Authentic Journeys on the Bay: The Chesapeake's Eastern Shore

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

Chesapeake City from Above

@bill_tha_thrill

The Ben Cardin C & D Canal Trail

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View from the Bayard House Restaurant in Chesapeake City

Day 1 - The Charms of Chesapeake City

Chesapeake City

Drive to Chesapeake City
Browse the unique shops and boutiques in this quintessential Bayfront town
Reel in lunch with a view at Chesapeake Inn and Marina
Walk or bike the paved Ben Cardin C&D Canal Trail
Reflect on your day over drinks and dinner at The Bayard House Restaurant
Be lulled to sleep by the sound of ships gliding through the canal at the Ship Watch Inn

Friends of Mount Harmon

Mount Harmon Plantation

Chesapeake Water Tours

Cruising on the C & D Canal with Chesapeake Water Tours

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Sunset on the C & D Canal in Chesapeake City

Day 2 - Tidewater Tales on Land and Water

Chesapeake City to Earleville and Galena

Wake up and enjoy breakfast (included) on the porch at The Ship Watch Inn
Drive to Mount Harmon Plantation for a tour of the tidewater plantation, manor house and nature preserve (30 minute drive)
Drive to Galena for a delightful lunch at Deep Blue at Kitty Knight, perched on the deck above the Sassafras River (20 minute drive)
Sip and savor Maryland wine with a trip to Crow Vineyard and Winery (10 minute drive)
Return to Chesapeake City (25 minute drive)
Cruise the historic C & D Canal on a guided tour with Chesapeake Water Tours and watch cargo being transported between ports.
Spend dinner time watching ships glide down the canal at Shaefer’s Canal House
Return to the Ship Watch Inn

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Blackwater National Wildlife Refuge

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

Local beer on tap at RAR Brewing Company

Day 3 - Waterside Natural Splendor

Chesapeake City to Cambridge

Enjoy breakfast (included) with a view at the Ship Watch Inn
Drive to Cambridge (1 hour 30 minutes)
Visit the Harriet Tubman Museum and Educational Center in downtown Cambridge
Lunch on rockfish bites or a crabby burger at Portside Seafood Restaurant
Take a scenic drive to see eagles and waterfowl at the Blackwater National Wildlife Refuge (20 minute drive south of Cambridge)
Experience a nostalgic nautically-themed dinner and find your culinary treasures at The Dive Club in Cambridge
Unwind with local hipsters at RAR Brewing
Spend the night in a fully restored 19th-century sea captain’s manor at The Cambridge House Bed and Breakfast

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.

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

Indulge in a full breakfast overlooking the pond at the Cambridge House Bed and Breakfast
Travel to and explore the Harriet Tubman Underground Railroad Visitor Center (20 minute drive south of Cambridge)
Stop for locally-sourced lunch at Emily’s Produce
Follow in Tubman’s footsteps on the Harriet Tubman Underground Railroad Scenic Byway, stopping at Brodess Farm, Bucktown Store, Madison, and Stewart’s Canal
Have a cozy dinner at Ava’s Pizzeria and Wine Bar
Check into the Hyatt Regency Chesapeake Bay
Enjoy a nightcap at Michener's Library at the Hyatt and sleep in luxury overlooking the Choptank River

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Waterman Barry Bruce Crab Scraping off Smith Island

Experience Smith Island

Boat Tour to Smith Island with Experience Smith Island

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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

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Sunset at Janes Island State Park

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Canoeing on the water trails 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