34 days in Hawaii Itinerary

34 days in Hawaii Itinerary

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Route & dates

34 days in Hawaii Itinerary

Start: San Francisco
Fly:  7 h 30 min
1
Honolulu, Oahu
— 5 nights
Fly:  2 h 15 min
2
Lihue, Kauai
— 5 nights
Fly:  2 h 30 min
3
Kailua-Kona, Island of Hawaii
— 5 nights
Drive:  1 h 45 min
4
Hilo, Island of Hawaii
— 3 nights
Fly + Bus:  3 h 15 min
5
Lahaina, Maui
— 5 nights
Travel:  3 h 15 min
6
Kaunakakai, Molokai
— 2 nights
Travel:  3 h
7
Lanai City, Lanai
— 2 nights
Travel:  3 h 15 min
8
Kihei, Maui
— 5 nights
Fly:  7 h 30 min
End: San Francisco

5
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Explore Honolulu's surroundings by going to Kailua Beach Park (in Kailua) and Haleiwa (Sunset Beach Park & Waimea Bay). The adventure continues: explore the different monuments and memorials at USS Arizona Memorial, take in the dramatic scenery at Manoa Falls, kick back and relax at Waikiki Beach, and discover the deep blue sea with a scuba or snorkeling tour.

For other places to visit, reviews, maps, and tourist information, go to the Honolulu trip website .

San Francisco to Honolulu is an approximately 7.5-hour flight. You can also do a combination of train and flight. Traveling from San Francisco to Honolulu, you'll gain 2 hours due to the time zone difference. Traveling from San Francisco in September, expect Honolulu to be somewhat warmer, temps between 88°F and 76°F. Wrap up your sightseeing on the 6th (Sun) early enough to travel to Lihue.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Kailua Beach Park
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach

5
nights
Lihue, Kauai

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Go for a jaunt from Lihue to Eleele to see Scuba & Snorkeling about 30 minutes away. There's still lots to do: take an unforgettable tour with a helicopter tour, contemplate the long history of Kilohana, stroll through Poipu Beach Park, and admire the sheer force of Opaekaa Falls.

To find photos, where to stay, more things to do, and other tourist information, you can read our Lihue day trip planner .

Fly from Honolulu to Lihue in 2.5 hours. Expect a daytime high around 86°F in September, and nighttime lows around 76°F. You will have some time to spend on the 11th (Fri) before leaving for Kailua-Kona.

Things to do in Lihue

Outdoors Tours Parks

Side Trips

Poipu, Kauai, Scuba & Snorkeling, Kayaking & Canoeing
Highlights from your plan
Kalapaki Beach ©
Kalapaki Beach
Helicopter Tours
Poipu Beach Park ©
Poipu Beach Park

5
nights
Kailua-Kona, Island of Hawaii

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 Papakōlea Green Sand Beach (in Naalehu), Hapuna Beach State Recreation Area (in Puako) and Pu'uhonua O Honaunau National Historical Park (in Honaunau). The adventure continues: fulfill a lifelong dream with a swim-with-the-dolphins experience, appreciate the views at Pololu Valley Lookout, get engrossed in the history at Kona Coffee Living History Farm, and tour the pleasant surroundings at Puako Petroglyph Archaeological Preserve.

To see traveler tips, more things to do, and more tourist information, refer to the Kailua-Kona trip builder website .

Getting from Lihue to Kailua-Kona by flight takes about 2.5 hours. September in Kailua-Kona sees daily highs of 87°F and lows of 76°F at night. You will have some time to spend on the 16th (Wed) before leaving for Hilo.

Things to do in Kailua-Kona

Outdoors Parks Nature

Side Trips

Island of Hawaii, Hapuna Beach State Recreation Area, Hula Daddy Kona Coffee, Pu'uhonua O Honaunau National Historical Park, Papakōlea Green Sand Beach
Highlights from your plan
Swim with Dolphins
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area

3
nights
Hilo, Island of Hawaii

Hilo ©
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.
You'll find plenty of places to visit near Hilo: Hawaii Volcanoes National Park (Devastation Trail, Kilauea Iki Trailhead, & more) and Jagger Museum (in Volcano). And it doesn't end there: admire the sheer force of Akaka Falls State Park, see the world from above with a helicopter tour, learn more about the world around you at Mokupapapa Discovery Center, and look for gifts at Hilo Coffee Mill.

To see photos, more things to do, other places to visit, and other tourist information, read our Hilo trip maker website .

You can drive from Kailua-Kona to Hilo in 2 hours. Alternatively, you can take a bus. Traveling from Kailua-Kona in September, you can expect nighttime temperatures to be slightly colder in Hilo, with lows of 71°F. Finish your sightseeing early on the 19th (Sat) so you can travel to Lahaina.

