14 days in Hawai'i for adventure lovers

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Shannon Delongchamp, Travel Agent in Ishpeming, MI

Shannon Delongchamp

Ishpeming, MI Travel Agent

Shannon Delongchamp

Ishpeming, MI · 2 Years of Experience

Paradise Travels with Shannon, an independent agent with Cruises & Tours, Unlimited, a Travel Leaders Network Affiliate Agency
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100% Recommended
Shannon did an excellent job planning our trip! My group and I had no worries whatsoever before, during, or after our trip. She was able to... Read More >
COUNTRIES VISITED:Hawaii
PLACES VISITED:Hawaii Island, Kauai Island, Maui Island, Oahu Island
SUGGESTED DURATION:14 Days
As a luxury Hawaiian travel planner, I specialize in designing seamless, multi-island itineraries that showcase the very bests of the Islands of Aloha. With extensive firsthand experience across Hawai‘i, I curate refined, personalized journeys that balance iconic highlights with exclusive experiences—so you can explore more while traveling effortlessly. From Oahu’s iconic shores of Waikiki, to Maui’s chill island vibe to Kaua‘i’s lush Hanalei Valley and the big Island’s active volcanoes. Whether you envision a private whale-watching or fishing charter, exclusive snorkeling excursions in crystal-clear reefs, or simply unwinding at a world-class oceanfront resort, every detail of your island escape will be meticulously planned and tailored to your unique vision of paradise.
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DAY1
Kauai Island
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Lihue, Kaua‘i
You will land in Lihue, the second largest town on Kaua'i. This charming little village is not only a hub of activity but also rich in cultural and historical significance. Relax on the beautiful white sands of Poipu Beach at your resort.
HIGHLIGHTS:
Relaxing on Poipu Beach
DAY2
Kauai Island
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Hanapepe, Kauai
Visit Hanapepe, a town amidst the sugar cane fields, and cross the famous Hanapepe Swinging Bridge. Take in the expanse of Waimea Valley from Puu Hinahina lookout point. Visit Kauai Coffee Plantation and see the process from blossoming, harvesting, to the final step of roasting. Sample the exclusive Hawaiian-grown coffees.
HIGHLIGHTS:
Coffee sampling at Kauai Coffee Plantation
DAY3
Kauai Island
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Helicopter tour of the Na Pali Coast
Take a private Island Helicopter tour exploring the rugged splendor of the Na Pali Coast, the deep colorful gorges of Waimea Canyon, and magnificent Manawaiopuna (Jurassic) Falls.
HIGHLIGHTS:
Helicoptor tour of Kaua'i to include the Manaqaiopuna Falls
DAY4
Oahu Island
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Hololulu International Market Place and Waikiki
Take a walk, or taxi down to Waikiki beach for some sun and surf. Do some shopping at the International Market Place in the heart of Honolulu. There you will find everything from name-brand luxury to local artist sales, along with many dining options for you to enjoy.
HIGHLIGHTS:
Retail therapy at the International Market Place.
DAY5
Oahu Island
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Honolulu city and the USS Arizona/Missouri Tour
Visit the Valor in the Pacific with the USS Arizona Memorial at Pearl Harbor, the USS Missouri, and a tour of Honolulu city. There, you will get the chance to see the Hawai'ian royal palace. The ?Iolani Palace was the royal residence of the rulers of the Kingdom of Hawai?i built in 1882 by King Kalakaua.
HIGHLIGHTS:
Pearl Harbor and the Valor of the Pacific
DAY6
Oahu Island
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Diamond Head and the North Shore
Hike Diamond Head for sweeping views of Waikiki’s coastline and the Pacific beyond. Conclude your day with signature Friday-night fireworks illuminating the shoreline of Waikiki. Take a drive to the North Shore to see the surfing capital of the world. This area is known for its legendary surfing and massive waves at spots like Pipeline, Waimea Bay, and Sunset Beach.
HIGHLIGHTS:
Diamond Head hike
DAY7
Oahu Island
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Luau and the Polynesian Cultural Center
Take a stop in and tour The Polynesian Cultural Center, offering insight into Pacific Island cultures. Take in an oceanfront luau for a traditional buffet (kalua pig, poi, and poke), interactive lessons, and a Polynesian performance featuring hula and fire-knife dancing.
