Insight Vacations
Hawaii With Oahu, Maui & The Big Island - Classic GroupHawaii’s traditional greeting, Aloha, embodies hospitality, respect, love and welcome. Experience the magic of these tropical islands and meet its gentle people on your unforgettable Hawaiian guided vacation. Look beyond the swaying hula dancers, ukuleles and floral shirts to celebrate local traditions and flavors. An incredible journey awaits as you get to know Oahu and Maui intimately while having time to relax at your oceanfront resorts.
Dining Summary- 4 Dinner with Wine (DW)
- 9 Breakfast (B)
- 3 Lunch (L)
Choice Highlights- Choose between two carefully selected activities
- Maui: Choose to visit the Haleakala National Park offering an astonishing volcanic landscape.
- Maui: Cruise to the scenic coastline of Lana i island and snorkel a dazzling coral reef, home to abundant sea life. Wild dolphins are found in bays and offshore, including acrobatic spinner dolphins, friendly bottlenose dolphins, and curious spotted dolphins. Sightings of humpback whales are also common from December to April.
Additional Included Highlights- Prices included economy inter-island airfares and all related charges for Honolulu - Kahului and Kahului - Kona. Flights are subject to change without notice until time of booking. Inter-island airlines charge a baggage handling fee of USD $25 per first checked suitcase on each inter-island flight. This fee is not covered by the prices is the responsibility of the guest. See Terms and Conditions for details.This trip experiences high elevations, we recommend guests with preexisting medical conditions talk with a doctor prior to travel.
Authentic Dining- Oahu: Dive into an al fresco, sustainably sourced Farm-to-Table lunch while enjoying epic views of the North Shore.
- Maui: You are invited to choose your own dining experience from a selection of restaurants for your Dine-Around evening. Your options include a magical evening at the Wailele Luau for a taste of traditional Polynesian cuisine and dance or one of your resort’s other acclaimed restaurants.
- Maui: If there were an award for "exceptional Maui restaurant in the unlikeliest of locations," Hali'imaile General Store would definitely take the cake. Instead, this longtime Maui dining classic has been lauded as everything from "Best Hawaiian Regional" to "Best Restaurant on Maui." Chef Beverly Gannon is Maui's favorite chef, bar none. One of Hawaii's most heralded chefs, this restaurant has drawn dining aficionados from around the world for over 32 years, as well as locals. Maui’s original farm-to-table restaurant, the menu exclusively features locally sourced Hawaiian produce, meats and products. Our dishes are an unique blend of fresh Hawaiian flavors, local Asian influences, and modern preparations.
Insight Choice- Maui: Choose to visit the Haleakala National Park offering an astonishing volcanic landscape.
- Maui: Cruise to the scenic coastline of Lana i island and snorkel a dazzling coral reef, home to abundant sea life. Wild dolphins are found in bays and offshore, including acrobatic spinner dolphins, friendly bottlenose dolphins, and curious spotted dolphins. Sightings of humpback whales are also common from December to April.
Insight Experiences- Maui: Visit one of the last working pineapple farms with a fun and knowledgeable Local Expert. Discover the impact these plantations had on the islands and sample some of the extra sweet Maui Gold variant.
- Kona: Join a Local Expert to learn about incredible Kona coffee. Enjoy a tasting of this gourmet specialty and see native plants, fruits and the organic coffee fields on your tour around the plantation.
Make Travel Matter- Oahu: MAKE TRAVEL MATTER® as you join an eco-tour with your Local Expert in a Hawaiian Legacy Forest and plant a native tree contributing to the healing of the local ecosystem. Your experience advances UN Global Goal 15: Life on Land.
Top Rated Highlights- Maui: Visit Ioa Valley State Park, burial site of Hawaii's chiefs for centuries
- Honolulu: Visit Pearl Harbor and step aboard the USS Arizona Memorial and recount the events that led the US to join World War II.
