Book a Charter Now

Sunset Sailing ($425)

Experience the Chesapeake Bay's legendary sunsets from the deck of a luxury sailboat. The golden hour painting the water as you glide through the evening waters with the privacy of your guests our crew and nowhere else to be.

Day Charter ($395-$695)

From morning breezes to afternoon winds, choose your perfect day on the Bay. Whether a half-day escape to explore hidden coves and historic harbors, or a full day of sailing, swimming, and discovering the Chesapeake with only your guests and our crew.

Overnight Stay ($325)

Your own private floating retreat. Spend the night (up to 4 people total) aboard Mañana in her slip at Rock Hall's premier marina. The unique experience of sleeping on a luxury sailboat, complete with full galley, cozy air conditioned cabins, and the peaceful sounds of the harbor at night.

MultiDay Charters (Email)

Beyond our standard charters: multi-day coastal cruises, bareboat rentals for licensed captains, sailing lessons from beginner to advanced, corporate events, wedding proposals, ash scattering ceremonies, and fully custom experiences—if you can imagine it on the Chesapeake, we can make it happen. Email us at captain@son-of-a-sailor.com to discuss longer charters.