9-Nights Hawaii with Oahu, Maui & the Big Island - Small Group from $6,563

Insight Vacations

OFFER ID 1556456

Hawaii With Oahu, Maui & The Big Island - Small 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)

Choice Highlights

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.

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: 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.

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

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.

9 nights from $6,563 per person

Itinerary

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Itinerary Details

Insight Vacations: Hawaii with Oahu, Maui & the Big Island - Small Group

Day 1 - Aloha Hawaii
After your arrival at Honolulu Airport, the traditional lei greeting at your Travel Director's Welcome Desk kicks off your Hawaii vacation. Your hotel during your time on Oahu was the setting for Blue Hawaii, Elvis Presley’s 1961 movie and it is the birthplace of the legendary cocktail of the same name. Tonight, join your Travel Director and fellow travelers for a dinner.
Accommodations: Hilton Hawaiian Village Waikiki Beach Resort, Oahu
Meals: Dinner

Day 2 - Pearl Harbor Relaxed Start
Enjoy a relaxed start this morning followed by a visit to the Pearl Harbor National Memorial, commemorating the tragic day of December 7th 1941. Walk through the Visitor Center and take a short boat ride to the USS Arizona Memorial, the final resting place of 1,102 sailors and marines. USS Arizona tickets are subject to NPS; ticket timing availability not known until the day before visit. Spend time at the superb visitor center and explore exhibits that recount the events that led the US to join World War II. As part of today's adventure, you'll see the Punchbowl National Memorial Cemetery of the Pacific. It honours all those who served in the US Armed Forces and lost their lives during WWII, the Korean War and the Vietnam War. Return to Waikiki and spend the rest of your day at leisure.
Accommodations: Hilton Hawaiian Village Waikiki Beach Resort, Oahu
Meals: Breakfast

Day 3 - A Trip Around Oahu Relaxed Start
After a relaxed start this morning, set out to explore Oahu on an exciting island tour. Take in the epic views from Pali Lookout towards the Kaneohe Bay and the Windward Coast. The valley below was the scene of a bloody battle in 1795 when King Kamehameha I extended his rule over the island with an army of 10,000 men. Journey beneath the towering Ko’olau Cliffs and along the rugged coastline. Join a MAKE TRAVEL MATTER® Experience with your Local Expert in a Hawaiian Legacy Forest and partake in the sacred planting ceremony of a native tree contributing to the healing of the local ecosystem. Delve into an al fresco, sustainably sourced picnic lunch while enjoying views of the Legacy Forest. Continue to North Shore where in the winter months waves can reach 30ft making it a favorite spot among big wave surfers worldwide. Visit Haleiwa, the social and artistic hub of the North Shore. Stroll among small boutiques and plantation-era buildings to soak up the laid-back ambiance. Finally, return to Waikiki after your eventful day and enjoy your evening at leisure.
Accommodations: Hilton Hawaiian Village Waikiki Beach Resort, Oahu
Meals: Breakfast, Lunch

Day 4 - Maui, the Valley Isle
Take a short flight to Kahului on Maui. This slice of Hawaiian island paradise offers magnificent nature and a wide variety of activities. Visit the awe-inspiring Iao Valley State Park and see the 1,200-foot landmark Iao Needle. This green-mantled rock outcropping overlooks sacred lands and was used as a burial site for Hawaii’s chiefs for centuries. In the evening 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, dance and storytelling, or one of the resort’s other acclaimed restaurants.
Accommodations: The Westin Maui Resort & Spa, Ka'anapali Beach, Maui
Meals: Breakfast, Dinner

Day 5 - Upcountry Maui
This morning, head to Upcountry Maui and discover a different face of the island. Visit one of the last working pineapple farms with a fun and knowledgeable Local Expert. Discover the deep impact these plantations had on the islands and sample some of the extra sweet Maui Gold variant. At its peak, Hawaii produced 75% of the world’s pineapples and the tropical fruit became a symbol for the state. Next we indulge in a Farm-to-Table lunch at the Hali’imaile General Store. Originally a plantation shop in the early 20th century, the restaurant is known for its outstanding island cuisine. Return to your resort and spend the evening at your leisure.
Accommodations: The Westin Maui Resort & Spa, Ka'anapali Beach, Maui
Meals: Breakfast, Lunch

Day 6 - Insight Choice in Maui
Explore Maui with Insight Choice. Choose to experience sunrise at Haleakala National Park, offering an astonishing volcanic landscape. Hear the Hawaiian legends about the active volcano and see the unique Haleakala Silversword plant. Alternatively, cruise to the scenic coastline of Lana'i island and snorkel a dazzling coral reef, home to abundant sea life. Tonight, get together with your Travel Director and fellow travelers for dinner.
Accommodations: The Westin Maui Resort & Spa, Ka'anapali Beach, Maui
Meals: Breakfast, Dinner

Day 7 - To the Big Island
Take a short flight to Hawai’i, the largest island of the archipelago. Upon arrival, spend time in easy-going Kailua-Kona, once the home of Kamehameha I, Hawaii’s great ruler. Travel from the beach to the coffee growing area of Kona and join a Local Expert to learn about Kona coffee. Enjoy a tasting of this gourmet specialty that only grows on the slopes of two local active volcanoes. See native plants, fruits and the organic coffee fields on your tour around the plantation. Continue to your luxurious resort accommodation and enjoy the rest of your day at leisure.
Accommodations: Hilton Waikoloa Village, Island of Hawai'i
Meals: Breakfast

Day 8 - The Volcanoes of Hawaii
After a relaxed start, get ready for an unforgettable journey to the volcano. After a luscious lunch enter the UNESCO World Heritage listed Hawai'i Volcanoes National Park. Hear the legends of Pele, the goddess of volcanoes and fire and the creator of the Hawaiian Islands. Stop by the magical Rainbow Falls on your way back to your resort.
Accommodations: Hilton Waikoloa Village, Island of Hawai'i
Meals: Breakfast, Lunch

Day 9 - A Day to Relax Relaxed Start
Enjoy a Relaxed Start and spend the day on island time, relaxing under the swaying palms. Lounge by the pool, enjoy a spa treatment, or snorkel in the local lagoon looking for the rare green sea turtles that call these waters home. Tonight, come together for dinner and toast to your travels.
Accommodations: Hilton Waikoloa Village, Island of Hawai'i
Meals: Breakfast, Dinner

Day 10 - Farewell Hawaii
Bid farewell to your fellow travelers and new friends and depart at leisure to the Kona airport filled with new memories and stories.
Meals: Breakfast

Featured Destinations

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.

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).

Oahu

Vacation Details

Valid Date Ranges

09/19/2026 - 09/28/2026

from $6,563 per person

* This departure has been designated a guaranteed departure by the operator, meaning that the minimum number of guests has been met, although still subject to weather and other conditions.

Prices Start At

from $6,563 per person

Length

9 Nights

Air City

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Vacation Rating

Deluxe

Remarks

Trip prices are per person, land only, based on double occupancy and reflect applicable discounts. Trip prices and discounts are subject to change. Airfare is additional. Tour prices, dates and itineraries are correct at the time of the website going live, however are subject to confirmation at the time of booking. Other restrictions may apply.

All fares are quoted in US Dollars.

OFFER ID

1556456

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