Insight Vacations
Hawaii with Oahu, Maui & the Big Island - Classic Group
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)
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.
| Day 1 |
Say "Aloha!" to the big city on Oahu's South Shore: Honolulu. This sunny capital city is the main portal to the larger Hawaiian archipelago, and the perfect base for exploring Oahu. Drinking in all the breathtaking scenery is just one part of the Honolulu experience — there's so much more: Waikiki's crescent beach, plus its shopping and dining; the 350-acre volcanic crater Diamond Head (climb to the top for amazing views); and Pearl Harbor National Memorial.
Be sure to take a scenic drive from the South Shore to the North Shore, and experience the Polynesian Cultural Center, the Dole Plantation (think pineapples!), as well as world-class snorkeling, shrimp carts, and shaved ice stands. |
| Day 2 |
Say "Aloha!" to the big city on Oahu's South Shore: Honolulu. This sunny capital city is the main portal to the larger Hawaiian archipelago, and the perfect base for exploring Oahu. Drinking in all the breathtaking scenery is just one part of the Honolulu experience — there's so much more: Waikiki's crescent beach, plus its shopping and dining; the 350-acre volcanic crater Diamond Head (climb to the top for amazing views); and Pearl Harbor National Memorial.
Be sure to take a scenic drive from the South Shore to the North Shore, and experience the Polynesian Cultural Center, the Dole Plantation (think pineapples!), as well as world-class snorkeling, shrimp carts, and shaved ice stands. |
| Day 3 |
Say "Aloha!" to the big city on Oahu's South Shore: Honolulu. This sunny capital city is the main portal to the larger Hawaiian archipelago, and the perfect base for exploring Oahu. Drinking in all the breathtaking scenery is just one part of the Honolulu experience — there's so much more: Waikiki's crescent beach, plus its shopping and dining; the 350-acre volcanic crater Diamond Head (climb to the top for amazing views); and Pearl Harbor National Memorial.
Be sure to take a scenic drive from the South Shore to the North Shore, and experience the Polynesian Cultural Center, the Dole Plantation (think pineapples!), as well as world-class snorkeling, shrimp carts, and shaved ice stands. |
| Day 4 |
Maui is a Hawaiian paradise offering an incredible variety of landscapes, experiences, and cultural traditions. Known for its valleys, beaches, and volcanic peaks, Maui attracts visitors who want to immerse themselves in nature and Hawaiian heritage. The island’s crown jewel is Haleakalā National Park, where the massive dormant volcano provides beautiful scenery and unforgettable sunrise views. Visitors can hike through the park or stargaze under one of the clearest night skies in the world. For beach lovers, Maui’s coastline offers something for everyone. Kaʻanapali Beach, with its soft golden sands and crystal-clear waters, is a favorite for sunbathing and snorkeling. Makena Beach is perfect for those seeking a quieter spot to relax. Surfing, paddleboarding, and even seasonal whale-watching from the shore are common activities on the island. During the winter months, humpback whales migrate to Maui’s warm waters. Maui is also home to one of the most scenic drives in the world: the Road to Hāna. The winding coastal route takes travelers through lush rainforests, past cascading waterfalls, and to charming small towns like Hāna itself. Along the way, stops like the Waiʻānapanapa Black Sand Beach and the Pools of ʻOheʻo (Seven Sacred Pools) provide great views. The journey is just as rewarding as the destination, with plenty of photo opportunities around every bend. The island’s vibrant cultural traditions are another highlight. Luaus invite visitors to experience traditional Hawaiian food, music, and hula dancing. Maui’s farmers' markets and farm-to-table dining options showcase the island’s agricultural riches, including fresh pineapples, macadamia nuts, and locally caught fish like mahi-mahi and ahi tuna. Stopping at small food stands along the way, such as those serving shave ice or banana bread, is a delicious way to explore the island’s flavors. |
| Day 5 |
Maui is a Hawaiian paradise offering an incredible variety of landscapes, experiences, and cultural traditions. Known for its valleys, beaches, and volcanic peaks, Maui attracts visitors who want to immerse themselves in nature and Hawaiian heritage. The island’s crown jewel is Haleakalā National Park, where the massive dormant volcano provides beautiful scenery and unforgettable sunrise views. Visitors can hike through the park or stargaze under one of the clearest night skies in the world. For beach lovers, Maui’s coastline offers something for everyone. Kaʻanapali Beach, with its soft golden sands and crystal-clear waters, is a favorite for sunbathing and snorkeling. Makena Beach is perfect for those seeking a quieter spot to relax. Surfing, paddleboarding, and even seasonal whale-watching from the shore are common activities on the island. During the winter months, humpback whales migrate to Maui’s warm waters. Maui is also home to one of the most scenic drives in the world: the Road to Hāna. The winding coastal route takes travelers through lush rainforests, past cascading waterfalls, and to charming small towns like Hāna itself. Along the way, stops like the Waiʻānapanapa Black Sand Beach and the Pools of ʻOheʻo (Seven Sacred Pools) provide great views. The journey is just as rewarding as the destination, with plenty of photo opportunities around every bend. The island’s vibrant cultural traditions are another highlight. Luaus invite visitors to experience traditional Hawaiian food, music, and hula dancing. Maui’s farmers' markets and farm-to-table dining options showcase the island’s agricultural riches, including fresh pineapples, macadamia nuts, and locally caught fish like mahi-mahi and ahi tuna. Stopping at small food stands along the way, such as those serving shave ice or banana bread, is a delicious way to explore the island’s flavors. |
| Day 6 |
