Hawaii is a tropical paradise with six unique and distinct islands, each with its own character, history, and attractions. Island hopping is a great way to experience the best of what Hawaii has to offer, from lush rainforests and breathtaking beaches to towering volcanoes and stunning waterfalls. Here’s a 10-day itinerary for island hopping in Hawaii, so you can explore the best of each island.
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Start Your Hawaii Vacation Itinerary in Oahu!
Start your journey on the island of Oahu, home to the state capital of Honolulu, the famous Waikiki Beach, and historic Pearl Harbor. Spend your first day exploring the city and the surrounding beaches, then head to the North Shore the next day to watch the world-renowned surfers ride the waves at Sunset Beach or the Bonzai Pipeline.
The First Day in Hawaii!
Start your day at the famous Waikiki Beach, located in the heart of Honolulu. Enjoy a leisurely morning on the beach or take a surf lesson. Waikiki is one of the best spots in Hawaii to learn to surf, with gentle waves and a variety of surf schools and rental shops available. After working up an appetite, grab brunch at one of the many beachside cafes, such as Hula Grill or Duke’s Waikiki.
After brunch, visit the nearby Honolulu Zoo, home to over 900 animals from around the world, including Komodo dragons, orangutans, and Hawaiian monk seals. If you’re traveling with children, the zoo also offers interactive exhibits and a petting zoo.
In the afternoon, visit the iconic Diamond Head State Monument. This volcanic crater is one of the most recognizable landmarks in Hawaii and offers breathtaking views of Waikiki and the Pacific Ocean. The hike to the top is moderate and takes about an hour, so be sure to bring plenty of water and wear comfortable shoes.
End your day with a visit to the historic Pearl Harbor National Memorial, where you can pay your respects at the USS Arizona Memorial and learn about the attack that launched the United States into World War II. The museum features exhibits and artifacts, as well as a documentary film about the events of December 7, 1941.
Day Number Two: North Shore
Begin your second day with a visit to the North Shore, home to some of the world’s best surfing beaches. Stop at the charming town of Haleiwa, where you can browse the galleries and shops, and enjoy breakfast at one of the local cafes, such as Coffee Gallery or Beet Box Cafe.
After breakfast, head to Waimea Bay, where you can watch surfers ride the massive waves during the winter months. If you’re feeling adventurous, you can even take a surf lesson with one of the local surf schools.
In the afternoon, visit the Polynesian Cultural Center, where you can learn about the rich culture and traditions of Hawaii and the Pacific Islands. The center features six different island villages, each with its own unique performances and exhibits. Be sure to catch the evening show, “Ha: Breath of Life,” which features a stunning display of Polynesian dance and music.
End your day with a visit to the Kualoa Ranch, a working cattle ranch that offers a variety of outdoor activities, including horseback riding, ATV tours, and zip lining. The ranch has been used as a filming location for many movies and TV shows, including “Jurassic Park” and “Lost,” and offers a behind-the-scenes tour of its Hollywood history.
…Then It’s On To Maui!
Fly to Maui, the second-largest island in the Hawaiian chain, known for its pristine beaches, waterfalls, and world-class resorts. Start your Maui adventure in the charming town of Lahaina, where you can stroll the streets and browse the galleries and shops. Then, take a scenic drive on the Road to Hana, a 64-mile stretch of winding roads, waterfalls, and breathtaking views.
Day Three: The Maui Portion
Start your the Maui portion of your Hawaii Vacation Itinerary in the charming town of Lahaina, located on the west coast of the island. Lahaina was once a bustling whaling town, and you can learn about its history at the Lahaina Whaling Museum or take a whale watching tour during the winter months. Stroll the streets and browse the galleries and shops, or simply relax on the beach and soak up the sun. You can also enjoy lunch or dinner at one of the many restaurants in town, such as Fleetwood’s on Front St., owned by musician Mick Fleetwood.
After exploring Lahaina, head to Ka’anapali Beach, one of the most popular beaches on Maui. Relax on the golden sand, swim in the crystal-clear waters, or take a stroll along the beachwalk. You can also explore the nearby Black Rock, a lava formation that juts out into the sea and is a popular spot for snorkeling and diving.
End your day with a sunset dinner at the famous Mama’s Fish House, located on the North Shore. This iconic restaurant offers fresh seafood and Polynesian-inspired cuisine in a stunning oceanfront setting. Be sure to make a reservation in advance, as this popular spot fills up quickly.
