sail the Bay on Anytime

Sail the Chesapeake Bay on Anytime

Chesapeake Bay sailing cruise

Affordable, fun Bay sailing! Helping make your sailing dreams come true... Call now!

The Chesapeake Bay sailing season is here. Reserve your private sailboat charter on "Anytime" today!

Click to reserve your space now... before it's too late! Sail the Bay today!

Overheard onboard Anytime...
"We had such a nice time... thank you for making us a great memory!"

Call Captain Walt anytime... 717-870-0548... and let him help you plan your unique sailing experience on the Chesapeake Bay!

Now you can custom design your own private yacht adventure and sail to just about anywhere on the Bay. Captain Walt Shoemaker proudly offers you the unique sailing experience of "Anytime"... a vintage Hinckley Bermuda 40 (B40) sail boat plying the waters of the Chesapeake Bay.

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.

Click to reserve your space for the current sailing season now!

"Anytime’s" charters range from single day sails to full week packages... and anything in between. This makes a great gift for birthdays, anniversaries or Fathers Day. “Anytime” is ideal for corporate charters, employee team building, romantic get aways, and family sailing adventure trips for up to 6 people.