19 days in Hawaii Itinerary

19 days in Hawaii Itinerary

Created using Inspirock Hawaii holiday maker

Plan created by another user.Make it yours

Route & dates

Start: San Antonio
Fly:  12 h 30 min
1
Hilo, Island of Hawaii
— 2 nights
Drive:  1 h 45 min
2
Kailua-Kona, Island of Hawaii
— 6 nights
Fly:  4 h
3
Lahaina, Maui
— 4 nights
Fly:  4 h 30 min
4
Haleiwa, Oahu
— 2 nights
Fly:  3 h
5
Lihue, Kauai
— 4 nights
Fly:  12 h 30 min
End: San Antonio

2
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.
Kick off your visit on the 13th (Tue): see the interesting displays at Lyman Museum, see the interesting displays at Pacific Tsunami Museum, thenlook for all kinds of wild species at Hawaii Tropical Botanical Garden, and finally make a trip to Pepeekeo Scenic Drive. On the next day, explore the fascinating underground world of Kaumana Caves Park, thenenjoy the sand and surf at Richardson Beach Park, thenkick back and relax at Carlsmith Beach Park, and finally admire the natural beauty at Liliuokalani Gardens.

To see where to stay, traveler tips, and more tourist information, read our Hilo online visit planner.

San Antonio to Hilo is an approximately 13-hour flight. The time zone difference when traveling from San Antonio to Hilo is minus 4 hours. Plan for a bit warmer nights when traveling from San Antonio in October since evenings lows in Hilo dip to 70°F. Cap off your sightseeing on the 14th (Wed) early enough to go by car to Kailua-Kona.

Things to do in Hilo

Parks Outdoors Beaches

Side Trip

Hawaii Tropical Botanical Garden
Find places to stay Oct 12 — 14:
Highlights from your plan
Hawaii Tropical Botanical Garden ©
Hawaii Tropical Botanical Garden
Richardson Beach Park ©
Richardson Beach Park
Liliuokalani Gardens ©
Liliuokalani Gardens

6
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.
You'll discover tucked-away gems like Punalu‘U Beach and Fishing Charters & Tours. You'll enjoy a bit of beach vacationing at Hapuna Beach State Recreation Area and Manini'owali Beach (Kua Bay). Explore Kailua-Kona's surroundings by going to Captain Cook (Kealakekua Bay & The Painted Church), Queen's Bath (in Princeville) and Honaunau (Pu'uhonua O Honaunau National Historical Park & Honaunau Bay). The adventure continues: look for all kinds of wild species at Kanaloa Octopus Farm, enjoy the sand and surf at 49 Black Sand Beach, tour the pleasant surroundings at Papakōlea Green Sand Beach, and experience rural life at Hula Daddy Kona Coffee.

To find maps, traveler tips, reviews, and more tourist information, read our Kailua-Kona day trip tool.

Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 86°F in October, and nighttime lows around 75°F. Wrap up your sightseeing on the 20th (Tue) early enough to travel to Lahaina.

Things to do in Kailua-Kona

Parks Nature Outdoors

Side Trips

Captain Cook, Honaunau, Kealakekua, Hapuna Beach State Recreation Area, Punalu‘U Beach
Find places to stay Oct 14 — 20:
Highlights from your plan
Fishing Charters & Tours
Punalu‘U Beach ©
Punalu‘U Beach
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area

4
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.
We've included these beaches for you: Napili Beach and Kapalua Beach. Escape the urban bustle at Ho'okipa Beach Park and Kamaole Beach Park II. Venture out of the city with trips to Wailea (Wailea Beach, Makena Beach, &more). Next up on the itinerary: kick back and relax at D.T. Fleming Park, make a trip to Hale Pa'ahao - Old Lahaina Prison, get interesting insight from Tours, and look for all kinds of wild species at Honolua Bay.

To find reviews, more things to do, where to stay, and more tourist information, you can read our Lahaina trip itinerary website.

Fly from Kailua-Kona to Lahaina in 4.5 hours. In October, plan for daily highs up to 84°F, and evening lows to 73°F. Cap off your sightseeing on the 24th (Sat) early enough to travel to Haleiwa.

Things to do in Lahaina

Parks Outdoors Beaches

Side Trips

Wailea, Kapalua, Ho'okipa Beach Park, Honolua Bay, Kamaole Beach Park II
Find places to stay Oct 20 — 24:
Highlights from your plan
Napili Beach ©
Napili Beach
Little Beach ©
Little Beach
Wailea Beach ©
Wailea Beach

2
nights
Haleiwa, Oahu

Haleiwa ©
Haleiwa is a North Shore community and census-designated place (CDP) in the Waialua District of the island of Oahu, City and County of Honolulu. Kick off your visit on the 25th (Sun): kick back and relax at Ehukai Beach Park, thenexplore the gorgeous colors at Banzai Pipeline, thentrek along Ehukai Pillbox Hike, and finally stroll through Lost Survivors Beach Camp. On the next day, kick back and relax at Mokuleia Beach Park, thenenjoy the sand and surf at Keawaula (Yokohama Beach), thentake in the dramatic natural features at Ka'ena Point State Park, and finally don't miss a visit to Wyland Galleries.

To find more things to do and other tourist information, read our Haleiwa trip planner.

Getting from Lahaina to Haleiwa by flight takes about 5 hours. Traveling from Lahaina in October, Haleiwa is a bit cooler at night with lows of 68°F. Finish your sightseeing early on the 26th (Mon) to allow enough time to travel to Lihue.

Things to do in Haleiwa

Parks Outdoors Beaches

Side Trips

Pupukea, Ka'ena Point State Park, Mokuleia Beach Park, Keawaula (Yokohama Beach)
Find places to stay Oct 24 — 26:
Highlights from your plan
Ehukai Beach Park ©
Ehukai Beach Park
Banzai Pipeline ©
Banzai Pipeline
Keawaula (Yokohama Beach) ©
Keawaula (Yokohama Beach)

4
nights
Lihue, Kauai

Lihue ©
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Get some historical perspective at Kilohana and Ninini Point Lighthouse Cache Site. You'll discover tucked-away gems like Wailua Falls and Kauai Path. The adventure continues: brush up on your knowledge of spirits at Koloa Rum Company, take an in-depth tour of Kauai Museum, kick back and relax at Kalapaki Beach, and take in the dramatic scenery at Opaekaa Falls.

Plan a trip to Lihue easily and quickly by telling Inspirock to suggest an itinerary.

Getting from Haleiwa to Lihue by flight takes about 4.5 hours. Traveling from Haleiwa in October, Lihue is a bit warmer at night with lows of 74°F. Wrap up your sightseeing on the 30th (Fri) early enough to travel back home.

Things to do in Lihue

Parks Outdoors Beaches

Side Trips

Poipu, Opaekaa Falls, Kauai Path
Find places to stay Oct 26 — 30:
Highlights from your plan
Koloa Rum Company ©
Koloa Rum Company
Maha'ulepu Heritage Trail
Maha'ulepu Heritage Trail
Wailua Falls ©
Wailua Falls

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