Hawaii looks straightforward on paper. Pick an island, find a good hotel and book the flights. In reality, there are quite a few decisions that can make a big difference to the trip.
The islands are very different from one another, hotel room categories can be surprisingly complicated, and moving between islands takes more time than the 40-minute flight suggests. Add restaurant reservations, rental cars, different weather from one side of an island to another and the flights from the mainland, and there is quite a bit worth working out before you book.
We book Hawaii regularly at Clements Travel, particularly Four Seasons, Rosewood, Ritz-Carlton, Andaz and the other higher-end resorts. This is the advice we tend to give our own clients, including where we think it is worth spending more and where it probably isn't.
Which Hawaiian Island Should You Visit?
There isn't one island that works for everyone. Maui is often a good starting point for a first Hawaii trip because you get excellent resorts without being tied to the resort. You can rent a car, go out for dinner, explore different parts of the island and still have plenty of days where you do very little.
Hawaii Island feels quite different. The distances are much greater, the landscape is more dramatic and several of the best resorts are destinations in their own right.
Oahu gives you Honolulu, Waikiki, restaurants, shopping, history and a much more urban side of Hawaii.
Kauai is greener, quieter and less developed, while Lanai is at the other end of the spectrum altogether. We often use Lanai at the end of a longer Hawaii trip when the idea is to stay somewhere excellent and not feel any particular need to leave.
How Many Islands Should You Visit?
This depends mainly on how long you have.
For a week, we'd normally stick with one. With around ten nights, two islands works well. With two weeks, three becomes much easier.
The reason isn't that inter-island flights are particularly long. They aren't. It's everything around them.
Checking out, getting to the airport, returning the rental car, flying, collecting the luggage, picking up another car and getting to the next hotel can use a large part of the day.
For a ten-night trip, we'd generally prefer five nights on Maui and five on Hawaii Island over trying to squeeze in a third stop. You see less on paper, but you have far more time to enjoy each place.
uld always rather give you five unhurried nights on each of two islands than have you checking off four islands on an exhausting sprint.
When to Visit Hawaii
Hawaii works year-round, although the experience changes depending on the season and, importantly, which coast you are staying on.
December through April is high season and also the main period for humpback whale watching. Winter brings much larger swells to north-facing shores, so ocean conditions can be quite different from summer.
June through August generally brings warmer days and calmer water in many areas, along with increased demand from families during school vacations.
Spring and fall can be very good times to travel. There is often better hotel availability outside the main vacation periods, and the islands can feel a little quieter.
Christmas and New Year is a different proposition altogether. The most popular resorts can fill a long way ahead and festive reservations frequently come with minimum stays, higher rates and much stricter deposit and cancellation conditions. For the top hotels, we like to start looking 9 to 12 months ahead.
Hawaii's Microclimates
One thing that catches people out is looking at a weather app for the whole island.
Hawaii has significant microclimates. Volcanic mountains create rain shadows, so you can have sunshine on one side of an island and heavy rain on another.
When we're looking at weather for a hotel, we're interested in the specific coast rather than the generic forecast for Maui or Hawaii Island.
Flights to Hawaii
One useful way to plan Hawaii is to work out the flights before deciding the order of the islands.
You don't necessarily need to arrive and depart from the same airport.
If you're combining Oahu and Maui, for example, you could fly from the mainland into Honolulu, travel from Oahu to Maui during the trip and then fly home directly from Maui.
The same can work with Kona and Kauai depending on your home airport and the routes operating on your dates.
It avoids flying back to Honolulu purely to connect home, and most major airlines allow you to price this as a multi-city itinerary.
Honolulu has by far the largest selection of flights, but Maui, Kona and Kauai also have nonstop service to the mainland.
Look at the Aircraft, Not Just the Cabin Name
This becomes more important if you're coming from the East Coast, Texas or the Midwest.
Some longer Hawaii flights operate with lie-flat Business or First Class seats. United, for example, uses Polaris-style lie-flat seats on selected Hawaii services. American also has lie-flat Business Class on some routes, while Delta operates Delta One on selected longer flights.
The aircraft is worth checking because two flights sold as First or Business Class can offer very different seats.
One might have a flat bed. Another might have a standard domestic First Class recliner.
Aircraft substitutions happen as well, so we look at the actual flight and seat map rather than assuming the cabin name tells the whole story.
From California, we wouldn't necessarily build the trip around finding a flat bed. From New York or another East Coast city, where you can spend around ten hours on the plane, it becomes far more relevant.
Arrival time is worth considering too. A better seat isn't necessarily worth arriving at 9 PM and losing the first evening at the hotel.
We normally look at the whole itinerary together: where you're starting, where you're finishing, what nonstop options exist and which routing uses the least amount of vacation time.
Hawaii Airports at a Glance
You don't automatically need to fly through Honolulu. Four of the five islands most commonly included in luxury Hawaii itineraries have airports with direct mainland service.