Day Four: The World’s LARGEST Volcano!
Begin your second day with a visit to Haleakala National Park, located on the eastern side of the island. Haleakala is home to the world’s largest dormant volcano, and its otherworldly landscape offers stunning views of the island and the sea beyond. You can hike along the trails, take a guided tour, or simply marvel at the breathtaking scenery.
After exploring Haleakala, head to the charming town of Makawao, known for its arts and crafts galleries and boutiques. This former cowboy town is now a hub of creativity and features unique shops and cafes, such as T. Komoda Store and Bakery, which has been serving up delicious baked goods since 1916.
In the afternoon, visit the Iao Valley State Park, located in Central Maui. The park is home to the iconic Iao Needle, a 1,200-foot rock formation that rises above the lush valley. You can hike the trails, learn about the history and culture of Hawaii at the park’s visitor center, or simply take in the beauty of the surroundings.
End your day with a visit to the Maui Ocean Center, located in the town of Ma’alaea. This aquarium features over 60 exhibits showcasing the unique marine life of Hawaii, including sea turtles, sharks, and stingrays. You can also take a behind-the-scenes tour or even participate in a shark dive or ray encounter.
Add Molokai to Your Hawaii Vacation Itinerary
Take a ferry to Molokai, the fifth-largest island in Hawaii, and known for its untouched natural beauty and rich history. Visit Kalaupapa National Historical Park, a remote peninsula that was once a leper colony, or hike to the highest sea cliffs in the world at the Halawa Valley.
Day Five: Molokai!
Start the Molokai portion of your Hawaii Vacation Itinerary with a visit to Kalaupapa National Historical Park, located on the northern coast of the island. This remote peninsula was once a leper colony, and you can learn about its history and the lives of its residents at the park’s visitor center. You can also take a guided mule ride down the steep trail to the peninsula or hike along the Kalaupapa Lookout Trail for stunning views of the surrounding cliffs and ocean.
After exploring Kalaupapa, head to the town of Kaunakakai, located on the southern coast of the island. This charming town is the hub of Molokai’s local culture and features unique shops and restaurants, such as Kanemitsu Bakery, known for its delicious hot bread and pastries.
In the afternoon, visit the Pala’au State Park, located in the center of the island. This park features a lush rainforest, towering waterfalls, and hiking trails that offer breathtaking views of the island. You can also learn about the history and culture of Molokai at the park’s museum, which features exhibits and artifacts from the island’s past.
End your day with a sunset dinner at the Hotel Molokai, located on the west coast of the island. This oceanfront restaurant offers fresh seafood and island-inspired cuisine in a laid-back atmosphere.
Molokai For One More Day
Begin your second day with a visit to the Halawa Valley, located on the eastern side of the island. This remote valley is home to the highest sea cliffs in the world and features a stunning waterfall that can only be accessed by hiking or kayaking. You can also learn about the history and culture of the valley at the Halawa Valley Cultural Preserve, which offers guided tours and workshops.
After exploring the Halawa Valley, head to the Papohaku Beach, located on the western coast of the island. This three-mile-long beach is one of the most beautiful and secluded beaches in Hawaii, with pristine white sand and crystal-clear waters. You can relax on the beach, swim in the ocean, or take a leisurely stroll along the shore.
In the afternoon, visit the Molokai Plumeria Farm, located in the town of Maunaloa. This farm features over 200 varieties of plumeria trees, as well as other tropical plants and flowers. You can take a guided tour of the farm and learn about the history and cultivation of plumeria, as well as purchase fresh flowers and leis.
End your day with a visit to the Coffees of Hawaii, located in the town of Kualapu’u. This coffee farm offers tours and tastings, as well as a variety of coffee blends and merchandise. You can also enjoy a light meal or snack at the cafe, which features a stunning view of the surrounding countryside.
Secluded Lanai!
Next, hop on a ferry to Lanai, the smallest inhabited island in Hawaii, and a secluded paradise that offers world-class golf, pristine beaches, and stunning natural beauty. Spend your days lounging on the beach or exploring the island’s rugged terrain on a Jeep tour.
Day 7:
Start your Lanai adventure with a visit to Hulopoe Beach, located on the southern coast of the island. This beautiful crescent-shaped beach features pristine white sand, crystal-clear waters, and excellent snorkeling and diving opportunities. You can also hike along the nearby trails or relax on the beach and soak up the sun.
