How to Plan Your First Hawaii Trip

So, you’ve decided to book a trip to Hawaii? First time? Let’s make it happen!

This guide cuts through the noise, focusing on the practicalities of planning your first trip to Hawaii. We’ll walk you through booking flights, choosing the right island(s), and finding budget-friendly accommodation, so you can focus on the fun: volcanoes, beaches, and island vibes.

Setting the stage

1. Figure out your Hawaii vacation budget

This first-time Hawaii vacation planner starts with your budget. You already know that you’ll need to pay for more than just airfare and accommodation. You’ll also need funds for activities, dining, and transportation, not to mention a buffer for souvenirs and assorted unexpected expenses.

Here’s a rough idea of how much it would cost to spend a week in Oahu during shoulder season. We’ve broken it into three price points: Budget, Mid-Range, and Luxury.

Remember, these are estimates. A lot depends on your destination, travel dates, and whether you use the cost-cutting ideas that we’ve included in this article.

Accommodation:

• Budget: $150/night per couple. Look for vacation rentals, hostels, or budget-friendly hotels outside the main Waikiki strip.
• Mid-Range: $250/night per couple. Consider moderately priced hotels with good amenities or vacation rentals in quieter areas.
• Luxury: $400/night per couple. Splurge on beachfront resorts, oceanfront suites, or private villas.

Activities:

• Budget: $50/day per couple. Focus on free or low-cost activities like hiking, snorkeling, visiting cultural sites, and picnicking on the beach.
• Mid-Range: $75/day per couple. Include paid activities like surfing lessons, boat tours, museum visits, and luau shows.
• Luxury: $150/day per couple. Go for private helicopter tours, dolphin encounters, scuba diving trips, and high-end spa treatments.

Food:

• Budget: $75/day per couple. Opt for casual dining, food trucks, grocery store picnics, and self-catering in your accommodation.
• Mid-Range: $100/day per couple. Enjoy a mix of casual and sit-down meals, exploring local restaurants and farmer’s markets.
• Luxury: $150/day per couple. Indulge in fine dining experiences, romantic beachside dinners, and chef-curated meals.

Transportation:

• Budget: $30/day per couple. Utilize public transportation (buses) and rely on walking or biking for short distances.
• Mid-Range: $40/day per couple. Rent bikes for some days and occasionally use taxis or ride-sharing services.
• Luxury: $50/day per couple. Rent a car for the week or hire a private driver for day trips or special occasions.

Other Expenses:

• Tipping: Generally 15-20% of restaurant bills, tour guides, and taxi fares. Budget around $10/day.
• Extras: Unexpected expenses happen! Allocate 10% of your total budget for things like souvenirs and miscellaeous costs.

Total Budget:

• Budget: $3,885 for the week, or $555/day
• Mid-Range: $5,950 for the week, or $850/day
• Luxury: $9,450 for the week, or $1,350/day

2. Choose when to travel

When is the best time to visit Hawaii? That depends on your priorities. Let’s explore the ideal times to travel, considering weather, budget, and crowds.

The best time to visit Hawaii for good weather

June, July, and August have the best weather. You’ll have minimal rain and perfect beach conditions. There will also be more people and higher prices.

The shoulder seasons (March-May) have good weather. Expect warm days and slightly lower costs. If you travel then, make sure your Hawaii packing list includes a rain jacket.

The cheapest time of year to visit Hawaii

It costs a lot to go to Hawaii. And if you go during a busy time, like Christmas or Spring Break, it might cost you even more.

The best time to visit Hawaii for budget travelers is during the shoulder season (after Easter through May and September through November). You’ll find better deals on accommodation and flights during these months, and flying mid-week can save you even more money.

When is Hawaii least crowded?

The quietest months in Hawaii for tourism are typically May, and September (after Labor Day) through November (excluding Thanksgiving). These are the best months for visitors who want to avoid large crowds and seek a more tranquil experience.

