Planning Your Hawaii Getaway

During these cold, wet, and sometimes snowy winter months, it’s easy to dream about running away to paradise. But why just dream. Right now is the ideal time to say Aloha to Hawaii.

Hawaii COVID-19 Travel Rules

Like all states, Hawaii has rules for traveling during the COVID-19 pandemic, but it still wants to welcome visitors.

As of March 4, 2021, the state will allow all domestic travelers to avoid quarantine if they provide a recent negative COVID-19 test. If there’s no test, then travelers will have to spend the first ten days in Hawaii looking at paradise from the comfort of their hotel room.If you’re island hopping, you may need to take another COVID-19 test before the next leg of your trip. To find out all of the COVID-19 rules, check out Hawaii’s COVID-19 portal.

Weather in Hawaii

When you pack for a trip to Hawaii, remember, the state is what we call tropical. That means temperatures are high, but so is humidity. In fact, Hawaii is home to one of the wettest places on earth, Wai’ale’ale, on the island of Kauai. Wai’ale’ale receives an average of 470 inches/1,094 centimeters of rain a year (Source: Hawaii-guide.com).

No matter what time of year you visit Hawaii, pack a rain poncho because you’ll run into wet weather. Even in its driest month, June, Hawaii receives an average of 3 inches/7.6 centimeters of rain (Source: Hawaii-guide.com).

Hawaii’s rain is usually sporadic, meaning it can be raining one minute and sunny the next.

As for temperature, January and February are the coldest months. Lows average 65°F/18.3°C and highs average 80°F/26.7°C. The hottest months are August and September, where lows average 72°F/22.2°C and highs average 86°F/30°C.

How to Save Money Traveling to Hawaii

Traveling to Hawaii can be pricy, especially if you’re flying from the East Coast. Here are some tips to make sure you’re saving the most money on airfare.

Skip Peak Times

According to Hopper, the cheapest flights to Hawaii are in January and February. That’s because it’s that small window between the winter holidays and spring break. Hopper says you’ll save an average of $175 if you fly in January and February compared to the high season.

The site Love Big Island has a differing opinion, saying, “In our opinion, the best time to avoid the crowds and find the cheapest tickets to the Big Island is between mid-April and May and in September and October.”

Since Hawaii has tropical weather even in the winter months, it’s an ideal destination for most travelers. That makes peak travel times almost year-round.

Fly on Weekdays

While Hawaii isn’t a weekend getaway kind of place, you’ll find many travelers try to bookend their Hawaiian vacations with weekends to get the most time possible on the islands.

If you’re looking to save money on airfare, be flexible with your travel dates. Midweek flights to and from Hawaii tend to be cheaper than those on Friday, Saturday, or Sunday.

Find the Buying “Sweet Spot”

Like most trips that you take, there is a “sweet spot” for buying plane tickets. That means you’re not shopping too soon and paying premium prices, plus you’re not shopping too late and buying tickets when most of them are gone already.

Love Big Island says, “On average, the best time to buy your ticket to Hawaii is between 21 and 121 days before departure, with the period between 40 and 50 days often mentioned as a golden rule.

Cheapest Island to Fly Into

When it comes to buying cheap airline tickets, you also want to remember that Hawaii is home to nearly a dozen airports. That means some islands are more affordable to fly into than others.

  • Daniel K. Inouye International Airport in Honolulu (HNL) on the island of Oahu
  • Kona International Airport (KOA) on the island of Hawaii (a.k.a. “The Big Island”)
  • Hilo International Airport (ITO) on the island of Hawaii
  • Kahului Airport (OGG) on the island of Maui
  • Hana Airport (HNM) on the island of Maui
  • Kapalua Airport (JHM) on the island of Maui
  • Lihue Airport (LIH) on the island of Kauai
  • Molokai Airport (MKK) on the island of Molokai
  • Kalaupapa Airport (LUP) on the island of Molokai
  • Lanai Airport (LNY) on the island of Lanai

The international airports, HNL on Oahu, KOA on Hawaii, and ITO on Hawaii, will be the easiest to get flights into because they are international airports and thus the cheapest.

If you plan to visit Oahu or Hawaii, then you’re set. If your destination is some of the other islands, like Maui, Kauai, or Lanai, then flying into one of the international airports and then taking an island hopper plane may be your best plan.

How to Travel Between Hawaiian Islands

If you’re looking to do the Hawaiian Islands in style, then odds are you’re going to want to visit more than one island. That’s because each island has a little something different to offer visitors. I’ll talk about that in just a few moments, but first, how do you travel between islands?

There are several ways to island-hop. You can go by helicopter, boat, or ferry. You can also do what most people do and take a plane.

