Favorite things, day 3: Hawaii

(All photos taken by me; message me for licensing.)

Sun, sand, beach, surf, ancient cultures, outdoors — there’s so much to love about Hawaii. An archipelago of 8 primary islands, it offers a great break far away from most things. For Americans, no passport required.

Hawaii is not a monolithic place. I recommend different parts of Hawaii depending on what you’re interested in. In order of my favorites.



Hiking for all skill levels, gorgeous waterfalls. Kauai has one of the most famous hikes in the world – the Kalalau Trail. It’s sandwiched between the cliffs of the Na Pali Coast and the Pacific Ocean. It is always crowded, often muddy. Still, you have to do it. For the more adventurous, there is a spur trail that will take you to a narrow ribbon of water falling off the cliffs. The spur trail is four miles round trip, strenuous and poorly marked.

I prefer the Pihea-Alakai Swamp trail in Kokee State Park.

Hotel recommendation: Princeville Resort (formerly St. Regis Princeville).



Beaches, beaches, beaches – by far the best beaches in the island. The road to Hana provides a windy path through lush forests and waterfalls.

Hotel recommendations: Fairmont Kea Lani, Andaz Maui.

Hotel recommendation if you’re trying to convince your significant other not to have kids: Grand Wailea, A Waldorf Astoria Resort.

Big Island


The Big Island is more low-key than its neighbor islands. The big highlight here is Hawaii Volcanoes National Park.

The Kilauea Iki Crater hike has you hike from the rim of the crater down into the crater floor and up the other side. One of the best hikes I’ve done.

It is a long way to the volcano from Kailua-Kona area, where most people stay. You should plan to spend one night near the volcano. Unfortunately, like near most national parks, the quality of the lodging leaves a lot to be desired.

Hotel recommendation: Fairmont Orchid.

Hotel non-recommendation: Hilton Waikoloa.


View from room Angelfish 3, Manele Bay Hotel

It’s not Maldives isolated, but it’s pretty isolated. There are basically two things to do on this island: golf and go to the beach.

This is where Bill Gates got married. He rented out every hotel room on the island and chartered all of the helicopters on nearby islands.

Ironically, Larry Ellison now owns more than 95% of the island.

I also saw Al and Tipper having breakfast here once.

There are two hotels, one on the beach and the other inland known for its golf courses. I don’t golf and I like the beach so I haven’t stayed there.

Hotel recommendation: Four Seasons Resort Lanai (formerly Manele Bay Hotel).



This is where most people go, partly because it’s the easiest to get to by air from most of the world. (From the West Coast, all of the above except Lanai, are accessibly nonstop.)

If you don’t vacation a lot, just need to get the hell out of a Midwestern ice scape and have kids in tow, this is probably a good place. You have city, sights (Pearl Harbor, most notably), beach, surf… a little bit of everything.

Waikiki Beach is one of the best known beaches in the world. It’s way too crowded for me. I try to avoid walking around Waikiki. Lots of kids and many, many planeloads and busloads of tourists from Japan.

I prefer to go the North Shore or Kailua areas. The Bellows Air Force Base beach is one of the most stunning beaches I’ve been to. Much of Lost was filmed on the North Shore.

Hotel recommendations: Royal Hawaiian, Westin Moana Surfrider. (I prefer the Royal Hawaiian, but it usually comes down to price.)

Hotel non-recommendation: Hilton Hawaiian Village.

I haven’t been to:

Molokai – I’ll get there some day.
Kahoolawe – It’s uninhabited and off limits.
Niihau – The Forbidden Island. It’s privately owned and you need an invite.


About Rakesh Agrawal

Rakesh Agrawal is Senior Director of product at Amazon (Audible). Previously, he launched local and mobile products for Microsoft and AOL. He tweets at @rakeshlobster.
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