Hawaiian Holiday Travel Tips


Holiday Travel Tips

What a difference a year makes. After months of pared down social gatherings, working from home, and time spent away from loved ones, many people are prioritizing travel to celebrate the 2021 holiday season. (And let’s face it, we all deserve a beachfront break!)

Whether you’re dreaming of a family vacation, a romantic getaway, or an epic adventure, here are our top tips for planning the perfect holiday trip to Hawaii.

Holiday Travel Tips

Take in Nature’s Seasonal Decorations

From an epic sunrise on Haleakala to the emerald-tinged swimming hole at Rainbow Falls, nothing beats the winter blues like the vibrant colors of the Hawaiian islands.  

Hawaii Island (“The Big Island”)

With five national parks and four distinct climate zones, the Big Island offers plenty of opportunities for exploration.

Located on the southeastern shore of the Big Island, Kilauea — one of the most active volcanoes in the world — is currently putting on a spectacular display of smoke and glowing lava. The latest eruption is happening within a closed area of Volcanoes National Park, but visitors can get a glimpse from spots like Kilauea Overlook, Uekahuna, Wahinekapu, Keanakako`i Crater, Kupina`i Pali and several locations along the Crater Rim Trail.

Take a drive through the Kona Coffee Belt to see poinsettias growing wild along the lush hillsides. Sometimes called the “Christmas flower,” these fiery harbingers of the holidays can grow up to 8 feet tall in their natural setting. While you’re in the area, take a tour of one of the local coffee farms to learn how the beans are grown and harvested along the slopes of Hualalai and Mauna Loa, then fuel up on the world famous brew before heading off on the next leg of your excursion.

Towering at over 13,500 feet, Mauna Kea offers Hawaii’s version of a winter wonderland. In just a matter of hours, visitors can go from the sandy beach to a snow capped mountain, where stargazing tours happen nightly near the summit’s Mauna Kea Observatory. Back down at sea level, take a nighttime dive with the manta rays in the calm ocean waters off Kona, an otherworldly experience you won’t soon forget. For an immersive experience of a cultural sort, dine on island fare under the stars while you thrill to the spectacle of traditional dance, theater and music at the Outrigger Kona Resort and Spa’s Feast & Fire Luau.

Holiday Travel Tips


From Waikiki to Waimanalo, Oahu is home to some of the most famous beaches in the world, and awash in Hawaiian culture.

For a twist on tradition, take a tour of the holiday lights at Honolulu Hale, catch a holiday hula show, or hang out on Waikiki Beach, where you just might catch a glimpse of Santa arriving by outrigger canoe. All of Kalakaua Avenue will be lit up in a merry extravaganza as well, so take a leisurely stroll or drive with the top down to soak in the warm trade winds. On December 12, cheer on the elite runners as they take to the streets of the capital city for the Honolulu Marathon.


Whether by land, sea or air, the beauty of Maui is on full display this time of year.

Hop on a catamaran to take part in some of the world’s best whale watching, which happens off of the Valley Isle’s coastline as humpbacks make their annual migration home from Alaska. Take to the skies for a private aerial tour of the Molokini Crater, or, if you prefer to keep your feet on the ground, opt for a chauffeured road trip along the road to Hana, one of the most breathtaking (and exhilarating) scenic drives on the planet. If you need a little holiday spirit, visit the island’s famed Lahaina Banyan tree, which is decked out in lights during the month of December . On December 5th, watch athletes sprint to the finish line at the “winner take all” XTERRA World Championship, the world’s premier off-road triathlon on Maui’s northwest coast.


From the world-famous rain forests to the dramatic coastline, Kaua`i is a hiker’s dream.

Explore the dramatic red cliffs and crested buttes of Waimea Canyon or head to the neighboring Koke`e State Park and follow the Awa`awapuhi Trail to the edge of Napali Coast's famous cliffs. Give the thrill-seekers the gift of adrenaline with activities like cave diving, zip lining and kayaking.

Holiday Travel Tips

Eat, Drink and Be Merry

From poke bowls and shave ice to barbecue to craft beer, there’s something to suit every palate in Hawaii.

On Oahu, local ingredients and regional flavors are on the menu at Hula Grill Waikiki, a favorite for both visitors and locals.

The local food scene on Oahu includes everything from five-star boîtes to casual eateries. Sip a Mai Tai while you drink in the ocean views at famed spots like Duke’s Waikiki, or enjoy a fun night out at Maui Brewing Co. in Waikiki, where the menu highlights craft brews, cocktails and from-scratch eats.

When it comes to food, Maui offers a bounty of tropical fruits, sustainably-sourced seafood and Hawaiian treats, all served in the spirit of aloha. Whether you choose to stop at a local food truck for a quick bite or prefer to linger over dinner, there are plenty of places to find Maui’s must-have dishes.

