Walking Maʻalaea Harbor, Maui | Reflections on Sailing & Schooner Life

Day one in Maui, and of course, I was drawn straight to the harbor. After nearly 24 hours of travel (including a mid-flight emergency where my old nursing skills kicked back in!), I landed at Maʻalaea Harbor — the second windiest harbor in the world. For me, this walk is more than just a look at boats. It's a connection to my roots. It's a grounding feeling of home, thousands of miles away from gypsy and my soul mate. It’s a reflection on why the ocean keeps calling me back — from growing up in Valdez, Alaska and Prince William Sound, to now living and creating aboard with Scott as we take on the unfolding journey of refitting our 80’ triple-masted Thomas Colvin schooner, The Alaskan Gypsy. It's about gratitude for the entire experience! Whether in the raw stillness of Alaska or the trade winds of Hawaii, the sea has always been my grounding place. Thanks for joining me in keeping Gypsy Life connected across oceans. Feel free to comment along as I'd love to share the journey with you! :) Chapters: 00:00 – Arriving at Maʻalaea Harbor (Not in the Shipyard Anymore!) 01:06 – Checking Out Maui’s Boats & Vessel Styles 02:48 – Why Our Steel “House on the Water” Stands Out 04:14 – Harbor Reflections + My Mid-Flight Nursing Story 05:27 – How It All Connects to Refitting The Alaskan Gypsy 07:41 – Growing Up in Valdez, Alaska (My Ocean Roots) 08:19 – Deckhand Summers in Prince William Sound 10:31 – Inspired by Liveaboard Sailors I Saw as a Kid 11:23 – Dreams Becoming Reality with Scott 12:04 – Returning to Hawaii: Childhood Memories & Now 14:35 – Exploring More of the Harbor Walk 17:14 – Tropical Harbors vs. Alaskan Harbors 19:10 – Finding Maui’s Longest Stretch of Beach 20:49 – Closing Reflections: Freedom, Schooner Dreams & Ocean Life