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The Perfect Weekend in Waikiki


3 Day Weekend - Waikiki, Hawaii

There’s nothing better for summer travel than an adventure to the islands of Hawaii. First up: Oahu’s vibrant neighborhood of Waikiki. This world-famous birthplace of modern surfing is home to great culture (and a little craft beer fun, too). Here’s our perfect itinerary for a fun-packed two or three-day weekend in Waikiki.


3PM | Cocktails in the Sand at Duke's Waikiki

The perfect start to your weekend in Waikiki? An afternoon cocktail and apps on the sand (we recommend the Luksosowa potato vodka infused Cucumber Mojito), overlooking the famed Diamond Head at the crowd-pleaser Duke’s. 
Duke’s at the Outrigger Waikiki Beach Resort; Reservations recommended

6PM | Live Music under the Stars at Kani Ka Pila Grille

After freshening up, head over to the newly reopened (and refreshed!) Outrigger Reef to check out the locals-love favorite Kani Ka Pila Grille for the main course—and live Hawaiian music under the stars. 
Kani Ka Pila Grille, Outrigger Reef Waikiki Beach Resort; Reservations recommended


8AM | Custom-roast Coffee at Hawaii’s most Instagrammed Coffeeshop

For an insta worthy lattes and lots of Aloha vibes, grab your morning coffee at one of the island’s coolest coffeeshops.
Hawaiian Aroma Caffee, Waikiki Beachcomber

10AM | Surf (or Sand) at Waikiki Beach

In Waikiki, it’s great to hit the beach early. Want to learn to ride the waves? Faith Surf School makes it easy. They also have stand-up paddleboarding and outrigger canoe surfing for all kinds of adventuring—or just lounge oceanside by the crystalline waters.
Faith Surf School, Outrigger Waikiki Beach Resort 


7PM | Dive-In Movie at Waikiki Beachcomber

Make it the perfect relaxing evening after a busy sun-kissed day with a movie night by the pool (think family-friendly classics like "Percy Jackson: Sea of Monsters"). Chill in the hot tub with a bit of bubbly and popcorn or apps from the poolside cafe.  
Poolside, Waikiki Beachcomber; Inquire at check-in for the latest movie line-up


6AM | Sunrise Hike at Diamond Head

For breathtaking panoramic views, this short (but fairly steep) hike up the Le’ahi (a.ka. Diamond Head) volcanic cone is a must. Make sure to arrive early to savor the early-morning stillness—and be able to snag a parking spot.
Diamond Head State Monument; Recommended to arrive just before park opens at 6AM as parking fills up quickly

9AM | Learning to Hula

If you still have a little energy left for hula-ing after your hike, spend your final morning giving this traditional Polynesian dance a try. Outrigger has a range of other cool (free) classes, too—from ukulele lessons to island wood carving and lei making—if you’re able to stay a little longer.
Hula Class, Waikiki Beach Walk Plaza; RSVP at Eventbrite.com 

11AM | Smoothie Bowls at Sunrise Shack

Replenish after the morning’s adventuring with an organic superfood smoothie bowls and bullet coffee at the super-cute Sunrise Shack. Created by a foursome of pro-surfers and bodyboarders, the Shack is more than just great food; it's definitely an experience (check out their cool merch onsite too).
Sunrise Shack, Outrigger Waikiki Beach Resort


3:30PM | Happy Hour at Maui Brewing Co.

For a little well-crafted happy hour, pop over to Hawaii’s largest craft brewery just steps from the ocean on the bustling Kalakaua Avenue. Try a Big Swell IPA or the new tequila-based Street Fighter Cocktail.
Maui Brewing Co., Waikiki Beachcomber; Reservations recommended



9AM | Breakfast at Hula Grill

Hula Grill is known for sourcing ingredients straight from the land and sea - and while it's open three meals a day, breakfast happens to be the ultimate treat here. From fresh papaya and local eggs to Acai Bowls and Strawberry Mochi Waffles, there's something for everyone.
Hula Grill Waikiki, Outrigger Waikiki Beach Resort; Reservations recommended

11AM | Snorkeling at Queen’s Beach

With 1,200 miles of stunning coral-reef coastline and turquoise waters, snorkeling is a must while in Waikiki. Check out the Marine Life Conservation District on the south end in front of Queen’s Beach to hang out with tropical reef fish like the Humuhumu'ele'ele and black triggerfish.
Marine Life Conservation District in front of Queens Beach, between the Kapahulu Groin and the Natatorium


Bonus on way out of town

For a bonus before you head out of town, swing by the famous statues of Duke Kahanamoku, the father of modern-day surfing (or the King Kamehameha statue a few miles north that's seen in various scenes of Hawaii Five-O).

Got kids? See our 3 Things Kids Will Love in Waikiki post, too!

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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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