Shown below is a sample cruising itinerary. Please also consult your charts and cruising guide when planning your charter.

Havre de Grace – A charming town located just off I-95 at the “Head of the Bay” with a downtown that is easily walkable from the waterfront. Tidewater Marina, home of BaySail School & Yacht Charters, is a full service marina with about 200 slips and moorings. Within just a few blocks of the marina there are several excellent restaurants, antique shops, Bed & Breakfasts, and a boardwalk on the bay with the Concord Point Lighthouse. Restaurant Suggestions: Tidewater Grille (410-939-3313), MacGregor’s (410-939-3002), Coakley’s Pub (410-939-8888), La Cucina (410-939-1401), Laurrapin Grille (410-939-4958),  and for breakfast VIntage Café (410.939.1333) or the Waffle House (410-939-4870).

Sassafras River – Has some good anchorages along the river plus good marinas & restaurants in Georgetown. Recommend Sailing Associates (410-275-8171) or Georgetown Marina (410-648-5112) for a slip or mooring. Skipjack Cove (410-275-2122) has slips and a restaurant.  Depending on the season, they may have a water taxi service (call for info). Another nice and convenient restaurant is the Granary (410-275-1603). Turner Creek is a good anchorage on the Sassafras. (Georgetown is about 3 hours from BaySail).

Still Pond – Quiet anchorage (no facilities) – Voted “Best of the Bay” by Chesapeake Bay Magazine readers last year. Please do NOT go “inside” because of shallow water. This anchorage is not good when wind is strong from the West or Northwest. (Still Pond is about 3 hours from BaySail).

Worton Creek – Worton Creek Marina (410-778-3282) for a slip. You may also anchor here. Good restaurant, Harbor House (410-778-0669) but they do not have a water taxi. Call first to check restaurant days of operation. (Worton Creek is about 4 hours from BaySail).

Fairlee Creek – We recommend visiting here on weekdays  because it can get crowded on weekends in the summer. You can either anchor or get a slip at Mears Great Oak Landing (410-778-2100) which has a restaurant and tiki bar on the weekends (call for hours). Please read Cruising Guide for directions on entering Fairlee Creek before you go in. Generally, on approach, follow the green can buoys but favor the shore. Then head for the sign that says, “Great Oak Landing” . When going through the cut, favor the northern shore because in recent years the cut has become a little wider.  (Fairlee Creek is about 5 hours from BaySail).

Rock Hall – Charming town with marinas, restaurants and shops. Please read Cruising Guide for directions on entering Rock Hall before you go in. For a slip we recommend Rock Hall Landing Marina (410-639-2224) and for dining we suggest Harbor Shack (410-639-9996) or Waterman’s Crabhouse (410-639-2261). When you are approaching Rock Hall harbor and you are in the channel before the breakwater, stay in the channel but keep close to the right side (favor the red day marker). Once you are past the breakwater and inside the harbor, use the channel that goes around the perimeter. (Rockhall is about 6 – 7 hours from BaySail).

Baltimore Inner Harbor – Bustling port with marinas, restaurants, shops, and attractions. The Inner Harbor Marine Center (410-837-5339) puts you right in the middle of the Inner Harbor action. (Inner Harbor is about 9 hours from BaySail).

Annapolis – Capitol of Maryland. Lots of marinas, restaurants, shops. The City Dock has been rebuilt and is an easy place to stay. Call 410-263-7973 for a slip or mooring. Slips are also available at Mears Marina Annapolis (410-268-8282) or Yacht Basin Company (410-263-3544) (Annapolis is about 8 hours from BaySail).

St. Michaels – Quaint town with good restaurants, shops, marinas and Maritime Museum. Recommend St. Michaels Harbor Marina (410-745-9001). (St. Michael’s is about 12 hours from BaySail).

Please Note: Conditions on the Chesapeake Bay can change. The above itinerary and directions are suggestions only. Skippers should consult professional cruising guides and charts and always use their own good judgment when sailing.