Dreaming of Hawaii but can’t decide which island to visit? Why not visit them all! This itinerary guides you through four of Hawaii’s most iconic islands – Oahu, Maui, Kauai, and the Big Island – packing in adventure, relaxation, and unforgettable experiences. Get ready for the ultimate island-hopping adventure!
Oahu: City Life Meets Surf Culture (4 Days)
Your Hawaiian adventure begins on Oahu, the “Gathering Place.” This island perfectly blends bustling city life with world-class surfing and historical landmarks. Honolulu International Airport (HNL) is your gateway, and renting a car is highly recommended for exploring the island at your own pace. Traffic can be a pain, especially during rush hour, so plan accordingly. Budget about $50-$80 per day for a mid-size rental car.
Day 1: Pearl Harbor and Waikiki Beach
Start your trip with a somber yet essential visit to Pearl Harbor. The Pearl Harbor National Memorial is free to enter, but securing a reservation in advance is crucial, especially during peak season. You can reserve tickets up to 60 days in advance on the National Park Service website. Allow at least 3-4 hours for a complete visit, including the USS Arizona Memorial. Reflect on this significant historical site and remember the events of December 7, 1941.
Afterward, head to Waikiki Beach, the iconic stretch of sand synonymous with Hawaiian tourism. Take a surfing lesson from one of the many surf schools lining the beach; a group lesson typically costs around $50-$75. If surfing isn’t your thing, relax on the beach, soak up the sun, or take a dip in the refreshing ocean. In the evening, enjoy a Mai Tai at a beachfront bar and watch the sunset over the Pacific. For dinner, try a local plate lunch at a casual eatery like Rainbow Drive-In (around $10-$15) for an authentic taste of Hawaiian cuisine.
Day 2: North Shore Surfing and Polynesian Culture
Today, venture to Oahu’s legendary North Shore, famous for its massive winter waves. During the winter months (November-February), professional surfers flock here to ride these giants. Visit iconic surf spots like Sunset Beach, Pipeline, and Waimea Bay. Even if you’re not a surfer, the sheer power of the waves is a sight to behold. Check the local surf report before you go, as conditions can vary greatly.
In the afternoon, immerse yourself in Polynesian culture at the Polynesian Cultural Center. This expansive park showcases the traditions and cultures of seven Polynesian island nations, including Hawaii, Samoa, Fiji, Tonga, Tahiti, and Aotearoa (New Zealand). Attend traditional demonstrations, learn about crafts, and enjoy a delicious luau with authentic Hawaiian food and entertainment. Tickets range from $80-$120, depending on the package you choose. Book in advance, especially if you want to attend the evening luau.
Day 3: Diamond Head and Coastal Exploration
Start your day with a hike to the summit of Diamond Head, an extinct volcanic crater offering panoramic views of Waikiki and the coastline. The hike is moderately challenging, taking about 1-2 hours roundtrip. There is a $5 entrance fee per vehicle, or $1 per pedestrian. Go early in the morning to beat the heat and crowds. Don’t forget to bring water and sunscreen.
After Diamond Head, explore the scenic coastline along the southeast side of Oahu. Visit Hanauma Bay for snorkeling (reservations required and a small fee applies), but be aware that it’s closed on Tuesdays and Wednesdays for conservation. Check the Hanauma Bay website for the latest information and reservation details. Alternatively, Makapu’u Point Lighthouse Trail offers stunning ocean views and whale watching opportunities during the winter months. In the evening, enjoy a fine dining experience at a restaurant in Waikiki or explore the vibrant nightlife scene.
Day 4: Island Art and Departure
Before heading to Maui, spend the morning exploring Honolulu’s arts and culture scene. Visit the Honolulu Museum of Art for a glimpse into Hawaiian and Asian art. Consider a visit to Iolani Palace, the only official residence of royalty in the United States, showcasing Hawaiian history and culture. Take a guided tour to learn more about the palace’s fascinating past; tour prices vary from $27.00 to $75.00 and should be booked in advance.
Grab a final plate lunch (Leonard’s Bakery is a must-try for malasadas!) before heading to Honolulu International Airport (HNL) for your short flight to Maui (OGG). Airlines like Hawaiian Airlines and Southwest offer frequent inter-island flights. Make sure to arrive at the airport at least 2 hours before your flight, especially if you have checked baggage. Expect inter-island flights to cost somewhere around $70 to $150 (depending on factors like season, time of booking, and airline).
Maui: The Valley Isle (4 Days)
Maui, known as the “Valley Isle,” is renowned for its stunning beaches, lush rainforests, and the majestic Haleakala volcano. Kahului Airport (OGG) is the main airport. Renting a car is a must for exploring Maui’s diverse landscapes.
