Chesapeake Bay

πŸ‡ΊπŸ‡Έ United States

Chesapeake Bay

Mid-Atlantic

Overview

America's inland sea: 200 miles of sheltered water from Baltimore to Virginia Beach, with Annapolis at its heart and a tradition of east coast sailing that predates the Republic.

The Chesapeake Bay is the largest estuary in the United States, stretching 200 miles from the Susquehanna River at its head to the Virginia Capes at its mouth. The bay is wide β€” up to 30 miles across β€” shallow in most areas, and dotted with tributaries, rivers, and creeks that multiply the navigable shoreline into thousands of miles of cruising ground. American sailing culture has its spiritual home here; Annapolis, on the bay's western shore, is the centre. Annapolis, home to the United States Naval Academy and a concentration of yacht clubs, charter companies, and marine businesses, is the primary charter base. The town's colonial-era harbour, framed by the Maryland State House dome, provides berths at several marinas and an anchorage in the Severn River. The charter fleet operates from Annapolis and from several points along the eastern and western shores. The Eastern Shore β€” the flat, agricultural peninsula between the bay and the Atlantic β€” provides the best cruising. The rivers and creeks that indent the shore, St Michaels, Oxford, Tilghman Island β€” are the traditional stops. St Michaels, a former shipbuilding town, has a maritime museum, a handful of restaurants, and visitor berths at the town dock. Oxford, across the Tred Avon River, is quieter β€” a ferry, an inn, and a yacht club. The Eastern Shore's character is rural, unhurried, and waterfront-oriented in a way that the more developed western shore is not. South from Annapolis, the bay widens toward the Virginia state line. Solomons Island, at the mouth of the Patuxent River, provides a midpoint stop with marinas and restaurants. The southern bay, below the Potomac River, is less chartered but offers Tangier Island β€” a Chesapeake fishing community accessible only by boat, with a culture and accent that preserve elements of colonial-era English. The wind is typically southerly in summer, 8-18 knots, providing a gentle thermal breeze on most afternoons. Thunderstorms can develop rapidly on summer afternoons, producing strong gusts and heavy rain that pass within an hour. The bay is shallow enough that wind-driven chop is the dominant sea state rather than ocean swell. Provisioning in Annapolis is comprehensive. The Eastern Shore towns have small markets. Blue crabs β€” steamed, picked, and formed into crab cakes β€” are the bay's culinary identity, available at nearly every waterfront establishment. Fuel and water are at all marinas.

Charter Companies

Charter company operating in Chesapeake Bay?

Reach sailors planning their next charter β€” featured placement on this page from $500/month.

Become a Charter Partner

Plan this trip

Flights to Baltimore/Washington International Airport

Search flights on Expedia.

Travel insurance

Get a quote from World Nomads.

Most travel policies exclude crew responsibility and damage to the chartered yacht itself β€” check the small print.

Transfers to Baltimore/Washington International Airport

Are you a transfer operator at Baltimore/Washington International Airport? List your business with Sail Marker β€” be discoverable to every charter customer planning a trip here.

Partner with us

Provisioning at Chesapeake Bay

Local supplier? Welcome packs, fresh provisions, alcohol delivery β€” be the trusted name at Chesapeake Bay.

Become a partner

Marinas & Charter Bases

Marina listings for this destination are being compiled.

Itinerary Routes

Suggested sailing itineraries are being prepared by our editorial team.

Related Guides

Editorial guides for this destination will appear here.

On the Ground

Provisioning, airport transfers, crew agencies, and chandleries serving Chesapeake Bay.

Provide services in Chesapeake Bay?

Provisioning, transfers, crew hire, equipment β€” from $100/month.

List Your Service