Sailing into the Wild Blue

One of the reasons we moved to Hawaii was to spend more time exploring the ocean, the wild blue. One of our favorite ways to do that is by sailing. I grew up sailing on the East Coast, right in the heart of Cape Cod. My grandmother Tutu taught Bryan how to sail when we were dating and he has been hooked on it since.

We’d been wanting to sail to Lanai for years now, as Bryan and I haven’t been back to the island since our honeymoon in 2008. We spoke with the fine folks at Trilogy and found out they do a sail adventure to Lanai on Mondays – Fridays (they don’t do weekends out of respect for the locals). Their commitment to the environment coupled with their family-friendly attitude won us over. There was nothing left to do but pick a day and play hooky for the day! We met the crew in Lahaina and boarded the boat right at sunrise.

The morning began with Mama Coon’s cinnamon rolls straight out of the oven. Its’ true what they say – food tastes better on a boat.

We made our way over to Lanai and found our snorkeling spot. The wind was calm and everyone was feeling brave, including Aria. After her man o war sting a week prior, Aria was feeling nervous about going back in the water but decided to put on her brave boots and just go for it. The water and fished lured her in and the crew was especially encouraging.

The water clarity was insane and the fish seemed to come closest to Aria as if they were applauding her brave efforts. She was stoked. Now, we’ve worked up an appetite – back to the boat for some more food!

We motored around the tip of the island and made our way to the harbor. There, we were greeted by a beautiful traditional Hawaiian chant as we hopped off the catamaran to explore the island. The surf was pumping (7 foot overhead!) but we found a lovely tide pool to swim in while the waves crashed just outside the reef.

Then, we hiked to the legendary Sweetheart Rock. The hike is a hot one but we stayed cool from swimming just beforehand. The tale of Sweetheart Rock (taken from Go Hawaii):

Legend tells of two lovers, a Hawaiian maiden named Pehe from Lahaina and a young warrior from Lanai named Makakehau. He was so taken with her beauty that whenever he laid eyes upon her they would mist up in tears. Hence his name: Maka (eyes) Kehau (mist). He took her back to Lanai and hid her in a sea cave at the base of Manele’s cliffs.
One day while gathering supplies he noticed a storm brewing and started back, only to find Pehe drowned by the surge of the storm waves. Stricken with grief, Makakehau gathered his beloved in his arms. He wailed out to the gods and his ancestors to help him climb the steep rock island where he eventually buried her. He then jumped from this 80-foot summit into the pounding surf below.

Before we knew it, it was lunch time at the pavilion. We showered off and walked our hungry bellies over to the shaded, grassy area. Lunch was incredible!

Our sail back to Maui was entirely relaxing and a good time to reflect on the day’s adventures. The crew served up ice cream for dessert and it kept us just cool enough as we docked back at the hot Lahaina harbor. Thank you, Trilogy, for a great day! You have made us want to live on a boat.

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