The summer after I graduated from college, I took my first trip to Hawaii. From the moment I walked off the plane, my entire body instantly relaxed, and it didn’t take much longer for me to fall in love with everything the islands have to offer — with beautiful beaches, award-winning restaurants, and a thriving international community, who wouldn’t?
A little over a year later, I packed my bags and moved to Hawaii. Since then, I’ve gotten married, bought my first house, and really made Hawaii my home. I know it probably sounds crazy, but I promise a visit to Hawaii will change your life, all you have to do is make the trip!
If you’ve been dreaming of an island vacation, consider this your ultimate guide to the Hawaii.
Did you know that there are eight major islands that comprise Hawaii? Each one has a unique personality with different experiences to offer. If you don’t already, you’ll be sure to have a favorite soon.
Nickname: “The Gathering Place”
Known for: Honolulu, Hawaii’s capital city
Must do: Surf at Waikiki Beach
Visit if: …you want it all: beaches, mountains, and a city.
Nickname: “The Valley Isle”
Known for: Black sand beaches
Must do: Drive the Road to Hana
Visit if: …the beach is your number one priority.
Nickname: “The Pineapple Isle”
Known for: Celebrity sightings
Must do: Splurge on a stay at a luxury resort
Visit if: …your ideal vacation includes lots of spa time.
Nickname: “The Friendly Isle”
Known for: The birthplace of hula
Must do: Visit the royal Kapuaiwa Coconut Grove
Visit if: …you like quirky, unique experiences.
Nickname: “The Big Island”
Known for: Kilauea, a volcano that erupted earlier this year
Must do: stargaze on Mauna Kea, the world’s tallest sea mountain
Visit if: …you want a front row seat to the power of nature.
Nickname: “The Garden Isle”
Known for: Waimea Canyon, the “Grand Canyon of the Pacific”
Must do: Sail the Napali Coast
Visit if: …you love outdoor activities like hiking and surfing.
Unfortunately, it’s almost impossible to visit all eight islands. Elizabeth Sinclair purchased Niihau, the “Forbidden Isle,” in 1864 and her descendants have controlled the island ever since. While helicopter tours and some hunting opportunities exist, you typically have to work as a government official, serve in the U.S. Navy, or be related to the Sinclairs to visit. Kahoolawe, the “Target Isle” is completely off limits to the public.
What to Pack
(Lots of) Swimsuits
Pack one more bathing suit than you think you’ll need. Suits will be on heavy rotation during your time here and you’ll want an extra one for when the others are inevitably wet, dirty, have gone missing, etc. While swimsuit boutiques are a dime a dozen in Hawaii, that doesn’t mean you’ll always find a style that’s flattering or fits correctly. Plus, a trip to the islands is the perfect excuse to order one or two (or a dozen) new suits.
It’s a no brainer that you should be wearing sunscreen (all day, errrr day). But did you know certain sunscreens contain ingredients that are damaging to coral and fish? Check labels for oxybenzone, octinoxate, and octocrylene before you pack. Unfortunately, you’ll find at least one of the above in most popular sunscreen brands, but a quick google search for “reef safe sunscreen” will point you in the right direction.
No matter which islands you visit, you’ll want to go on at least one hike, (I’ll spare you the details about the time I flew to another island, only packed slides, and had to rummage through the world’s smallest Walmart for men’s hiking boots). You don’t need to invest in fancy hiking boots if you don’t think you’ll ever use them again in the future. For most hikes, a pair of sneakers with solid traction will do the trick. If you’re unsure, research a hike’s level of difficulty before deciding which pair you’ll bring.
I can’t recommend packing a Turkish towel enough. Unlike its traditional counterparts, Turkish towels are incredibly thin, quick to dry, and are extremely versatile. Use it as a beach towel, a picnic blanket, or even a wrap for cooler nights.
If I could only give you one piece of advice when it comes to packing for a Hawaiian vacation, it’s this: only pack what you can fit in a carry-on. I know, I know, but hear me out. First, you’ll be glad you skipped the notoriously long wait at the baggage carousel after a long flight. Second, packing light gives you more flexibility when it comes to transportation, visiting other islands, or even where you’ll spend the night (beach camping is slightly less appealing when you’re dragging 50 pounds of luggage through the sand).