Hawaiian Airlines has flights to most of the islands at least once a day, so you’ll have plenty of options. Southwest Airlines also flies between the islands.

If you don’t want to move from hotel to hotel every time you visit a new island, then consider taking a cruise. The ship travels from island to island at night, which means you have the entire day to explore.

Which Hawaiian Islands Should I Visit?

All of this leads to the big question, which island should I visit? With the follow-up question, should I see more than one island?

The length of your trip will determine whether you visit just one island or more than one. According to U.S. News, “The general rule of thumb when visiting Hawaii is traveling to one island per week. You can push it. With five days, you can do a quick sampler of two islands. But each island is diverse and filled with far more than a week’s worth of things to see. The best way to experience Hawaii is to devote at least five days to each island.”

Once you have the length of your trip squared away, it’s time to tackle the more challenging question. Which island do you choose?


Oahu is the island with the most to do. Home to Honolulu and Waikiki, Oahu has a little bit of everything.

Diamond Head

 You can take a hike to the top of the famed Diamond Head volcanic crater. It gets packed with tourists later in the day, so make that the first item on your morning to-do list.

Dole Plantation Tour

 The Dole Plantation Tour offers anything and everything pineapple-related. See how the famed pineapples are grown and take a walk through the pineapple maze. Then, browse the massive gift shop and be sure to leave some room for the company’s famed Dole Whip, frozen yogurt made with Dole pineapples.

Hanauma Bay Snorkeling

Take a dip in Hanauma Bay and see some of the amazing sea life that Hawaii has to offer. Take some snorkeling gear so you can stay underwater longer. It’s worth it. Not only do you run into sea turtles and tropical fish, but you can also pay extra to go on dolphin excursions and whale watching trips.

North Shore

Surf’s up at one of the most famous surfing spots on the islands. North Shore tends to be for serious surfers. If you’re not an experienced surfer, you can still watch some skilled wave riders.

Pearl Harbor & the USS Arizona Memorial

A trip to Oahu is not complete without a visit to Pearl Harbor and the USS Arizona Memorial. It is an emotional feeling to stand right above where the USS Arizona sank when the Japanese attacked Pearl Harbor. You will not regret the visit.

Polynesian Cultural Center

For an authentic Hawaiian cultural experience, look no further than the Polynesian Cultural Center. There you’ll experience a traditional Hawaiian luau with native Polynesian dancers.

Shrimp Trucks

While you’re visiting the North Shore, make sure you detour to one of the island’s famed shrimp trucks. Places like Giovanni’s Shrimp Truck serve up large piles of shrimp on hefty mounds of rice.


The nightlight in Waikiki is the hottest on the island. There’s also high-end shopping to keep you busy.


Many people consider Kauai the best island of the Hawaiian Islands to visit because of its beautiful beaches and plenty to keep you busy.

The Beaches

Go Hawaii has a complete list of the beautiful beaches on Kauai. You can head to Anini Beach Park if you’re looking for white sandy beaches with tranquil waters. 

If you’re looking to surf, then Kealia Beach Park is a great choice. Its sandbar bottom makes for some great waves.

Helicopter Tours

Since you can’t see much of the island by car, you need to rely on a helicopter to get the best view of Kauai. There are plenty of companies that offer helicopter tours of the island so you can get an aerial view of the lush landscape.


 A majority of the island is inaccessible by car, so you’ll need to take a hike if you want the island’s best views. Kokee State Park and Waimea Canyon have trails for hikers of every skill level.

Jurassic Park Filming Locations

Those lush images are the same ones caught in the Jurassic Park movies. According to Islands.com, most of the Jurassic Park filming locations are right on Kauai.


According to Go Hawaii, kayaking is a must-do during a visit to Kauai.

“Kauai is home to the only navigable rivers in Hawaii, so kayaking is an integral part of a unique Kauai vacation,” according to the Go Hawaii site. “Relax and take in the exquisite scenery as you paddle down the Wailua River. This popular river for kayaking weaves by lush, jungle landscapes along with the island’s East Side. Other river routes include the Huleia River from Nawiliwili Harbor in Lihue, as well as the Hanalei River on the North Shore, the longest on the island.”


You will not regret spending time in Koloa, an old plantation town on the south shore of Kauai. Koloa is home to the Koloa Rum Company, as well as some awesome shave ice.

Mountain Biking & ATVing

If you’d rather get around on wheels, then mountain biking or ATVing may be more your speed. Along with hiking trails, there’s plenty of trails for wheeled vehicles as well.

Poipu Beach

A visit to Poipu Beach doesn’t just include nice sand, but incredible animals. Sea turtles and seals often end up sunning themselves on the beach. If you’re looking for a glimpse of Hawaii’s wildlife without getting in the water, then Poipu is a great place to start.