Maui is a Hawaiian paradise offering an incredible variety of landscapes, experiences, and cultural traditions. Known for its valleys, beaches, and volcanic peaks, Maui attracts visitors who want to immerse themselves in nature and Hawaiian heritage. The island’s crown jewel is Haleakalā National Park, where the massive dormant volcano provides beautiful scenery and unforgettable sunrise views. Visitors can hike through the park or stargaze under one of the clearest night skies in the world. For beach lovers, Maui’s coastline offers something for everyone. Kaʻanapali Beach, with its soft golden sands and crystal-clear waters, is a favorite for sunbathing and snorkeling. Makena Beach is perfect for those seeking a quieter spot to relax. Surfing, paddleboarding, and even seasonal whale-watching from the shore are common activities on the island. During the winter months, humpback whales migrate to Maui’s warm waters. Maui is also home to one of the most scenic drives in the world: the Road to Hāna. The winding coastal route takes travelers through lush rainforests, past cascading waterfalls, and to charming small towns like Hāna itself. Along the way, stops like the Waiʻānapanapa Black Sand Beach and the Pools of ʻOheʻo (Seven Sacred Pools) provide great views. The journey is just as rewarding as the destination, with plenty of photo opportunities around every bend. The island’s vibrant cultural traditions are another highlight. Luaus invite visitors to experience traditional Hawaiian food, music, and hula dancing. Maui’s farmers' markets and farm-to-table dining options showcase the island’s agricultural riches, including fresh pineapples, macadamia nuts, and locally caught fish like mahi-mahi and ahi tuna. Stopping at small food stands along the way, such as those serving shave ice or banana bread, is a delicious way to explore the island’s flavors. |
| Day 7 |
Located on the island of Maui, Kahului serves as the island's vibrant commercial hub and a gateway to many of its top attractions, offering visitors an exciting blend of local culture, historic sites, and easy access to Maui’s stunning landscapes. The town is a short drive from some of the island’s most striking destinations, including the majestic Haleakalā National Park and the nearby Hana Highway, with its lush rainforests and hidden waterfalls. For those looking to enjoy the island's coastline, Kahului’s beaches won’t disappoint. Kanaha Beach Park, located just outside of town, is a prime spot for watersports like windsurfing, kitesurfing, and stand-up paddleboarding. The gentle waters make it an ideal location for beginners, while more seasoned adventurers can take advantage of the area’s windy conditions. Nearby, the Maui Ocean Center offers a fascinating glimpse into the diverse marine life that inhabits the waters around Maui. With exhibits showcasing everything from sea turtles to vibrant coral reefs, it’s a great way for families and visitors of all ages to learn more about the island’s underwater world. The dining scene in Kahului is another highlight, with a strong emphasis on local ingredients and fresh seafood. Popular Hawaiian dishes like the "plate lunch" and Maui's iconic poke bowls are bursting with island flavors and are staples that shouldn’t be missed. |
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| Day 10 |
Kailua-Kona, a picturesque seaside town on the west coast of Hawaii's Big Island, is a haven for travelers seeking both adventure and tranquility. Known simply as "Kona" to locals, this vibrant destination is celebrated for its rich history, volcanic landscapes, and inviting beaches. Kailua-Kona's iconic oceanfront Ali'i Drive is the heartbeat of the town, lined with charming shops, art galleries, and a plethora of dining options that range from fresh seafood to authentic Hawaiian cuisine. The town’s year-round sunny weather makes it perfect for snorkeling in crystal-clear waters, exploring ancient Hawaiian temples, or simply relaxing on the white sands of Kamakahonu Beach. For history enthusiasts, Kailua-Kona offers a fascinating glimpse into Hawaii's past. The town is home to the historic Hulihe‘e Palace, once the summer residence of Hawaiian royalty. Today, the palace serves as a museum showcasing Victorian artifacts from the era of King Kalākaua and Queen Kapi‘olani, offering a unique window into Hawaii's royal heritage. Nearby, the Mokuaikaua Church, the oldest Christian church in Hawaii, stands as a testament to the island's cultural crossroads. Built in 1820 from lava rock and coral, this church tells the story of early missionaries who arrived on Hawaiian shores. Adventure awaits just beyond the town’s borders. The clear waters off Kailua-Kona are known for some of the best snorkeling and diving spots in the Hawaiian Islands, especially at Kealakekua Bay, where you can swim among vibrant coral reefs teeming with tropical fish and even spot spinner dolphins. For a truly unforgettable experience, embark on a night dive or snorkel tour to see the majestic manta rays that glide gracefully through the waters—a mesmerizing encounter that has been called one of the world's most awe-inspiring underwater adventures. A fun fact about Kailua-Kona is that it is home to the world-famous Kona coffee, considered among the best in the world. The fertile volcanic slopes of the nearby Kona coffee belt provide the ideal conditions for cultivating this premium coffee, renowned for its smooth flavor and rich aroma. Visitors can tour local coffee farms to learn about the unique production process, sample freshly brewed Kona coffee, and even take part in the annual Kona Coffee Cultural Festival, celebrating the island's coffee heritage with parades, tastings, and farm tours. Whether you’re savoring a cup of Kona coffee, exploring historic landmarks, or diving into the deep blue sea, Kailua-Kona offers an authentic taste of the Hawaiian spirit. |
| Travel Dates | Price | ||
|---|---|---|---|
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01/24/26 - 12/05/26 |
Starting At $6,950 |
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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.
