Florida Keys Yo-Yo, Part 1: Kayaking Key Largo To Key West. Intro and Days 1-2.
In early January 2026, I was recapping my 2025 adventures, longing once again for the outdoors. For the past 5 years, I’d begun my hiking season earlier and earlier, to the extent that I started my Desert Winter Thru Hike at the end of January, nearly 1 year prior. While I didn’t really want to repeat a 1500 mile winter thru-hike again this year, a mini staycation / thru-hike seemed like the perfect way to satisfy my immediate wanderlust. So I began studying the logistics of hiking the Florida Keys Overseas Heritage Trail, which lies conveniently in my backyard. Pretty quickly, I added more ambitious plans to also paddle my sea kayak to Key West, making it a paddling /[…]
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