The Only Hawaii Itinerary You’ll Ever Need

Hawaii’s beauty makes it easy to dream about visiting, but planning the perfect Hawaii itinerary can be overwhelming. From deciding what to see and do with your limited time, to knowing how to make the most of each island, there are a lot of choices that can make or break your trip. As someone who works in the Hawaii travel industry and visits frequently, I’ve learned some of the best ways to help you create an unforgettable experience. Whether you have just a long weekend or two full weeks, I’ve got you covered with ways to make the most of Hawaii’s aloha spirit. Let’s get planning!

How to Plan Your Hawaii Itinerary

Planning a Hawaii itinerary can feel a bit like being in a candy store. Everything looks amazing, but you can’t have it all in one go (unless you’ve got unlimited time, which… if you do, teach me your ways!). Here’s how to break it down and get the best bite out of paradise.

Choosing the Right Islands to Visit Based on Trip Length

First, consider how much time you have. Once you know that, you can decide which islands you want to visit. If you need more help choosing the right island(s), check out my post on The Best Hawaiian Island for You.

• 3 days: Stick to one island—trying to see more than one will leave you feeling rushed. Each island has a unique flavor, so savor it!
• 4-5 days: Add a day trip to another island—get a taste without overdoing it.
• 5-7 days: Aim for two islands—it’s totally manageable, and you’ll feel like you really got to know the place.
• 10 plus days: You can try to go for all four major islands. The more time, the merrier! Just know that each island’s got its own rhythm, and planning with that in mind will make your trip perfect.

3 Days in Hawaii: Stick to One Island

If you’re doing a quick trip, just pick one island. I know it might feel like you’re missing out, but you’ll end up spending your precious time in airports and cars instead of living it up. Here are some suggested 3-day itineraries for each of the four major islands. 

Oahu: Waikiki Beach, Pearl Harbor, Diamond Head, and North Shore Exploration

Here’s how you can break down your 3 days on Oahu. You can check-out my full 3 Day Oahu itinerary for more details.

• Day 1: Ocean Adventures and Luau Magic: Start with breakfast at Orchids, then dive into ocean adventures like surfing or snorkeling at Hanauma Bay, and end the day with a traditional Hawaiian luau at Paradise Cove.
• Day 2: Road Trip to the North Shore’s Laid-Back Vibes: Begin your day with a trip to the North Shore. Check out the famous waves and take some time to explore the small beach towns. Later, stop by the Dole Plantation or relax at one of the North Shore’s stunning beaches.
• Day 3: Hike, History, Shopping, and Sunset: Start your day at Pearl Harbor, then enjoy some shopping at Ala Moana Center, and wrap up with a delicious dinner while watching the sunset.

Maui: Road to Hana, Kāʻanapali, and Haleakalā National Park

Three days on Maui? Here’s how I’d spend it. Be sure to check-out my full guide on for 3 days on Maui.

• Day 1: Drive the Road to Hana: It’s twisty and might make you a bit motion-sick, but it’s absolutely worth it. You’ll experience waterfalls, beaches, and banana bread—it’s like a Hawaiian sampler platter.
• Day 2: Kāʻanapali: Start with breakfast at an oceanfront cafe, then explore Whalers Village for some shopping. Relax on Kāʻanapali Beach, enjoy snorkeling near Black Rock, and end your day with a sunset dinner at a beachfront restaurant.
• Day 3: Sunrise at Haleakalā: Pull yourself out of bed super early for a sunrise at Haleakalā. Be sure to reserve your spot in advance, as reservations are required. It’s a once-in-a-lifetime experience—almost like visiting another world.

Big Island: Volcanoes National Park, Kona Coffee Farms, and Black Sand Beaches

Three days on the Big Island is perfect for adventurers. See below for quick tips, or check out the full itinerary here.

• Day 1: Volcanoes National Park: Kick things off with a visit to Volcanoes National Park. Seeing lava flow at night is both peaceful and powerful, offering an experience that will humble you.
• Day 2: Kona Coffee and Manta Rays: Spend the morning touring Kona coffee farms. Even non-coffee drinkers, like me, find these tours fascinating. In the evening, join a manta ray night snorkel for an unforgettable underwater adventure. I had the opportunity to do this with my mom recently, and it’s one of the coolest experiences we’ve ever had. 
• Day 3: Punalu’u Black Sand Beach: Visit Punalu’u Black Sand Beach, a surreal spot with its dark sands and sea turtles chilling like they own the place (which, honestly, they do!). Relax and take in the beauty of this unique setting.

