Spend five days on the island of Oahu in the majestic state of Hawaii with Vacations by Marriott. Relax under palm trees on arguably the most famous beach on the island, Waikiki Beach, or take a dip in the Pacific Ocean. Learn how to surf, know where to shop, and discover must-see attractions thanks to our itinerary below. Browse our Oahu vacation packages, pack your bags, and we’ll see you near the water!

Day One: You arrive at Honolulu International Airport late in the morning, pleased that the time zone has given you a couple of additional hours on this, your first day on the island of Oahu. You collect the luggage and make your way toward the Waikiki Beach Marriott Resort & Spa, which is located right across the street from one of the most famous stretches of beach in the world. You take a short walk along the beach under the sun, then retreat to the resort’s pool for a couple of hours. You glance up, watch the palms sway, and exhale. Later, you don some island attire and head downstairs to d.k. Steak House, which is nothing like your average hotel restaurant. You dig into a juicy, dry aged steak accompanied by jumbo shrimp, and realize you’ll sleep very well tonight.

Day Two: Yesterday’s walk on Waikiki Beach was inspiring, as you watched surfers gracefully glide toward shore, with wave after wave rolling through the warm, clear water. A chat with the staff after breakfast has you convinced – you’re learning to surf today. The instructor begins with some tips on balance points and the basic stance required, and paddles you out to “Canoes,” where for a hundred years or more, thousands of others just like you have ridden their first wave. The instructor gets you in position, and with a little push from behind, you’re up and riding. The experience is addicting; as soon as you catch a wave, you want another! The entire experience is so exhilarating that you make a dinner reservation at Duke’s Canoe Club, where over a plate of Macadamia Crusted Mahi Mahi you watch surfers ride their last waves of the day before darkness falls.

Day Three: This morning you’ve decided to rent a car and see more of the island. Hertz has a rental desk right near the lobby of the resort, and within a few minutes you’re rolling toward the North Shore with the top down. On the way, you stop at the Dole Plantation, where you work your way through the world’s largest walkable maze, then cool off with some Dole Whip – a refreshing pineapple treat. A little while later, you arrive on the North Shore and work on your tan at Waimea Bay, then grab lunch at the Kua Aina Sandwich Shop. After a stop at the Matsumoto General Store for Hawaiian shave ice, you continue to the island’s windward side, stopping for pics at Kualoa Ranch, Chinaman’s Hat and the Pali Lookout before dropping back downhill to the twinkling lights of Honolulu.

Day Four: You’re back on Waikiki Beach today and decide to join a group for a short outrigger canoe paddle. Outriggers have been used by the Polynesian people for hundreds of years as a means of transportation and exercise, and your paddle is capped off with a nicely-ridden wave back toward shore. A little later, you spend the afternoon doing some shopping at the dozens of shops lining Kalakaua Avenue, and in the open-air Royal Hawaiian Shopping Center, which offers everything from the latest gadgets at the Apple Store to high-end handbags at Salvatore Ferragamo. And as the sun begins to set, it’s back to the beach to board a catamaran for a sunset sail. With a warm breeze blowing and a cool drink in hand, you watch the sun dip below the Pacific at the end of another great day on Oahu.

Day Five: You’ll be returning to the mainland this afternoon, so you get up early and head to nearby Diamond Head Crater for a hike to the top of the iconic peak overlooking Waikiki and the island’s south shore. With your hat and sunscreen on and water bottle in hand, you work your way from the bottom of the crater up the trail for about three-quarters of a mile, passing by bunkers used in World War II and finally reaching the peak. The view from the top is incredible, with all of Waikiki spread out below you and views of the island’s west side to your right, and the southern coastline to the left. You take (and post!) a few pictures, then enjoy the downhill hike back to where you began. It’s a great way to complete your visit to Oahu – Hawaii’s “Gathering Place.”