Dreaming of Hawaii? Don’t just pick one island, experience them all! This itinerary guides you through an unforgettable Hawaiian island-hopping adventure, packed with insider tips, must-do activities, and practical information to make your trip seamless.
Deciding Which Islands to Visit
First things first: which Hawaiian islands will you conquer? Each island offers a unique vibe and set of experiences. Our recommended itinerary focuses on four main islands: Oahu, Maui, Kauai, and the Big Island (Hawaii Island). This combination gives you a taste of everything from bustling city life to serene beaches and volcanic landscapes.
Oahu: Known as “The Gathering Place,” Oahu is a perfect starting point. It’s a blend of city life in Honolulu and Waikiki, historic sites like Pearl Harbor, and world-class surfing on the North Shore. Think of it as your Hawaiian welcome party – full of energy and options.
Maui: “The Valley Isle” is famed for its stunning beaches, including the iconic Ka’anapali Beach, lush landscapes, and the breathtaking Road to Hana. Maui offers a laid-back atmosphere and is ideal for romance, adventure, and relaxation.
Kauai: If you’re craving dramatic scenery, then “The Garden Isle” is your paradise. Kauai boasts the awe-inspiring Na Pali Coast, Waimea Canyon (the “Grand Canyon of the Pacific”), and stunning beaches. It’s an outdoor enthusiast’s dream.
Big Island (Hawaii Island): This island lives up to its name! “The Big Island” offers active volcanoes, diverse ecosystems, black sand beaches, and even snow-capped mountains in the winter. It’s a land of contrasts and raw natural beauty.
Island Hopping Logistics: Flights and Ferries
Getting between the islands is usually done best by plane. Multiple airlines, like Hawaiian Airlines and Southwest, offer inter-island flights. These flights are relatively short (usually 30-50 minutes) and frequent. Booking in advance, especially during peak season, is essential for the best prices. Keep an eye out for sales and consider signing up for airline loyalty programs.
Ferries used to be a more common option, but now only one primarily operates between Maui and Lanai. If Lanai is on your radar (and it’s a fantastic little island!), consider a day trip from Maui using the Maui-Lanai Ferry. Otherwise, stick to flights for inter-island travel.
Pro Tip: Pack light! Inter-island flights often have baggage fees, so minimizing your luggage will save you money. Roll your clothes to maximize space and consider using packing cubes.
The Ultimate 14-Day Hawaiian Island Hopping Itinerary
This itinerary is a suggestion and can be adjusted based on your interests and budget. The estimated cost per person for this trip, excluding international flights, could range from $3,500 to $7,000 depending on your style of accommodation, dining preferences, and activity choices. Always book accommodations and activities in advance where possible, especially during peak season.
Days 1-3: Oahu – Pearl Harbor, Waikiki, and the North Shore
Fly into Honolulu International Airport (HNL) on Oahu. Pick up your rental car (essential for exploring the islands) and head to Waikiki.
Accommodation: Choose from a range of hotels in Waikiki, from budget-friendly options to luxurious resorts. Outrigger Reef Waikiki Beach Resort and Hyatt Regency Waikiki Beach Resort & Spa are popular choices. Airbnb is also a good option for more space and potentially lower costs.
Day 1: Immerse yourself in history at Pearl Harbor. Book your tickets online in advance through the National Park Service website to guarantee entry and avoid long lines. In the afternoon, relax on Waikiki Beach, take a surf lesson, or explore the shops and restaurants along Kalakaua Avenue. Enjoy a sunset cocktail at a beachfront bar.
Cost: Pearl Harbor tickets (USS Arizona Memorial) are free, but reservation fees may apply. Surf lessons start around $75-$100. Dinner can range from $20 to $50+ per person.
Day 2: Hike Diamond Head crater for panoramic views of Waikiki and the coastline. The hike is moderately challenging and takes about 1-2 hours round trip. In the afternoon, visit Iolani Palace, the only official residence of royalty in the United States. Consider an evening luau with Polynesian dances and traditional Hawaiian food. Germaine’s Luau and Polynesian Cultural Center are popular choices, often costing $100-$200 per person.
Directions to Diamond Head: From Waikiki, take Kalakaua Avenue east, then turn left onto Diamond Head Road. The entrance to Diamond Head State Monument is on the right.
Day 3: Take a drive up to the North Shore, famous for its big waves (especially during the winter months). Visit iconic surf spots like Sunset Beach, Pipeline, and Waimea Bay. Watch experienced surfers ride the waves (November to February). Snorkeling and swimming are great during calmer periods. Have lunch at a shrimp truck (Giovanni’s Shrimp Truck is a classic) and enjoy the laid-back North Shore vibe. Consider a visit to the Dole Plantation for a taste of Hawaiian history and a pineapple ice cream treat.
North Shore Tip: Parking can be challenging at popular beaches. Arrive early or be prepared to walk a bit. Always check surf reports before entering the water.
