21 days in Hawaii Itinerary

21 days in Hawaii Itinerary

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Route & dates

21 days in Hawaii Itinerary

Start: Rome
Fly:  27 h
1
Honolulu, Oahu
— 2 nights
Bus:  30 min
2
Kailua, Oahu
— 2 nights
Bus + Fly:  2 h
3
Lihue, Kauai
— 4 nights
Fly + Taxi:  1 h 15 min
4
Kihei, Maui
— 3 nights
Bus + Fly:  2 h 15 min
5
Kailua-Kona, Island of Hawaii
— 6 nights
Drive:  2 h
6
Hilo, Island of Hawaii
— 1 night
Fly:  28 h
End: Rome

2
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.
Kick off your visit on the 18th (Sun): kick back and relax at Waimea Bay, then let your taste buds guide you at a local gastronomic tour, and then appreciate the views at Nuuanu Pali Lookout. Here are some ideas for day two: stroll through Kapiolani Regional Park, hike along Koko Crater Trail, then get to know the fascinating history of Makapuu Lighthouse Trail, and finally buy something for everyone on your list at Ala Moana Center.

To find photos, where to stay, maps, and more tourist information, read our Honolulu trip planner.

Rome, Italy to Honolulu is an approximately 27-hour combination of car and flight. Traveling from Rome to Honolulu, you'll gain 11 hours due to the time zone difference. Plan for somewhat warmer nights when traveling from Rome in June since evenings lows in Honolulu dip to 27°C. Wrap up your sightseeing by early afternoon on the 20th (Tue) to allow time for the car ride to Kailua.

Things to do in Honolulu

Parks Outdoors Trails

Side Trips

Waimea Bay, Nu’uanu Pali
Highlights from your plan
Koko Crater Railway Trail ©
Koko Crater Railway Trail
Makapuu Lighthouse Trail ©
Makapuu Lighthouse Trail
Kapiolani Regional Park ©
Kapiolani Regional Park

2
nights
Kailua, Oahu

Kailua ©
Kailua is a census-designated place (CDP) in Honolulu County, Hawaii, United States. Kailua Beach Park has been added to your itinerary. On the 20th (Tue), stroll through Lanikai Beach, then enjoy the sand and surf at Kailua Beach Park, then tour the pleasant surroundings at Sandy Beach Park, and finally browse the eclectic array of goods at Kailua Farmers Market. Keep things going the next day: stop by Manoa Chocolate Hawaii, stop by Kalapawai Market, contemplate in the serene atmosphere at Laie Hawaii Temple, then kick your exploration up a notch at some of the top local zipline courses and adventure parks, then kick back and relax at Sunset Beach Park, and finally look for gifts at Muumuu Heaven.

To see reviews, maps, photos, and tourist information, use the Kailua trip itinerary planner.

Kailua is very close to Honolulu. Expect a daytime high around 32°C in June, and nighttime lows around 26°C. Wrap up your sightseeing by early afternoon on the 22nd (Thu) to allow enough time to travel to Lihue.

Things to do in Kailua

Outdoors Parks Beaches

Side Trips

Laie Hawaii Temple, Sunset Beach Park, Sandy Beach Park
Highlights from your plan
Lanikai Beach ©
Lanikai Beach
Kailua Beach Park ©
Kailua Beach Park
Sunset Beach Park ©
Sunset Beach Park

4
nights
Lihue, Kauai

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. You'll discover tucked-away gems like Zipline and Na Pali Coast State Park. Escape the urban bustle at Kalalau Trail and Kauai Coffee Company. Get out of town with these interesting Lihue side-trips: Aunty Liliko'i (in Waimea), Hawaiian Trading Post (in Lawai), Poipu Shopping Village (in Poipu) and Hanalei (Ching Young Village Shopping Center & Hanalei Valley Lookout). Next up on the itinerary: kick back and relax at Tunnels Beach, admire the sheer force of Wailua Falls, look for gifts at Island Soap & Candle Works, and shop like a local with Seductions of Kauai Gallery.

To see other places to visit, reviews, photos, and tourist information, go to the Lihue itinerary builder.

Traveling by combination of bus and flight from Kailua to Lihue takes 2 hours. In June, plan for daily highs up to 32°C, and evening lows to 26°C. Wrap up your sightseeing on the 26th (Mon) early enough to travel to Kihei.