After exploring Hulopoe Beach, head to the Garden of the Gods, located in the center of the island. This unique landscape features towering rock formations and red dirt that make for a stunning and surreal view. You can hike along the trails and explore the area, or simply take in the beauty of the surroundings.
In the afternoon, visit the Lanai Cultural and Heritage Center, located in the town of Lanai City. This museum features exhibits and artifacts that showcase the unique history and culture of Lanai, including its plantation era and Hawaiian heritage. You can also browse the museum’s gift shop, which offers locally made crafts and souvenirs.
End your day with a sunset dinner at the Four Seasons Resort Lanai, located on the western coast of the island. This luxurious resort features world-class dining and breathtaking ocean views, making for a memorable dining experience.
Day 8:
Begin your second day with a visit to the Puu Pehe, also known as the Sweetheart Rock, located on the southern coast of the island. This iconic landmark features a stunning sea stack and a legend of a tragic love story, making for a romantic and picturesque view. You can also explore the nearby trails and take in the beauty of the surrounding cliffs and ocean.
After exploring Puu Pehe, head to the Munro Trail, located in the center of the island. This scenic drive takes you through the heart of Lanai’s rugged landscape, offering stunning views of the island and the sea beyond. You can also hike along the trails and explore the area, or simply take in the beauty of the surroundings.
In the afternoon, visit the Lanai Cat Sanctuary, located in the town of Lanai City. This unique sanctuary is home to over 600 cats, making for a fun and memorable experience. You can learn about the sanctuary’s mission and meet some of its furry residents, or even adopt a cat to take home with you.
End your day with a visit to the Lanai Pine Sporting Clays, located on the eastern side of the island. This shooting range offers a unique and exhilarating experience, with stunning views of the island and the opportunity to practice your shooting skills.
Complete Your Journey on the Big Island of Hawaii
End your island hopping adventure on the Big Island, home to the world’s most active volcano, Kilauea, and a wealth of outdoor activities. Explore the volcanic landscape of Hawaii Volcanoes National Park or take a dip in the crystal-clear waters at Hapuna Beach. Finish your trip with a traditional Hawaiian luau, complete with hula dancing and fire-knife performances.
Day 9:
Start your Big Island adventure with a visit to Hawaii Volcanoes National Park, located on the southeastern coast of the island. This park is home to two active volcanoes, Kilauea and Mauna Loa, and offers visitors a unique opportunity to see the power and beauty of nature up close. You can hike along the trails, learn about the park’s geology and history at the visitor center, or even take a helicopter tour for a bird’s-eye view of the volcanoes.
After exploring the national park, head to Punaluu Beach, located on the southeastern coast of the island. This black sand beach is famous for its stunning beauty and unique color, and is a great spot for swimming, sunbathing, or simply taking in the beauty of the surroundings.
In the afternoon, visit the town of Hilo, located on the northeastern coast of the island. This charming town is the cultural hub of the Big Island and features unique shops and restaurants, such as the Hilo Farmers Market, which offers fresh local produce and crafts. You can also learn about the history and culture of the island at the Lyman Museum and Mission House, which features exhibits and artifacts from the island’s past.
End your day with a sunset dinner at the Ocean Sushi Deli, located in the town of Kailua-Kona. This restaurant offers fresh sushi and Japanese-inspired cuisine in a stunning oceanfront setting, making for a memorable dining experience.
Day 10:
Begin your second day with a visit to the Waipio Valley, located on the northern coast of the island. This remote valley features lush rainforests, towering waterfalls, and stunning views of the ocean and the surrounding cliffs. You can hike along the trails, take a guided horseback ride, or even go on a helicopter tour for a unique perspective of the valley.
After exploring the Waipio Valley, head to the Kohala Coast, located on the western coast of the island. This area is home to some of the most beautiful beaches on the Big Island, such as Hapuna Beach and Mauna Kea Beach, both of which offer stunning views and excellent snorkeling opportunities.
In the afternoon, visit the Puukohola Heiau National Historic Site, located in the town of Kawaihae. This site features a historic temple built by King Kamehameha I, as well as exhibits and artifacts that showcase the history and culture of the island. You can also explore the nearby trails and take in the beauty of the surrounding countryside.