Kauai: Waimea Canyon, Wailua Falls, and Relaxing at Hanalei Bay

Kauai, the Garden Isle, is my personal favorite. In three days, you’ll feel like you’ve unplugged and stepped into a screensaver. Here’s a full itinerary for 3 days on Kauai.

• Day 1: Waimea Canyon and Nā Pali Coast: Explore Waimea Canyon, nicknamed the Grand Canyon of the Pacific. It’s vibrant and colorful, with far fewer crowds than other popular spots. In the afternoon, take a boat or helicopter tour to experience the breathtaking Nā Pali Coast with its dramatic cliffs and stunning ocean views.
• Day 2: Wailua Falls: Take a trip to Wailua Falls—worth the stop for some breathtaking views and photos. You can even consider kayaking on the Wailua River for an adventurous way to experience the lush surroundings.
• Day 3: Hanalei Bay: End your time by relaxing at Hanalei Bay. It’s peaceful, postcard-perfect, and ideal for winding down into serious vacation mode.

4-5 Days in Hawaii: Add a Day Trip to a Neighbor Island

If you’ve got 4-5 days, you can add in a little extra—base yourself on one island, and sneak in a day trip to another. You could even consider flying to the second island the night before to maximize your time for exploring.

Here are some suggested 3-day and day trip combinations:

• 3 Days on Oahu + Day Trip to Maui: Spend 3 days exploring Oahu’s highlights, then take a day trip to Maui to drive part of the Road to Hana or relax on Kaanapali Beach.
• 3 Days on Maui + Day Trip to the Big Island: Enjoy 3 days on Maui with activities like the Road to Hana and Haleakalā, then take a day trip to the Big Island to visit Volcanoes National Park.
• 3 Days on Kauai + Day Trip to Oahu: Immerse yourself in Kauai’s scenic beauty for 3 days, then take a day trip to Oahu to see Pearl Harbor and hike Diamond Head.
• 3 Days on the Big Island + Day Trip to Kauai: Spend 3 days on the Big Island enjoying Volcanoes National Park and Punalu’u Black Sand Beach, then take a day trip to Kauai to explore Waimea Canyon and the Nā Pali Coast.

5-7 Days in Hawaii: Break Up the Trip to See Two Islands

With 5-7 days in Hawaii, you can start to really see what makes each island special—spend a few days exploring two islands and dive a bit deeper. You can experience city life, adventure, beaches, and take things at a pace that feels right—less like you’re racing and more like you’re flowing with the island vibes.

Here are some suggested two-island itineraries:

• 3 Days on Oahu + 2 Days on Maui: Spend 3 days exploring Oahu’s major sites like Waikiki, Pearl Harbor, and the North Shore, then fly to Maui for 2 days of adventure on the Road to Hana and sunrise at Haleakalā.
• 3 Days on Maui + 2 Days on the Big Island: Start with 3 days on Maui, experiencing Wailea and Kaanapali Beach. Then, hop over to the Big Island for 2 days to explore Volcanoes National Park and Punalu’u Black Sand Beach.
• 3 Days on Kauai + 2 Days on Oahu: Immerse yourself in Kauai’s stunning landscapes, including Waimea Canyon and Hanalei Bay, then spend 2 days in Oahu visiting Diamond Head, Waikiki, and Pearl Harbor.
• 2 Days on the Big Island + 3 Days on Kauai: Begin on the Big Island with visits to Volcanoes National Park and manta ray snorkeling, then fly to Kauai for 3 days to take in Waimea Canyon, the Nā Pali Coast and Hanalei Bay.

10 or more Days in Hawaii: See All Four Major Islands

If you have 10 or more days, you can explore all four of Hawaii’s main islands without feeling rushed. This approach allows you to savor each island’s unique vibe and get a full sense of the diversity Hawaii has to offer.

