21 days in Hawaii Itinerary

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Honolulu, Oahu
— 7 nights
Koloa, Kauai
— 3 nights
Kailua-Kona, Island of Hawaii
— 3 nights
Hilo, Island of Hawaii
— 2 nights
Lahaina, Maui
— 4 nights


Honolulu, Oahu — 7 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Discover out-of-the-way places like Lanikai Beach and Makapuu Lighthouse Trail. You'll explore and learn at USS Arizona Memorial and Bishop Museum. Explore the numerous day-trip ideas around Honolulu: Haleiwa (Waimea Bay & Waimea Valley), Shark's Cove (in Pupukea) and Kailua Beach Park (in Kailua). The adventure continues: tour the pleasant surroundings at Koko Crater Railway Trail, kick back and relax at Waikiki Beach, stroll the grounds of National Memorial Cemetery of the Pacific, and hit the best photo ops around with an inspiring photography tour.

For reviews, maps, and more tourist information, read Honolulu trip itinerary builder website.

Milan, Italy to Honolulu is an approximately 23-hour flight. The time zone difference when traveling from Milan to Honolulu is minus 11 hours. When traveling from Milan in April, plan for a bit warmer days and much hotter nights in Honolulu: temperatures range from 33°C by day to 25°C at night. Cap off your sightseeing on the 2nd (Tue) early enough to catch the flight to Koloa.
Parks · Outdoors · Beaches · Historic Sites
Side Trips

Koloa, Kauai — 3 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Explore hidden gems such as Wailua Falls and Na Pali Coast State Park. Get outdoors at Hanalei Beach and Shipwreck Beach. Explore Koloa's surroundings by going to Waimea (Polihale State Park & Waimea Canyon State Park) and Boat Tours & Water Sports (in Kekaha). There's still lots to do: hike along Maha'ulepu Heritage Trail, stroll through Poipu Beach Park, and take in the dramatic natural features at Spouting Horn.

Plan a Koloa trip in moments using our itinerary builder.

You can fly from Honolulu to Koloa in 2.5 hours. May in Koloa sees daily highs of 32°C and lows of 25°C at night. Finish up your sightseeing early on the 5th (Fri) so you can catch the flight to Kailua-Kona.
Parks · Outdoors · Nature · Beaches
Side Trips

Kailua-Kona, Island of Hawaii — 3 nights

Heart of the Kona Coast

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.
We've included these beaches for you: Pu'uhonua O Honaunau National Historical Park and Hapuna Beach State Recreation Area. Kealakekua Bay and Mokuaikaua Church are good opportunities to explore the local culture. And it doesn't end there: see what you can catch with a fishing tour, contemplate the long history of Puako Petroglyph Archaeological Preserve, experience rural life at Greenwell Farms, and take in the awesome beauty at Mauna Kea.

For other places to visit, ratings, photos, and other tourist information, go to the Kailua-Kona trip itinerary planner.

Getting from Koloa to Kailua-Kona by flight takes about 2.5 hours. In May, plan for daily highs up to 33°C, and evening lows to 26°C. Cap off your sightseeing on the 8th (Mon) early enough to go by car to Hilo.
Parks · Outdoors · Nature · Beaches
Side Trips

Hilo, Island of Hawaii — 2 nights

America's Wettest City

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.
Kick off your visit on the 9th (Tue): admire the sheer force of Rainbow Falls, examine the collection at Pacific Tsunami Museum, admire the natural beauty at Hawaii Tropical Bioreserve and Garden, then take in nature's colorful creations at Liliuokalani Gardens, and finally enjoy the sand and surf at Richardson Beach Park. Here are some ideas for day two: stop by Hilo Coffee Mill, then explore the striking landscape at Thurston Lava Tube (Nahuku), then trek along Kilauea Iki Trailhead, and finally contemplate the geological forces at Kīlauea.

To find photos, traveler tips, maps, and tourist information, refer to the Hilo driving holiday planning website.

Traveling by car from Kailua-Kona to Hilo takes 2 hours. Alternatively, you can take a bus. Plan for little chillier nights when traveling from Kailua-Kona in May since evenings lows in Hilo dip to 22°C. Wrap up your sightseeing on the 10th (Wed) to allow time to fly to Lahaina.
Parks · Nature · Outdoors · Beaches
Side Trips

Lahaina, Maui — 4 nights

Crown Jewel of Maui

Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
Explore hidden gems such as Napili Beach and Ho'okipa Beach Park. You'll enjoy a bit of beach vacationing at Wailea Beach and Kamaole Beach Park III. Explore the numerous day-trip ideas around Lahaina: Wailea (Makena Beach, Scuba & Snorkeling, &more) and Maui Specialty Chocolate (in Kahului). There's much more to do: tour the pleasant surroundings at Kapalua Coastal Trail, walk around Lahaina Banyan Court, and kick your exploration up a notch at some of the top local zipline courses and adventure parks.

For photos, ratings, reviews, and tourist information, go to the Lahaina visit planner.

You can fly from Hilo to Lahaina in 2.5 hours. May in Lahaina sees daily highs of 32°C and lows of 24°C at night. Wrap up your sightseeing by early afternoon on the 14th (Sun) to allow enough time to fly back home.
Outdoors · Parks · Beaches · Wildlife
Side Trips

Hawaii travel guide

Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.