Day 5: Road to Hana
Dedicate a full day to the legendary Road to Hana, a winding coastal highway that’s a must-do on Maui. This scenic drive is about 64 miles long and features over 600 curves and 54 bridges, passing by waterfalls, lush rainforests, and stunning coastal views. Start early to avoid the crowds and allow plenty of time to stop at the numerous viewpoints, hiking trails, and swimming holes. Some popular stops include Twin Falls, the Garden of Eden, and the Pools of Ohe’o (Seven Sacred Pools), if open (check conditions beforehand). Do research on the Pools of Ohe’o because swimming is sometimes restricted. Drive carefully, as the road can be narrow and winding. Pack snacks, water, and swimwear. Consider downloading an offline map or app like Shaka Guide to enhance your experience with audio commentary and navigation.
Day 6: Haleakala Sunrise and Upcountry Maui
Wake up before dawn and drive to the summit of Haleakala National Park to witness a breathtaking sunrise. This is an unforgettable experience, as the sun rises above the clouds, painting the sky in vibrant colors. Reservations are required for sunrise viewing and can be made up to 60 days in advance on Recreation.gov. Dress warmly, as temperatures at the summit can be surprisingly cold, even in summer. Afterwards, explore Upcountry Maui, visiting the charming town of Makawao and the Surfing Goat Dairy for a unique experience. Take a tour and meet the adorable goats, and sample some of their delicious goat cheeses. In the afternoon, relax on one of Maui’s beautiful beaches or try windsurfing at Ho’okipa Beach Park, known for its strong winds and sea turtles.
Day 7: Snorkeling at Molokini Crater and West Maui Beaches
Embark on a snorkeling excursion to Molokini Crater, a partially submerged volcanic crater teeming with marine life. Numerous tour operators offer trips to Molokini, typically including snorkeling gear, breakfast, and lunch. Book in advance, especially during peak season. Snorkelers will see a lot of tropical fishes, corals, and maybe even turtles. In the afternoon, explore the beaches of West Maui, such as Kaanapali Beach and Kapalua Bay. Kaanapali Beach is known for its soft sand and clear water, while Kapalua Bay offers a more secluded and picturesque setting. Watch the cliff diving ceremony at Black Rock (Pu’u Keka’a) at Kaanapali Beach for a cultural show.
Day 8: Whale Watching and Departure to Kauai
If you are visiting Maui during whale season (November-May), be sure to take a whale watching tour. Humpback whales migrate to the warm waters of Hawaii to breed and calve, and seeing these gentle giants is an awe-inspiring experience. Do check the local tour operators to compare and book options.
Spend the afternoon relaxing on your favorite beach before heading to Kahului Airport (OGG) for your flight to Lihue Airport (LIH) on Kauai. Again, Hawaiian Airlines and Southwest will be your main options for flights. Arrive two hours prior to your flight and budget between $70 to $150.
Kauai: The Garden Isle (4 Days)
Kauai, also known as the “Garden Isle,” is the oldest and greenest of the main Hawaiian Islands. Its dramatic landscapes, stunning coastline, and lush rainforests make it a paradise. Upon arrival at Lihue Airport (LIH), pick up your rental car – a necessity for exploring the island.
Day 9: Waimea Canyon and Kokee State Park
Start your Kauai adventure with a visit to Waimea Canyon, often referred to as the “Grand Canyon of the Pacific.” This geological wonder offers breathtaking views of deep canyons, colorful cliffs, and cascading waterfalls. Drive along Waimea Canyon Drive, stopping at the various viewpoints to admire the scenery. Continue to Kokee State Park, where you can explore hiking trails through lush forests and enjoy panoramic views of the Na Pali Coast. Pack a picnic lunch and enjoy the serenity of this natural playground.
Day 10: Na Pali Coast Boat Tour or Helicopter Tour
Experience the majestic Na Pali Coast from a unique perspective by taking a boat tour or helicopter tour. These tours offer stunning views of the towering sea cliffs, hidden valleys, and cascading waterfalls that make the Na Pali Coast so famous. Boat tours allow you to get up close to the coastline and offer snorkeling or swimming opportunities, while helicopter tours provide a bird’s-eye view of the dramatic landscape. Book your tour in advance, as they tend to sell out quickly, especially during peak season. Prices vary depending on the tour and the operator, but expect to pay around $150-$250 for a boat tour and $250-$400 for a helicopter tour.
