50 days in Hawaii Itinerary

50 days in Hawaii Itinerary

Created using Inspirock Hawaii vacation planner
Make it your trip
Fly
1
Honolulu, Oahu
— 11 nights
Fly
2
Koloa, Kauai
— 10 nights
Fly
3
Lahaina, Maui
— 11 nights
Fly
4
Hilo, Island of Hawaii
— 6 nights
Drive
5
Kailua-Kona, Island of Hawaii
— 11 nights
Fly

S M T W T F S
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12

Honolulu, Oahu — 11 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.
You'll find plenty of places to visit near Honolulu: Pupukea (Pu’u O Mahuka Heiau State Monument & Ehukai Beach Park), Haleiwa (Sunset Beach Park, Waimea Valley, &more) and Kailua (Kailua Beach Park & Lanikai Beach). The adventure continues: explore the different monuments and memorials at USS Arizona Memorial, buy something for everyone on your list at Ala Moana Center, hit the best photo ops around with an inspiring photography tour, and make a trip to Battleship Missouri Memorial.

To see other places to visit, photos, more things to do, and more tourist information, go to the Honolulu journey tool.

Newark to Honolulu is an approximately 11-hour flight. The time zone changes from Eastern Standard Time (EST) to Hawaii-Aleutian Standard Time (HST), which is usually a -5 hour difference. Plan for somewhat warmer temperatures traveling from Newark in September, with highs in Honolulu at 88°F and lows at 76°F. Finish up your sightseeing early on the 2nd (Sun) so you can catch the flight to Koloa.
more
Parks · Outdoors · Beaches · Historic Sites
Side Trips

Koloa, Kauai — 10 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Venture out of the city with trips to Waimea (Waimea Canyon State Park, Puu Hinahina Lookout, &more), Hanalei (Hanalei Valley Lookout & Hanalei Beach) and Na Pali Coast State Park (in Wainiha). There's much more to do: kick your exploration up a notch at some of the top local zipline courses and adventure parks, look for all kinds of wild species at Kauai Safaris, take in the dramatic scenery at Hanakapiai Falls, and kick back and relax at Poipu Beach Park.

For traveler tips, photos, maps, and tourist information, refer to the Koloa vacation builder app.

You can fly from Honolulu to Koloa in 2.5 hours. In October, daytime highs in Koloa are 84°F, while nighttime lows are 74°F. Finish up your sightseeing early on the 12th (Wed) so you can catch the flight to Lahaina.
more
Parks · Outdoors · Nature · Beaches
Side Trips

Lahaina, Maui — 11 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.
Get out of town with these interesting Lahaina side-trips: Makawao (Ho'omana Spa Maui & Maui Veterans Cemetery), Ocean Vodka Organic Farm and Distillery (in Kula) and Ho'okipa Beach Park (in Paia). Spend the 13th (Thu) exploring the striking scenery along Hana Highway - Road to Hana. There's lots more to do: see some colorful creatures with a scuba or snorkeling tour, take in the dramatic natural features at Haleakala Crater, enjoy the sand and surf at Ka'anapali Beach, and admire the majestic nature at Iao Valley.

For maps, ratings, photos, and more tourist information, refer to the Lahaina trip itinerary planning app.

Traveling by flight from Koloa to Lahaina takes 2.5 hours. Expect a daytime high around 84°F in October, and nighttime lows around 73°F. Cap off your sightseeing on the 23rd (Sun) early enough to catch the flight to Hilo.
more
Outdoors · Parks · Beaches · Scenic Drive
Side Trips

Hilo, Island of Hawaii — 6 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.
Change things up with these side-trips from Hilo: Laupahoehoe Beach Park (in Laupahoehoe), Hawaii Volcanoes National Park (Keanakakoi Crater Overlook, Devastation Trail, &more) and Waipiʻo Valley Lookout (in Honokaa). There's still lots to do: take in nature's colorful creations at Liliuokalani Gardens, shop like a local with Hilo Farmers Market, meet the residents at Mokupapapa Discovery Center, and see the world from above with a helicopter tour.

For traveler tips, other places to visit, reviews, and tourist information, go to the Hilo journey planner.

Traveling by flight from Lahaina to Hilo takes 2.5 hours. October in Hilo sees daily highs of 84°F and lows of 70°F at night. Finish your sightseeing early on the 29th (Sat) so you can drive to Kailua-Kona.
more
Parks · Outdoors · Trails · Nature
Side Trips

Kailua-Kona, Island of Hawaii — 11 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.
Explore the numerous day-trip ideas around Kailua-Kona: Hapuna Beach State Recreation Area (in Puako), Honaunau (The 1871 Trail & Pu'uhonua O Honaunau National Historical Park) and Naalehu (Papakōlea Green Sand Beach & Paradise Meadows Orchard & Bee Farm Home of Hawaii's Local Buzz). There's still lots to do: fulfill a lifelong dream with a swim-with-the-dolphins experience, relax in the rural setting at Heavenly Hawaiian Kona Coffee Farm, explore the fascinating underground world of Kula Kai Caverns, and contemplate in the serene atmosphere at Mokuaikaua Church.

To see more things to do, photos, traveler tips, and other tourist information, read our Kailua-Kona trip itinerary builder tool.

You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. In October in Kailua-Kona, expect temperatures between 86°F during the day and 75°F at night. Wrap up your sightseeing on the 9th (Wed) early enough to fly back home.
more
Outdoors · Parks · Beaches · Historic Sites
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.
more