Destinations, Hawaii, Maui

Sunrise on the Sea: Sailing from Maui to Lana’i

January 26, 2015

For these two parents used to waking up to care for a little one in the middle of the night, it felt like a pretty slick maneuver, hopping out of bed at 5:15am and making a dash for the beach. There we were: driving down from Ka’anapali to the Lahaina Harbor for a 6am check-in at the boat while Lucie stayed back at the condo with her grandparents. (Queue: “Freedom!!!”)

It’s not especially hard to wake before dawn in Hawaii when your internal clock is still hanging on to west coast time. It’s also not terribly hard to convince your husband to come sail from Maui to Lana’i when you mention that the crossing includes fresh baked cinnamon rolls, coffee, and whale watching…and probably dolphin sightings, too.

I knew that traveling to Hawaii with a little one meant saying the goodbye-version-of-Aloha to jam-packed days of adventure. In fact, I intentionally let go of almost all my normal trip planning exercises and instead focused simply on anticipating a week in the sunshine with family.

That said, when the opportunity for one big splurge came along…I couldn’t resist.

A few weeks before the trip, my cousin Sam and his wife Marissa invited us to join them in making bookings (remember, we went to Maui with 30 family members!). They’d taken a Trilogy Excursions half-day snorkel tour to Molokini crater on their honeymoon a few years back and held high hopes for the same company’s day long adventure to Maui’s neighboring island of Lana’i.

I saved a little chunk of change by making my reservation a week in advance, and when we departed for Hawaii a few days later, I enjoyed having the little adventure tucked as an ace up my sleeve. Even if the every other day of the vacation revolves around chasing Lucie in circles, I thought, I know I have one blissful eight hour getaway on the books.


On our pre-dawn morning, I swung the rental van into the parking lot near the harbor, and our troupe of five (Sam, Marissa, Ted, and my cousin Riley and I) walked down to the waterfront, checked in with Captain Caleb, and boarded the catamaran.


Almost as soon as we left shore, the crew began making the rounds with warm cinnamon rolls. This friendly British Columbian, Anthony, works a pretty great gig as a breakfast-serving whale-watching expert in Hawaii during the North American winter and spring and then as a guide back in Canada during the summer and fall. (No word on whether the Canadian tours serve fourth-generation-recipe cinnamon rolls on board, though.)



My cousin-in-law Marissa (so glad you married in the family!), my Cousin Sam, and Ted and me… (Riley: M.I.A. Possibly filling his bottomless cup of coffee below deck?)


“It’s a fourteen mile trip across the water from harbor to harbor,” they told us. Far enough to feel like a true journey, but close enough to allow us time to arrive and explore with plenty of hours remaining in the day.

Peaceful and quiet.

We skimmed across the ocean, waiting for the sun, watching for whales, and relishing the warmth of ceramic mugs in our fingers and the smell of coffee and salt water in the air.


















Once we reached the coast of Lana’i, we disembarked and walked up the hill and around the corner to Hulopo’e Beach Park and Marine Preserve, a private little paradise shared by locals and by the Four Seasons Lanai at Manele Bay.

Dating back to Trilogy’s initial 1973 trips to the island, they’ve honored an agreement to avoid bringing people to snorkel on weekends and holidays in order to leave it quietly uncrowded for the locals to enjoy. They’re the only private company with permission to bring guests to the beach, and we felt like we had paradise to ourselves.

The seclusion was delightful. I rolled out a beach mat on the warm sand, and while others grabbed snorkel gear and slipped into the water to take in the flora and fauna of the sea, I sunk my toes into the sand and escaped into my book.

A bit later, Ted and I looked at each other and decided yes, yes we were going to splurge just a little bit more.

Coffee at the Four Seasons? A worthy reason for a little hike up the beach trail.





Sipping a humble coffee from the balcony dining soon turned into sharing a split-order of Ahi benedict…because…well, when in Hawaii.

Also, let it be noted: Ted has a mad crush on the chairs at The Four Seasons at Manele Bay…

…and I had a mad crush on the full-length mirrors and my laughably comfortable pants.

