The Hawaiian Islands are like a cluster of siblings, each with its unique attributes. From black sand beaches to rocky shores, unique volcanic formations to vast forests, ancient cultures to urban panache, luxury resorts to snug little shacks, visiting each island is a phenomenal experience.
The setting, weather, and landscapes of Hawaii are straight out of a Disney movie, and choosing one place for a staycation is hard. This guide will help you shortlist some towns in some of the most spectacular islands of Hawaii.
A tropical staycation awaits you. Keep reading to know more!
Top Islands for a Staycation in Hawaii
Each island in Hawaii is so unique in terms of natural vistas, attractions, and beaches. To help you decide which island city is ideal for your next staycation, here is a list of top islands and towns in Hawaii, each with a different feel and something special to offer.
Hawaii- The Big Island
The Big Island went from being one of the most sought-after islands in Hawaii to a forgotten spot. The Big Island may not be for those looking for an Instagram vacation, but for staycationers, it is a dreamy destination unparalleled to any other island in Hawaii.
This geographically remarkable island shelters everything from pristine black sand beaches to magnificent snow-capped mountains, mesmerizing lava deserts to lush rainforests.
The active, fire-oozing Kilauea volcano has been increasing the island’s landmass since 1983, which means, Big Island is only growing bigger and more majestic. The Big Island has hiking trails and state parks, the hues of sand, and natural vistas that you have seen nowhere else in the world.
Key Experience:
Hawaii Volcanoes National Park, Akaka Falls, Waipio Valley, Coconut Island, Kona Coffee Living History Farm, and Hawaiian luau.
Where to Stay in Hawaii (Main Island) on a Staycation
Naalehu
The southernmost spot in the USA, Naalehu, is a small town with fewer than 1000 residents. Perfect for staycationers looking to get away from some of the large and more commercial cities on Big Island. Naalehu is a sleepy little town where you can visit a few local restaurants, bars, & bakeries, and soak in the beauty of nature surrounding this place.
Hawi
Perched on the northernmost tip of Big Island, Hawi is the perfect town to plan a staycation. The delightful art galleries, restaurants, boutique shops, brightly colored sugar plantations, and a small business district vibe make it a fantastic staycation destination. If you want to do something adventurous on your beach staycation, you can also tour the nearby Kohala fruit farm or ride the Kohala zip lines.
Honokaa
Once a major town, known for its profitable sugar industry, is now a charming historic downtown. Honokaa has quieted down ever since the factory was shut and now houses a community theater, restaurants, and lively shops. Honokaa hosts Western Week every May, a lively celebration of the town’s history of ranching, with live music, a festival, and rodeo events.
Best Time to Visit the Hawaii Big Island
September to November is a great time to plan a staycation to Big Island. The room rates dip as the season is almost over by this time, but try to plan your staycation in September and October because November is the rainiest month on Big Island. If you’re here during this time, make sure to go to the Kona Coffee Cultural Festival.
December to March (winter months) is another prime time to visit Big Island. The whale-watching season is at its peak from January. The hotel rates drop and you may get a room for as cheap as $200 a night.
June to August is the peak season owing to the perfect beach weather during these months. If you are planning a trip during these months, be sure to book the flights and lodging in advance.
Lanai
Lanai is blessed with surreal landscapes and other-worldly marvels of nature. With over 89,000 acres of countryside, 400 miles of drive trails, and 18 miles of secluded beaches, Lanai is the perfect place to go on an off-the-grid staycation. The sandy remote beaches, unique rock formations, and striking underwater reefs of Lanai make it an exemplary staycation destination in nature’s lap.
The best part is that it is a grand adventure to reach some of the most iconic places in Lanai as the path is paved and you might even need an off-roading vehicle. The island is great for rejuvenating and revitalizing, trying world-class cuisine and luxury accommodations.
Key Experience:
Shipwreck Beach, the Munro Trail, Garden of the Gods, Poaiwa Petroglyphs, Hulopoe Bay, and Lanai Culture and Heritage Center.
Where to Stay in Lanai on a Staycation: Lanai city
Famed as Pineapple Island because of its largest pineapple produce in the world, Lanai city is the central city on the island. Once home to the Mormon colony, this charming small town is perched 1700ft above sea level. Several restaurants serve authentic Hawaiian cuisine, and there are art galleries, jewelry shops, and coffeehouses to explore on your staycation. You can also take biking tours, visit nearby bays, and indulge in other outdoor activities, such as horseback riding, and golf.