Wailua Falls

If you just have to see a waterfall on your visit to Hawaii, look no further than Wailua Falls. It’s a double-tiered waterfall that’s breathtaking to see. Better yet, it’s easy to get there. There’s no need to hike in. You can park close by and take a short walk to the falls.


A two-island hop away from Oahu is the island of Maui, the state’s second-largest island.According to Go Hawaii, “Maui, known also as “The Valley Isle,”…[is] beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales (during winter months), farm-to-table cuisine, and the magnificent sunrise and sunset from Haleakala.”

Haleakala National Park

When you visit Maui, take the time to visit Haleakala National Park. You’ll see everything from a bamboo forest, native birds, and the famed Haleakala Crater.

The crater formed after eons of erosion and lava flows. Combined, they create a unique natural sight.

Ka’anapali Beach

“Ka’anapali Beach is a mile-long, spectacularly perfect beach that is home to seven resorts, high-end shopping, various restaurants, and activities,” reads the Maui Guidebook. If you’re looking to experience the perfect Hawaiian beach, this is where you want to go.

Kapalua Coastal Trail

According to the hiking site, “Kapalua Coastal Trail is a 2.5 mile heavily trafficked out and back trail located near Lahaina, Maui, Hawaii that offers scenic views and is good for all skill levels. The trail is primarily used for walking and running.”

In other words, this is where you want to be.

Maui Brewing Company

Beer lovers will love a visit to the Maui Brewing Company, where you’ll find the handcrafted Big Swell IPA and the Bikini Blonde Lager. For underage drinkers, there are handcrafted sodas available.

Maui Swap Meet

A decades-old tradition makes for excellent souvenir shopping. The Maui Swap Meet has a little bit of something for everyone.

Nakalele Blowhole

Don’t get too close because the Nakalele Blowhole isn’t the safest place to visit, but it’s great to see. When the tide rises, waves crash into the blowhole, launching jets of water through the blowhole and high into the air.

Road to Hana

Filled with fantastic scenery and lush landscapes, a drive down Maui’s Hana Highway is a must-do. The “Road to Hana,” as it’s called, is an all-encompassing experience. 

“In order to truly experience Hana, it helps to know more about the history and legends of the area. You may find out that there are legendary stories associated with each spot where Gods have left their mark, and historic battles have been fought,” according to the Road to Hana website.

Hawaii (Big Island)

Hawaii is the biggest island of the Hawaiian Islands. Not only is the island much larger than the other ones in the island chain, but it’s filled with a variety of climates and terrain.

According to Go Hawaii, “You can travel through all but four of the world’s different climate zones here, ranging from Wet Tropical to Polar Tundra, a result of the shielding effect and elevations of the massive volcanoes Maunakea and Maunaloa. From the many geological features at Hawaii Volcanoes National Park to the snow-capped heights of Maunakea; from the lush valleys of the Hilo and Hamakua Coasts to the jet-black sands of Punaluu Beach, the island of Hawaii is an unrivaled expression of the power of nature. How ever you decide to experience the island, it is sure to leave you humbled!”

Akaka Falls

 It’s a short but steep walk to see Akaka Falls, but it’s worth the trip. You’ll walk through lush tropical vegetation to see the twin falls that plunge 442 feet.

Farm Tours

Known for Kona coffee, Hawaii also grows items that are hard to find in any other place. Love Big Island suggests that you take farm tours while on the Big Island. Hawaiians cultivate macadamia nuts, taro (the root used in poi), and seahorses, among other things.

Kilauea Volcano

One of the most awe-inspiring and frightening sights on Hawaii is a look at the Kilauea Volcano. An active volcano, you never know when Kilauea will erupt and where the lava will flow.

Lava Tubes

If you can’t get to Hawaii when there’s an active volcano, then check out the island’s lava tubes.

According to Love Big Island, “Exploring lava tubes is a great way to get to know more about the volcanic processes that continue to shape the Big Island, especially when there is no lava flowing on the surface. Because they are easy to access and have a fascinating formation history (rivers of lava!), they are a perfect family outing, but more hard-core and multiple-hour spelunking guided tours are also possible.”

Kona Coffee

Caffeine lovers would be remiss to miss out on one of the best coffees in the world. Kona coffee is one of the most expensive coffees in the world because it can only be grown in one place. Kona.

Manta Ray Night Dives

According to the site Love Big Island, a night dive with the manta rays is one of the most memorable dives on the planet. Not only do you get to see the big fish up close, but you get to watch them in action.

Mauna Kea Summit

Located 14,000 feet above sea level, a drive to the summit of Mauna Kea will give your breathtaking views of the Big Island. If you plan to go, be prepared to spend the majority of the day on the drive. It’s two hours to the summit with winding roads.


