Eastern Shore

Kent Island

Kent Island is all about the Eastern Shore Lifestyle. Surrounded by water and abundant wildlife such as nesting eagles, blue herons and nature trails with deer, fox, rabbit and the elusive Black squirrel.  Kent Island allows one to simply relax and nurture one’s inner soul. Kayaking, crabbing, biking, strolling on beaches, collecting sea glass is a way of life on the quiet shores of Kent Island.

Check out our Boozy Kent Island Tour!

- Chesapeake Bay Environmental Center & Visitors Center

- Kent Narrows

- Cross Island Trail

- Historic Kent Manor

- The Chesapeake Bay Beach Club

- Shopping

- Dining

- Accommodations




Take a lazy stroll down our tree lined streets, stop in our unique art galleries and boutiques and dine in one of our visitor friendly coffee shops and renowned restaurants. Indulge in a cozy stay in one of our gracious Victorian Bed and Breakfast or Historic Inns, enjoying a leisurely morning breakfast before exploring the 8th Best Small Town in America. 

- Tidewater Inn

- Historic Downtown

- Talbot Historical Society

- Adkins Arboretum 

- Avalon Theater

- Shopping

- Dining

- Accommodations


St. Michaels


St. Michaels is a picturesque harbor on Maryland's Eastern Shore and was named as one of the Top 10 Best Small Coastal Towns in America by USA Today.  Its harbor and some homes date back to the mid-1600's, and is home to the Chesapeake Bay Maritime Museum where you can immerse yourself in our maritime history.  

Check out or Boozy St. Michaels Tour!

- Inn at Perry Cabin

- Tilghman Waterman's Museum

- Classic Motor Museum

- Chesapeake Bay Maritime Museum

- Shopping

- Dining

- Accommodations 



A charming, tree-lined and waterbound village with a population of less than 1000, Oxford is one of the oldest towns in America and has a long history in maritime activities. Early in the day, you will still find local watermen at the town dock unloading the catch of the day. You can watch the sailboats arriving from all over the bay to dine at the various local restaurants our town has to offer. 

- Oxford Bellevue Ferry: America's Oldest Privately Owned Ferry

- Robert Morris Inn

- The Oxford Museum

- Shopping

- Dining

- Accommodations