Ridiculous as it sounds, we finished our breakfast just in time for lunch.

We walked back to the sandy beach, rolled up our mats, packed up our sunscreen and books and bags, and took a short return van ride down to the pavilion on the marina where the Trilogy crew had prepared a chicken BBQ complete with heaping piles teriyaki noodles, and generous slices of juicy yellow pineapple. (Perhaps a hat-tip to history? Previously, Dole owned the majority of the island and tended plantations supplying 75% of the world’s pineapples!)




My cousin Sam and his wife Marissa, after a full morning of snorkeling and a pre-sail lunch.


Surprise, surprise: Captain Caleb (an eight year veteran of Trilogy Excursions) grew up near Dallas, Oregon before relocating to work somewhere with a tad more sunshine.


Natural ginger supplements to battle post-lunch seasickness. I figured it couldn’t hurt to take a few and be safe instead of sorry?

Time sped up once we left shore and headed eastward.


My cousin Riley and Ted, momentarily at the helm.

After encountering a pod of spinner dolphins and watching their energetic play, the crew turned us out to open water and unfurled the sails.

Adults and kids alike ate ice cream in the sunshine while offers of Moloka‘i Mules, Lana‘i Tais, and seasonal beers came to the passengers 21 and older.



About an hour later, Lahaina Harbor appeared bright and lively on our approach.


By the time we stepped off the boat and back to land, the sun was high in the sky, dawn was a distant memory…and I daresay we were starting to miss Lucie just a little bit.

A solid, satisfying adventure: good food and good company, beautiful scenes and a peaceful unwinding, a break from the daily rhythm, and a chance to be away from the baby long enough to make reunion all the sweeter.

Let me tell you, she was pretty stinking cute when we got back, especially when we suited her up in her little rashguard to go splash in the resort pool. But I’ll save that for another post…

For now, it’s just we twoOregonians, joined at the hip once again, out exploring the world.


Two kidless-for-the-day (and pasty-pale-white) Oregonians: Happily escaping reality on a little mini-getaway in the tropics.

Thanks so much to Trilogy Excursions for sponsoring this post; thanks to Captain Caleb, first mate Koa, and Chad and Anthony for the truly exceptional service; and thanks to my cousins for the great recommendation. And thanks to my parents for watching little babyOregonians for the day! Though kids 13-18 are 25% off, and kids 3-12 are 50% off, and kids Lucie’s age are absolutely free, we were pretty giddy to experience a full day of fun with zero responsibility for diaper bags and snacks and kiddie-sunscreen.

Sail Trilogy Discover Lana’i /// Take the “Crew’s Favorite” sunrise sailing, if you can: cinnamon rolls and coffee, fresh fruit and whale watching, snorkeling in a private cove (or heading up to the Four Seasons!), enjoying a catered BBQ lunch, and drinking Moloka‘i Mules and Lana‘i Tais on deck in the afternoon sunshine on the beautiful Pacific Ocean. @sailtrilogy

Four Seasons Resort Lanai at Manele Bay. Beautiful seclusion. Kind staff. And killer Ahi benedict.

“Unexpected stories from unexpected places” – a collection of shorts from Lonely Planet. /// If you can’t get away to sail in Hawaii just yet, try Tales from Nowhere (pictured above on the beach at Lana’i). I bought it in the Powell’s Bookstore travel section during one particularly angsty-wanderlusty pre-RTW phase, and I still pick it up from time to time to be momentarily transported to remote corners of the world. Example: while sitting on the beach on Lana’i, I took a trip to Easter Island. Never underestimate the power of words.

Lastly, if you’re interested in glimpses of real life on a sailboat, check out the documentary Maidentrip (currently on Netflix), and then go explore my South African friend Kate’s photos from life on the sea: @abrandnewlife.

Question time! Would you:

a) willingly get up before dawn on vacation in Hawaii? (Be honest.)
b) choose to split the Four Season’s Ahi benedict with your significant other or eat it all yourself? (If money were no object, I’d probably have ordered three servings.)
c) like Trilogy’s recipe for Ma’s famous cinnamon buns? (Well, you’re in luck: Here you go.)

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