Hawaii is a great place to visit any time of the year, and there are a wide array of accommodations, travel styles, and activities to enjoy. It actually can be a bit overwhelming to plan a Hawaii trip, given all the options! But don’t worry, because Legacy Travel Designs has a whole host of partners and connections that we work with to curate the perfect adventure for you and your traveling companions. Below is a sample itinerary for a first visit to Hawaii, with stops on Oahu and Maui.
After your traditional lei greeting at the airport, grab your rental car or private transfer and head over to your hotel on Oahu’s famous Waikiki Beach. Settle in, have a mai tai, and enjoy dinner at one of Waikiki’s many wonderful restaurants.
Go for a hike up to Diamond Head crater, where you can get sweeping views of Oahu and its shoreline. You can go on your own or have a guide show you around. You can even take an eBike tour of the Waikiki area on the way to Diamond Head! Enjoy some beach relaxation time in the afternoon, then head out for a sunset cocktail cruise along the shores of Oahu.
Today is the day to appreciate the history and culture of Oahu and the peoples of the South Pacific. Visit Pearl Harbor and it’s museums and World War II memorials. Take a tour of Iolani Palace in Honolulu, the home of Hawaii’s last reigning monarchs. In the evening, experience a traditional Hawaiian luau.
Take a quick 45-minute flight from Honolulu to Kahului Airport on Maui, then head to your villa or hotel along the coast. Check out the beach, the nearby village for shopping, and have dinner at your resort or at one of the many restaurants or food stands that serve authentic cuisine from many different cultural influences in Hawaii.
For many, snorkeling at Molokini Crater is a “must-do” on their Maui vacation. This sunken crater has created the perfect area for relaxing on a sailing catamaran and viewing the sea creatures and coral below. You also could take a day trip to the nearby island of Lanai, which has some wonderful ocean adventure options.
Hire a guide or join a group tour for a full day on the world-famous road to Hana, where you’ll experience the byway’s lush farms, scenic overlooks, and rich Hawaiian history. Try to keep your jaw from dropping as you proceed along this iconic north-Maui route, passing postcard-perfect scenery at Wai’anapanapa State Park, Ho’okipa Beach Park, and Waikani Falls. Continue on to Ke’anae, a historic Hawaiian hamlet known for its fisherman and photo-worthy atmosphere, and see the final resting place of aviator Charles Lindbergh.
You’ll have to get up early to catch the sunrise from the summit at 10,023 feet, but it will be worth it to have the experience of a lifetime at Haleakala National Park. Most tours provide transportation and breakfast, along with park entrance fees and cold weather gear to use as you await the majestic beauty of a sunrise you are not likely to forget. You’ll be back at your hotel or villa by noon-time, where you can have a leisurely lunch and then a nice nap on the beach in the afternoon!
Head into the interior of Maui to explore a pineapple plantation or take a coffee and chocolate tour. The samples alone are worth the drive! Finish your time in Hawaii with a bird’s eye view of the island on a helicopter tour. You’ll see waterfalls, beaches, cliffs, and volcanoes as well as some of the other islands in the distance.
As you leave Hawaii, treasure the unique experiences you’ve had, and start planning for your next visit!
We’ll create your perfect vacation recipe from scratch, sourced from the finest ingredients below, and add our special sauce.
Art and Culture
Meeting the Locals
Rest and Relaxation
Indigenous Craft Workshops
We’ll add personalized surprises sprinkled throughout.
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