Days 4-6: Maui – Road to Hana, Haleakala, and Beaches
Fly from Honolulu to Kahului Airport (OGG) on Maui. Pick up your rental car.
Accommodation: Stay in West Maui (Ka’anapali, Lahaina) or South Maui (Kihei, Wailea). West Maui offers beautiful beaches and resorts, while South Maui is known for its calmer waters and condo rentals. The Hyatt Regency Maui Resort & Spa in Ka’anapali and the Grand Wailea in Wailea are luxurious options.
Day 4: Embark on the legendary Road to Hana. Start early (around 7 AM) to avoid traffic. This scenic drive is full of waterfalls, lush rainforests, and breathtaking coastal views. Make sure your rental car insurance covers unpaved roads (important for some sections of the loop). Pack snacks, water, and a swimsuit. Must-see stops include Twin Falls, the Garden of Eden Arboretum, and the Pools of Ohe’o (Seven Sacred Pools – check for accessibility before you go, though). Plan for a full day of driving – it will take at least 8-10 hours to complete the round trip.
Road to Hana Tip: Drive slowly and be respectful of local residents. Pull over to let faster cars pass. Download an offline map (like the Shaka Guide app) to help navigate without cell service.
Day 5: Witness the sunrise from the summit of Haleakala National Park. You’ll need to make a reservation in advance via the National Park Service website as entry is now limited. Dress warmly – it can be very cold at the summit, even in summer. After sunrise, explore the park’s hiking trails, such as the Sliding Sands Trail or the Halemau’u Trail. In the afternoon, relax on one of Maui’s beautiful beaches. Ka’anapali Beach is perfect for swimming and sunbathing. Consider a snorkeling or scuba diving trip to Molokini Crater, a partially submerged volcanic crater teeming with marine life.
Cost: Haleakala National Park entrance fee is $30 per vehicle. Molokini snorkeling trips range from $100-$150 per person.
Day 6: Learn to surf at Lahaina, West Maui or visit the Maui Ocean Center to discover the underwater world of Hawaii. Alternatively, go whale watching on a boat tour (seasonal, December to May), or simply relax on the beach and soak up the sun. Visit the historic whaling town of Lahaina, stroll along Front Street, and browse the art galleries and shops. Enjoy a sunset dinner at a restaurant overlooking the ocean.
Days 7-9: Kauai – Na Pali Coast, Waimea Canyon, and Beaches
Fly from Kahului (OGG) to Lihue Airport (LIH) on Kauai. Pick up your rental car.
Accommodation: Stay in Poipu (South Shore) or Princeville (North Shore). Poipu offers sunny weather and calm beaches, while Princeville is known for its lush scenery and dramatic coastline.
Day 7: Take a boat tour along the Na Pali Coast. This is the best way to see the towering cliffs, sea caves, and waterfalls of this breathtaking coastline. Several tour operators offer half-day or full-day tours, including snorkeling and lunch. Captain Andy’s and Holo Holo Charters are reputable choices. Book in advance, especially during peak season. If you prefer, you can hike a portion of the Kalalau Trail for a closer view of the Na Pali Coast, but be prepared for a strenuous hike.
Na Pali Coast Tip: Choose a boat tour that departs from Port Allen for a shorter ride to the Na Pali Coast, or from the North Shore (Princeville) during calm summer months. Motion sickness medication is recommended for those prone to seasickness.
Day 8: Explore Waimea Canyon, the “Grand Canyon of the Pacific.” Drive up to the canyon rim for stunning views of the colorful cliffs and deep valleys. Hike one of the canyon’s many trails, such as the Canyon Trail or the Cliff Trail. In the afternoon, visit Kokee State Park, which offers more hiking trails and panoramic views. Consider a picnic lunch at one of the park’s scenic overlooks.
Waimea Canyon Tip: Bring layers of clothing, as the weather can change quickly at higher elevations. Wear comfortable hiking shoes and bring plenty of water.
Day 9: Relax on one of Kauai’s beautiful beaches. Poipu Beach is perfect for swimming, sunbathing, and snorkeling. Lydgate Beach Park offers a protected lagoon for families with young children. Hanalei Bay is a picturesque beach with views of the mountains. Consider a kayaking trip up the Wailua River to the Fern Grotto, a cave adorned with ferns.
Days 10-13: Big Island – Volcanoes National Park, Black Sand Beaches, and Stargazing
Fly from Lihue (LIH) to either Kona International Airport (KOA) or Hilo International Airport (ITO) on the Big Island. Kona is on the west side of the island and Hilo is on the east side, so choose your arrival airport based on your initial plans. You’ll want a car for this island so consider where you want to begin.
Accommodation: Stay in Kona (West Side), Hilo (East Side) or Volcano Village (near the National Park). Kona offers sunny weather and luxury resorts, Hilo is known for its lush rainforests and waterfalls, and Volcano Village is a quiet retreat near Volcanoes National Park. The Fairmont Orchid on the Kohala Coast and Volcano House Hotel within Volcanoes National Park are excellent choices.
