This fall, Nauti Daddy Sailing Co. transforms the Chesapeake Bay into our own cozy‑gay getaway. Over seven days we’ll drift between historic villages, vibrant harbors, and quiet anchorages — including a sail though Baltimore Harbor — letting the fall colors and cool breezes set the vibe. Every day brings a new slice of the bay, and every night brings new connections.

Onboard, Chef Davey keeps the boys warm and happy with autumn‑themed meals, hot cider, and cocoa under the stars. Mornings are made for hot coffee, comfy grey sweatpants, and the kind of lingering conversations that give those sweats a little more of a story to tell. Afternoons hopefully bring sunshine and speedos, or less, warming ourselves in the last warm days of the Chesapeake. And plenty of blankets nearby for spontaneous cuddle puddles if it's too cold! Evenings unfold with music, flirty banter, laughter, and that gentle mischief that always seems to spark when gay men gather on the water.

We return to Annapolis just in time to celebrate Annapolis Pride weekend together, connected, glowing, with new, authentic friendships for life. 

Fall warmth, gay pride, and gray sweatpants, this is autumn Nauti Daddy Sailing Company style