Best Time to Visit Hawaii Chart

Factor	Peak Season (June-August)	Shoulder Season (April-May & Sept-Nov)	Low Season (November-March)
Weather	Hot, sunny	Pleasant	Cool, rainy
Prices	Highest	Moderate	Lowest
Crowds	Most	Less	Least
Surfing	Good swells for experienced surfers	Smaller swells good for beginners	Biggest swells ideal for experienced surfers
Whale Watching		Rare	Excellent

ⓘ TLDR: If you’re looking for a balance between crowds, pricing, and weather, visiting Hawaii in April/May or between Labor Day and Thanksgiving (the shoulder season) is a great bet.

3. Decide how many days you will spend in Hawaii

In our opinion, it’s not worth going to Hawaii for just a few days. To begin with, the shortest nonstop flight to Hawaii from Los Angeles (LAX) takes approximately 5.5 hours and will be even longer from anywhere else. Not to mention, your body will also have to deal with the time change. Trust us: Jet lag is no fun.

If you want your vacation to Hawaii to be worthwhile, you should plan to spend at least a week there. That should be enough time to enjoy the attractions and culture … assuming you’re only visiting one island.

If your Hawaii itinerary includes multiple islands, you’ll need two weeks or more. You’ll lose half a day of sightseeing time while you change hotels and fly there, so plan accordingly.

See our 7 Day Oahu itinerary for many more tips.

4. Select the Hawaiian island you want to visit

Hawaii has eight main islands and six of them are tourist destinations. Every island has its own unique vibe and culture that you may experience firsthand.

TLDR: Everybody has their own opinion on which Hawaiian island is the best. But most visitors decide between Maui vs. the Big Island for a first Hawaii visit.

Not sure which Hawaiian island to choose? The first thing you need to do is to figure out what your priorities are. Then, do some research on what the various islands have to offer so you can tailor your first-time trip to Hawaii to your interests.

But don’t go crazy. As fun as it might sound, island hopping isn’t the best use of your holiday time. Staying on one island not only streamlines your itinerary but also saves on transportation costs.

TRAVEL STYLE	OAHU	MAUI	HAWAII	KAUAI	LANAI	MOLOKAI
Adventure & Ecotourism		✓	✓	✓
Beaches	✓	✓	✓	✓	✓	✓
Culture	✓		✓		✓	✓
Diving & Snorkeling	✓	✓	✓
Escape				✓		✓
Family	✓	✓		✓
Food	✓	✓
Golf & Spa	✓		✓	✓	✓
Honeymoon/Relaxation		✓
Nightlife	✓
Shopping	✓		✓

ⓘ According to The Hawaii Vacation Guide, Oahu and the Big Island (Hawaii) are the most affordable islands. Maui is one of the most expensive.

Booking the essentials

ⓘ SUPER IMPORTANT TIP: It is not uncommon for popular attractions, airlines, and hotels to be completely booked up, especially during peak travel times. Make reservations well in advance to avoid being disappointed.

5. Book your flights

Now that you know when you’re going and how long you’ll be there, it’s time to book your flight. But booking a flight to Hawaii involves more than finding the cheapest ticket. Baggage fees, transfers, and seat preference cost extra on many airlines, so you’ll need to factor those into the price.

You can researches prices on flight aggregators like Skyscanner, Google Flights, and CheapOair. They save you time and money by searching the web for the most advantageous airline schedules and prices. You can also set up price alerts so you’ll be notified if there are any price drops.

To save even more money, check out the airfare on different days of the week to see how prices change. More often than not, fares will be cheaper mid-week.

Flying from a nearby airport can also save you money. For example, there are different prices for flights to Hawaii from the three main airports in the Greater New York City Area.

Interesting fact: The three U.S. cities with the lowest airfares to Honolulu are Oakland, Los Angeles, and Seattle.

6. Choose where to stay

No matter what your budget is, Hawaii has countless accommodation options for you to choose from. You’ll find everything from beach bungalows to luxury resorts, rental homes, hotels, and more.

Staying beachfront offers stunning views and instant access to the ocean, but the tradeoff is that it’s often more expensive. If being on the water isn’t important to you, book something that’s a few blocks inland. Those accommodations can be more affordable and offer a quieter experience.