- Honolulu: See the Punchbowl National Memorial Cemetery of the Pacific, honoring all those who served in the US Armed Forces and lost their lives during World War II, the Korean War and the Vietnam War.
- Oahu: On your journey around Oahu take in epic views from Pali Lookout. Travel beneath the towering Ko’olau Mountains and along the rugged Windward Coast. Reach the North Shore and visit Haleiwa, the social and artistic hub of the North Shore.
- Maui: Visit the awe-inspiring Iao Valley State Park and see the 1,200-foot (366 meter) landmark Iao Needle, overlooking the final resting place of Hawaii’s native chiefs.
- Hawaii: Visit the UNESCO World Heritage listed Hawai'i Volcanoes National Park. Take in sights along Crater Rim Drive for views of the Kilauea Caldera.
Featured Destinations
The Island of Hawaii
The Island of Hawaii
Twice as large as all of the other major Hawaiian Islands combined, the The Island of Hawaii (the Big Island) is also the youngest of the island chain. At some 800,000 years of age, it's also still growing. The Hawaii Volcanoes National Park contains one of the world's most active volcanoes which continues to pour into the sea adding to the shoreline. From its snow capped peaks to its black, white and green sand beaches the island is really a study in contrasts. Rocky deserts and lush rainforests. Peaceful bays and rolling pasture land. Luxurious orchids and waterfalls on the windward side, and areas on the western slopes where the world famous Kona coffee is grown. The Island of Hawaii is the place for adventure. Horseback riding in Waimea. Golf everywhere. Snow skiing (really!) at Mauna Kea. The ocean is gorgeous at any time of year. Kona is the marlin fishing capital of the Pacific. Or maybe the quaint shops and restaurants of Hilo, will be enough to keep you thoroughly entertained. The Big Island is also the place for history. All over the island you'll see petroglyphs, and heiau, ancient places of worship. The royal summer palace and the first Christian church in Hawaii will take you back in time. From the rainbows and waterfalls of the windward side to the sun drenched beaches of the Kona/Kohala Coast, the Big Island is vibrant and alive. And wherever you go, you'll find the spirit of Aloha. Of course, you'll find all of the amenities, attractions, activities, and accommodations that will fit any pocketbook and life style. You'll also find a physical beauty, a depth of cultural heritage, and a spiritual warmth that is without equal. Whatever you're looking for in a Hawaiian vacation, the Island of Hawaii offers some great moments that could last a lifetime. Because Hawaiian weather varies very little throughout the year, the weather you'll experience on the Big Island depends more on location than time of year. The wide variety of climates and the resulting range of temperatures and rainfall across the island are due primarily to differences in elevation and exposure to the moist northeasterly trade winds. The average day-time temperature in the coastal resort areas ranges from the mid 80's (29.4 C)in the summer months of May to October to the mid to low 70's (23.9-26.1 C) during the winter months of November to April.
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Destination Guide
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Oahu
Oahu
Oahu is "The Gathering Place." It has more hotels, more restaurants, and more major attractions than all of the other islands put together. Our major city, Honolulu, is here. So is the "World's Best Beach" at Waikiki.
Honolulu is sophisticated, lively, and breathtaking. It has more in the way of arts, culture, and entertainment. It has an abundance of galleries, nightclubs, and museums, a major zoo, aquarium, Iolani Palace (the only royal palace on U.S. soil), Pearl Harbor, the Arizona Memorial... the list goes on and on.
The day-time high temperatures in Honolulu during the summer range from an average of 85 to 87 degrees F (29.4-30.6 C) with night-time lows of 70 to 74 (21.1-23.3 C). Winter day-time high temperatures in the city are 70 to 74 degrees F (21.1-23.3 C) and night-time lows are 65 to 69 degrees (18.3-20.6 C). Travelers may want to pack a light jacket and pants for strolling on the cooler winter evenings. Hikers planning to trek through some of Oahu's higher elevations should be aware that there is a 3.5 degree drop in temperature for every thousand foot rise above sea level. Its a good idea then to carry along a couple of layers of light clothing for these higher elevations, especially in the winter months.