How to Get There
The Hawaiian Islands are the most remote chain of islands in the entire world, so it’s understandable that flights from the mainland have been expensive and peppered with unnecessary layovers for years. But, with major airlines adding more non-stop flights from both the West and East Coast, it’s never been easier or cheaper to visit. (Travel + Leisure magazine recently reported flights from Los Angeles to Honolulu for as little as $280!).
Regardless of where you live, there are plenty of tried and true ways to save money on a flight. One of the simplest ways is to be flexible with the location you fly into. There are four major airports, all of which offer inter-island flights. Just keep in mind that Hawaii’s busiest seasons are the winter (particularly the holiday season), and the summer months, so you can expect flights to be slightly more expensive during those times.
Where to Stay
There’s no shortage of hotels on most of the islands and there’s generally a wide variety of price points for every budget; however, the smaller the island, the less hotels available. For this reason, you should always book in advance if possible.
AirBnb isn’t always the cheaper option in Hawaii, but definitely allows you to save in other ways (most have kitchens, laundry machines, and free scuba/snorkel/beach gear for guests to use). You’ll also more likely to get a lot more space for your money this way.
While camping is one of the most affordable and rewarding ways to experience a night on an island, it is illegal in some areas and requires permits in others. Always check online for state parks rules. If you’re interested in camping, I’d recommend doing in on the Big Island.
Things to Know
Hawaii takes great pride in protecting the environment. Be advised that you’ll have to purchase shopping bags (15 cents) at any stores and your coffee will probably be served to you with a paper straw. While it may seem like a major inconvenience, those small efforts make a big difference in keeping our oceans clean.
Dining out in Hawaii can induce a bit of a sticker shock if you don’t already live in a major city like New York or Los Angeles. Expect to pay at least $25 for almost every meal — not including alcohol.
The exceptions: local food trucks and diners! If you need to save a little money, look for “Local Grindz” — you’ll get a lot of food for a fraction of the cost.
Speaking of food, there are some things you simply MUST eat while visiting the islands. The first are malasadas, Portuguese doughnuts that are wildly popular with tourists and locals alike. They generally come coated in a variety of flavored sugars and/or custard fillings.
Other sweet treats to try include shaved ice, Ted’s Bakery pies, and fresh fruit. Once you’ve satisfied your sweet tooth, head to the local gas station for Hawaii’s most popular savory snack: spam musubi (a slice of grilled Spam on top of a block of rice, wrapped in nori). While it’s not for everyone, you have to try it at least once.
Respect the Culture
Before Hawaii was a state, it was a sovereign nation with a royal family. Ever since the last reigning queen was violently overthrown by a group of Americans farmers, Hawaii’s been fighting to preserve its customs and traditions. It’s important to remember that Hawaiian culture isn’t American culture; take time to educate yourself about Hawaii’s rich history. Most importantly, be wary of cultural appropriation.
Island Hopping 101
There’s something about the phrase “island hopping” that adds instant glamour to any vacation. Luckily, you don’t have to be rich and famous to get around Hawaii — you just have to plan accordingly.
As epic as it would be to hit all six of the major islands on one short trip, the (pineapple) juice just wouldn’t be worth the squeeze. Instead, treat your trip like a Choose Your Own Adventure novel: use what you know of each island and prioritize what you’d like to see, do, and eat from there. Just keep in mind the cost of traveling (inter-islands flights, ferry rides, rental cars, etc.).
Need some help? Here’s how a local would island hop:
Day 1: Honolulu (Oahu)
Morning: Arrive early in the morning to make the most of your first day in Oahu. Catch a ride straight from the airport to Kono’s Honolulu — this local chain serves up the best breakfast burritos, including the Haleiwa Bomber made with 12-hour slow-roasted pulled kalua pork. While you’re waiting for your order, cross the street to Leonard’s Bakery to sample its famous malasadas.
Afternoon: Check into your hotel in downtown Waikiki, (yes, the neighborhood is touristy. But that’s because it’s located near all the best stuff). Once you’re settled, spend the afternoon exploring all Waikiki has to offer. Your only solid plans tonight are a sunset cruise on board the No Hoku II Catamaran and a dinner reservation at House Without a Key, an iconic Honolulu dinner spot.
Local tip: Since the majority of your time will be spent downtown, save a little money here by forgoing a rental car. Ubers are notoriously fast in Honolulu (seriously — don’t even call one until you’re downstairs and waiting), and most attractions are in walking distance from the hotels.