Get Swept Up in Romance

With its endless bounty of magic, beauty and adventure, Hawaii is a paradise for lovers.

Whether you’re planning a romantic getaway, an epic proposal, a walk down the aisle, or the first days of your happily ever after, there are plenty of opportunities for couples looking to escape and connect this holiday season.

December is the most popular month for marriage proposals, and you don’t have to look far to find a stunning backdrop where you can pop the question. Some of our favorite “marry me” spots can be found on the Big Island. If you’re ready to exchange I dos or renew your vows, Outrigger’s team of wedding planners is always at the ready to help you plan the perfect ceremony. The Hawaiian vow renewals take place on the beach, and are complimentary for guests. It’s truly a magical experience.

Plan Ahead

With travel on the rebound, Hawaii is among the most in-demand destinations for holiday vacation seekers in 2021. Hardly surprising, considering that winter on the islands includes stunning seasonal displays, an array of cultural events and near-perfect weather.

Bottom line: This is not the year to wait for a last-minute deal.

If you are planning to travel to Hawaii for the holidays, be sure to check the latest entry requirements on Hawai`i’s Safe Travel Program, designed to prevent the spread of COVID-19.

At Outrigger, we’re committed to providing you with a worry-free trip to paradise. Our Outrigger Clean Commitment promises the highest standards of health and safety and we look forward to welcoming you for a safe and relaxing stay.