Day 10: Explore Volcanoes National Park. Witness the power of nature at Kilauea volcano, one of the world’s most active volcanoes. Hike the Kilauea Iki Trail, which takes you across the floor of a dormant volcano crater. Visit the Jaggar Museum for views of the Halema’uma’u crater (check for eruption activity). Drive along Crater Rim Drive, stopping at various overlooks. Check the park’s website for current conditions and safety information.
Volcanoes National Park Tip: Wear sturdy shoes, bring water, and be prepared for volcanic fumes. Consider a nighttime visit to see the glow from the Halema’uma’u crater (if active). As of late 2023, the volcano has been relatively active. Always check alerts and closures.
Day 11: Visit Punalu’u Black Sand Beach, where you might spot endangered Hawaiian green sea turtles basking in the sun. Be respectful and maintain a safe distance from the turtles. In the afternoon, drive to the Kona side of the island. Visit a coffee plantation and sample Kona coffee, known for its rich flavor.
Day 12: Snorkel or scuba dive at Kealakekua Bay, where Captain Cook first landed in Hawaii. This bay is known for its clear waters and abundant marine life. Several tour operators offer boat trips to the bay, including snorkeling gear and lunch. Alternatively, relax on one of the Kona Coast’s beautiful beaches, such as Hapuna Beach or Kahalu’u Beach Park.
Day 13: Ascend to the summit of Mauna Kea for incredible stargazing opportunities. Attend a stargazing program at the Mauna Kea Visitor Information Station (VIS) located at around 9,200 feet elevation. Note that the summit (13,796 feet) is sacred and requires 4-wheel drive vehicle access, and children under a certain age should not ascend to that altitude. At the VIS you can look through telescopes and learn about the night sky. Dress warmly – it can be very cold at the summit.
Mauna Kea Tip: If you plan to drive to the summit, rent a 4-wheel drive vehicle and make sure it is properly geared for off-road driving. Spend some time at the VIS to acclimatize to the altitude before ascending to the summit. Make sure your car has good brakes; they will be tested on your descent.
Day 14: Departure
Fly out of either Kona International Airport (KOA) or Hilo International Airport (ITO), depending on your chosen itinerary.
Alternative Activities and Considerations
- Learn to Hula: Many hotels and cultural centers offer hula lessons.
- Attend a Lei-Making Workshop: Learn the art of crafting beautiful flower leis.
- Try Local Cuisine: Venture beyond the tourist spots and try some local favorites like poke, plate lunch, and shave ice.
- Respect Local Culture: Be mindful of Hawaiian traditions and customs. Ask before taking photos of people and avoid trespassing on private property.
- Consider a Helicopter Tour: For a bird’s-eye view of the islands, a helicopter tour is an unforgettable experience (especially over Kauai’s Na Pali Coast). Budget around $300-$400 per person.
- Hiking Permits: For certain hiking trails, especially on Kauai, you may need to obtain a permit in advance. Check the state’s Department of Land and Natural Resources website.
- Travel Insurance: Consider travel insurance that covers trip cancellations, medical emergencies, and lost luggage.
Frequently Asked Questions
What is the best time of year to visit Hawaii?
The best time to visit Hawaii depends on your preferences. The peak season is during the winter months (December to April) when the weather is generally drier and cooler, but prices are higher. The shoulder seasons (April to June and September to November) offer pleasant weather and fewer crowds.
How much does it cost to island hop in Hawaii?
The cost of island hopping in Hawaii varies depending on your travel style, choice of accommodation, and activities. A rough estimate for a 14-day trip, excluding international flights, can range from $3,500 to $7,000 per person. This estimate includes flights, accommodation, rental cars, activities, and food.
Do I need a rental car on each island?
Yes, a rental car is highly recommended on each island, especially on Maui, Kauai, and the Big Island, to explore at your own pace. Oahu has a more extensive public transportation system, but a car is still useful for exploring the North Shore and other parts of the island.
What should I pack for island hopping in Hawaii?
Pack light, comfortable clothing, swimwear, sunscreen, a hat, sunglasses, insect repellent, hiking shoes, and a light jacket for cooler evenings. Don’t forget your camera and a reusable water bottle.
Is it safe to drink tap water in Hawaii?
Yes, tap water is generally safe to drink in Hawaii. However, if you have concerns, you can purchase bottled water or use a water filter.
What are some cultural practices I should be aware of?
Respect local culture by removing your shoes before entering someone’s home, asking permission before taking photos of people, and avoiding trespassing on private property. Be mindful of noise levels, especially in residential areas.
<!– References
References List:
- Hawaii Department of Business, Economic Development & Tourism (DBEDT)
- National Park Service
- Go Hawaii Official Website
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Ready to turn this itinerary into reality? Start planning your Hawaiian island-hopping adventure today! Book your flights, reserve your accommodations, and prepare for an unforgettable experience. Aloha!