Here is a suggested itinerary for seeing all four islands in 10 days:

• Days 1-3: Oahu: Start your journey in Oahu, visiting iconic sites like Waikiki Beach, Pearl Harbor, and the North Shore.
• Days 4-6: Maui: Fly to Maui for a few days to drive the Road to Hana, relax on Kaanapali Beach, and witness the sunrise at Haleakalā.
• Days 7-8: Big Island: Spend two days on the Big Island exploring Volcanoes National Park and snorkeling with manta rays.
• Days 9-10: Kauai: End your trip on Kauai, taking in the beauty of Waimea Canyon and the Nā Pali Coast for a perfect finale to your Hawaiian adventure.

Insider Tips for a Perfect Hawaii Vacation

Best Times to Visit Hawaii for Weather, Events, and Deals

Hawaii is a wonderful destination year-round, but there are certain times that stand out for fewer crowds, great weather, and better deals:

• April to early June, and September to early November: These months are considered the best times to visit. You’ll enjoy perfect weather, fewer tourists on the beaches, and often better prices on hotels. Plus, it’s a great time for activities like surfing, whale watching, or enjoying local festivals.
• Busy Season (Winter and Summer): If you can only travel during peak times like winter or summer, don’t worry—it’s still amazing! Just be prepared for larger crowds at popular spots and most-likely higher prices.

For a detailed breakdown of Hawaii’s seasons, check out my full guide on the best time to visit Hawaii.

Getting Around Hawaii: Flights, Ferries, and Tips

• Inter-Island Travel: You don’t necessarily have to start and end your trip on the same island. While Oahu has the most flights, other islands also offer non-stop options to and from the mainland. Use a multi-destination flight search to help you figure out your best route. Hawaiian Airlines and Southwest offer frequent short flights, typically under an hour. Flight costs usually range from $50 to $150, but booking early or using comparison tools like Google Flights can help you find the cheapest options.  
• Maui-Lanai Ferry: For the Maui-Lanai route, there is a convenient ferry option. The ferry runs a couple of times a day, and the journey takes a little over an hour.
• Pack Light: Traveling light will make managing luggage much easier across multiple islands, reducing hassle during transfers, especially when considering the agricultural inspections required at Hawaii airports. These inspections can make handling a lot of luggage even more cumbersome. 

Renting a Car in Hawaii

• Public Transport: Public transport in Hawaii is limited. Uber and Lyft are available, but may be restricted depending on your location. 
• Renting a Car: Renting a car is essential if you plan to explore beyond Waikiki. Attractions are spread out, and buses are infrequent.

How to Save Money: Find Deals on Accommodations, Activities, and Dining

• Travel During Shoulder Seasons: April to June, and September to November offer the best deals.
• Book Group Accommodations: Airbnb or Vrbo are often a steal if you’re traveling with friends or family. Just make sure you understand all of the fees upfront. 
• Don’t Underestimate Food Trucks: Some of the best meals can be found from a truck by the beach—like fresh fruit bowls that capture the island’s natural flavors.
• Be Selective with Tours: Tours can get pricey, so it’s important to choose wisely. Focus on experiences that are truly unique to Hawaii, like a helicopter ride over the Nā Pali Coast or a manta ray night snorkel on the Big Island. For simpler activities, like a walking tour of Honolulu, you can often go self-guided to save money while still having an enriching experience.

Packing Essentials for Hawaii

• Casual Attire: Pack your flip-flops, comfy shorts, and a couple of nice outfits for dinners out.
• Hiking Gear: Essential if you plan on exploring (which you should!).
• Reef-safe Sunscreen: It’s not just a suggestion—it’s a rule. You’ll be thankful you have it while snorkeling at Hanauma Bay or exploring Maui’s coral reefs.

Respecting Hawaiian Culture and the Environment

Hawaii isn’t just a vacation spot—it’s home to many people, with a rich culture and delicate ecosystems. Here’s a few ways you can show your respect: 

• Learn Hawaiian Phrases: Show respect by learning a few Hawaiian phrases (like “mahalo” for thank you).
• Respect Sacred Spots: Be mindful of sacred areas and always leave the beaches and trails as you found them.
• Do Not Touch Wildlife: Please, don’t touch the turtles or monk seals—they need their space, and it’s illegal.

Whether you’re visiting for a few days or planning a two-week island-hopping adventure, Hawaii offers a blend of natural beauty, cultural richness, and unforgettable experiences. With this Hawaii itinerary, you can create the perfect trip to suit your time and travel style. Book your flights, pack your bags, and let the aloha spirit transform your vacation. Aloha!