Day 11: Poipu Beach and Spouting Horn
Spend the day relaxing and exploring the south shore of Kauai. Poipu Beach is consistently ranked as one of the best beaches in the United States, known for its golden sand, clear water, and monk seal sightings. Swim, sunbathe, snorkel, or try stand-up paddleboarding. Nearby, visit Spouting Horn, a natural blowhole that shoots water high into the air with a roar. In the evening, enjoy a delicious meal at one of Poipu’s many restaurants or attend a traditional Hawaiian luau.
Day 12: Secret Falls and Departure to the Big Island
Embark on a kayaking adventure to Secret Falls (Uluwehi Falls) along the Wailua River. This hidden waterfall is accessible only by kayak and a short hike through the rainforest. Rent a kayak from one of the outfitters along the Wailua River and paddle upstream to the trailhead. The hike to the waterfall is moderately challenging, but the reward is well worth it – a refreshing swim in the pool beneath the cascading falls.
After returning, grab some lunch and head towards the Lihue Airport (LIH) for your flight to Kona International Airport (KOA) on the Big Island. Be at the airport 2 hours early and budget the same price tag on flights to the Big Island as per the previous inter-island flights.
The Big Island: The Adventure Isle (4 Days)
The Big Island, officially known as Hawaii Island, is the largest and youngest of the Hawaiian Islands. It offers a diverse range of landscapes, from active volcanoes to black sand beaches and snow-capped mountains. Upon arrival at Kona International Airport (KOA) or Hilo International Airport (ITO), pick up your rental car, as you will need it to get around to see the vast different island climates.
Day 13: Hawaii Volcanoes National Park
Dedicate a full day to exploring Hawaii Volcanoes National Park, home to Kilauea, one of the world’s most active volcanoes. Drive along Crater Rim Drive, stopping at the various viewpoints to admire the volcanic landscapes. Visit the Jaggar Museum to learn about volcanic activity and Hawaiian volcanology.
Take a hike along the Kilauea Iki Trail (4 miles, moderate) with a descent into a volcanic crater. Hike through the Thurston Lava Tube (Nāhuku), a 500-year-old lava cave. In the evening, try to catch a glimpse of the glow from the Halema’uma’u crater, if visible, or attend a ranger program to learn more about the park’s geology and ecology. Check the park’s website for the latest advisories and closures, as volcanic activity can change rapidly. The entrance fee is $30 per vehicle, valid for 7 days.
Day 14: Kona Coffee Farms and Black Sand Beaches
Start your day with a visit to the Kona Coffee Belt, a region known for its world-renowned coffee beans. Take a tour of one of the local coffee farms, learn about the coffee-making process, and sample some of the delicious Kona coffee. Some farms offer free tours and tastings. After your coffee fix, head to Punalu’u Black Sand Beach to see black sands. Watch for Hawaiian green sea turtles resting on the warm sand. Remember to keep a respectful distance from the turtles and avoid disturbing them. Swimming is possible here, but the surf can be rough.
Day 15: Stargazing at Mauna Kea
Experience the magic of stargazing at Mauna Kea, the tallest mountain in Hawaii and one of the best places in the world for astronomical observation. Drive to the Mauna Kea Visitor Information Station (VIS) at 9,200 feet, where you can learn about the observatories and the research being conducted on Mauna Kea.
For those with a 4-wheel drive vehicle, you can continue to the summit (13,796 feet) for an even better stargazing experience. Note that this is a high-altitude environment, and it is important to acclimate to the altitude before ascending to the summit. Spend at least 30 minutes at the VIS before continuing to the summit. Dress warmly, as temperatures at the summit can be below freezing, even in summer.
Day 16: Waterfalls and Departure
Before heading to Kona International Airport (KOA) for your flight home, spend the morning exploring the waterfalls near Hilo on the east side of the island. Rainbow Falls is easily accessible and offers stunning views of the cascading water. Akaka Falls State Park features two impressive waterfalls, Akaka Falls (442 feet) and Kahuna Falls (100 feet). Take a short hike through lush rainforest to reach the waterfalls. After viewing the waterfalls, head to the airport well in advance of your scheduled flight.
Accommodation Tips
Accommodation costs vary greatly depending on the island, location, and type of lodging. On Oahu and Maui, expect to pay more for hotels and resorts in popular tourist areas. Kauai and the Big Island offer a wider range of options, including vacation rentals, condos, and budget-friendly hotels. Consider booking accommodations well in advance, especially during peak season.