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Outrigger Reef Waikiki Beach Resort | Hawaii
  • Home of Hawaiian Music, Kani Ka Pila Grille
  • Renovated modern guest rooms
  • Immersive cultural activities
  • Voyager 47 Club Lounge
Waikiki Beachcomber by Outrigger | Hawaii
  • Hawaii’s first and only craft hotel
  • Home of The Beachcomber Originals
  • Hawaiian Aroma Caffe, Waikiki’s most Instagrammed coffee shop
  • Island’s longest bar at Maui Brewing Co
Outrigger Waikiki Beach Resort | Hawaii
  • Beachfront location
  • Home of Duke’s Waikiki
  • Hawaii’s best live music venue, Blue Note Hawaii
  • Voyager 47 Club Lounge
Waikiki Malia by Outrigger |Hawaii
  • Intimate retreat for adventure seekers
  • Easy access to Waikiki Beach
  • Choice for value-minded families and groups
  • Spacious guest rooms and studios
  • Offering connecting rooms and kitchenettes
OHANA Waikiki East by Outrigger | Hawaii
  • Spacious guest rooms with kitchenettes
  • Ideal for large groups or families
  • Steps to Waikiki Beach and International Market Place
  • Onsite restaurants – Appetito Craft Pizza & Wine Bar and Tanaka of Tokyo
Airport Honolulu Hotel | Hawaii
  • Only half a mile from Daniel K. Inouye International Airport
  • Pet friendly
  • Convenient for business travelJust minutes from Pearl Harbor
Waikiki Shore by Outrigger | Hawaii
  • Only resort condo directly on Waikiki Beach
  • Sweeping panoramic ocean views
  • Family friendly
  • Perfect for extended stays
  • Ability to select a specific condo unit
Regency on Beachwalk Waikiki by Outrigger | Hawaii
  • Intimate, boutique style condo resort
  • Situated in the Waikiki Beach Walk shopping and dining district
  • Ability to select a specific condo unit
Honua Kai Resort & Spa | Maui
  • 38 tropical beachfront acres
  • 3-acre aquatic playground
  • AAA Four Diamond Award accredited
  • Luxury, 1, 2 and 3 bedroom suites on Kaanapali Beach
The Kapalua Villas Maui | Hawaii
  • Located on 22,000-acre Kapalua Resort
  • Choose from 3 beaches and 11 restaurants
  • Ocean and golf room views
  • Offering two magnificent golf courses
  • Ability to select a specific condo unit
Palms at Wailea Maui by Outrigger | Hawaii
  • Located within the world-famous Wailea Resort community
  • A short drive from the Shops at Wailea and beaches
  • Near Wailea’s most renowned restaurants
Royal Kahana Maui by Outrigger | Hawaii
  • Ocean view of Molokai and Lanai
  • Boasts oceanfront pool
  • Private lanai
  • Ability to select a specific condo unit
2 Bedroom Partial Ocean View|Kaanapali Maui at the Eldorado by Outrigger
  • Fronts the fairways of Kaanapali Beach Resort
  • Short walk from Whalers Village
  • Featuring three swimming pools
  • Ability to select a specific condo unit
Aina Nalu Lahaina by Outrigger | Maui
  • Boutique-style condos in heart of Lahaina
  • Two blocks away from Front Street
  • Walking distance to shops and restaurants
Napili Shores Maui by Outrigger | Hawaii
  • Offering stunning views of Lanai and Molokai
  • Newly renovated condos
  • Oceanfront on property dining at the Gazebo Restaurant
Waipouli Beach Resort & Spa Kauai by Outrigger | Hawaii
  • Heated river pool running through two-acre property
  • Features flumed water slides
  • Ability to select a specific condo unit
Kiahuna Plantation Resort Kauai by Outrigger | Hawaii
  • Cottage-style beachfront condos
  • Complimentary access to Poipu Athletic Club
  • Ability to select a specific condo unit
Lae Nani Resort Kauai | Hawaii
  • Oceanfront condos
  • Includes an ocean pool within a natural stone breakwater
  • Adjacent to the Coconut MarketPlace
Welcome to Outrigger Kona Resort and Spa
Watch the majestic manta rays that swim through Keauhou Bay. Or spend your day relaxing at the spa. It all starts here, on Hawaii Island.
Fairway Villa Waikoloa by Outrigger | Hawaii Island
  • Guests treated to infinity pool and lava rock whirlpool
  • Surrounded by Robert Trent Jones Jr. designed golf course
  • Selection of on property dining options
Kohala Coast Vacation Rentals by Outrigger | Hawaii Island
  • Five distinct properties to choose from
  • Ability to select a specific condo unit
  • Close to upscale King’s Shops and Queen’s Market Place
  • Golf at Beach Course
Kanaloa at Kona by Outrigger | Hawaii Island
  • Set on 18 oceanfront acres
  • Boasts 3 swimming pools and 2 tennis courts
  • Ability to select a specific condo unit
Royal Sea Cliff Kona by Outrigger | Hawaii Island
  • Set on a lava rock bluff
  • Panoramic views of the Kona coast
  • 5-minute drive to restaurants and shops
  • Ability to select a specific condo unit
Castaway Island, Fiji Resort | Outrigger Hotels & Resorts
  • Beachfront bures
  • Complimentary beach services
  • Kava ceremony welcomes guests
  • Wood-carving guest activity
  • Enjoy Meke traditional song and dance
Outrigger Fiji Beach Resort | Outrigger Hotels & Resorts
  • Beachfront bures
  • Offering Meimei nanny service
  • Talai butler service available
  • Named #1 Family Resort
  • Amazing firewalking ceremony
  • Outrigger Mauritius Beach Resort | Outrigger Hotels & Resorts
    • Luxury beachfront suites
    • Mauritian Rum tasting experience
    • Dance to Sega music
    • Relax on private beach
    • Complimentary kid’s club
    Evening at Outrigger Koh Samui Beach Resort
    • Located beachfront on Lamai Beach
    • 2 swimming pools
    • Fitness center
    • Restaurants and in-room dining
    • 3 meeting rooms
    Garden Suite - living area | Outrigger Khao Lak Beach Resort
    • Located beachfront on Bangsak Beach
    • Swimming pool
    • Fitness center
    • Restaurants and in-room dining
    • 3 meeting rooms
    Plunge Pool Suite | Outrigger Surin Beach Resort
    • Located on Surin Beach
    • Boutique resort
    • 2 swimming pools
    • Restaurant and in-room dining
    Aerial View | Outrigger Maldives Maafushivaru Resort
    • Luxury resort in the Maldives
    • Choose from beachfront villas or over-water villas
    • Numerous dining options, including our signature restaurant Moodhu Grill
    • Fully equipped PADI and SSI dive center
    Waikiki Beach | Hawaii
    • Famous for Waikiki Beach
    • Hike Diamond Head Crater
    • Take a historical journey at Pearl Harbor
    • Birthplace of legendary surfer Duke Kahanamoku
    • Home to Iolani Palace, US’s only royal place
    Experience a gorgeous Maui sunset
    • Voted “Best Island in the US”
    • Home to Haleakala volcano
    • Famed for whale watching during the winter months
    • Famous scenic stretch road to Hana
    • Mile long of sandy shore at Kaanapali Beach
    Beaches of Kauai | Hawaii
    • Nicknamed the Garden Island
    • Known for lush valleys, waterfalls and hiking trails
    • Has more beaches than any other Hawaiian Island
    • Most hiking trails than an other Hawaiian Island
    • Largest coffee plantation in the US
    Hawaii Island (Big Island)
    • Often referred to as the “Big Island”
    • Kilauea volcano is the most active and largest in the world
    • Known for black sand beaches
    • Grows most of the world’s macadamia nuts
    • Home to some of the world’s largest telescopes
    Aerial view | Castaway Island Fiji
    • Beachfront bures
    • Authentic cultural experiences
    • Family-friendly accommodations
    • Beach & water activities
    Outrigger Thailand | Outrigger Hotels & Resorts
    • Accommodations in Koh Samui, PhangNga and Surin Phuket
    • Exotic cuisine featuring aromatic spices and fresh ingredient
    • More than 40,000 temples throughout the country
    • Unique variety of wildlife and nature
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