Things to do in Lihue

Parks Outdoors Shopping

Side Trips

Koloa, Kauai, Hanalei, Poipu, Hawaiian Trading Post
Highlights from your plan
Shipwreck Beach ©
Shipwreck Beach
Na Pali Coast State Park ©
Na Pali Coast State Park
Wailua Falls ©
Wailua Falls

3
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've now added Kamaole Beach Park III to your itinerary. Eschew the tourist crowds and head to Wailea Beach and Ulua Beach. Visiting Zipline and Wailea Beach Path will get you outdoors. Explore the numerous day-trip ideas around Kihei: Kapalua (D.T. Fleming Beach Park & Kapalua Beach), Ali'i Kula Lavender Farm (in Kula) and Hana (Charles Lindbergh's Grave & Red Sand Beach (Kaihalulu Beach)). There's much more to do: kick back and relax at Kamaole Beach Park II, take in the architecture and atmosphere at Keawala'i Congregational Church, see some colorful creatures with a scuba or snorkeling tour, and stroll through Makena Beach.

To see other places to visit, where to stay, more things to do, and more tourist information, you can read our Kihei travel itinerary planner.

Do a combination of flight and taxi from Lihue to Kihei in 1.5 hours. In June, plan for daily highs up to 35°C, and evening lows to 24°C. Wrap up your sightseeing on the 29th (Thu) to allow time to travel to Kailua-Kona.

Things to do in Kihei

Outdoors Parks Beaches

Side Trips

Wailea, Kula, Kapalua, Scuba & Snorkeling, Charles Lindbergh's Grave
Highlights from your plan
D.T. Fleming Park ©
D.T. Fleming Park
Wailea Beach Path ©
Wailea Beach Path
Wailea Beach ©
Wailea Beach

6
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.
Give yourself a bit of retail therapy at Big Island Bees and Kailua Candy Company. Discover out-of-the-way places like Pu'uhonua O Honaunau National Historical Park and Manini'owali Beach (Kua Bay). Get out of town with these interesting Kailua-Kona side-trips: Hapuna Beach State Recreation Area (in Kohala Coast), Honaunau Bay (in Honaunau), Waikoloa (Anaehoomalu & Waikoloa Beach Resort), South Point (Ka Lae) and Green Sand Beach (in Naalehu) and Kealakekua Bay (in Captain Cook). Next up on the itinerary: stroll through Punaluu Black Sand Beach, stop by Original Donkey Balls Factory and Store., admire the verdant scenery at Pololu Valley Lookout, and relax in the rural setting at Hula Daddy Kona Coffee.

To see other places to visit, more things to do, and other tourist information, go to the Kailua-Kona tour planner.

Traveling by combination of taxi, flight, and bus from Kihei to Kailua-Kona takes 2.5 hours. In June, plan for daily highs up to 34°C, and evening lows to 27°C. Finish your sightseeing early on the 5th (Wed) to allow enough time to drive to Hilo.

Things to do in Kailua-Kona

Parks Outdoors Beaches

Side Trips

Kealakekua, Holualoa, Honaunau, Island of Hawaii, Captain Cook
Highlights from your plan
Punalu‘U Beach ©
Punalu‘U Beach
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area

1
night
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.
Start off your visit on the 5th (Wed): stop by Hilo Farmers Market, learn about winemaking at Volcano Winery, explore the wealth of natural beauty at Kilauea, trek along Kilauea Iki Trail, then stop by Big Island Candies, and finally pause for some serene contemplation at St. Joseph Catholic Church,. Keep things going the next day: stop by Hilo Coffee Mill, enjoy the sand and surf at Richardson Beach Park, then take in nature's colorful creations at Liliuokalani Park and Gardens, and finally whizz through the canopy at some of the top local zipline courses and adventure parks.

For ratings, traveler tips, more things to do, and other tourist information, read our Hilo trip planner.

Getting from Kailua-Kona to Hilo by car takes about 2 hours. Other options: take a bus. Plan for slightly colder nights when traveling from Kailua-Kona in July since evenings lows in Hilo dip to 24°C. Finish your sightseeing early on the 6th (Thu) so you can travel back home.

Things to do in Hilo

Parks Outdoors Nature

Side Trips

Hawaii Volcanoes National Park, Hilo Coffee Mill, Big Island Candies, Volcano Winery
Highlights from your plan
Kīlauea ©
Kīlauea
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Richardson Beach Park ©
Richardson Beach Park

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