Best Time to Visit Lanai
The best time to visit Lanai is between June and November, the region’s warmest and driest months. However, the weather on the island remains pleasant all year round. Lanai sees the least amount of rain as compared to the other Hawaiian islands, making it one of the best places to plan a staycation any time of the year. Although for the whale-watching season, you’ll want to plan your trip between January and April.
Kauai
Azure waters, sublime sunsets, serene beaches, and glorious skies, Kauai is the tropical paradise you envision for a staycation. The oldest island in the Hawaiian island chain, Kauai is a rural fusion of luxury. No over-the-top luxury or buzz, Kauai is for staycationers who want to explore the best of nature.
Kauai is a small place to explore, with only two major highways, some places can only be accessed on foot. Although, the best way to explore Kauai is through boat tours.
Kauai is not among the cheapest islands in Hawaii. The hiking trails are paid, and the room rates shoot up to $500 a night during the season. Although there’s enough picturesque nature in Kauai that you can explore for free if you’re willing to broaden your budget for this staycation, you can find memorable experiences like a helicopter ride of the island, cruise, and snorkeling.
Key Experience:
Waimea Canyon, Kilauea Lighthouse & Wildlife Refuge, Local Markets, and Snorkel, Surf & Swim.
Where to Stay in Kauai on a Staycation: Hanalei
Nestled in northern Kauai, Hanalei is a few minutes west of Princeville. This small town has a unique history, with a Russian imperial presence that occupied forts in a nearby town. Known for stunning beaches and a myriad of possibilities for outdoor adventure such as windsurfing, zip-lining, hiking, river-rafting, and snorkeling, Hanalei is a fun and active town for a staycation. From casual food truck dining to ukulele concerts, music festivals, and local boutique stores, Hanalei is a hippie town with resort-free and a laid-back staycation vibe.
Best Time to Visit Kauai
The ideal time to visit Kauai is between September and November or from April to June when the weather is breezy and airfare & hotel rates drop. December to March is the peak season among travelers who want to escape the chillier weather. The rates go higher from June to August as this the peak season for family vacations.
If you’re planning a staycation between September to November, you can experience the Kauai Mokihana Festival, Kauai Marathon, and Alakai Festival (October).
Oahu
A fusion of Eastern and Western cultures and a blend of world-craft luxury and mesmerizing scenery, Oahu is one of the most sublime places in Hawaii. The urban feel of cities balanced with laid-back surf towns (Fun fact: Surfing was invented in Oahu), Oahu welcomes all kinds of staycationers. Blue waters, meandering hikes, the islands’ many activities, eclectic restaurants, a host of cultural and historic sites, and sprawling white-sand beaches, make Oahu one of its kind Hawaiian destinations and undoubtedly one of the most popular one.
Oahu flawlessly brings together the ancient Hawaiian traditions and unparalleled luxury that makes discovering Oahu delightful.
Key Experience:
Corsair Plane Wreck Dive Site, Polynesian Cultural Center, Iolani Palace, USS Arizona Memorial, Waikiki neighborhood, North Shore, The Queen Theater, and Honolulu city.
Where to Stay in Oahu on a Staycation: Haleiwa
Honolulu attracts millions of visitors each year. If you want to stay away from the crowds and find a quiet escape in the most populated Hawaiian Island, Haleiwa is THE place for you. Haleiwa is tucked on the North Shore of Oahu and is only 1-hour from Waikiki. A timeless gem, Haleiwa still looks as it looked a decade ago. Haleiwa is famed as the surfing capital of the world because of its perfect waves and protected coastlines. Guided water activities like snorkeling, kayaking, and stand-up paddleboarding to fun hikes around the north shore, from the vibrant downtown and quirky shops to mouth-watering eateries, Haleiwa has all the ingredients for a perfect staycation recipe.
Note: Several attractions are operating with limited capacity, some require you to pre-book a space, and some are unavailable.
Best Time to Visit Oahu
Known as the ‘Gathering Place’, Oahu gets the most crowded of all Hawaiian Islands. It is difficult to avoid the crowds here but you can find pockets of emptier beaches in April, May, September, and early October. If you are planning a visit during these months, you can enjoy the Lantern Floating at Moana Beach Park and the month-long Aloha Festival celebrating Hawaiian heritage with music, dance, and historical showcases. Oahu has excellent weather year-round, so you can plan a visit any time of the year. If you plan a staycation in January or February, you can enjoy the Chinese New Year celebration that features lion dances, night festivals, and fireworks, and the Honolulu Festival.