HIGHLIGHTS:
Luau on the beach
DAY8
Maui Island
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Arrive at your resort on Maui and Haleakala Sunset
Once you settle into your Maui resort, head out and drive to see the sunset at the summit of Haleakala. You may see some endangered Nene geese and silver sword plants. Then, head to the Haleakala Observatory and learn about the climate on Maui. If you look out the windows in the far distance, you will see the summits of Mauna Loa and Mauna Kea on the Big Island of Hawai'i! Now it's time to sit back and enjoy the sunset like you have never seen it before, as it dips below the clouds and into the vast ocean.
HIGHLIGHTS:
Sunset at Haleakala
DAY9
Maui Island
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Molokini Snorkel and Whale Watch, Maui Ocean Center
Snorkel Molokini and adventure with the turtles, and many tropical fish on this little outcrop of a volcanic rim! Then jump on a large ocean raft to witness humpback whales in their natural habitat. If you are lucky, maybe one will break the water in front of your boat and do what the naturalists describe as "spyhopping!" Immerse yourself in the marine life at Maui Ocean Center. You can take a tour or walk around the aquarium on your own. There is a touch tank, where you can feel the unique skin of a starfish! The jellyfish exhibit is amazing as well! A must-do is the Humpbacks of Hawai’i exhibit and sphere, where you can sit back and watch humpbacks in 3-D.
HIGHLIGHTS:
Seeing the humpback whales up close.
DAY10
Maui Island
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The Road to Hana
Take the iconic 64-mile Road to Hana, featuring more than 600 curves through lush rainforest, cascading waterfalls, and dramatic coastal scenery. Along the way, you’ll encounter striking red and black sand beaches as you circle the island. Numerous pull-offs invite you to stop for short hikes into the rainforest, where hidden waterfalls and scenic overlooks await. Keep an eye out for the stunning rainbow-painted eucalyptus trees lining portions of the road. At journey’s end, reward yourself with some of Hawai‘i’s best—and most famous—banana bread.
HIGHLIGHTS:
The colorful eucalyptus trees on the way to Hana
DAY11
Maui Island
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Iao Valley State Monument
Drive to the ?Iao Valley State Monument, where you can see the ‘Iao Needle, a stunning, emerald-covered lava rock pinnacle rising from the valley floor. On your way back, stop at the Kepaniwai Park & Heritage Gardens in Wailuku. Enjoy a serene walk through the distinct garden areas representing Hawaii's various immigrant cultures, including beautiful Japanese, Chinese, and Korean sections with pagodas, tea houses, and pavilions.
HIGHLIGHTS:
The beautiful hike to the Iao Needle
DAY12
Hawaii Island
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Hawai‘i Volcanoes National Park
Discover Hawai‘i Volcanoes National Park, home to Mauna Loa—the world’s largest volcano—and Kilauea, one of the most active. Walk through the ancient Nahuku lava tube. Swim alongside majestic manta rays as they glide gracefully through the night waters.
HIGHLIGHTS:
Volcanoes National Park
DAY13
Hawaii Island
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Deep sea fishing and a visit to Hilo
Visit Hilo on the charming, rainier side of the island to see Rainbow Falls, and explore the Kaumana Caves, then stop into the Hilo Farmers Market at the end of the day for some fresh produce. Try some rambutans if they are in season! Charter a boat to go deep sea fishing for Blue Marlin, Yellow fin Tuna (Ahi), Mahi Mahi (Dorado), and Ono (Wahoo).
HIGHLIGHTS:
Deep sea fishing and enjoying freshly caught Mahi Mahi
DAY14
Hawaii Island
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Enjoying the beach at Kona
Before heading home, take time to stroll along the beaches of Kona. Soak in the coastal views, watch for whales breaching offshore during the season, and take in the last of the Hawaiian Aloha spirit.
HIGHLIGHTS:
The Hawaiian Sun
FINAL THOUGHTS
If you are seeking a luxury, multi-island Hawaiian vacation designed just for you. With my experience, your Hawaiian journey becomes more than a vacation—it becomes an effortless, immersive, luxury adventure you’ll cherish for a lifetime.