Hawaii with Oahu, Maui & the Big Island - Classic Group

Hawaii’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 (D)
- 9 Breakfast (B)
- 3 Lunch (L)
- Choose between two carefully selected activities
- Maui: Visit 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.
- 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.
- 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.
- Maui: Visit 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.
- 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.
- 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.
- 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 366 m (1,200 ft) 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.
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ID: 9001734
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ID: 8923392
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ID: 9000231
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ID: 9001734
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Find the journey right for you with our selection of tour styles. Whether you're looking to see a number of destinations in a single tour, explore a single destination in depth or you want to take the road less traveled, we have the perfect holiday for you.
Discovery Journeys
Discovery Journeys are the ideal style for first-time travelers, showing you the very best your destination has to offer. Each tour will introduce you to multiple countries in one journey.
Regional Journeys
Travel deeper by picking one place that you’ve always longed to visit. Our Regional Journeys are carefully planned to let you explore one region or country in depth, in order to really know its people, traditions and culture.
Country Roads
Step off the beaten track and discover a different side of your destination. Steering clear of the well-trodden tourist trail, our Country Roads program sends you off to hidden retreats and unexpected adventures with lots of local flavor.
Easy Pace
Love full days at leisure while on holiday? Take more time to explore on your own, with a minimum of three nights in each destination and plenty of free time - including more Relaxed Starts - built into the itinerary.
Special Interest Tours
Explore our collection of Special Interest Tours that are themed around particular local festivals, events or cultural interests. These tours include stops at the Chelsea Flower Show in England, Oktoberfest in Germany and more.
Group Travel
Private Custom Groups
We offer the option to customize your own group tour. Our dedicated team of travel experts will create a tailor-made itinerary to suit your needs.
Groups on Set Departures
Pricing Scales to your group size. Our group sizes have no upper limits and our competitive pricing scales according to your group size and your budget.
Our history of traveling sustainably
OVER A DECADE OF POSITIVE IMPACT
There are few things more stylish and elegant than being a responsible tourist. That's why sustainable and responsible tourism is at the heart of what we do. As a premium travel brand, we recognize that it's our duty to set the right example. We work diligently to leave a positive impact on the planet, its people, and its wonderful wildlife. To cement our commitment, we created our 5-year How We Tread Right sustainability strategy and our not-for-profit organization, the TreadRight Foundation.
OUR COMMITMENT
- Sustainability and conservation: We ensure that we’re protecting our invaluable landscapes and natural resources.
- Cultural preservation: We ensure that the true economic benefit of travel is felt by local communities.
- Protection of our world’s wildlife: We advocate for the highest standard of ethical wildlife experiences.
Our 5-year sustainability strategy
HOW WE TREAD RIGHT
Our 5-year How We Tread Right sustainability strategy is based on 11 measurable goals anchored to the United Nations Sustainable Development Goals, which address the issues of climate change, sustainable food production, waste reduction, travel experiences, diversity and inclusion, and wildlife.
By traveling with Insight Vacations, you're supporting a responsible travel company that truly works hard to make a difference.
How you have a positive impact
MAKE TRAVEL MATTER®️ Experiences
Travel is education and experience is the best teacher. Our MAKE TRAVEL MATTER®️ Experiences teach you about the world all while making it better. Whether that's through supporting local economies, preserving age-old traditions, or advancing conservation efforts for native ecosystems. Find out more about how you can be a truly sustainable traveler.
Climate Action
OUR JOURNEY TO NET ZERO
Since the inception of our sustainability strategy, the global community has continued to rally in response to the urgent need for climate action. We're committed to achieve net zero greenhouse gas (GHG) emissions by the year 2050. Our dedication to this goal is outlined in our Climate Action Plan, with science-based targets that address our carbon footprint. We are proud of the fact that, alongside our sister brands, we became the first global tour operator to have near-term, long-term and net zero targets that are validated by the Science Based Target initiative (SBTi). Gain a deeper insight into our Climate Action Plan and how we're meeting our targets.
Our strategic plan
DIVERSITY, EQUITY AND INCLUSION
We believe diversity is the foundation of meaningful travel. We set out with a curious mind, and the desire to meet new people, hear fresh perspectives and experience different cultures. Embracing and empowering diversity, equity and inclusion in all areas of life requires a conscious effort – whether at home, at work, or in our communities.
At the Travel Corporation (TTC), our Diversity, Equity and Inclusion (DEI) journey started many years ago, with the development of our DEI strategy. We’ve formalized goals in the following areas: People & Culture, Product & Experiences, and Marketing & Communications, to ensure we’re upholding our end.
Find the journey right for you with our selection of tour styles. Whether you're looking to see a number of destinations in a single tour, explore a single destination in depth or you want to take the road less traveled, we have the perfect holiday for you.
Discovery Journeys
Discovery Journeys are the ideal style for first-time travelers, showing you the very best your destination has to offer. Each tour will introduce you to multiple countries in one journey.
Regional Journeys
Travel deeper by picking one place that you’ve always longed to visit. Our Regional Journeys are carefully planned to let you explore one region or country in depth, in order to really know its people, traditions and culture.
Country Roads
Step off the beaten track and discover a different side of your destination. Steering clear of the well-trodden tourist trail, our Country Roads program sends you off to hidden retreats and unexpected adventures with lots of local flavor.
Easy Pace
Love full days at leisure while on holiday? Take more time to explore on your own, with a minimum of three nights in each destination and plenty of free time - including more Relaxed Starts - built into the itinerary.
Special Interest Tours
Explore our collection of Special Interest Tours that are themed around particular local festivals, events or cultural interests. These tours include stops at the Chelsea Flower Show in England, Oktoberfest in Germany and more.
Group Travel
Private Custom Groups
We offer the option to customize your own group tour. Our dedicated team of travel experts will create a tailor-made itinerary to suit your needs.
Groups on Set Departures
Pricing Scales to your group size. Our group sizes have no upper limits and our competitive pricing scales according to your group size and your budget.
Our history of traveling sustainably
OVER A DECADE OF POSITIVE IMPACT
There are few things more stylish and elegant than being a responsible tourist. That's why sustainable and responsible tourism is at the heart of what we do. As a premium travel brand, we recognize that it's our duty to set the right example. We work diligently to leave a positive impact on the planet, its people, and its wonderful wildlife. To cement our commitment, we created our 5-year How We Tread Right sustainability strategy and our not-for-profit organization, the TreadRight Foundation.
OUR COMMITMENT
- Sustainability and conservation: We ensure that we’re protecting our invaluable landscapes and natural resources.
- Cultural preservation: We ensure that the true economic benefit of travel is felt by local communities.
- Protection of our world’s wildlife: We advocate for the highest standard of ethical wildlife experiences.
Our 5-year sustainability strategy
HOW WE TREAD RIGHT
Our 5-year How We Tread Right sustainability strategy is based on 11 measurable goals anchored to the United Nations Sustainable Development Goals, which address the issues of climate change, sustainable food production, waste reduction, travel experiences, diversity and inclusion, and wildlife.
By traveling with Insight Vacations, you're supporting a responsible travel company that truly works hard to make a difference.
How you have a positive impact
MAKE TRAVEL MATTER®️ Experiences
Travel is education and experience is the best teacher. Our MAKE TRAVEL MATTER®️ Experiences teach you about the world all while making it better. Whether that's through supporting local economies, preserving age-old traditions, or advancing conservation efforts for native ecosystems. Find out more about how you can be a truly sustainable traveler.
Climate Action
OUR JOURNEY TO NET ZERO
Since the inception of our sustainability strategy, the global community has continued to rally in response to the urgent need for climate action. We're committed to achieve net zero greenhouse gas (GHG) emissions by the year 2050. Our dedication to this goal is outlined in our Climate Action Plan, with science-based targets that address our carbon footprint. We are proud of the fact that, alongside our sister brands, we became the first global tour operator to have near-term, long-term and net zero targets that are validated by the Science Based Target initiative (SBTi). Gain a deeper insight into our Climate Action Plan and how we're meeting our targets.
Our strategic plan
DIVERSITY, EQUITY AND INCLUSION
We believe diversity is the foundation of meaningful travel. We set out with a curious mind, and the desire to meet new people, hear fresh perspectives and experience different cultures. Embracing and empowering diversity, equity and inclusion in all areas of life requires a conscious effort – whether at home, at work, or in our communities.
At the Travel Corporation (TTC), our Diversity, Equity and Inclusion (DEI) journey started many years ago, with the development of our DEI strategy. We’ve formalized goals in the following areas: People & Culture, Product & Experiences, and Marketing & Communications, to ensure we’re upholding our end.
About Insight Vacations

