The Fashionable Frequent Flyers

Listen, we get it! This is a very daunting question. With only a limited amount of vacation time available, planning the perfect Hawaiian vacation begins with choosing the right island(s) for you! Linda and I have been fortunate enough to have had a year out in Hawaii, and that time has allowed us to visit five of the eight islands. It has been an absolute blessing, and also, it has given us a decent amount of insight to pass along. This post will provide our take on what each of the islands offers (in broad strokes) in the hopes that it will help you make a decision. Ideally, to the extent possible, we’d recommend planning a trip to two or three islands so that you can maximize your experience!

Kauai – The Garden Isle

Kauai is the oldest of the Hawaiian islands, and, in our view, by far the most lush — hence the name, the garden isle. It is incredibly green and incredibly beautiful. This island is home to Waimea Canyon (colloquially known as the Grand Canyon of the Pacific), Limahuli Gardens and Preserve, and the gorgeous Na Pali Coast. Kauai is small, easily commutable, and full of beautiful rainbows around every bend. To date, this is our favorite island and our favorite activity on the island is without question the Na Pali coast tour hosted by Blue Ocean Adventures.

Maui – The Valley Isle

Maui is the second largest of the Hawaiian islands and is the island most frequented for romantic vacations. The resorts in Wailea are absolutely breathtaking and the perfect setting for a honeymoon, anniversary, or any sort of bae-cation. But don’t be fooled, Maui has a lot more to offer — it isn’t called the valley isle for nothing. The Road to Hana is spectacular and has numerous amazing offerings, including many many waterfalls (most of which are accessible and you can swim in), the seven sacred pools, the red sand beach, the black sand beach, the Garden of Eden, and a flurry of food stands along the way. Maui is also the best island to do whale watching in the winter, and the snorkeling in Molokini Crater was pretty awesome too. Our favorite activity was definitely the Haleakala Sunrise — What! A! Sight!

Hawai’i Island – The Big Island

As is obvious from its name, this is the largest of the Hawaiian islands and the island which had the most recent volcanic eruption. You’ll spend a large amount of your time on the island commuting given its vast size, and you’ll be struck by how much of the land is covered with black lava rock. In our view, this is the best island to do marine activities. The snorkeling is top-notch because the reefs are well-maintained. You can also swim with manta rays and dolphins, both of which are amazing experiences. The Big Island also offers numerous black sand beaches, and a green sand beach, and is home to the southernmost point in the United States. Volcano National Park is an amazing place to visit with numerous experiences, as is the City of Refuge for some cultural learning. The waterfalls on the Big Island are huge and inaccessible, but a sight to see. Our favorite activity was swimming with dolphins 🙂

Oahu – The Gathering Place

Oahu is home to approximately 80% of the population of the State of Hawaii, and, in our view, offers a decent balance and representative slate of activities offered on the various Hawaiian islands. Granted, there are no black, red, or green sand beaches on Oahu, but there are amazing white sand beaches, amazing hiking trails, and pretty awesome marine activities such as swimming with sharks and dolphins. You can learn to surf, sail, and fish, and if that doesn’t sound very exciting to you, you can skydive or learn to pilot a plane (and tour the island). Waikiki is basically the Hawaiian Time Square, so if you’re interested in high-end shopping, this is the place for you (and the sales tax here is much lower than mainland US). Most importantly, this is the perfect place to chill with family and have a nice beach cookout. That’s basically the Oahu island pass time!

Lanai – The Pineapple Island

Lanai is the smallest of the islands we have visited, and perhaps the most unique. The island is basically comprised of three segments: 1) Sensei Lanai, the Four Seasons resort in the mountains; 2) the town center, which is approximately two blocks; and 3) the Four Seasons Lanai beach resort. The island is owned almost in its entirety by Larry Ellison. While a lot of Lanai is undeveloped, the two segments where the Four Seasons operate are extremely lavish. The two resorts are similar, but also very different. Four Seasons Lanai is more akin to a resort in Waimea in Maui, whereas Sensei is an adults-only hotel with its focal point on health and wellness. Lanai is centrally located and at one point on the island, you can see all the other islands. Our favorite activity on the island was the couples spa hale experience at Sensei.

We hope this helps! If you’d like to see more photos of what the various experiences we’ve described above look like, check out our Instagram feeds and follow us for more luxury travel and adventure content.