34 days in Hawaii Itinerary

34 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner

Plan created by another user. Make it yours
Fly
1
Honolulu, Oahu
— 5 nights
Fly
2
Lihue, Kauai
— 5 nights
Fly
3
Kailua-Kona, Island of Hawaii
— 5 nights
Drive
4
Hilo, Island of Hawaii
— 3 nights
Fly
5
Lahaina, Maui
— 5 nights
Unknown
6
Kaunakakai, Molokai
— 2 nights
Unknown
7
Lanai City, Lanai
— 2 nights
Unknown
8
Kihei, Maui
— 5 nights
Fly

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5
nights
Honolulu, Oahu

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.
Get out of town with these interesting Honolulu side-trips: Haleiwa (Sunset Beach Park & Waimea Bay) and Kailua Beach Park (in Kailua). There's still lots to do: stroll the grounds of USS Arizona Memorial, discover the deep blue sea with a scuba or snorkeling tour, steep yourself in history at Battleship Missouri Memorial, and take in the pleasant sights at Diamond Head State Monument.

Ask Inspirock to suggest an itinerary and make planning a trip to Honolulu fast, fun, and easy.

San Francisco to Honolulu is an approximately 8-hour flight. You'll gain 2 hours traveling from San Francisco to Honolulu due to the time zone difference. Prepare for a bit warmer weather when traveling from San Francisco in September: high temperatures in Honolulu hover around 88°F and lows are around 76°F. Finish your sightseeing early on the 6th (Sun) so you can travel to Lihue.

Things to do in Honolulu

Parks · Outdoors · Beaches · Historic Sites

Side Trips

5
nights
Lihue, Kauai

Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Step out of Lihue to go to Eleele and see Scuba & Snorkeling, which is approximately 30 minutes away. The adventure continues: take an unforgettable tour with a helicopter tour, tour the pleasant surroundings at Kalapaki Beach, play a few rounds at Hokuala Golf Course, and take in the dramatic scenery at Opaekaa Falls.

For where to stay and other tourist information, read our Lihue road trip planning site.

You can fly from Honolulu to Lihue in 2.5 hours. Expect a daytime high around 86°F in September, and nighttime lows around 76°F. On the 11th (Fri), you'll have the morning to explore before heading off to Kailua-Kona.

Things to do in Lihue

Outdoors · Tours · Parks · Beaches

Side Trips

5
nights
Kailua-Kona, Island of Hawaii

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.
Venture out of the city with trips to Hapuna Beach State Recreation Area (in Puako), Pu'uhonua O Honaunau National Historical Park (in Honaunau) and Papakōlea Green Sand Beach (in Naalehu). The adventure continues: get close to the beloved marine mammals with a swim-with-the-dolphins experience, see what you can catch with a fishing tour, take your sightseeing to a higher altitude at Mauna Kea, and get engrossed in the history at Kona Coffee Living History Farm.

To find where to stay, more things to do, traveler tips, and tourist information, read Kailua-Kona route planner.

Traveling by flight from Lihue to Kailua-Kona takes 2.5 hours. September in Kailua-Kona sees daily highs of 87°F and lows of 76°F at night. On the 16th (Wed), you'll have the morning to explore before heading off to Hilo.

Things to do in Kailua-Kona

Outdoors · Parks · Beaches · Nature

Side Trips

3
nights
Hilo, Island of Hawaii

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.
Explore the numerous day-trip ideas around Hilo: Jagger Museum (in Volcano) and Hawaii Volcanoes National Park (Devastation Trail, Kilauea Iki Trailhead, &more). There's much more to do: admire the sheer force of Akaka Falls State Park, look for gifts at Hilo Coffee Mill, take an unforgettable tour with a helicopter tour, and get up close and personal with brilliant marine life at Mokupapapa Discovery Center.

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

You can drive from Kailua-Kona to Hilo in 2 hours. Alternatively, you can take a bus. Expect a bit cooler evenings in Hilo when traveling from Kailua-Kona in September, with lows around 71°F. Finish your sightseeing early on the 19th (Sat) so you can travel to Lahaina.

Things to do in Hilo

Parks · Nature · Outdoors · Trails

Side Trips

5
nights
Lahaina, Maui

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.
Lahaina is known for wildlife, nightlife, and adventure. Your plan includes some of its best attractions: see some colorful creatures with a scuba or snorkeling tour, stop by Lahaina Front Street, stroll through Napili Beach, and kick back and relax at Kapalua Beach.

To find reviews, maps, more things to do, and other tourist information, go to the Lahaina trip planning app.

You can fly from Hilo to Lahaina in 3.5 hours. Expect a daytime high around 86°F in September, and nighttime lows around 74°F. Finish up your sightseeing early on the 24th (Thu) so you can travel to Kaunakakai.

Things to do in Lahaina

Outdoors · Parks · Beaches · Tours

Side Trips

2
nights
Kaunakakai, Molokai

Kaunakakai is a census-designated place (CDP) in Maui County, Hawaii, United States. Venture out of the city with trips to Molokai (Papohaku Beach Park & Halawa Valley) and Kepuhi Beach (in Maunaloa). There's still lots to do: look for gifts at Purdy's All-Natural Macadamia Nut Farm, tour the pleasant surroundings at Murphy's Beach, don't miss a visit to United States Postal Service, and take in the architecture and atmosphere at St. Joseph's Church.

For photos, reviews, maps, and other tourist information, refer to the Kaunakakai online visit planner.

Use the Route module to find suitable travel options from Lahaina to Kaunakakai. In September, plan for daily highs up to 85°F, and evening lows to 73°F. Wrap up your sightseeing by early afternoon on the 26th (Sat) to allow enough time to travel to Lanai City.

Things to do in Kaunakakai

Outdoors · Parks · Beaches · Nature

Side Trip

2
nights
Lanai City, Lanai

Lanai City is a census-designated place (CDP) on the island of Lanai, in Maui County, Hawaii, United States. Get ready for a full day of sightseeing on the next day: identify plant and animal life at Lanai Cat Sanctuary, shop like a local with Mike Carroll Gallery, then walk around Dole Park, and finally tour the pleasant surroundings at Nature & Parks.

To find out how to plan a trip to Lanai City, use our trip itinerary maker.

Use the Route module to find suitable travel options from Kaunakakai to Lanai City. Traveling from Kaunakakai in September, expect slightly colder with lows of 68°F in Lanai City. Finish your sightseeing early on the 28th (Mon) to allow enough time to travel to Kihei.

Things to do in Lanai City

Parks · Outdoors · Beaches · Adventure

Side Trip

5
nights
Kihei, Maui

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.
Explore the numerous day-trip ideas around Kihei: Haleakala Crater (in Haleakala National Park) and Ho'okipa Beach Park (in Paia). The adventure continues: get up close and personal with brilliant marine life at Maui Ocean Center, admire the majestic nature at Iao Valley, kick back and relax at Kamaole Beach Park II, and stroll through Wailea Beach.

To see other places to visit, photos, maps, and tourist information, read Kihei tour itinerary maker website.

Explore your travel options from Lanai City to Kihei with the Route module. When traveling from Lanai City in September, plan for a bit warmer days in Kihei, with highs around 90°F, while nights are about the same with lows around 72°F. Finish up your sightseeing early on the 3rd (Sat) so you can travel back home.

Things to do in Kihei

Parks · Outdoors · Beaches · Tours

Side Trips

Hawaii travel guide

4.3
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.