16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

Created using Inspirock Hawaii vacation builder

Make it your trip
Fly
1
Honolulu, Oahu
— 5 nights
Fly
2
Lihue, Kauai
— 3 nights
Fly
3
Kailua-Kona, Island of Hawaii
— 1 night
Drive
4
Hilo, Island of Hawaii
— 2 nights
Fly
5
Kihei, Maui
— 4 nights
Fly

S M T W T F S
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4

Honolulu, Oahu

— 5 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.
Venture out of the city with trips to Haleiwa (Pupukea Beach Park, Sunset Beach Park, &more). There's lots more to do: stroll the grounds of USS Arizona Memorial, see some colorful creatures with a scuba or snorkeling tour, contemplate the long history of Battleship Missouri Memorial, and stroll through Diamond Head State Monument.

To see traveler tips, photos, and other tourist information, go to the Honolulu road trip planning app.

Chicago to Honolulu is an approximately 12-hour flight. Traveling from Chicago to Honolulu, you'll gain 4 hours due to the time zone difference. Prepare for much hotter weather when traveling from Chicago in November: high temperatures in Honolulu hover around 84°F and lows are around 72°F. Wrap up your sightseeing on the 18th (Thu) to allow time to travel to Lihue.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trip

Lihue, Kauai

— 3 nights
Lihue or LÄ«hue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. You'll find plenty of places to visit near Lihue: Hanalei Beach (in Hanalei), Waimea Canyon State Park (in Waimea) and Na Pali Coast State Park (in Wainiha). The adventure continues: kick your exploration up a notch at some of the top local zipline courses and adventure parks, explore the striking landscape at Spouting Horn, see the world from above with a helicopter tour, and enjoy the sand and surf at Poipu Beach Park.

For ratings, reviews, maps, and tourist information, use the Lihue day trip planner.

You can fly from Honolulu to Lihue in 2.5 hours. November in Lihue sees daily highs of 81°F and lows of 71°F at night. Wrap up your sightseeing on the 21st (Sun) to allow time to travel to Kailua-Kona.

Things to do in Lihue

Parks · Outdoors · Beaches · Nature

Side Trips

Kailua-Kona, Island of Hawaii

— 1 night

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.
On the 22nd (Mon), relax in the rural setting at Heavenly Hawaiian Kona Coffee Farm, then kick back and relax at Kahaluu Beach, then get a new perspective on things with Boat Tours & Water Sports, and finally take in the waterfront at Kailua Pier.

To find ratings, reviews, and other tourist information, read Kailua-Kona road trip site.

Getting from Lihue to Kailua-Kona by flight takes about 2.5 hours. In November in Kailua-Kona, expect temperatures between 84°F during the day and 73°F at night. Finish your sightseeing early on the 22nd (Mon) so you can drive to Hilo.

Things to do in Kailua-Kona

Outdoors · Tours · Wildlife · 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.
Start off your visit on the 23rd (Tue): get up close and personal with brilliant marine life at Mokupapapa Discovery Center, then cruise along Devastation Trail, then hike along Kilauea Iki Trailhead, and finally explore the striking landscape at Thurston Lava Tube (Nahuku). Get ready for a full day of sightseeing on the 24th (Wed): take in the dramatic scenery at Rainbow Falls, get a taste of the local shopping with Hilo Farmers Market, then take in nature's colorful creations at Liliuokalani Gardens, then stop by Basically Books, and finally admire the sheer force of Akaka Falls State Park.

For other places to visit, more things to do, where to stay, and more tourist information, read Hilo vacation maker tool.

Drive from Kailua-Kona to Hilo in 2 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in November, Hilo is little chillier at night with lows of 68°F. Finish up your sightseeing early on the 24th (Wed) so you can travel to Kihei.

Things to do in Hilo

Parks · Nature · Outdoors · Shopping

Side Trip

Kihei, Maui

— 4 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.
Get out of town with these interesting Kihei side-trips: Zipline (in Kula), Haleakala Crater (in Haleakala National Park) and Maui Veterans Cemetery (in Makawao). Spend the 25th (Thu) exploring the striking scenery along Hana Highway - Road to Hana. There's still lots to do: look for all kinds of wild species at Wildlife Areas, get engrossed in the history at Story of Hawaii Museum, walk around Lahaina Banyan Court, and meet the residents at Maui Ocean Center.

For traveler tips, other places to visit, and tourist information, use the Kihei trip itinerary planner.

Traveling by flight from Hilo to Kihei takes 3 hours. Expect a daytime high around 84°F in November, and nighttime lows around 68°F. Finish up your sightseeing early on the 28th (Sun) so you can travel back home.

Things to do in Kihei

Outdoors · Parks · Scenic Drive · Tours

Side Trips

Hawaii travel guide

4.4
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.