PREMIUM TOURS FOR CURIOUS TRAVELERS
Insight Vacations is a premium tour operator that promises a superior experience from start to finish, with an elevated level of detail and attention at every step. Discover more about the Insight Vacations premium travel experience.
PREMIUM EXPERIENCES
Exclusive, crafted experiences that get you up close and personal to every destination. Enjoy Insider Access before and after opening-hours and skip the line access at key sights. Take your pick from one, two or three curated Insight Choice experiences. Plus, Insightful Encounters with Local Experts and Specialists that add even more life, color and storytelling for a truly enlightening experience.
PREMIUM DINING
Whether you’re being welcomed into the workspaces of chefs or taking your seat at top-rated restaurants, you’ll find yourself dining on regional favorites with a seasonal twist. Take your seat for wine-paired meals and enjoy indulging your preferences from a curated choice of restaurants on Dine-Around evenings. Get hands-on with Cooking Demonstrations and enjoy an industry-leading vegetarian offering at every mealtime.
About Insight Vacations

PREMIUM TOURS FOR CURIOUS TRAVELERS
Insight Vacations is a premium tour operator that promises a superior experience from start to finish, with an elevated level of detail and attention at every step. Discover more about the Insight Vacations premium travel experience.
PREMIUM EXPERIENCES
Exclusive, crafted experiences that get you up close and personal to every destination. Enjoy Insider Access before and after opening-hours and skip the line access at key sights. Take your pick from one, two or three curated Insight Choice experiences. Plus, Insightful Encounters with Local Experts and Specialists that add even more life, color and storytelling for a truly enlightening experience.
PREMIUM DINING
Whether you’re being welcomed into the workspaces of chefs or taking your seat at top-rated restaurants, you’ll find yourself dining on regional favorites with a seasonal twist. Take your seat for wine-paired meals and enjoy indulging your preferences from a curated choice of restaurants on Dine-Around evenings. Get hands-on with Cooking Demonstrations and enjoy an industry-leading vegetarian offering at every mealtime.