Day 2: Kailua (Oahu)
Morning: If your mental picture of Hawaii includes turquoise water, white sandy beaches, and palm trees swaying in the tropical breeze, a trip to Oahu’s is a must. Start your day by hiking the famous Lanikai Pill Boxes. The hike is moderately easy and only takes about 20 minutes to get to the first lookout. Once you get to the top, make sure to snap a souvenir picture before heading down.
Afternoon: Spend the rest of your day lounging around Lanikai Beach. If you’d rather get moving, kayaks are available for rent. You can choose between kayaking the 5 mile loop around Kailua Bay or just a short trip out to the Mokes (also known as the Twin Islands) and back. For dinner, head up the road to Hawaii’s popular sandwich chain Maui Mike’s.
Local tip: Kailua is a pretty good distance from Honolulu. Instead of paying for an Uber, take TheBus, Hawaii’s public bus system. You can catch it anywhere in Honolulu and ride it to straight to Lanikai Beach for around $5.50.
Day 3: Lahaina (Maui)
Morning: Check out of your hotel, check into your flight, and say goodbye to Oahu — time to island hop! After a short 40 minute flight, you’ll arrive in Maui (via Kapalua Airport). You’ll want a car to explore this island, so pick one up at the airport before driving to the cozy beach town of Lahaina. On the way, stop at one of the many fruit stands for a breakfast smoothie.
Afternoon: With plenty of locally owned boutiques, dessert spots, and coffee shops, Lahaina feels like a tropical version of Martha’s Vineyard, you could easily spend the whole afternoon exploring the town. When you do get hungry head to Fleetwood’s on Front St., and ask to be seated on the rooftop bar — you’ll get great food and an even better view.
Day 4: Road to Hana (Maui)
Morning and Afternoon: Similar to the Pacific Coast Highway (you know, that road they’re always driving on in Big Little Lies), the Road to Hana is a scenic route along the coast of Maui. The 64 mile cliff-side drive can be done over the course of several days, so don’t try see it all at once. The more you want to drive, the earlier the in the morning you should leave.
Local tip: Take it from a local, sometimes you’ve just got to be a tourist. Such is this case when driving Hana Highway. Download an audible guide to listen to while you drive. The guide will point out must see sights, mile by mile.
Day 5: Lanai City (Lanai)
Morning: Today is all about relaxing, so you’re taking a day trip to luxurious Lanai. Catch the 9:15am ferry and arrive in Lanai approximately an hour later. Your only stop this morning is the Four Seasons for some serious pampering, like a deep tissue massage or a more modestly priced manicure. #treatyoself
Afternoon: Take a short hike from the Four Seasons to Puu Pehe, (also known as Sweetheart Rock). The Hawaiian legend tells the story of a young warrior from Lanai who fell in love with a young maiden from Lahaina. Their story ends tragically with the warrior burying his love on the rock island before jumping off it himself. Puu Pehe is especially beautiful around sunset, and you may even see spinner dolphins swimming around it. Just make sure to leave in time to catch the last ferry back to Maui (6:45pm!).
Day 6: Kona (Big Island)
Morning: No trip is complete without a visit to the actual island of Hawaii. Fly from Lahaina into Kona for your first day there (you’ll want to reserve a car on this island, too). Take some time this morning to learn about Hawaii’s history and tour its former royal grounds at the Pu’uhonua O Hōnaunau National Historical Park.
Afternoon: If you’re a coffee drinker, Kona is the place for you! Drive to Holualoa in the slopes of Kailua-Kona for an afternoon of coffee tasting. With over 600 coffee farms in the area, it’s safe to say that Kona is to coffee what Napa is to wine. Buy a few souvenir bags of your favorite for brewing at home.
Local tip: Instead of spending the night in Kona, head out early and stay in Hilo. This will allow you to get up earlier in the morning and beat the crowds at Hawaii Volcanoes National Park.
Day 7: Hilo (Big Island)
Morning and Afternoon: It’s hard to believe that in the United States there’s an active volcano, much less three. Luckily, seeing is believing, and today you’re visiting Hawaii Volcanoes National Park. There are two drives through the park: Crater Rim Drive and Chain of Craters Road. The former is faster, but you’ll want to take Chain of Craters for optimal views. The 38-mile round trip drive passes through rainforests, dried lava fields, and ends at the coastline.
Then its time to say goodbye. Pick up some postcards for the flight home and head to the airport. Until next time, Hawaii!