Your Perfect Week in Waikiki Is Waiting


Week in Waikiki  | Hawaii Itinerary

A week in Waikiki sure sounds like heaven right about now! While some people prefer to whip through Waikiki during a three-day weekend, others like to soak up island vibes on full-week getaways. Giving yourself a full week means more hikes, lazy beach days and lingering lunches without feeling like you're being squeezed for time. Check out some itinerary inspiration for your week of bliss.

Things to Do in Waikiki During the Day

See Diamond Head

You'll be eager to show off photos from paradise soon after you land! Get your well-deserved bragging out of the way first thing by visiting one of Waikiki's most Instagrammable spots when you get within view of Diamond Head. As Hawaii's most recognizable landmark, Diamond Head puts you in an aloha state immediately with help from lush coastal views. Trekking the Diamond Head Crater Hike trail will also help you settle into your new role as a jet-setting paradise explorer.

Week in Waikiki  | Hawaii Itinerary

Scoop Your Way Through an Acai Bowl

More than just a place to grab refreshing and healthy fare, Sunrise Shack Waikiki is a movement (and has some killer smoothies!). This celebrated snack spot is home to picture-worthy acai bowls that people from all over the world pine over on social media. It also happens to be the unofficial "watering hole" for local foodies seeking the best organic bullet coffee and smoothie bowls in Hawaii. Fuel up among the local surfers who consider this "the spot."

Bike the Waikiki Loop

Proof that you can explore so much of beautiful Waikiki even if you don't have a car, the Waikiki Loop is a stunning bike route spanning 4.3 miles. Don't worry if you don't know where to get a bike in Waikiki—there are more than 20 bikes shops to choose from along the route.

Week in Waikiki  | Hawaii Itinerary

Be a Beach Baby

Let's get to the real reason why you want to spend a whole week in Waikiki. You want to check out all of the beaches at least once! Make sure your list covers Gray's Beach, just in front of the Outrigger Reef Waikiki Beach Resort, and other must-visit beaches like the Royal Hawaiian Beach, Kuhio Beach Park (Prince Kuhio Beach) and Sans Souci Beach at Diamond Head.

In addition to putting in some quality time resting on the sand, you should take advantage of the many opportunities for swimming, snorkeling, boarding, surfing and canoeing along the two-mile waterfront stretch that shapes stunning Waikiki. You might even bump into a surfing star like Robert “Wingnut” Weaver from Endless Summer or the iconic Kelly Slater.

Take in the Culture

Go beyond the beaches and sand to experience Hawaii’s thriving, diverse culture. Try age-old activities alongside new ones as part of Outrigger Reef Waikiki Beach Resort's free cultural activities lineup—think hula dancing (it's easier than you think), lei-making (it's all about the love!), and bamboo stamping (perfect for all ages).

Visit the Waikiki Aquarium

Get curious about clownfish, sharks, coral and all of the other forms of life that make Hawaiian's ecosystem the vibrant jewel that it is. The aquarium's coral farm is a highlight. You'll understand why preserving the natural beauty of the Pacific is so important to locals after spending an afternoon at the aquarium.

Things to Do in Waikiki at Night

Order the Hula Pie at Duke's Waikiki

Nights out in Waikiki are all about dining in at one of the coolest foodie spots! No local restaurant is as legendary as Duke's Waikiki. Offering ocean views that can be enjoyed while you dine on favorites like lobster, panko-crusted calamari and coconut-ginger braised seafood, Duke's has lively ambiance that's made livelier by its great selection of beers, wines and cocktails. It's a crime to finish up your meal without ordering the world-famous Duke's Hula Pie featuring ice cream, hot fudge, whipped cream and toasted macadamia nuts with a chocolate cookie crust.

Relax at Maui Brewing Co.

As Hawaii's largest craft brewery, Maui Brewing Co. delivers the best assortment of island-brewed beers in a chic, open-air setting. It's a wonderland for beer lovers with 36 craft and specialty beers on tap. And it's just as great for foodies too, with fresh, locally-sourced ingredients and artisanal fare perfect for happy hours that extend to an evening out.

Listen to Live Local Music

From restaurants to beachfront bars, there are so many great spots to see live music in Waikiki. Celebrate the local tradition of “kanikapila” at Kani Ka Pila Grille, where you can enjoy live music nightly from some of Hawaii's most talented rising stars. Stay at Duke's after the hula pie for a famous Mai Tai and local music alongside stunning views of Diamond Head (and for a special treat, come just before sunset for a spectacular view of Hawaii’s famous sunset). And segue from sun-drenched afternoon beers at Maui Brewing Company to nighttime fun, with more local music plus cool craft beer and scratch-kitchen staples.

Week in Waikiki  | Hawaii Itinerary

A Waikiki Adventure Doesn't Have to Be Wishful Thinking

There's never been a better time to turn a fantasy Waikiki itinerary into a solid vacation plan. Pamper yourself to a full week of savoring fruity delectables, sharing the waves with pro surfers and finding blissful clarity on Pacific precipices. 

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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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