Our first morning in Key West started with phone calls home – catching up with family, showing off the new anchorage. During one call with my parents, we realized our mooring line was chafing badly. Oops. Quick fix: we swapped it for a bridle setup (probably what we should have done from the start).
Barrett changed the oil while I tackled other chores, and then we packed up for an adventure. Dinghying over to Key West Bight, we bought a day pass to leave our wonderful dinghy, Squeasel, at the dock and hopped on a bus to the beach.
There, we met up with friends – Megan, Jon, and their son Thomas. The plan was a beach BBQ, but another group had claimed the grill and fire Jon had started and refused to share. Classic curveball. Instead, the night morphed into sushi appetizers by the ocean, followed by dinner at their house. The kids got to play, the adults caught up, and laughter filled the evening. Sometimes the best memories come from plans gone sideways.
Our week in Key West unfolded in a groovy rhythm – a mix of work, play, and wandering.
Highlights included:
- Fresh baked donuts at the docks.
- Uniquely cruiser laundry and provisioning experiences.
- Shopping, splash pad adventures, and long lunches.
- Spotting horseshoe crabs in the marina.
- Daily dolphin sightings around the anchorage.
- Sunset after sunset that left us in awe.
- Making phone calls on a vintage, yet functional, pay phone (for free) at Pepe’s Cafe.
- The kids chatting with folks on the wharf, spouting fish facts as tarpon and parrotfish swirled below.
- Meeting local artists, enjoying delicious food around town, and exploring Mallory Square.
- A slightly rolly but beautiful Father’s Day sail north to Marathon.
Like most of our favorite stops, this one felt like more than just a stopover – it felt like a little chapter of our story. A Key West address, even if only for a week.
Sailing Agora 
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