Spend your first day of your Hawaii vacation getting to know Honolulu and the famed Waikiki Beach, with its waterfront bars and restaurants.
Where to stay: While in Oahu, choose between the elegant 5-star Kahala Hotel and Resort, located far enough outside of Honolulu to be tranquil and quiet, but close enough for trips to Waikiki Beach and its beachfront bars. Or, head a little further out to the North Shore and check into Ocean Villas at Turtle Bay, with its sea views and palm-fringed lawns leading to a private beach.
Transportation: Rent a car in Oahu as part of a Hawaii package deal to get out and experience the island’s natural beauty and remote, uncrowded beaches – both today and tomorrow.
From Honolulu, it’s a little over 20 minutes’ drive southwest to Hanauma Bay, famed for its incredible snorkeling. About 30 minutes’ drive northwest is Waimanalo, the island’s longest beach where you can try surfing on a traditional outrigger canoe.
In the evening, there is nothing more Hawaiian – or more romantic – than listening to live music and watching a hula dance at sunset. In Waikiki, there’s a free Kuhio Beach Hula Show held three times a week at the Hula Mound along Kalakaua Ave.
We suggest heading for the Windward Coast first; it’s just a 30-minute drive east from Honolulu but feels a world away. There’s enough to do in this area to fill a whole day; however, you could also spend just a few hours here then drive another 50 minutes to Hawaii’s North Shore, known for its surfing and laidback atmosphere.
After 3 days on Oahu, it’s time to hop on a flight to Maui. Flights between Oahu and Maui are frequent and take around 40 minutes. To get the most out of your time on Maui, pick up a rental car at the airport to have the freedom to explore.
Where to stay: Options in Kihei include smaller boutique hotels such as the luxurious, adults-only Hotel Wailea, Relais & Chateaux, or larger resorts such as Fairmont Kea Lani Maui, which has an adults-only swimming pool and excellent selection of bars and restaurants.
You will need a car to travel from your hotel to the starting points of these guided adventures, so we recommend renting a car for your daytrip around Maui.
For your last night, we recommend a sunset cruise with one of the many companies that depart from nearby Maalaea harbor to end your 5-day getaway. In the evening, catch a flight from Maui back to Oahu to make your connection home.
Jul 1 - Jul 2
We loved this hotel! Steps from the beach, amazing pool, the housekeeping service was incredible and the rooms were clean and modern.
Jun 8 - Jun 9
Beautiful and close to beach two blocks they even had beach towels and chairs to use
Jul 1 - Jul 2
Our family of 6 stayed in two adjoining rooms in the Tapa Tower for six nights on a last-second trip, which coincided with the State of Hawaii's response to COVID-19. As a result, there were certain activities we were unable to enjoy during our trip, such as eating in restaurants during the last ...
^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.