20 days in Hawaii Itinerary

20 days in Hawaii Itinerary

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Route & dates

20 days in Hawaii Itinerary

Start: Ubud, Bali
+2
Bus + Foot + Fly:  9​h 30​min
1
Honolulu, Oahu
— 4 nights
Fly:  2​h 45​min
2
Wailea, Maui
— 4 nights
Bus + Fly:  5​h 30​min
3
Kailua-Kona, Island of Hawaii
— 3 nights
Drive:  1​h 45​min
4
Hilo, Island of Hawaii
— 3 nights
Fly:  3​h
5
Kapaa, Kauai
— 2 nights
+2
Drive + Fly + Drive:  26​h
End: Ubud, Bali

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.
You'll enjoy a bit of beach vacationing at Waikiki Beach and Kailua Beach Park. Get in touch with nature at Diamond Head State Monument and Hanauma Bay Nature Preserve. Venture out of the city with trips to Lanikai Beach (in Kailua), Haleiwa (Sunset Beach Park & Waimea Bay) and Banzai Pipeline (in Pupukea). And it doesn't end there: admire the sheer force of Manoa Falls, take some stellar pictures from Puu Ualakaa State Park, enjoy the sand and surf at Ala Moana Beach Park, and take a memorable drive along Makapu'u Point.

To find reviews, traveler tips, maps, and more tourist information, go to the Honolulu journey builder site .

Ubud, Indonesia to Honolulu is an approximately 23.5-hour combination of bus and flight. The time zone changes from Central Indonesia Time to Hawaii Standard Time, which is usually a -18 hour difference. Traveling from Ubud in April, expect Honolulu to be a bit cooler, temps between 33°C and 25°C. Cap off your sightseeing on the 4th (Mon) early enough to travel to Wailea.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Kailua, Haleiwa, Banzai Pipeline, Makapu'u Point
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
Kailua Beach Park ©
Kailua Beach Park

4
nights
Wailea, Maui

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Relax by the water at Wailea Beach and D.T. Fleming Park. Step out of the city life by going to Haleakala Crater and Makena Beach. Change things up with these side-trips from Wailea: Ho'okipa Beach Park (in Paia) and Wai'anapanapa State Park (in Hana). It doesn't end there: kick back and relax at Maluaka Beach and stop by Sweet Paradise Chocolatier.

To find more things to do, other places to visit, where to stay, and more tourist information, use the Wailea trip planner.

Traveling by flight from Honolulu to Wailea takes 3 hours. Alternatively, you can do a combination of flight and taxi; or do a combination of flight and car. In May in Wailea, expect temperatures between 35°C during the day and 23°C at night. Wrap up your sightseeing on the 8th (Fri) early enough to travel to Kailua-Kona.

Things to do in Wailea

Parks Beaches Outdoors

Side Trips

Ho'okipa Beach Park, Haleakala Crater, D.T. Fleming Park, Wai'anapanapa State Park, Tutu's Pantry
Highlights from your plan
Haleakala Crater ©
Haleakala Crater
Wailea Beach ©
Wailea Beach
Wai'anapanapa State Park ©
Wai'anapanapa State Park

3
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.
For shopping fun, head to Waikoloa Beach Resort or Queens' Market Place. We've included these beaches for you: Hapuna Beach State Recreation Area and Honaunau Bay. Take a break from Kailua-Kona with a short trip to Anaehoomalu in Waikoloa, about 40 minutes away. Next up on the itinerary: get close to the beloved marine mammals with Big Island Divers, see Kona Boys, relax in the rural setting at Hula Daddy Kona Coffee, and stroll through Manini'owali Beach (Kua Bay).

To find more things to do, where to stay, photos, and tourist information, refer to the Kailua-Kona online holiday builder .

Getting from Wailea to Kailua-Kona by combination of bus and flight takes about 5.5 hours. Other options: do a combination of car and flight. Expect a daytime high around 33°C in May, and nighttime lows around 26°C. Wrap up your sightseeing on the 12th (Tue) early enough to drive to Hilo.

Things to do in Kailua-Kona

Parks Outdoors Beaches

Side Trips

Waikoloa, Kahaluu Beach, Honaunau Bay, Hapuna Beach State Recreation Area, Kona Boys
Highlights from your plan
Honaunau Bay ©
Honaunau Bay
Hapuna Beach State Recreation Area ©
Big Island Divers ©
Big Island Divers

3
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.
Relax by the water at Laupahoehoe Beach Park and Honoli'i Beach Park. Visiting Kilauea Iki Trailhead and Akaka Falls State Park will get you outdoors. Go for a jaunt from Hilo to Hawaii Volcanoes National Park to see Kīlauea about 54 minutes away. There's still lots to do: take in the dramatic scenery at Rainbow Falls, admire the natural beauty at Liliuokalani Gardens, stop by Hilo Hatties, and stroll through Richardson Beach Park.

For more things to do, photos, traveler tips, and tourist information, read our Hilo holiday planning app .

You can drive from Kailua-Kona to Hilo in 2 hours. Another option is to take a bus. Traveling from Kailua-Kona in May, expect slightly colder with lows of 22°C in Hilo. Finish up your sightseeing early on the 15th (Fri) so you can travel to Kapaa.

Things to do in Hilo

Parks Nature Outdoors

Side Trips

Hawaii Volcanoes National Park, Laupahoehoe Beach Park
Highlights from your plan
Akaka Falls State Park ©
Akaka Falls State Park
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Laupahoehoe Beach Park ©
Laupahoehoe Beach Park

2
nights
Kapaa, Kauai

Kapaa ©
Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
On the 16th (Sat), take in the dramatic scenery at Opaekaa Falls, steep yourself in history at Menehune Fishpond, then kick back and relax at Shipwreck Beach, and finally tour the pleasant surroundings at Poipu Beach Park. Get ready for a full day of sightseeing on the 17th (Sun): kick back and relax at Tunnels Beach and then admire the majestic nature at Hāʻena State Park.

To see traveler tips, ratings, more things to do, and tourist information, read Kapaa online trip itinerary planner .

Traveling by flight from Hilo to Kapaa takes 3 hours. In May, plan for daily highs up to 32°C, and evening lows to 25°C. Wrap up your sightseeing on the 17th (Sun) to allow time to travel back home.

Things to do in Kapaa

Parks Beaches Outdoors

Side Trips

Kauai, Poipu
Highlights from your plan
Poipu Beach Park ©
Poipu Beach Park
Tunnels Beach ©
Tunnels Beach
Shipwreck Beach ©
Shipwreck Beach

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