21 days in Hawaii Itinerary

21 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner
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— 5 nights
— 3 nights
— 2 nights
— 3 nights
— 6 nights


Kihei — 5 nights

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.
Kids will appreciate attractions like Maui Ocean Center and Iao Valley. Change things up with these side-trips from Kihei: Lahaina (Zipline, Ka'anapali Beach, &more). Spend the 20th (Sun) exploring the striking scenery along Hana Highway - Road to Hana. And it doesn't end there: kick back and relax at Wailea Beach, play a few rounds at Maui Nui Golf Club, soothe aching muscles at some of the top local wellness centers, and tour the pleasant surroundings at Kamaole Beach Park III.

To find photos, more things to do, other places to visit, and other tourist information, use the Kihei tour planning website.

Singapore, Singapore to Kihei is an approximately 20-hour flight. The time zone changes from Singapore Standard Time (SGT) to Hawaii-Aleutian Standard Time (HST), which is usually a -18 hour difference. In November, Kihei is little chillier than Singapore - with highs of 34°C and lows of 23°C. Finish your sightseeing early on the 23rd (Wed) so you can fly to Hilo.
Outdoors · Parks · Scenic Drive · Beaches
Side Trips

Hilo — 3 nights

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.
Kids will appreciate attractions like Akaka Falls State Park and Rainbow Falls. Venture out of the city with trips to Hawaii Volcanoes National Park (Kilauea Iki Trailhead, Devastation Trail, &more). There's much more to do: admire the natural beauty at Liliuokalani Gardens, take in the exciting artwork at Banyan Gallery, take a memorable drive along Banyan Drive, and stroll around Carlsmith Beach Park.

To find photos, maps, other places to visit, and tourist information, you can read our Hilo route maker.

Traveling by flight from Kihei to Hilo takes 2.5 hours. November in Hilo sees daily highs of 32°C and lows of 23°C at night. Cap off your sightseeing on the 26th (Sat) early enough to go by car to Kailua-Kona.
Parks · Nature · Outdoors · Shopping
Side Trips

Kailua-Kona — 2 nights

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.
Kick off your visit on the 26th (Sat): take in the waterfront at Kailua Pier, then get close to the beloved marine mammals with a swim-with-the-dolphins experience, then kick back and relax at Hapuna Beach State Recreation Area, and finally tour the pleasant surroundings at Mauna Kea Beach. Get ready for a full day of sightseeing on the 27th (Sun): get engrossed in the history at H.N. Greenwell Store Museum, enjoy the sand and surf at Kahaluu Beach, take in the spiritual surroundings of Mokuaikaua Church, then look for all kinds of wild species at Kona Cloud Forest, then stop by Mountain Thunder Coffee Plantation, and finally play a few rounds at Mauna Lani Resort .

To see where to stay, traveler tips, maps, and other tourist information, go to the Kailua-Kona online driving holiday planner.

Drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. In November in Kailua-Kona, expect temperatures between 34°C during the day and 26°C at night. Cap off your sightseeing on the 28th (Mon) early enough to catch the flight to Kapaa.
Outdoors · Parks · Beaches · Wildlife
Side Trips

Kapaa — 3 nights

Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
Bring the kids along to Waimea Canyon State Park and Kayaking & Canoeing. Get out of town with these interesting Kapaa side-trips: Poipu (Prince Kuhio Park, Spouting Horn, &more), Na Pali Coast State Park (in Wainiha) and Hanalei Beach (in Hanalei). There's much more to do: see the world from above with a helicopter tour, relax and rejuvenate at some of the best spas, take some stellar pictures from Sleeping Giant Trail, and relax in the rural setting at Lydgate Farms Kauai Chocolate.

To see traveler tips, more things to do, reviews, and other tourist information, use the Kapaa road trip site.

Traveling by flight from Kailua-Kona to Kapaa takes 2.5 hours. In November in Kapaa, expect temperatures between 32°C during the day and 25°C at night. Wrap up your sightseeing by early afternoon on the 1st (Thu) to allow enough time to fly to Honolulu.
Parks · Outdoors · Nature · Beaches
Side Trips

Honolulu — 6 nights

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Attractions like USS Arizona Memorial and Sunset Beach Park make great kid-friendly stops. Explore the numerous day-trip ideas around Honolulu: Waimea Bay (in Haleiwa), Byodo-In Temple (in Kaneohe) and Kailua Beach Park (in Kailua). There's much more to do: tour the pleasant surroundings at Waikiki Beach, hike along Diamond Head State Monument, listen to music at Polynesian Cultural Center, and explore the different monuments and memorials at National Memorial Cemetery of the Pacific.

For reviews, other places to visit, ratings, and more tourist information, use the Honolulu visit planner.

Getting from Kapaa to Honolulu by flight takes about 2.5 hours. In December, daytime highs in Honolulu are 32°C, while nighttime lows are 24°C. On the 7th (Wed), you'll have the morning to explore before heading back home.
Parks · Outdoors · Beaches · Historic Sites
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.

Island of Hawaii travel guide

Scuba & Snorkeling · Swim with Dolphins · Beaches
The Big Island
Aptly nicknamed the "Big Island," the Island of Hawaii features sunny, black-sand beaches on the western side by Kona and a tropical rain forest on the eastern by Hilo. In between, the massive mountain Maunaloa covers half the island, and Kilauea, one of the world's most active volcanoes, erupts continuously. Twice as large as all the other Hawaiian Islands combined, this big chunk of land in the Pacific manages to retain a laid-back atmosphere despite its immense popularity with tourists. Instead of spending your entire vacation at one of the island's luxurious tourist resorts, go on tours of this Pacific haven's coffee and macadamia nut plantations and working ranches, or explore its nature reserves and rugged trails.

Kauai travel guide

Scuba & Snorkeling · Zipline · Beaches
The Garden Isle
The northernmost of Hawaii's major islands, Kauai earned the nickname "Garden Island" because of its abundance of lush greenery and tropical plants, watered frequently with plentiful rainfall. Kauai's landscape continues to suffer from powerful erosion, resulting in natural attractions that include plunging canyons, tall mountain peaks, and the longest sandy coastline of all the Hawaiian islands. Offering a mild tropical climate and pristine wilderness areas largely unspoiled by mass tourism, Kauai is a great vacation destination for visitors eager to escape Hawaii's more crowded tourist resorts. For a genuine Kauai experience, join the locals for one of their famous traditional meat and vegetable feasts, prepared in underground pits lined with hot rocks.

Oahu travel guide

Beaches · Cemeteries · Scuba & Snorkeling
The Gathering Place
A top cultural and vacation destination within the Hawaiian Islands, Oahu is home to over 85 percent of the state's population. Aptly nicknamed the "Gathering Place," the island is truly at the heart of Hawaii, featuring the busy city of Honolulu and its surrounding districts. Visitors to Oahu can enjoy all the modern conveniences of a large city, while remaining within walking distance of secluded beaches, picturesque parks, high mountain peaks, and quaint little towns. To experience the laid-back side of Hawaii, take a trip away from the tourist hotspot of Waikiki, the island's most crowded neighborhood.