Due to the high cost, long travel time, and diverse destinations among the island chain, planning a trip is challenging for a Hawaii trip planner. A bad itinerary means a waste of time. But for planning, traditional trip planner websites can only provide recommendations, itinerary templates, and must-do lists. They can't make decisions or make an itinerary automatically. That's what an AI trip planner can help you with.
With AI, you can not only get an editable itinerary in minutes, but also connect planning with real execution, like booking flights and hotels. In this article, you will get a step-by-step roadmap to plan a personalized itinerary to Hawaii with our free trip planner.
Best Time to Visit Hawaii
People come to Hawaii mainly because of the awesome weather here. Hawaii is in the tropics, where the length of day and temperature are relatively uniform. The hot season starts from June to October, but it is never unbearably hot. And the relatively cool season starts from December to March. Any month can be a great time to visit Hawaii. So when to go to Hawaii mainly depends on your schedule, the places you want to visit, and your budget.
Peak Tourist Season
Summer, from June to August, and Winter, from mid-December to January, are peak seasons in Hawaii. Thus, prices for airfare and accommodations are at their highest. In particular, the last two weeks of December and the first week of January are prime times for travel, and hotels and flights are often booked to capacity. For budget-limited travelers and outdoor adventure lovers, it may not be a good time.
Low Tourist Season
Late Spring, from mid-April to mid-June, and Fall, from September to November, are the shoulder seasons with fewer crowds and lower prices of flights and hotels. It will be to get reservations for excursions, rental cars, and restaurants. Don't worry, Hawaii is a beautiful place to visit all year round.
How Many Days for a Trip to Hawaii
It depends on how many islands you want to explore and the purpose of the trip. Usually, 5-6 days for one island. If you focus on adventures like hiking, snorkeling, and outdoor activities, 10-14 days is needed. But if you just want to relax on beaches, 5-6 days is sufficient.
How to Plan Your Trip with an AI Trip Planner
The functions of an AI trip planner are powerful. With natural language processing (NLP), AI can understand users' needs through the information they input, and then generate editable and personalized itineraries automatically. What's more, the AI trip planner uses intelligent algorithms to scan real-time flight prices across the web, which helps users find more economical flights. And for hotels, AI makes it easier to find what you want, whether luxury resorts, cozy boutique hotels, or budget-friendly options.
Step 1: Input your requirements
Here is a simple prompt for you to start planning. You can also use your own words.
Prompt for a 6-day honeymoon trip
My wife and I would like to plan a 10-day honeymoon trip with a budget of around ＄6000 to Hawaii in February 2026, departing from Los Angeles. We’d love to spend our time mainly on the Big Island and Maui. The travel pace should be moderate. We want a romantic and relaxing itinerary with a moderate pace. There are some special activities that we want to experience: sunset, whale watching, hiking, and beautiful beaches.
Step 2: Adjust the itinerary
After the itinerary is generated, what you should do is check and adjust the plan to make sure the final plan is exactly what you want. Whether you want to add or remove activities or adjust your budget, tell it what you need.
Step 3: Select your flights and hotels, and book them directly
Compared to traditional trip planner websites, you don't need to compare the price of flights and hotels yourself, jumping between different tabs endlessly. The AI trip planner automatically scans the best options across the web and presents you with clear choices.
Step 4: Share your itinerary with your fellow travelers
Click the "share" button, and your fellow travelers who are not with you can also know the itinerary instantly. Moreover, they can check the travel plan anytime during the trip.
Here is the itinerary I got for the romantic honeymoon! With a personalized itinerary, reasonable and directly bookable flights, hotel arrangements, and thoughtful tips, the honeymoon will be smooth and stress-free.
Where to Stay and Explore in Hawaii
Oahu
Oahu, also called "The Gathering Place". The majority of Hawaii’s population is concentrated here. East and West cultures come together here and are deeply rooted in the values and traditions of the Native Hawaiian people. The island is convenient with different transportation options for travelers to explore Oahu's regions and diverse activities.
Best for families, foodies, culture and history aficionados, and also romance seekers. But the island, especially Honolulu and Waikiki, can be busy and congested, with traffic problems at times.
Hawaii Island
This is the youngest island in the Hawaiian chain, and is commonly known as the Big Island, nearly twice as big as all of the other Hawaiian Islands combined. Due to the high elevation and barrier effect of Mauna Kea and Mauna Loa, Hawaii’s two most famous volcanoes, you can experience eight of the world's 13 ecosystems here.
Hawaii Island is perfect for adventure seekers, nature lovers, families with children who want kid-friendly activities, and lovers seeking romance. However, the island is large, and many of the attractions are far apart, making a rental car essential.
Maui
Maui has some of the best beaches in Hawaii, with soft white sand and crystal-clear waters. Popular spots include Kaanapali Beach and Wailea, and also offer a mix of outdoor activities, cultural experiences, and relaxation. You can hike, bike, snorkel, or simply enjoy the sunset.
