17 days in Oahu, Island of Hawaii & Maui Itinerary

17 days in Oahu, Island of Hawaii & Maui Itinerary

Created using Inspirock Hawaii attractions planner
Make it your trip
Fly
1
Honolulu
— 4 nights
Fly
2
Kailua-Kona
— 4 nights
Fly
3
Hana
— 2 nights
Drive
4
Ka'anapali
— 5 nights
Fly

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Honolulu — 4 nights

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 explore the less-touristy side of things at Koko Crater Railway Trail and Scuba & Snorkeling. Your cultural itinerary includes sights like National Memorial Cemetery of the Pacific and Queen Emma Summer Palace. Explore the numerous day-trip ideas around Honolulu: Laie Hawaii Temple (in Laie), Waimanalo (Bellows Field Beach Park & Waimanalo Beach) and Kailua Beach Park (in Kailua). And it doesn't end there: kick back and relax at Sunset Beach Park, tour the pleasant surroundings at Kapiolani Regional Park, explore the different monuments and memorials at Valley of the Temples, and get to know the fascinating history of Makapuu Lighthouse Trail.

To find where to stay, photos, and more tourist information, go to the Honolulu trip itinerary planner.

Tampa to Honolulu is an approximately 12.5-hour flight. You'll gain 5 hours traveling from Tampa to Honolulu due to the time zone difference. Expect a daytime high around 88°F in September, and nighttime lows around 76°F. You'll set off for Kailua-Kona on the 27th (Tue).
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Outdoors · Parks · Beaches · Historic Sites
Side Trips

Kailua-Kona — 4 nights

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.
Do some cultural sightseeing at Pu'uhonua O Honaunau National Historical Park and The Painted Church. We've included these beaches for you: Hapuna Beach State Recreation Area and Honaunau Bay. Explore Kailua-Kona's surroundings by going to Captain Cook (The Captain Cook Monument & Kealakekua Bay) and Waikoloa (49 Black Sand Beach & Waikoloa Petroglyph Preserve). The adventure continues: enjoy the sand and surf at Manini'owali Beach (Kua Bay), admire the verdant scenery at Waipio Valley, take in the spiritual surroundings of Mokuaikaua Church, and fulfill a lifelong dream with a swim-with-the-dolphins experience.

To find more things to do, traveler tips, photos, and tourist information, read our Kailua-Kona sightseeing planner.

Traveling by flight from Honolulu to Kailua-Kona takes 2.5 hours. Alternatively, you can fly. In September, daily temperatures in Kailua-Kona can reach 87°F, while at night they dip to 76°F. You will leave for Hana on the 1st (Sat).
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Parks · Outdoors · Beaches · Nature
Side Trips

Hana — 2 nights

Hana is one of the most isolated communities in Hawaii, with a permanent population of just over 1,000 people.
Kick off your visit on the 1st (Sat): kick back and relax at Red Sand Beach - Kaihalulu Beach, then indulge in some personalized pampering at Luana Spa Retreat, and then explore the different monuments and memorials at Wananalua Congregational Church. On your second day here, view the masterpieces at Laura Mango, trek along Sliding Sands Trail, then take your sightseeing to a higher altitude at Haleakala Crater, and finally explore the striking landscape at Ke‘anae Point.

To find traveler tips, more things to do, ratings, and tourist information, refer to the Hana trip planner.

Traveling by flight from Kailua-Kona to Hana takes 3.5 hours. Traveling from Kailua-Kona in October, expect slightly colder with lows of 70°F in Hana. You will leave for Ka'anapali on the 3rd (Mon).
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Parks · Nature · Outdoors · Trails
Side Trips

Ka'anapali — 5 nights

Perched at the western tip of Maui, the tourist hub of Ka'anapali offers a range of resorts and activities revolving around the beach.
You'll enjoy a bit of beach vacationing at Kapalua Beach and D.T. Fleming Park. Museum-lovers will appreciate Karen Lei's Gallery and Maui Hands. There's much more to do: explore the striking landscape at Nakalele Blowhole, kick your exploration up a notch at some of the top local zipline courses and adventure parks, tour the pleasant surroundings at Oneloa Bay, and kick back and relax at The Spa at Black Rock.

To find ratings, reviews, and more tourist information, go to the Ka'anapali online travel planner.

You can drive from Hana to Ka'anapali in 3 hours. Alternatively, you can do a combination of taxi and bus. In October in Ka'anapali, expect temperatures between 84°F during the day and 73°F at night. On the 8th (Sat), you're off to home.
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Outdoors · Parks · Beaches · Trails
Side Trips

Oahu travel guide

4.3
Beaches · Cemeteries · Scuba & Snorkeling
The Gathering Place
A top cultural and vacation destination within the Hawaiian Islands, Oahu is home to over 85 percent of the state's population. Aptly nicknamed the "Gathering Place," the island is truly at the heart of Hawaii, featuring the busy city of Honolulu and its surrounding districts. Visitors to Oahu can enjoy all the modern conveniences of a large city, while remaining within walking distance of secluded beaches, picturesque parks, high mountain peaks, and quaint little towns. To experience the laid-back side of Hawaii, take a trip away from the tourist hotspot of Waikiki, the island's most crowded neighborhood.
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Island of Hawaii travel guide

4.5
Scuba & Snorkeling · Swim with Dolphins · Beaches
The Big Island
Aptly nicknamed the "Big Island," the Island of Hawaii features sunny, black-sand beaches on the western side by Kona and a tropical rain forest on the eastern by Hilo. In between, the massive mountain Maunaloa covers half the island, and Kilauea, one of the world's most active volcanoes, erupts continuously. Twice as large as all the other Hawaiian Islands combined, this big chunk of land in the Pacific manages to retain a laid-back atmosphere despite its immense popularity with tourists. Instead of spending your entire vacation at one of the island's luxurious tourist resorts, go on tours of this Pacific haven's coffee and macadamia nut plantations and working ranches, or explore its nature reserves and rugged trails.
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Maui travel guide

4.5
Scuba & Snorkeling · Beaches · Zipline
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.
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