Here is a rough estimate of accommodation costs per night (on average), though prices can fluctuate:
- Budget: $100-$150 (hostels, budget hotels, Airbnbs outside tourist centers)
- Mid-Range: $150-$300 (standard hotels, condos, well-located Airbnbs)
- Luxury: $300+ (resorts, high-end hotels, luxury vacation rentals)
Food and Drink
Hawaiian cuisine is a delicious blend of Polynesian, Asian, and Western influences. Be sure to try local specialties such as poke, kalua pig, laulau, poi, and shave ice. Plate lunches are a great way to sample a variety of Hawaiian dishes at an affordable price. Food trucks are also popular, offering a wide range of cuisines, from Korean BBQ to vegan options.
Don’t forget to try Kona coffee, grown on the slopes of the Big Island, and local craft beers from breweries across the islands. Enjoy a Mai Tai or other tropical cocktail at a beachfront bar while watching the sunset.
Here’s a rough estimate on food costs per person per day:
- Budget: $30-50 (mostly self-catering, food trucks, plate lunches)
- Mid-Range: $50-100 (mix of restaurants, casual dining, some self-catering)
- Luxury: $100+ (fine dining, cocktails, eating out for most meals)
Budget Considerations
This multi-island adventure requires careful budgeting. Inter-island flights, rental cars, accommodations, activities, and food can add up quickly. Here’s a breakdown of potential costs (per person for 16 days/15 nights) without airfare from the mainland:
- Flights between islands (4 flights): $280 – $600
- Rental cars (4 islands, avg $60/day): $960
- Accommodation (avg $200/night, mid-range): $3,000
- Activities & tours (avg $100/day): $1,600
- Food & drinks (avg $80/day): $1,280
- Miscellaneous (gas, souvenirs, etc.): $500
Total (estimated mid-range): $7,620 – $7,940
This is just a general estimate, and your actual costs may vary depending on your travel style, preferences, and time of year. Saving on accommodation and meals will bring the price down.
Packing Essentials
- Lightweight and breathable clothing
- Swimsuits and beach cover-ups
- Hat, sunglasses, and sunscreen (reef-safe is recommended)
- Hiking shoes and sandals
- Rain jacket or umbrella
- Reusable water bottle
- Snorkel gear (optional)
- Insect repellent
- Camera and extra batteries
FAQ Section
What is the best time of year to visit Hawaii?
The best time to visit Hawaii depends on your priorities. The weather is generally pleasant year-round, but the peak season is from mid-December to April and June to August. During these times, expect higher prices and more crowds. Shoulder seasons (April-May and September-November) offer a good balance of pleasant weather and fewer crowds. Whale watching season is from November to May, with peak sightings in January and February.
Is it necessary to rent a car on each island?
Yes, renting a car is highly recommended on each island, especially Maui, Kauai, and the Big Island. Public transportation is limited, and many of the best attractions are located outside of the tourist areas. Oahu has a more extensive public transportation system, but a car is still recommended for exploring the North Shore and other parts of the island. Ensure you book your rental in advance, especially during peak season, to secure the best rates. Don’t forget to check the rental car company’s policies regarding driving on unpaved roads, as some restrictions may apply.
Are inter-island flights expensive?
Inter-island flights can range from $70-$150 and are not super expensive, but the cost can add up when traveling between multiple islands. To save money, book in advance and compare prices from different airlines like Hawaiian Airlines and Southwest. Be flexible with your travel dates and times, and consider flying during off-peak hours. Check for any baggage fees or other additional charges that may apply.
What are the best activities for families with children?
Each island offers a wealth of family-friendly activities. On Oahu, visit the Honolulu Zoo, the Waikiki Aquarium, or the Polynesian Cultural Center. Maui has the Maui Ocean Center, the Sugar Cane Train, and numerous beautiful beaches for swimming and snorkeling. On Kauai, take a boat tour of the Na Pali Coast, visit the Kauai Coffee Company, or explore Waimea Canyon. The Big Island has Hawaii Volcanoes National Park, the Imiloa Astronomy Center, and several black sand beaches.
For younger children, consider activities like building sandcastles, tide pooling, and attending a luau with traditional Hawaiian music and dance. Older children and teenagers may enjoy surfing lessons, zip-lining, or hiking to waterfalls.
Is it safe to drink tap water in Hawaii?
Yes! Tap water in Hawaii comes from rainwater and groundwater, and it is safe to drink in the state with the Hawai’i Department of Health stringently monitoring water quality across each county.
References
- National Park Service, Pearl Harbor National Memorial
- Polynesian Cultural Center
- Recreation.gov, Haleakala Sunrise Reservations
- Honolulu Museum of Art
- Iolani Palace
- Hawaii Department of Health Water Quality
Ready to turn this island-hopping dream into reality? Start planning your trip today! Book your flights, accommodations, and activities in advance to secure the best prices and availability. Pack your bags, grab your sense of adventure, and get ready for an unforgettable journey through the Hawaiian Islands. Aloha!
