50 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner
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1
Honolulu, Oahu
— 12 nights
Fly
2
Koloa, Kauai
— 10 nights
Fly
3
Kihei, Maui
— 12 nights
Fly
4
Hilo, Island of Hawaii
— 4 nights
Drive
5
Kailua-Kona, Island of Hawaii
— 11 nights
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Honolulu, Oahu — 12 nights

Big Pineapple

Give yourself a bit of retail therapy at Ala Moana Center and Ko Hana Distillers. You'll get in some beach time at Waikiki Beach and Kapiolani Regional Park. You'll find plenty of places to visit near Honolulu: Kapolei (Ko Olina Golf Club & Ihilani Spa), Haleiwa (Pupukea Beach Park, Sunset Beach Park, &more) and Pupukea (Pu’u O Mahuka Heiau State Monument, Banzai Pipeline, &more). There's much more to do: stroll the grounds of USS Arizona Memorial, discover the deep blue sea with a scuba or snorkeling tour, take in the pleasant sights at Diamond Head State Monument, and explore the activities along Hanauma Bay Nature Preserve.

For more things to do, photos, and other tourist information, use the Honolulu route app.

Denver to Honolulu is an approximately 8.5-hour flight. You'll gain 3 hours traveling from Denver to Honolulu due to the time zone difference. Plan for much warmer temperatures traveling from Denver in November, with highs in Honolulu at 84°F and lows at 72°F. Finish your sightseeing early on the 13th (Sun) so you can fly to Koloa.
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Koloa, Kauai — 10 nights

Give yourself a bit of retail therapy at Talk Story Bookstore and Poipu Shopping Village. You'll get in some beach time at Poipu Beach Park and Anini Beach. You'll find plenty of places to visit near Koloa: Hanalei (Hanalei National Wildlife Refuge, Havaiki Oceanic and Tribal Art, &more), Na Pali Coast State Park (in Wainiha) and Waimea (Puu Hinahina Lookout, Aloha 'n Paradise Espresso Bar, &more).

To see ratings, reviews, traveler tips, and other tourist information, use the Koloa sightseeing planning website.

Traveling by flight from Honolulu to Koloa takes 2.5 hours. In November, daily temperatures in Koloa can reach 81°F, while at night they dip to 71°F. Finish your sightseeing early on the 23rd (Wed) so you can fly to Kihei.
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Kihei, Maui — 12 nights

We've included these beaches for you: Wailea Beach and Ka'anapali Beach. Head to Tamura's Fine Wine & Liquors and Village Galleries in Lahainafor some retail therapy. You'll find plenty of places to visit near Kihei: Haleakala Crater (in Haleakala National Park), Lahaina (Lahaina Banyan Court, Lahaina Galleries, &more) and Kula (Zipline & Maui Stargazing). Spend the 5th (Mon) exploring the striking scenery along Hana Highway - Road to Hana. And it doesn't end there: enjoy the sand and surf at Kapalua Beach, tour the pleasant surroundings at Makena Beach, play a few rounds at Makena Golf Courses, and admire the majestic nature at Iao Valley.

Plan a Kihei trip in moments using our itinerary builder.

You can fly from Koloa to Kihei in 2.5 hours. In November in Kihei, expect temperatures between 84°F during the day and 68°F at night. Wrap up your sightseeing on the 5th (Mon) to allow time to fly to Hilo.
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Hilo, Island of Hawaii — 4 nights

America's Wettest City

Give yourself a bit of retail therapy at Hilo Farmers Market and Volcano Art Center Gallery. Venture out of the city with trips to Steam Vents (in Pahoa), Uncle Robert's Awa Bar and Farmers Market (in Kaimu) and Hawaii Volcanoes National Park (Nature & Wildlife Tours, Kilauea Iki Trailhead, &more). And it doesn't end there: look for gifts at Big Island Candies, take in the exciting artwork at Extreme Exposure Fine Art Gallery, take in the dramatic scenery at Rainbow Falls, and immerse yourself in nature at Akaka Falls State Park.

To plan Hilo vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by flight from Kihei to Hilo takes 2.5 hours. In December, plan for daily highs up to 80°F, and evening lows to 65°F. Cap off your sightseeing on the 9th (Fri) early enough to go by car to Kailua-Kona.
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Kailua-Kona, Island of Hawaii — 11 nights

Heart of the Kona Coast

We've included these beaches for you: Hapuna Beach State Recreation Area and Pu'uhonua O Honaunau National Historical Park. Give yourself a bit of retail therapy at Big Island Bees and Discovery Antiques. You'll find plenty of places to visit near Kailua-Kona: Waimea (Waialea Beach & Isaacs Art Center Museum and Gallery), Anaehoomalu (in Waikoloa) and Naalehu (Ka Lae Light, Papakōlea Green Sand Beach, &more). There's still lots to do: get close to the beloved marine mammals with a swim-with-the-dolphins experience, play a few rounds at Mauna Lani Resort , view the masterpieces at Trudy's Island Arts, and kick back and relax at Mauna Kea Beach.

Use Inspirock's suggestions to plan your Kailua-Kona trip and find the best activities and attractions for your vacation.

You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 82°F in December, and nighttime lows around 70°F. Wrap up your sightseeing by early afternoon on the 20th (Tue) to allow enough time to fly back home.
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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.
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