Hawaii Island is the one where the airport choice needs particular attention because KOA and ITO are on opposite sides of a very large island. For most of the major luxury resorts on the western side, KOA is the airport we use. Maui also has smaller airports at Kapalua and Hana, but OGG is the main airport for the vast majority of visitors.
Passport and REAL ID Requirements for Hawaii
For travelers flying from the U.S. mainland, Hawaii is a domestic flight, so U.S. citizens do not need a passport specifically to travel there. TSA identification requirements still apply. Since May 7, 2025, travelers aged 18 and over using a state-issued driver's license or identification card at airport security generally need a REAL ID-compliant document. A passport or another TSA-accepted form of identification can also be used.
Children under 18 generally aren't required to present identification to TSA when traveling domestically with an adult, although individual airlines can have their own requirements. If you're flying to Hawaii from outside the United States, the normal U.S. immigration and entry requirements apply.
Traveling Between the Hawaiian Islands
For most island combinations, flying is the practical option. There isn't a regular passenger ferry system connecting all the main Hawaiian islands. Lanai is an exception because it can be reached by air, including Lanai Air, and there is also passenger ferry service from Maui.
When we're putting together a multi-island trip, we look at the entire transfer rather than simply choosing the shortest flight. Connections, airport transfers, luggage and rental cars all need to be included in the calculation.
Rental Car or Private Transfers?
We are fans of renting a car in Hawaii, particularly on Maui, Kauai and Hawaii Island. The biggest reason is freedom. You can go out for dinner, stop at a beach, change your plans halfway through the day or drive somewhere because somebody mentioned it over breakfast.
There is also a financial argument for it. Private airport transfers to places such as Wailea, the Kohala Coast and Princeville can become expensive, and depending on the dates, a rental car for the week can sometimes cost around the same as the airport transfers alone. We have access to corporate car rental rates as well, so we can compare those against the public rates.
On Oahu it depends on where you're staying. If you're spending a few days in Waikiki and don't plan to leave very often, paying for a car to sit in the hotel garage doesn't make much sense. Lanai is different again because the resorts provide transportation around the island and 4x4 rentals are available when you want to explore independently.
Hotel parking should be included in the calculation because valet or self-parking at higher-end Hawaii hotels can easily add $40 to $65 or more per night. The other disadvantage to renting is the airport collection process. Lines can sometimes be long during busy arrival periods, and for some clients a private transfer is worth paying for simply to walk out of the airport and leave.
If you're traveling with children, car seats need to be considered for both rental cars and private transfers. Hawai'i state law requires children up to 10 years old to be secured in an appropriate child passenger restraint or booster seat unless they are over 4'9" tall. Children under 4 need an appropriate child safety seat, while children under 2 need to be secured in a rear-facing car seat. This also applies when using private transfer services, so if you're arranging airport transportation, make sure the transfer company knows the ages of the children in advance and can provide the correct seats.
Restaurants in Hawaii
If there are restaurants you really want to visit, this is one part of the trip we'd look at early. Mama's Fish House on Maui is probably the best-known example, with good dinner times often disappearing months ahead. It's also worth checking where the restaurant is in relation to the hotel. Mama's is on Maui's North Shore near Paia, while many of the luxury resorts are down in Wailea, so dinner there involves a reasonable drive each way and is better planned as part of the day.
That doesn't mean we think every meal should be reserved before you arrive. Hawaii has excellent poke counters, bakeries, food trucks, farmers markets and smaller local restaurants. We'd normally secure the restaurants that are difficult to get into and leave plenty of space for everything else.
Luxury Hotels and Room Categories in Hawaii
Hawaii is interesting because many of its best luxury hotels aren't new. Four Seasons, Rosewood, Ritz-Carlton, Montage, Auberge Resorts Collection and other major brands occupy some extraordinary pieces of coastline. We don't put too much weight on the age of the original building. We're more interested in when the rooms were last renovated, how well the hotel is being maintained, the quality of the staff and whether the property is still operating at the level its price suggests.
Room categories are where Hawaii can become surprisingly complicated. There is no standard definition of Ocean View. At one hotel it can mean a wide, unobstructed Pacific view. Somewhere else it might be an angled view between buildings, and at another property the ocean might only be visible from one part of the balcony. The price difference can be substantial.
Whether we think the upgrade is worthwhile depends on the particular hotel, where the rooms are positioned and how much time you're likely to spend on the lanai. Sometimes we'd absolutely pay more for the view. Other times, we'd take a well-positioned Garden or Mountain View room and use the difference for another night, dinner, a boat charter or something else during the trip. This is an area where knowing the hotel and its room categories can be very useful.