No other American city could offer you the opportunity to surf the world's biggest waves, snorkel a lagoon, hike into a dormant volcano, golf at a dozen championship courses, and catch the sunset from a five-star restaurant. All within an hours drive of your hotel room.
The key to enjoying Oahu, as with most of the islands, is mobility. The Bus circles the island for only a dollar. Or rent a car and get out to see the 'real' Hawaii... the gentle waterfalls, and the craggy peaks. Discover the 'undiscovered' beaches. Boogey board at Makapuu. Ride a horse at Turtle Bay. Watch the surfers at the Pipeline. Or sample a little fresh pineapple juice. Have fun! Get wet! This is Hawaii. It's an adventure!
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Destination Guide
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Maui
Maui
Travelers who can go anywhere in the world come back to Maui again and again, because their Maui moments are some of the most treasured of their lives. The majestic leaps of Maui's humpback whales are the perfect symbol for the magic of this island, where natural wonders set your spirit free and the warm aloha of Maui's people fills your heart with a sense of belonging.
Maui's prime resort areas are Kapalua, Kaanapali, Kihei, Wailea and Makena. Strung like jewels on the sunny western and southern shores of Maui, they offer pristine beaches and a wide range of hotel and condominium accommodations. At serene, secluded Hana, you'll discover Hawaii the way it used to be.
The best golf in paradise is yours to enjoy on Maui. There are challenges for players of all skill levels and incredible views no matter where you play, from the public courses to the championship layouts of Maui's Golf Coast. Plus, nowhere else in the world will you find the array of oceansports and activities that Maui offers.
Then there are the 42 miles of world famous beaches, ranging Only on Maui... from the little jewel of Red Sand Beach to the black sand beach at Waianapanapa State Park. The best snorkeling is at Honolua Bay or the small islet of Molokini, a submerged crater.
For the nature enthusiast, Maui has breathtaking hiking trails. The Hawaii Nature Center in Iao Valley is a good starting place. The rangers at Haleakala National Park lead free nature walks, both at the 10,000 foot summit of Maui's awe-inspiring, long-dormant volcano and at Oheo Gulch with its famous Seven Pools.
One of the best ways to experience Upcountry Maui is on horseback. The green pastures and sweeping vistas will remind you of range land in Wyoming. And Makawao town provides a taste of the "Old West."
Discover the fascinating artifacts of Maui's ancient culture at the Bailey House Museum or explore the island's heiau ruins (Hawaiian religious temples). If you get a chance, don't miss the performance of hula kahiko (ancient hula) by one of Maui's hula halau (hula schools).
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Destination Guide
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Valid Date Ranges
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March 2025
| 03/01/2025 |
03/10/2025 |
$6,306 per person
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| 03/15/2025 |
03/24/2025 |
$5,706 per person
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| 03/22/2025 |
03/31/2025 |
$5,706 per person
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April 2025
| 04/05/2025 |
04/14/2025 |
$6,306 per person
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May 2025
| 05/03/2025 |
05/12/2025 |
$6,306 per person
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| 05/10/2025 |
05/19/2025 |
$6,306 per person
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June 2025
| 06/14/2025 |
06/23/2025 |
$6,306 per person
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| 06/28/2025 |
07/07/2025 |
$6,306 per person
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July 2025
| 07/12/2025 |
07/21/2025 |
$6,306 per person
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| 07/26/2025 |
08/04/2025 |
$6,306 per person
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August 2025
| 08/09/2025 |
08/18/2025 |
$6,306 per person
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| 08/23/2025 |
09/01/2025 |
$6,306 per person
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September 2025
| 09/06/2025 |
09/15/2025 |
$6,306 per person
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| 09/13/2025 |
09/22/2025 |
$6,306 per person
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