Best for beach lovers, snorkeling enthusiasts, couples seeking a mix of relaxation and adventure, and travelers who enjoy good food and nightlife. Yet, Maui is a popular destination, and some areas can feel crowded, especially during peak season.
Kauai
Kauai is sometimes called the "Garden Island". As the oldest and northernmost island in the Hawaiian chain, the island is draped in emerald valleys, sharp mountain spires, and jagged cliffs aged by time and the elements. With diverse wildlife and untouched tropical rainforests, Kauai is a paradise for outdoor enthusiasts.
Best for families and couples who want a laid-back and culturally rich atmosphere in its small towns, and outdoor enthusiasts. But as a more rural island, Kauai is way more expensive than Maui and Oahu.
Top Things to Do in Hawaii
What You Can Do on Hawaii Island
A sample route for a 2-day trip to Hawaii Island:
🚩 Hilo Framers Market → Volcanoes Park → Kaulana Manu Nature Trail
- Hilo Farmers Market
A good place to buy locally-grown produce, like fresh tropical fruits. Sometimes you can also find crafts made by local artists and great Hawaiian snacks.
- Hawaiʻi Volcanoes National Park
From the wettest rainforests east of the Kilauea Caldera to the driest deserts west of Uekahuna, Hawaii Volcanoes is suitable for every type of visitor. A good place for visitors to explore the park in all types of environments and weather.
- Kaulana Manu Nature Trail
One of the most beautiful and pristine native Hawaiian forests for hiking, only 0.6 miles long, is very friendly for families with young kids, and also for photographers with heavy gear.
- Buying Local Hawaiian Coffee
Hawaii's climate and soil are naturally excellent for producing great coffee. You can buy them in local grocery stores and specialty retailers. Before buying, you'd better sample different types to find your favorite flavor.
What You Can Do on Maui
This is also a sample route for a 2-3 day winter trip to Maui:
🚩 Haleakala National Park → Ka’anapali Beach → Whale Watch
- Witness Maui’s Most Spectacular Sunrise
Haleakala National Park, also known as the "House of the Sun". You can witness a sunrise from the top of Haleakala, a volcano 9,740 feet high above sea level!
Tip: Make sunrise reservations in advance, and bring warm layers.
- Ka’anapali Beach
Ka’anapali Beach stands as one of North America’s most spectacular beaches with three miles of white sand and crystal clear water. An ideal spot for both relaxation and adventure, like snorkeling. The beach is free for access, but parking costs $5–10.
- Whale Watch (Winter only)
Every year, an estimated 10,000 to 12,000 North Pacific humpback whales migrate over 3,000 miles from Alaska to Hawaii for warm, safe waters for breeding and calving. The best time for whale watching on Maui is from January to March.
What You Can Do on Kauai
A sample route for a 1-day trip to Kauai, mainly on the North Shore of Kauai:
🚩 Kuilau Ridge Trail → Taste of Hawaii → Hanalei Town
- The Kuilau Ridge Trail and Na Pali Coast Views
The Kalalau Trail, 11 miles long, is known for being one of the most stunning hikes in the world, with lush valleys, ancient Hawaiian settlements, and towering sea cliffs.
- Explore Hanalei Town
Located in northern Kauai, Hanalei Town has timeless beauty, from historic places to contemporary art galleries. Visitors can enjoy water sports, exploring shops and food trucks, and scenic drives through Hanalei Valley.
- Try Acai Bowl and Poke Bowl
Acai Bowl is a must-try food in Hawaii. After hiking or sunbathing, there is nothing better than a refreshing, tropical acai bowl. Poke bowls are seemingly everywhere in Hawaii, typically served over a base of rice or other grains, with a variety of sauces and other toppings like ahi tuna or octopus.
Transportation Tips for Hawaii
On the Islands
Renting a car is best for exploring most of each island. Some car rental apps might be more affordable than traditional car rentals. For public transportation, buses only. Good choice for budget-limited travelers, but it’s also the slowest option. Taxis are convenient for short distances. Lyft and Uber are also very popular on Oahu!
Interisland Travel
Almost all travel between Hawaii's islands is by plane. Interisland flights are short and frequent. Flight times range from 20 to 50 minutes, depending on the route. The ferry is limited, only five times a day between Maui and Lanai.
Notes
- Rental cars are in high demand, so please plan ahead to secure a reservation.
- You can use your valid foreign driver’s license to drive in Hawaii for up to one year from your entry date.
Final Thoughts
Hawaii offers diverse islands, stunning landscapes, and endless activities, but planning a trip can be overwhelming. Traditional websites only provide recommendations, while an AI trip planner like iMean creates a personalized, editable itinerary in minutes, including flights, hotels, and practical tips.
If you want a personalized, editable day-by-day itinerary for Hawaii