What to Pack and Hawaii's Agricultural Rules
Hawaii is relaxed, including at most higher-end resorts, so normal resort clothing will cover most situations. The less obvious thing to pack is something warm if you're going up Haleakala on Maui or spending time at higher elevations on Hawaii Island. Sunrise at Haleakala can be very different from sitting beside the pool in Wailea a few hours later.
Sunscreen is another Hawaii-specific consideration. The state restricts the sale and distribution of sunscreens containing oxybenzone and octinoxate. We normally suggest bringing mineral sunscreen using ingredients such as zinc oxide or titanium dioxide rather than relying purely on products marketed as reef friendly.
Hawaii also has agricultural controls designed to protect its environment. Fresh fruit, vegetables, plants and seeds may need to be declared when arriving, while packaged foods are generally easier. When flying from Hawaii back to the U.S. mainland, checked and carry-on luggage goes through USDA agricultural inspection at the airport. If you've bought fruit or other agricultural products during the trip, check whether they can travel before packing them. You'll often see approved pineapples and other products packaged specifically for mainland travelers.
Five Hawaii Itineraries We Like
Maui + Hawaii Island: 10 Nights
Five nights on Maui followed by five nights on Hawaii Island is probably our favorite combination for a first Hawaii trip. Maui gives you a good mixture of resort time, driving, restaurants and exploring, then Hawaii Island changes the scenery completely with black lava landscapes and the large resorts of the Kona and Kohala coasts. Five nights on each gives you enough time to enjoy both without constantly thinking about the next checkout.
Maui + Lanai: 9 Nights
Five nights on Maui followed by four on Lanai works particularly well for a honeymoon. Do the more active part first on Maui, with a rental car, restaurants and days out, then move to Lanai for the final four nights. The contrast works well because by the time you reach Lanai, you've already done most of the driving and sightseeing you wanted to do.
Hawaii Island + Lanai: 10 Nights
Five nights on Hawaii Island and five on Lanai is a much more resort-focused trip. Hawaii Island has some exceptional large-scale resorts along the Kona and Kohala coasts, while Lanai feels smaller and much more removed from everything. We'd look at this combination for someone choosing Hawaii primarily for the hotels, weather and downtime rather than trying to cover a long list of sights.
Oahu + Hawaii Island: 9 Nights
Three nights on Oahu followed by six on Hawaii Island works well for families. Oahu gives you Honolulu, Pearl Harbor, restaurants and some of the historical side of Hawaii, then you move to Hawaii Island and stay in one place for six nights. You get two very different parts of Hawaii without moving the family every few days.
Oahu + Kauai + Maui: 14 Nights
If you have two weeks and want to see three islands, we'd start with three nights on Oahu, move to Kauai for four nights and finish with a full week on Maui. Oahu gives you Honolulu and sightseeing, Kauai changes the pace and scenery completely, and seven nights on Maui leaves enough time for both the hotel and exploring the island.
A Few Things Worth Knowing Before You Book
Changing islands takes longer than the flight time suggests, so we normally treat an inter-island move as a travel day rather than putting anything important around it. Hawaii Island is also much larger than many people expect, and driving times should be checked before planning days out. The same applies to ride-shares. Uber is easy enough in Honolulu but isn't something we'd want to depend on in some of the more remote parts of Kauai or Hawaii Island.
Popular restaurants are worth dealing with early, particularly if somewhere like Mama's Fish House is important to the trip, but we wouldn't reserve every meal. Ocean conditions also change with the seasons, especially on north-facing shores during winter, and higher elevations can be cold enough that warm clothing is useful.
We also wouldn't fill every day with activities. One of the reasons we like renting a car is that you can leave an afternoon open, see what the weather is doing and decide where you want to go once you're there. Hawaii is a very easy place to enjoy without having every hour accounted for.
Planning Your Hawaii Trip with Clements Travel
You don't need to work all of this out before contacting us. Tell us where you're flying from, who's traveling, your approximate dates, the kind of hotels you like and roughly what you want to spend. We'll narrow down the islands and give you a selection of hotels and room categories that fit the trip.
We work directly with many of Hawaii's leading luxury hotels through Four Seasons Preferred Partner, Rosewood Elite, Marriott STARS & Luminous, Hyatt Privé, Virtuoso and other luxury hotel programs. Depending on the hotel and program, our clients can receive benefits including daily breakfast for two, $100 or more in hotel credit, room or suite upgrades, and early check-in and late checkout. Our Guest Experience team also works with the hotel before arrival, particularly for honeymoons, anniversaries, birthdays and other celebrations.
There are no Clements Travel booking fees for luxury hotel reservations. You pay the hotel directly, normally at the same published rate available from the hotel itself, while receiving the additional benefits available through our preferred hotel programs. We can also help with everything around the hotel, including deciding which islands work together, flights, rental cars, private transfers, restaurant planning and working out which room categories are worth paying more for.
Planning a Hawaii trip? Contact Clements Travel with your dates, budget and where you're flying from, and we'll put together a selection for you.