End your day with a visit to the Kona Brewing Company, located in the town of Kailua-Kona. This brewery offers tours and tastings, as well as a variety of locally made beers and pub food. You can also enjoy the stunning ocean views from the brewery’s outdoor patio.
Island hopping in Hawaii is a once-in-a-lifetime adventure that allows you to experience the best of each island. With this itinerary, you can explore the bustling city of Honolulu, the pristine beaches of Maui, the untouched natural beauty of Molokai, the secluded paradise of Lanai, and the volcanic landscape of the Big Island. From relaxing on the beach to hiking to the highest sea cliffs in the world, Hawaii offers something for everyone. So, pack your bags and get ready for the adventure of a lifetime in paradise.
10 Day Hawaii Vacation Itinerary Checklist:
Day 1-2: Oahu – Hawaii Vacation Itinerary
- Explore Waikiki Beach, take a surf lesson or rent a surfboard
- Visit Honolulu Zoo, home to over 900 animals from around the world
- Hike Diamond Head State Monument for a breathtaking view of Waikiki and the Pacific Ocean
- Visit Pearl Harbor National Memorial and pay respects at the USS Arizona Memorial
- Go to the North Shore to watch surfers ride the waves at Sunset Beach or the Bonzai Pipeline
- Stop at the charming town of Haleiwa and have breakfast at one of the local cafes
- Visit Waimea Bay to watch surfers ride the massive waves during the winter months
- Go to the Polynesian Cultural Center, where you can learn about the rich culture and traditions of Hawaii and the Pacific Islands
- Visit Kualoa Ranch, a working cattle ranch that offers a variety of outdoor activities
Day 3-4: Maui – Hawaii Vacation Itinerary
- Visit Lahaina, a former bustling whaling town, and learn about its history at the Lahaina Whaling Museum
- Visit Ka’anapali Beach, one of the most popular beaches on Maui
- Go to Black Rock, a lava formation that juts out into the sea and is a popular spot for snorkeling and diving
- Explore Haleakala National Park, home to the world’s largest dormant volcano
- Visit the charming town of Makawao, known for its arts and crafts galleries and boutiques
- Go to Iao Valley State Park, home to the iconic Iao Needle
- Visit the Maui Ocean Center, an aquarium featuring over 60 exhibits showcasing the unique marine life of Hawaii
Day 5-6: Molokai – Hawaii Vacation Itinerary
- Visit Kalaupapa National Historical Park, a remote peninsula that was once a leper colony
- Take a guided mule ride down the steep trail to the peninsula or hike along the Kalaupapa Lookout Trail
- Visit the town of Kaunakakai, the hub of Molokai’s local culture
- Explore the Pala’au State Park, home to a lush rainforest, towering waterfalls, and hiking trails
- Visit the Molokai Plumeria Farm, which features over 200 varieties of plumeria trees and other tropical plants and flowers
- Go to the Coffees of Hawaii, a coffee farm that offers tours and tastings, as well as a variety of coffee blends and merchandise
Day 7-8: Lanai – Hawaii Vacation Itinerary
- Visit Hulopoe Beach, a beautiful crescent-shaped beach with excellent snorkeling and diving opportunities
- Explore the Garden of the Gods, which features towering rock formations and red dirt
- Visit the Lanai Cultural and Heritage Center, which features exhibits and artifacts that showcase the unique history and culture of Lanai
- Visit Puu Pehe, also known as the Sweetheart Rock, which features a stunning sea stack and a legend of a tragic love story
- Drive along the Munro Trail, which takes you through the heart of Lanai’s rugged landscape
- Visit the Lanai Cat Sanctuary, which is home to over 600 cats
- Go to the Lanai Pine Sporting Clays, a shooting range with stunning views of the island and the sea beyond
Day 9-10: Big Island – Hawaii Vacation Itinerary
- Visit Hawaii Volcanoes National Park, home to two active volcanoes, Kilauea and Mauna Loa
- Explore Punaluu Beach, a black sand beach famous for its stunning beauty and unique color
- Visit the town of Hilo, the cultural hub of the Big Island, and learn about the history and culture of the island at
Scott Sweeney is the creator of Virtual Hawaii 360. Scott is a professional marketer and a lifelong Hawaii enthusiast. Scott splits time between Oahu and Dayton, Ohio. In addition to his marketing endevours, he is also a published Ukulele musician.
