Sail the Bay

Mimosas and Memories...
A romantic overnight Bed and Breakfast Sail for two

Back by popular demand! Experience romance on the Bay with an intimate get-away for two... and a unique bed and breakfast sailing experience. Enjoy an evening sail and overnight stay on "Anytime"... a vintage 1972 Hinckley Yawl Bermuda 40 Mark III sailboat plying the waters of the Chesapeake Bay.

Relax uptop in the cockpit and relish the cool night breeze, then retire below deck and enjoy hot chocolate or warm cider by Anytime's fireplace. Sleep comfortably in the private fore V-berth. Rise to the smell of fresh coffee and a made-to-order breakfast. Then back to home port. A relaxing respite from the daily grind... and a unique bed and breakfast sail get-away-from-it-all.

Booking dates are available on Friday and Saturday nights from May until mid-November. The cost is $650.00 per couple. One couple per night.

Reservation Form...

Reservations are on a first-come, first-served basis. To expedite your reservation request fill out this form completely.


Your email address (This is never shared with anyone outside of

Your Telephone (Enter as XXX-XXX-XXXX)

What is the best time to reach you?

What dates are you considering?

Comments or questions about destinations or trip plans


Please note: Anytime's Captain, by law, cannot provide alcoholic beverages. If you bring the champagne, we'll supply the OJ for Mimosa's!

You can also call Captain Walt anytime... 717-870-0548... and let him help you plan your unique experience on the Chesapeake Bay!

"Anytime’s" standard charters range from single day sails to full week packages... and anything in between. The fare includes the full services of Captain and one crew, all food and snacks, non-alcoholic beverages, clean linens, pillows, and towels. Dockage if elected over anchoring, applicable taxes, and tips are an additional expense.

Please note:
The total amount of passengers allowed for any charter is 6.

Visit idyllic hidden harbors. Watch the local watermen work their crab pots. See the Great Blue Heron stalk its prey, and watch Osprey dive for fish. Get away from it all... or join the party in bustling harbors like Baltimore, Annapolis, or the Solomon's.