Sailing the Beautiful Chesapeake Bay from Rock Hall, MD

Sailing the Beautiful Chesapeake Bay from Rock Hall, MDSailing the Beautiful Chesapeake Bay from Rock Hall, MDSailing the Beautiful Chesapeake Bay from Rock Hall, MD
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Sailing the Beautiful Chesapeake Bay from Rock Hall, MD

Sailing the Beautiful Chesapeake Bay from Rock Hall, MDSailing the Beautiful Chesapeake Bay from Rock Hall, MDSailing the Beautiful Chesapeake Bay from Rock Hall, MD
Home
the boat
Charters
Deliveries
Contact
Lessons
More
  • Home
  • the boat
  • Charters
  • Deliveries
  • Contact
  • Lessons
  • Home
  • the boat
  • Charters
  • Deliveries
  • Contact
  • Lessons

Chartering 101

All Sails

  • Depart from Osprey Point Marina unless otherwise agreed upon.  I can relocate for a fee or even make it a one way trip.  Don't be afraid to ask if you are feeling adventurous.
  • Maximum of 6 guests, I can arrange for additional boats to accommodate your party or we can do multiple sailings to get everyone out on the water.
  • BYOB - bring your favorite, don't bring too much of it.  It doesn't get better with excess.  Prep as much as you can, remember the boat is moving, nothing stays on the table.
  • Leave your pets at home.
  • Gift Certificates are good for one year after date indicated.
  • Don't watch the weather, that guy sucks.

Day and Sunset Sails

Charters can be scheduled morning, mid-day, and sunset (times vary with seasons).

I will work with you, give me a heads up. Also, don’t be late, the clock starts when you are scheduled and we will return on time.

Full Day Sails

Full day charters will be seven hours long and scheduled at your convenience.  You can decide the itinerary, we can sail all day or choose to anchor at one of the many gunk holes where you can relax.  There are a couple of places where we can go for lunch if that's what you want to do.  Typically that only works during the week, not many 50ft parking spaces available on the weekends.


Multiday Sails

Choose a destination such a Baltimore, Annapolis, Havre de Grace, St. Mikes, etc. and we plan the trip around sailing there.  The Chesapeake Bay is truly a gem, anchorages abound and if you really want to get away that's not a problem.  This type of trip is best discussed over the phone so don't hesitate to call.

In addition to the charter fee you're responsible for:

  • Marinas
  • Fuel and pump out
  • Feeding the captain


Team Building

Bring your office team out for a day on the water, 9a-5p. Learn basic sail racing strategies and compete in a mock race against the clock or another boat. Teams can crew in groups up to six per boat. Learn crew positions, tacking, jibing, on a windward/leward course. Food and drink available, additional charges apply if you want the boat(s) staged in another port such as Annapolis, Baltimore, Saint Michael's, etc...

Stay In town!

Osprey Point Inn

Blue Heron Oyster House

Blue Heron Oyster House

The Inn is located at the marina complete with rooms, resturant, pool....I highly recommend it.  Excellent breakfast! Reservations require. 

Blue Heron Oyster House

Blue Heron Oyster House

Blue Heron Oyster House

Excellent fare, casual dining with indoor and outside seating.  Rooms and ice cream too!  I go to the BHOH multiple times a week.

Main Stay

Blue Heron Oyster House

Places to Stay

Live music, open mic night, the occasional movie.  It's an eclectic place for sure.  

Places to Stay

Places to Stay

Places to Stay

Make it a weekend and enjoy the Eastern shore.  Lodging  Resturants

Things to do

Places to Stay

Things to do

Kent County has many events throughout the year, don't miss Pirates and Wenches Weekend!

Rock Fishing

Places to Stay

Things to do

Numerous fishing charters in town, come catch a prized and taste rock fish.  aka Striped Bass

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