Classic Chesapeake Cruise
September 17 - 23, 2026
Early Board September 16
Rock Hall, Annapolis, Choptank River, Oxford Maryland
Join us for a cruise to several iconic Chesapeake destinations. We’ll moor in Annapolis Harbor - where we can enjoy the skyline, watch the boat parade or take a five minute water taxi to the historic downtown and the U.S. Naval Academy. We’ll sail to the Choptank River, taking the fun (and sometimes nail-biting) shortcut through Knapps Narrows, and we’ll spend a day in Oxford, one of Maryland’s oldest and most charming waterfront towns. This sail promises to be classic and historic – visiting both the Eastern and Western shores of the Chesapeake, the busy maritime port of Annapolis, and the bucolic Oxford.
The Plan
We’ll start our sail in Rock Hall, Maryland on Wednesday, September 16th. Plan on arriving at Haven Harbour Marina in the late afternoon to stow gear and head out to dinner at one of the favorite spots in Rock Hall.
Annapolis, Maryland waterfront
Tursday, September 17th
Thursday morning, after our skippers meet and check out the boats, we will sail down the Bay for a 17 nm sail to Annapolis. We’ll grab a mooring ball and enjoy the sights and sounds of this capital city.
Friday, September 18th
Friday is a 22 nm sail to Dun Cove on the Choptank River. We’ll navigate through Tilghman Island via Knapps Narrows - a shortcut designed for vessels navigating from the northern
Chesapeake Bay into the Choptank River (that would be us). We’ll anchor for the night in Dun Cove and enjoy our traditional raft up appetizer-dinner party.
Saturday, September 19th
We’ll make our way to lovely Oxford – a 12 nm trip through the Choptank River and up the Tred Avon River. The Safe Harbor Marina will be our home until Monday. They have a pool with Tred Avon views, courtesy bikes and shuttles to help us explore quaint Oxford, grills, a bathhouse, and a comfortable clubhouse. And, of course, we can always do some day-sailing if we want.
Charming Oxford, Maryland
Sunday, September 20th
Layover day to enjoy the marina’s amenities, explore Tred Avon, or go for a sail.
Monday, September 21st
Aptly named Knapps Narrows, Maryland
On Monday we’ll reverse our course to start heading home. We’ll anchor again at Dun Cove.
Tuesday, September 22nd
We’ll once again navigate Knapps Narrows (now that we are old hands at this shortcut) on our way back to a mooring ball in Annapolis.
Wednesday, September 23rd
It’s an early sail back to Rock Hall, where we’ll fuel up, pump out, and head for home.
The Boats
Two identical Catalina 445s have been reserved from Haven Charters in Rock Hall. Both have three cabins and two head and, while docked air conditioning, in the rare event it might be needed.
The cost of this trip is $1,100.00 per person (Skippers and Trip Leader: $588.00). The price includes charter fees and two nights’ slip fees and two nights’ mooring fees . Provisioning, fuel, pump-out, and all other incidentals are additional and will be handled by each boat’s crew.
The deposit for this trip is $100.00. Please make your check payable to The Sailing Club, Inc. and mail it, along with your completed two-page Reservation/Release Form, to Anne Marie Kelly at the address below. Reservations will be processed beginning April 13, 2026 with a random draw of those received by that date. All reservations received after that date are on a first come, first served basis. The balance of $1,100.00 is due on August 3, 2026. The Club’s standard thirty-day cancellation policy applies for this event.
A pre-trip meeting will be held a couple of weeks before the trip, at a time and place to be announced. All crew members should make every effort to attend in order to meet your crewmates, plan your meals, and make travel plans.
Please review the Club’s trip signup procedure and policies in the Trip Information Package.
Trip Leader
Anne Marie Kelly
29 Bethpage Drive
Skillman, New Jersey 98558
609-955-6757
annemariekelly@verizon.net
Assistant Trip Leader
Jan Cornelius
165 Brooktondale Rd
Brooktondale, NY 14817
607-342-6528
JanCCornelius@gmail.com
Please note that sailing conditions are dynamic, that your safety,
and that of your crewmates, depends on your good physical health and agility.
