Great Chesapeake Bay Loop Trip Ideas

We invite you to visit and explore Maryland’s Great Chesapeake Bay Loop, which skirts the largest estuary in the United States. Sail the Bay’s sparkling waters; breathe in her slightly salty air; taste the flavors of her fresh seafood bounty and local produce from the farms that line her shores; and enjoy her quaint 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.

No matter if you are looking for a quiet escape off-the-beaten-path at a cozy inn, a relaxing stay at a luxury hotel, a rustic camping or cabin experience, or a culturally-enriching holiday at a historic inn, the Great Chesapeake Bay Loop is the perfect destination. 

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

Unique Chesapeake Experiences: Bayside Adventure and Luxury

Who says you can’t do it all? Try active Bay adventures, sample local and authentic culinary delights, experience exciting nightlife and entertainment, and relax and pamper yourself at luxury hotels and spas. 

Explore jewels of the Chesapeake such as Baltimore, Annapolis, Kent Narrows and Easton. 
106 miles, 5 days, 6 nights - Plan Your Trip

Authentic Journeys on the Bay: The Cultural Explorations

Bring the family on this “historically” fun getaway. Explore charming Chesapeake Bay towns and discover watermen’s lifeways and lore. See iconic Chesapeake Bay sights on historic ships and learn Maryland’s best kept secrets. 

See these quintessential Chesapeake Bay towns: Annapolis, St. Michaels, Cambridge, Crisfield/Smith Island, and Chesapeake City.

The Heart of the Chesapeake: Annapolis to St. Michaels and Oxford, 109 miles, 5 days, 4 nights - Plan Your Trip 

The Chesapeake's Eastern Shore: Chesapeake City to Cambridge, Crisfield and Smith Island, 271 miles plus a ferry trip, 7 days, 6 nights - Plan Your Trip

An Outdoor Odyssey: Paddling, Pedaling and Playing on the Bay

Lace up your hiking boots and pack your paddle. Uncover hidden natural treasures on an off-the-beaten-path excursion through unique environments, showcasing the Chesapeake’s scenic beauty. 

Discover picturesque waterside Bay towns in Edgewater, Solomons, Leonardtown, Dameron, Scotland, and Smith Island.

The Chesapeake's Western Shore: Annapolis to Solomons and Leonardtown, 139 miles, 5 days / 4 nights - Plan Your Trip

Off the Grid Island Getaway on the Chesapeake Bay: Ridge to Ewell on Smith Island, 59 miles plus a ferry trip, 6 days / 5 nights - Plan Your Trip