Kai Caverns
Swim with Dolphins
Hapuna Beach State Recreation Area ©

9
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 Hilo's surroundings by going to Laupahoehoe Beach Park (in Laupahoehoe), Hawaii Volcanoes National Park (Thurston Lava Tube (Nahuku), Kilauea Iki Trailhead, & more) and Volcano (Jagger Museum & Akatsuka Orchid Gardens). There's still lots to do: take in the dramatic scenery at Akaka Falls State Park, take in nature's colorful creations at Liliuokalani Gardens, see the interesting displays at Pacific Tsunami Museum, and take an unforgettable tour with a helicopter tour.

To find maps, more things to do, other places to visit, and more tourist information, you can read our Hilo trip planner.

You can drive from Kailua-Kona to Hilo in 2 hours. Another option is to take a bus. Traveling from Kailua-Kona in May, Hilo is a bit cooler at night with lows of 22°C. Finish your sightseeing early on the 3rd (Wed) so you can travel to Kihei.

Things to do in Hilo

Parks Outdoors Trails

Side Trips

Hawaii Volcanoes National Park, Volcano, Steam Vents, Laupahoehoe Beach Park, Hawaii Tropical Botanical Garden
Highlights from your plan
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Akaka Falls State Park ©
Akaka Falls State Park
Liliuokalani Gardens ©
Liliuokalani Gardens

9
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.
Change things up with these side-trips from Kihei: Haleakala Crater (in Haleakala National Park), Kapalua Beach (in Kapalua) and Lahaina (Zipline, Ka'anapali Beach, & more). And it doesn't end there: cruise along Hana Highway - Road to Hana, tour the pleasant surroundings at Makena Beach, kick back and relax at Wailea Beach, and take an unforgettable tour with a helicopter tour.

To find other places to visit, traveler tips, maps, and tourist information, use the Kihei road trip planning app .

Do a combination of flight and taxi from Hilo to Kihei in 1.5 hours. Alternatively, you can do a combination of bus and flight. In June, daytime highs in Kihei are 36°C, while nighttime lows are 25°C. Finish up your sightseeing early on the 12th (Fri) so you can travel to Kapaa.

Things to do in Kihei

Outdoors Parks Beaches

Side Trips

Lahaina, Wailuku, Maui, Wailea, Ho'okipa Beach Park
Highlights from your plan
Punakea Palms Coconut Farm ©
Punakea Palms Coconut Farm
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana
Haleakala Crater ©
Haleakala Crater

8
nights
Kapaa, Kauai

Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Get out of town with these interesting Kapaa side-trips: Waimea Canyon State Park (in Waimea), Poipu (Poipu Beach Park, Spouting Horn, & more) and Na Pali Coast State Park (in Wainiha). There's still lots to do: capture your vacation like a pro with an inspiring photography tour, enjoy the sand and surf at Hanalei Beach, stroll through Kauai Path, and look for all kinds of wild species at Kalalau Trail.

Start your trip to Kapaa by creating a personalized itinerary on Inspirock.

Traveling by flight from Kihei to Kapaa takes 1.5 hours. June in Kapaa sees daily highs of 33°C and lows of 26°C at night. Cap off your sightseeing on the 20th (Sat) early enough to travel to Honolulu.

Things to do in Kapaa

Parks Outdoors Tours

Side Trips

Kauai, Poipu, Koloa, Hanalei, Lihue
Highlights from your plan
Photography Tours
Waimea Canyon State Park ©
Waimea Canyon State Park
Scuba & Snorkeling

11
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.
Venture out of the city with trips to Pu’u O Mahuka Heiau State Monument (in Pupukea), Haleiwa (Sunset Beach Park, Waimea Bay, & more) and Kailua (Kailua Beach Park & Lanikai Beach). There's still lots to do: stroll the grounds of USS Arizona Memorial, explore and take pictures at Diamond Head State Monument, look for all kinds of wild species at Hanauma Bay Nature Preserve, and kick back and relax at Waikiki Beach.

To find maps, reviews, more things to do, and other tourist information, read Honolulu trip planner .

Traveling by flight from Kapaa to Honolulu takes 2.5 hours. In June, plan for daily highs up to 35°C, and evening lows to 27°C. Finish your sightseeing early on the 1st (Wed) to allow enough time to travel back home.

Things to do in Honolulu

Outdoors Parks Museums

Side Trips

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

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