Maui
Sandwiched between the Big Island and the tiny Molokai Island, Maui offers just the right amount of fun, leisure, adventure, luxury, bustle, and serenity. Maui boasts distinctive landscapes, intriguing culture & history, a plethora of wildlife, and notable beaches.
There are tons of things you can do on a staycation in Maui, from dancing with the hula dancers to lounging on the beaches, from snorkeling among the sea turtles to playing golf along the coast.
Maui is divided into five regions:
South Maui- Beaches, trails, scenic drives, and the famous Wailea Beach
West Maui- Kaanapali Beach and Nakalele Blowhole
East Maui- Scenic coastline and Haleakala–the world’s largest dormant volcano
Central Maui- Iao Valley State Park (former tribal battlegrounds)
North Shore- Surf culture, fine-dines, and Paia town
Key Experience:
Haleakala National Park, Makena Beach State Park, snorkeling tours, and helicopter tours.
Where to Stay in Maui on a Staycation: Lahaina
Lahaina was once the capital of the entire Hawaiian Kingdom and the historic charm pertains through the city to date. A huge section of the city is a designated historic district and has been preserved for visitors. A staycation in Lahaina means a peek inside the olden times, that reflects in every corner of the city. Lahaina’s Front Street has a number of interesting shops, art galleries, and ocean-front restaurants. The city also has several theatres that feature and highlight the local dances, customs, and costumes. The scenic views of the ocean and the mountains, the upbeat nightlife and entertainment galore, the rich history and cultural significance of Lahaina make it an exceptional choice for a staycation in Maui.
Best Time to Visit Maui
Shoulder season, fall and spring is the perfect time to plan a trip to Maui. April through May and September through November enjoys a temperate climate, lower lodging rates, and lesser crowds, you can enjoy Maui at its best. Maui hosts some amazing festivals, like East Maui Taro Festival and Maui Steel Guitar Festival during April. You can enjoy the Maui Ukulele Festival in September if you plan a staycation in the fall. However, if you want to surf, winter is the best time to visit. Book as early as possible to save cost, as it is the priciest month to travel to Maui.
Molokai
A lesser-known Hawaiian destination, Molokai is the fifth-largest island with fewer tourists and minimum commercialization. If you want to experience the true Hawaiian way of life and live the Aloha spirit, Molokai is the right place for you. It offers a rare glimpse into what Hawaii was like before tourism took over and buried its authentic essence.
With dirt roads, untouched expanses, and countryside, Molokai is a quiet tropical town to experience authentic Hawaiian culture and interact with the natives of the land.
Go on a Hawaiian cultural tour to dive deeper into the ancient lifestyle. Unlike other islands of Hawaii, Molokai is not for luxury beach vacations but is a secluded island with a homely warmth and immersive culture.
Key Experience:
Soaring Sea Cliff, Halawa Valley Cultural Hike, Kalaupapa National Historical Park, and the Hawaiian heritage.
Where to Stay in Molokai on a Staycation: Kaunakakai
One of the lesser-known islands of Molokai, Kaunakakai boasts a Hawaiian cowboy vibe. The town has a history of fishing, ranching, and farming. Kaunakakai is not one of those Hawaiian islands where you can find luxurious resorts, countless activities, and fancy restaurants. It is for those staycationers who want a quiet getaway in a remote beach place.
Just 12mi (19km) north of Kaunakakai is Kalaupapa, a town that served as a colony for exiled lepers for nearly a century. Today, the Kiowea Beach Park on the west end of town is a lovely place to see Kapuaiwa, an ancient royal coconut grove.
Best Time to Visit Molokai
Molokai experiences great temperatures throughout the year. You can plan a staycation any time, so if you are planning a staycation across all Hawaiian islands, then plan the months for your other destinations first. If you want to avoid the crowd, like any other Hawaiian islands, avoid summer (July to September). However, this is also the most pleasant time to visit Molokai, find quieter and remote places in Molokai if you want to plan a summer staycation.
Tip: Plan a trip in June, the weather is pleasant and the summer tourists are yet to arrive.
Hawaii is the paradise that can boldly claim to have everything, making it a must-visit for all kinds of staycationers. If you have ideas and a list of things you want to do, then it is easier to pick the season and month of your trip. But if you want to discover Hawaii without plans and let the place surprise you, then just find the best and cheapest month to travel for a staycation and leave. No matter how and when you travel to Hawaii, it will encapsulate you forever. Aloha!