ⓘ BOOKING TIP: You can search for resorts and hotels on Booking and vacation rentals on Vrbo.

The price tag isn’t the whole story, though. Taxes bite in Hawaii (up to 18%!), and hotels often tack on resort fees for Wi-Fi, pools, or gym access. Rental condos might surprise you with cleaning charges, and parking is another cost to consider. Read the fine print before you book that beachfront dream.

We always read other guests’ reviews to get an idea of how they liked the place. Look for more recent feedback to get a more accurate picture of what your stay might be like.

7. Plan how you’ll get around the island

The first thing you’ll need to figure out is how to get from the airport to your lodging. If you’re renting a car or your hotel offers a shuttle service, you’re set.

If not, your options are to hail a cab, use an app like Uber or Lyft, or book an airport transfer service like Kiwitaxi. Go for the transfer service if you want the most convenient option. There’s something to be said for knowing that your driver will be waiting for you inside the airport, holding a sign with your name on it.

As to how to get around the island during your week in Hawaii, that depends on your budget and how much you plan to do. Yes, you can rely on public transportation, but the full Hawaiian experience requires a car.

We’ve had good experiences with Discover Cars and highly recommend them. Just keep in mind that rental cars are in high demand in Hawaii. You’ll need to book yours ASAP to ensure you will get the vehicle you want.

If you don’t want to drive, public buses offer a budget-friendly way to get around on Oahu, Maui, Kauai, and the Big Island. Taxis or ride-sharing apps like Holoholo, Lyft, and Uber are a faster, more flexible option. Just be warned: Finding a cab or rideshare to take you back to your hotel from a remote area can be a major challenge.

There are no public buses on Lanai or Molokai, but there are cabs and shuttles that can take you around. We recommend renting a 4WD on Lanai. With 400 miles of unpaved roads, the island begs for off-road adventures. You can also use a 4WD vehicle on Molokai, though taxis and shuttles should be fine for most journeys.

8. Buy travel insurance

In just the last few years, Hawaii has experienced cyclones, fires, and volcanic eruptions. Think about all the people who had to cancel their trips and didn’t get their money back!

This is one place where investing in travel insurance is worth it. There’s nothing like having peace of mind for unexpected situations. Policy coverage can include trip cancellations, medical emergencies, and lost belongings, too.

You can compare policies from providers like Ekta and World Nomads to find the one that aligns best with your needs and travel plans.

Planning your adventures

9. Create an itinerary

Crafting a well-balanced itinerary is key to maximizing your Hawaiian experience. Consider dedicating certain days to exploring local attractions, mixing in some relaxation on the beaches, and leaving room for spontaneous discoveries.

Check out our Maui and Oahu articles for plenty of itinerary ideas. They will help you prioritize activities that align with your interests, whether it’s hiking to scenic viewpoints, snorkeling in crystal-clear waters, or indulging in local cuisine.

Also, a travel guide like this one will give you lots more ideas than we can cover in any article.

10. Choose your activities and excursions

Whichever island you choose, rest assured that there are plenty of free things to do, as well as tours and activities that will make your vacation truly memorable.

Research and book activities and excursions in advance to secure your spot. Whether it’s a snorkeling tour, a scenic helicopter ride, or a traditional Hawaiian luau, having a plan in place ensures you won’t miss out on popular experiences. Check cancellation policies in case of any unexpected changes to your schedule.

Most local companies have good tours on offer. You can find many of them listed on Viator and Get Your Guide.

ⓘ TIP: If you plan to stay on Oahu, be sure to read our 7 Day Oahu Itinerary next.

Frequently asked questions about visiting Hawaii for the first time

In conclusion

We hope we’ve helped you out! Planning your first trip to Hawaii might feel a bit overwhelming, but you can do it! Trust us: With the right mindset and preparation, it can turn into a truly unforgettable experience. So, get ready to have an amazing time!

We really hope you’ll fully immerse yourself in the rich culture and stunning nature of Hawaii! Don’t be afraid to try new things like the delicious local cuisine and exciting adventure activities. More importantly, don’t forget to savor every single moment of your trip!

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