Sailboat racing past Thomas Point Lighthouse
Getty Images

Sailboat racing past Thomas Point Lighthouse.

Plan Your Getaway on the Great Chesapeake Bay Loop

Sailboat racing past Thomas Point Lighthouse
Getty Images

Sailboat racing past Thomas Point Lighthouse.


Chesapeake Bay Map

This map of Maryland and surrounding states shows the area of the Chesapeake Bay and its shorelines dotted with historic waterfront towns.

Come visit and explore Maryland’s Chesapeake Bay, the largest estuary in the United States and a place of serene beauty. Breathe in her slightly salty air; taste the flavors of her fresh seafood bounty and the farms that line her shores; enjoy her waterfront towns; talk to the locals, some of whom have lingering accents from their ancestors who settled the area over 300 years ago; and feel the freedom of escaping land and being on her waters.

To help you plan your Chesapeake Bay getaway, here are some trip ideas to get the most memories per mile.

Take a Chesapeake Bay Storyteller Tour

Travel Around the Chesapeake Bay

Visit Quintessential Chesapeake Bay Towns

25 Can’t Miss Things To Do Along The Great Chesapeake Bay Loop

Stay Along the Great Chesapeake Bay Loop


Aerial View of Oxford


Cove Point Lighthouse
Matthew McKinney

Cove Point Lighthouse

Historic Inn on the Eastern Shore
The Inn at Perry Cabin by Belmond

Inn at Perry Cabin by Belmond

Watermark Cocktail

Watermark Cocktail

Sailing on Chesapeake Bay
Melvin P. Heyes

Island Chill Yacht Charters

Bay Bridge sunset

Chesapeake Bay Bridge

To begin your exploration, select one or more QUINTESSENTIAL CHESAPEAKE BAY TOWNS as the starting point for your adventure. Each town has its own personality and displays a distinct personality. Some provide a serene retreat, while others beat with the thriving energy of the city.

Charming main streets with locally-inspired architecture lure you to peruse unique shops and galleries where you will be greeted by friendly staff. Seafood restaurants entice with the aroma and flavors of the day’s fresh catch.  And there are places to feed the mind and curiosity too, at numerous maritime and decoy museums.

Along the way, stroll along the waterfront and sail on a historic oystering vessel or sightsee on a charter boat. Take a guided tour with a Chesapeake Bay Storyteller  to get a behind-the-scenes look at the Bay and its treasures. Tour one of the Chesapeake’s iconic screwpile lighthouses . These beacons have protected mariners for centuries from the notorious shallow Bay waters.

Birders and hunters flock here seeking the nearly one million waterfowl that stop to feed and rest on the Chesapeake during their annual migration. An extensive network of  national wildlife refuges and state parks, along with a large trail system, provide numerous places for you to get outside and marvel at the beauty of the region. With wetlands, sandy beaches, hundreds of rivers and creeks and open waters to explore, the Chesapeake Bay is home to an incredible diversity of flora and fauna that are a photographer’s dream.

Along your journey, thread together several towns or points of interest by traveling on one of MARYLAND’S SCENIC BYWAYS. Come back and explore a new area each time until you’ve seen them all!