Things to do in Hilo

Parks Nature Outdoors

Side Trips

Hawaii Volcanoes National Park, Jagger Museum, Hilo Coffee Mill
Highlights from your plan
Akaka Falls State Park ©
Akaka Falls State Park
Kilauea Iki Trailhead ©
Kilauea Iki Trailhead
Kipuka Puaulu (Bird Park) Trail ©
Kipuka Puaulu (Bird Park) Trail

5
nights
Lahaina, Maui

Lahaina ©
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: cruise along Hana Highway - Road to Hana, make a trip to Lahaina Banyan Court, see some colorful creatures with a scuba or snorkeling tour, and enjoy the sand and surf at Napili Beach.

For photos, ratings, where to stay, and tourist information, use the Lahaina online trip itinerary maker .

Traveling by combination of flight and bus from Hilo to Lahaina takes 3.5 hours. Alternatively, you can fly; or do a combination of bus and flight. In September, daytime highs in Lahaina are 86°F, while nighttime lows are 74°F. Finish your sightseeing early on the 24th (Thu) so you can travel to Kaunakakai.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Kapalua, Hana Highway - Road to Hana, Parasailing & Paragliding
Highlights from your plan
Punakea Palms Coconut Farm ©
Punakea Palms Coconut Farm
Scuba & Snorkeling
Hana Highway - Road to Hana ©
Hana Highway - Road to Hana

2
nights
Kaunakakai, Molokai

Kaunakakai ©
Kaunakakai is a census-designated place (CDP) in Maui County, Hawaii, United States. Change things up with a short trip to Kepuhi Beach in Maunaloa (about 40 minutes away). There's much more to do: immerse yourself in nature at Papohaku Beach Park, stroll through Murphy's Beach, take an in-depth tour of Molokai Museum and Cultural Center, and admire the verdant scenery at Halawa Valley.

To find maps, reviews, traveler tips, and other tourist information, go to the Kaunakakai online travel route builder .

Explore your travel options from Lahaina to Kaunakakai with the Route module. In September in Kaunakakai, expect temperatures between 85°F during the day and 73°F at night. Wrap up your sightseeing by early afternoon on the 26th (Sat) to allow time for travel to Lanai City.

Things to do in Kaunakakai

Outdoors Parks Beaches

Side Trip

Molokai
Highlights from your plan
Halawa Valley ©
Halawa Valley
Purdy's All-Natural Macadamia Nut Farm ©
United States Postal Service ©
United States Postal Service

2
nights
Lanai City, Lanai

Lanai City ©
Lanai City is a census-designated place (CDP) on the island of Lanai, in Maui County, Hawaii, United States. On the 27th (Sun), you'll have a packed day of sightseeing: look for all kinds of wild species at Lanai Cat Sanctuary, then view the masterpieces at Mike Carroll Gallery, then stroll around Dole Park, and finally do some rugged touring at local off-road trails.

To see other places to visit, photos, more things to do, and other tourist information, you can read our Lanai City online travel route planner .

Explore your travel options from Kaunakakai to Lanai City with the Route module. Traveling from Kaunakakai in September, plan for little chillier nights in Lanai City, with lows around 68°F. Finish your sightseeing early on the 28th (Mon) so you can travel to Kihei.

Things to do in Lanai City

Parks Outdoors Beaches

Side Trip

Hulopoe Beach
Highlights from your plan
Mike Carroll Gallery ©
Mike Carroll Gallery
Lanai Cat Sanctuary ©
Lanai Cat Sanctuary
Hulopoe Beach ©
Hulopoe Beach

5
nights
Kihei, Maui

Kihei ©
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.
Step out of Kihei with an excursion to Haleakala Crater in Haleakala National Park--about 1h 25 min away. There's lots more to do: get up close and personal with brilliant marine life at Maui Ocean Center, kick back and relax at Kamaole Beach Park II, whizz through the canopy at some of the top local zipline courses and adventure parks, and indulge your thirst for a good beer at Maui Brewing Company.

For traveler tips, reviews, more things to do, and other tourist information, read our Kihei trip planner .

The Route module can help you plan travel from Lanai City to Kihei. Expect a bit warmer weather when traveling from Lanai City in September: highs in Kihei hover around 90°F, while lows dip to 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

Side Trips

Wailuku, Haleakala Crater, Wailea Beach, Ho'okipa Beach Park
Highlights from your plan
Kamaole Beach Park III ©
Kamaole Beach Park III
Haleakala Crater ©
Haleakala Crater
Maui Ocean Center ©
Maui Ocean Center

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