Chesapeake City
Dick Legates chesapeakecity.com

Authentic Journeys on the Bay: Cultural Explorations Option 2

Chesapeake City
Dick Legates chesapeakecity.com

 
Chesapeake City to Cambridge, Crisfield and Smith Island, 271 miles plus a ferry trip, 7 days, 6 nights
 

 

Chesapeake City from Above

Chesapeake City from Above

The Ben Cardin C & D Canal Trail
@bill_tha_thrill

The Ben Cardin C & D Canal Trail

View from the Bayard House Restaurant in Chesapeake City
@engineerin.ginger

View from the Bayard House Restaurant in Chesapeake City

Day 1 - The Charms of Chesapeake City

Chesapeake City

 

Mount Harmon Plantation
Friends of Mount Harmon

Mount Harmon Plantation

Cruising on the C & D Canal with Chesapeake Water Tours
Chesapeake Water Tours

Cruising on the C & D Canal with Chesapeake Water Tours

Sunset on the C & D Canal in Chesapeake City
@austinbndr28

Sunset on the C & D Canal in Chesapeake City

Day 2 - Tidewater Tales on Land and Water

Chesapeake City to Earleville and Galena

 

National Wildlife Refuge
@abitslippy3

Blackwater National Wildlife Refuge

The Harriet Tubman Mural by Michael Rosato outside the Harriet Tubman Museum and Educational Center

The Harriet Tubman Mural by Michael Rosato outside the Harriet Tubman Museum and Educational Center

Local  beer on tap at RAR Brewing Company

Local  beer on tap at RAR Brewing Company

Day 3 - Waterside Natural Splendor

Chesapeake City to Cambridge

 

Harriet Tubman Boat sculpture at The Harriet Tubman Underground Railroad Visitors Center
Governor’s Office Official Photo

Harriet Tubman sculpture at The Harriet Tubman Underground Railroad Visitor Center

Inside the Bucktown Store on the Harriet Tubman Underground Railroad Scenic Byway.

Inside the Bucktown Store on the Harriet Tubman Underground Railroad Scenic Byway.

Sunset on the Choptank River at the Chesapeake Hyatt
@hyattchesapeake

Sunset on the Choptank River at the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina

Day 4 - Find Your Way to Freedom

Cambridge

Waterman Barry Bruce Crab Scraping off Smith Island
@jilljasutaphotography

Waterman Barry Bruce Crab Scraping off Smith Island

Boat Tour to Smith Island with Experience Smith Island
Experience Smith Island

Boat Tour to Smith Island with Experience Smith Island

A Crab Shanty in Tylerton on Smith Island
@erocrunfaster

A Crab Shanty in Tylerton on Smith Island

Day 5 - Chesapeake Timeless Traditions

Crisfield and Smith Island

  • Drive to Crisfield (1 hour and 15 minutes from Cambridge)
  • Meet your tour guide at the Crisfield dock
  • Tour the “Island Out of Time” with Chesapeake Bay Storyteller Experience Smith Island 
  • Enjoy the freshest crab cake in Maryland for lunch (included with your tour)
  • Watch a hands-on crabbing demonstration at a working watermen’s crab shanty and learn about the iconic Chesapeake Bay Blue Crab
  • See a cake baking demonstration and get a Smith Island Cake to take home with you
  • Tour the Smith Island Cultural Center
  • Hop back on board and return to the dock at Crisfield
  • Enjoy a dinner of local specialties at the Water’s Edge Cafe
  • Stop for provisions and resupply in Crisfield at the Food Lion
  • Head to Janes Island State Park and check into your cabin

 

Sunset at Janes Island State Park
@ericatylerphotography

Sunset at Janes Island State Park

Canoeing on the water trails at Janes Island State Park
@sugarantelope

Canoeing on the water trails at Janes Island State Park

Kayaks at Janes Island State Park

Kayaks at Janes Island State Park

Day 6 -  Maryland’s Best Kept Secret

Janes Island
  • Wake up in tranquility at Janes Island State Park
  • Head to the Janes Island Observation Tower for 360-degree views of your island getaway
  • Rent a kayak, paddle board or canoe to get out on the more than 30 miles of water trails in the park
  • Enjoy a picnic lunch on the water or weigh anchor and find your spot
  • Try your hand at crabbing or fishing at the Janes Island Marina
  • Enjoy a spectacular sunset over the water from your cabin porch
  • Cook the day’s catch at your cabin or head back to Crisfield for dinner at From Scratch
  • Relax under the stars with a campfire

 

Stories of Maryland's Chesapeake Bay

Chesapeake Bay Storytellers guide book with photo of a sail boat

A Collection of Memories, Moments and Inspiration

Download Guide

Maryland's Great Chesapeake Bay Loop Getaway Guide

Maryland's Great Chesapeake Bay Loop Getaway Guide

Find a treasure trove of ways to explore the Bay, and meet our skilled Chesapeake Bay Storytellers.

Download Guide