Oahu is littered with historic sites that tell the story of its passage from independent island to Hawaiian kingdom to statehood. Many are easily made into a small circle-island tour.

It is easy to do a walking tour of historic sites in central Honolulu, to take a history trolley tour that departs from Waikiki and extends through Chinatown, or to add the bus tour of town to a Pearl Harbor visit. If you want to reach out further, though, some very special locations are best reached by car. I have recently taken two versions of a circle-island tour, one shorter than the other.

The first trip leaves Honolulu toward Pearl Harbor, then up to the Dole Plantation. A stop here includes much information about the role of pineapple and plantations in Hawaii history. It is a demonstration farm rather than an actual factory. We then went to the North Shore, driving until the road ends at Kaena point, which held spiritual significance for Native Hawaiians. Returning along the Kamehameha Highway, we paused at Turtle Bay before driving along the coast. We did not stop at the Kauola Ranch, but it now offers a “Lands and Legacies” tour that would be a nice addition. We drove up to the Pali overlook before doubling back to continue along the coast past the Makapu’u Lighthouse and ending at the airport.

A shorter version of this trip also departed from Honolulu but headed up the Pali highway with a stop at the Queen Emma Summer Palace. This quick, inexpensive tour was a highlight for our guests with an interest in Hawaii history. After a stop at the Pali overlook, we headed for the Valley of the Temples near Kaneohe to see the visually and spiritually impressive Byodo-In Temple. We turned onto the Kamehameha Highway in time to see the pirate ship Queen Anne’s Revenge still at the dock from the recent filming of Pirates of the Caribbean IV. From this point, we followed the Kam highway along the coast, as we had with the longer tour. However, since we had more time, stopped for photos at the blow hole and Sandy Beach.

The trade-off for the shorter tour is that you circle only a small part of the island. However, you do get out of town and spend less time driving while still experiencing significant moments in Hawaii history.


  1. From a completely biased point of view, I say the Windward side of the island is where you should visit. It will bring loads of different eateries (Mr. Lee’s and the diner next to Happy’s), historical sites (Kaneohe Bay, Heeia pier), mom and pop stores (shout out to Hygenic and Waikane), beaches (Kailua – Lanikai …. ), and just an all-around good time. Enjoy!!

  2. If you have time, the drive up to the North Shore and all the way down the Windward side is just beautiful. I do this drive with any friends/family visiting me for the first time, it is a must. I like them to see the more rural areas and character of each part of the island outside of the city. You get a feel for how different and just beautiful each part of the island really is.

Leave a Reply

Click for the BBB Business Review of this Travel Agencies & Bureaus in Honolulu HI
Travel Industry Logos