While not large, Molokai is still home to the tallest sea cliffs in the world, offering up incredible views of the Pacific Ocean.

Halawa Valley

A visit to Halawa Valley doesn’t just include amazing views but an inside look at the Hawaiian people’s culture and history.

Kalaupapa Overlook

You can’t visit the Kalaupapa Overlook without a tour guide, but it’s worth the money. Not only do you get amazing views, but for a little extra, you can take a mule ride to the bottom.

Kanemitsu Bakery Hot Bread

Famed for its fresh hot bread, the Kanemitsu Bakery is the kind of place you line up late at night or very early in the morning. It’s so popular, it even has its own Wikipedia page.

Kumimi Beach

If you’re looking for a calm place to go snorkeling, look no further than Kumimi Beach.

According to the Visit Molokai Blog, you should visit Kumimi Beach (a.k.a. Murphy’s Beach) during mid-and high-tide.

Molokai Plumeria Farm

Plumerias are a flower that screams Hawaii. A trip to the Molokai Plumeria Farm, and you can see how the flowers are made. You can also get your own cutting to take a little piece of the islands back home with you.

Post A Nut

Forget sending a postcard when you can send a coconut instead. Post A Nut promises to design, paint and then mail a coconut to anyone, anywhere in the world.


If you want to escape to paradise truly, then Lanai may be your ideal choice. Only a small population of Hawaiians live on Lanai, and tourists tend to visit the islands listed above more.

According to Meet Hawaii, “Backcountry hikes, four-wheel drives off beaten paths and welcoming beaches make Lanai feel like a private paradise, offering one of Hawaii’s most diverse travel experiences in a setting far removed from the more populated resort areas. Above all else, Lanai’s sense of privacy lends itself to reflections and forward-looking…”

Keahiakawelo “Garden of the Gods”

Keahiakawelo, more commonly known as the “Garden of the Gods” is a desolate landscape that looks very much out of place among the ordinarily lush and verdant hills of Hawaii. Still, it is magnificent in its desolation, and so it’s a sight not to be missed. Before you go, read this article in Hawaii Magazine, highlighting the storied history of Keahiakawelo.

Hulopoe Bay

Considered one of the best beaches in the world, Hulopoe Bay is one of the most popular places to visit on Lanai. There is plenty of space for sunbathers and plenty to see for snorkelers. However, a word of warning, the waters at Hulopoe Bay are safe in the summer but too dangerous during the winter months. It’s still worth the visit in the winter, but don’t expect the trip to include swimming.


Take a look back at Lanai’s past with a visit to Keomuku. Now uninhabited, Keomuku used to be a fishing village and once headquartered the Maunalei Sugar Company. According to Fodor’s, “After the company failed, the land was abandoned. Although there are no other signs of previous inhabitation, its church, Ka Lanakila O Ka Malamalama, built in 1903, has been restored by volunteers. Visitors often leave some small token, a shell or lei, as an offering.”

Lanai Cat Sanctuary

Located in Lanai City, the Lanai Cat Sanctuary was founded in 2004 to sterilize Lanai’s street cats. Since Lanai doesn’t have an animal shelter, that dream has now grown into a sanctuary for cats, as well as native birds. Volunteers at the Lanai Cat Sanctuary rescue cats from all over the island, including nesting grounds for native and endangered birds.

Lanai Cultural and Heritage Center

 Learn more about the culture and history of Lanai and its people at the Lanai Cultural and Heritage Center.

Mike Carroll Gallery

In 2001, artist Mike Carroll moved from Chicago to Lanai and used the islands for inspiration in his later works. The Mike Carroll Gallery highlights his depictions of Hawaii.

Munro Trail

Whether you hike or drive the 12.8-mile-long trail, it’s well worth it. The top of the Munro Trail marks the highest point of the island of Lanai. According to Fodor’s, “…on clear days you’ll be treated to a panorama of canyons and almost all the Hawaiian Islands.” Be sure to pack water if you plan to make the trek; there’s none available on the route.

Shipwreck Beach

Shipwreck Beach, so named because of the rusty barge that sits just off the coast, is one of Lanai’s better beaches to visit. Maui Magazine takes a look at what makes the beach so unique. If you plan to head out there, be sure to allow some time to visit Keomuku. It’s on the way.

Puu Pehe “Sweetheart Rock”

Like many places on Lanai, Puu Pehe, also known as “Sweetheart Rock,” is filled with history. According to the site Aloha Hawaii, Puu Pehe is the site of a tragic love story. Nowadays, it’s one of the most iconic places in Lanai to visit.

Written by Erika Towne

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