Maryland: Eastern Shore & Chesapeake Bay

6 days
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4.9/5 Excellent
100+ reviews  
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Group Tour
You won’t find another cycling tour like this splendid spin along Maryland’s Chesapeake Bay! With our deep local connections, VBT brings you a unique adventure featuring Southern warmth and hospitality. In the quaint coastal village of Rock Hall, you’ll be treated like family by your charismatic local innkeepers. Here, you might choose to relax—sipping cockta...
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Trip type
Group Tour
Lodging level
Premium - 4 star
Physical level
Trip pace
Full schedule


    • Sail the eastern shores with Captain Ed aboard the skipjack HM Krentz
    • Feast on the region’s famous seafood
    • Ride through the Blackwater National Wildlife Refuge, a haven for more than 250 bird species, and learn about Harriet Tubman at the newly opened Underground Railroad State Park and Visitor Center
    • Travel on the country’s oldest privately owned ferry (since 1760), across the Tred-Avon River between Oxford and Bellevue
    • Cycle the quiet country roads leading to the charming small towns of Oxford, St. Michaels, Rock Hall, and Easton

What's this trip about?

    You won’t find another cycling tour like this splendid spin along Maryland’s Chesapeake Bay! With our deep local connections, VBT brings you a unique adventure featuring Southern warmth and hospitality. In the quaint coastal village of Rock Hall, you’ll be treated like family by your charismatic local innkeepers. Here, you might choose to relax—sipping cocktails by the water, taking a dip in the saltwater pool, or listening to the piano in your inn’s charming parlor. Pedaling the cheerful inlets of Chesapeake Bay, you’ll pass stately bayside homes, spin through the Blackwater National Wildlife Refuge, and visit the Harriet Tubman Underground Railroad State Park. For the quintessential Maryland experience, you’ll meet a local fisherman and cruise on his traditional skipjack while listening to spirited tales of life on the water.  


Itinerary focusActive and Outdoor Sports
Group sizeSmall Group - max of 20 people
Age range13 to 80 years
Flights and transportN/A
Start CityEaston
End CityEaston

Travel Themes

  • Birding
  • Cycling & Biking
  • Nature & Wildlife
  • Photography


  • North America
  • United States


  • Belleview
  • Cambridge
  • Chesapeake Bay
  • Chestertown
  • Eastern Shore
  • Easton
  • Maryland
  • Oxford
  • St. Michaels


  • Cycling
  • Wildlife viewing

Trip includes

    • 5 nights in charming country inns
    • 11 meals: 5 breakfasts, 3 lunches, 3 dinners
    • Transportation from Baltimore/Washington International Airport to Easton
    • Transportation from Rock Hall to Baltimore/Washington International Airport
    • Custom VBT Bike and Helmet
    • Two Local, Bilingual Trip Leaders
    • Support Vehicle
    • Luggage Transportation
    • Ride with GPS and Daily Route Notes
    • Welcome Reception
    • Facilitated Cultural Experiences
    • Your Choice of VBT Branded Gear for Your Adventure


Travel Map
DAY 1: Arrive in Easton / VBT Bicycle Vacation begins

VBT provides a shuttle from Baltimore-Washington International Airport (BWI) to the Tidewater Inn in Easton, departing at 1:00 p.m.

Travel to Easton and the Tidewater Inn where your group and trip leaders will meet at 3:00 p.m. for a safety and bike-fitting ses...

DAY 2: Ride the Oxford & St. Michaels Trail / Sail on the HM Krentz / Self-Guided visit to the Chesapeake Bay Maritime Museum

Today you are in for a treat. The Oxford/St. Michaels Loop is considered one of the premiere biking routes on the East Coast. You will ride a clockwise route from your inn, through Oxford, a 17th-century town with a long tradition of boat building. Cutts and Case Boat...

DAY 3: Ride through Blackwater National Wildlife Refuge / Harriet Tubman Underground Railroad State Park

Leaving Easton this morning, shuttle 30 minutes to nearby Cambridge. Today’s ride starts in front of the town’s Harriet Tubman ‘take my hand’ mural.

Our scenic ride takes place in the Blackwater National Wildlife Refuge. Called one of the “Last Great Places” by...

DAY 4: Ride the farmlands of Kent County / Crow Vineyard & Winery / Eastern Neck Wildlife Refuge

More than half of the land in Kent County is devoted to farming. Spend the morning riding through its peaceful agricultural terrain.

Pedal past rows of wheat, corn, and soybeans on shaded lanes leading down to rewarding views of the Sassafras River and Turner’s...

DAY 5: Ride to Chestertown

After breakfast, ride north today to Chestertown, a historic colonial town on the Chester River. Chestertown was founded in 1705 and was one of Maryland’s six Royal Ports of Entry. In the mid-18th century, it was the second leading port in Maryland. The town’s shippin...

DAY 6: VBT Bicycle Vacation ends / Departure

Your Eastern Shore biking vacation concludes mid-morning at the inn. Your included shuttle will take you back to Baltimore-Washington International Airport (BWI), arriving around 12:00 p.m. We suggest a flight out of BWI no earlier than 2:00 p.m. For guests who parked...

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Dates & Availability

Price From $2,545
Price per day$424
Last Updated: 4/12/2024
Start Date
End Date
Shared Room
Single Supplement
21 Apr 2024
26 Apr 2024
05 May 2024
10 May 2024
12 May 2024
17 May 2024
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26 May 2024
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02 Jun 2024
07 Jun 2024
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27 Sep 2024

Check Current Availability, prices, specials with VBT Bicycling Vacations.

The total tour cost includes the tour price (regular or promotional) and the compulsory local payment. The promotional price is subject to change. Check directly with the operator for the latest price offer. The tour operator requires you to pay only the tour price to purchase your travel. The compulsory local payment will be paid when you join the trip. All prices are based on double, twin or triple share occupancy. Solo passengers will be accommodated in a double, twin or triple room according to availability with a passenger(s) of the same gender. Single supplement only needs to be paid if the passenger does not want to share and requests their own room. Discounts can only be applied at the time of booking and cannot be added at a later date, regardless of any changes made to the original booking.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

VBT Bicycling Vacations Reviews & Ratings

4.9/5  Excellent
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Tour Operator

VBT Bicycling Vacations

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Since 1971, VBT has crafted immersive and authentic biking vacations for active travelers. When you travel with VBT, you’re not just another tourist—you’re a traveler. With us, you’ll experience your destination with the help of a local, bilingual trip leader with a passion for sharing their home with you. You’ll eat in local restaurants, stay in accommodations that have been family-owned for generations and cycle through vineyards, olive groves, and medieval villages. 

With VBT, you won’t just visit a place—you’ll immerse yourself in it. You might follow a centuries-old pasta recipe while taking a cooking class in Rome—or learn a folk dance in Croatia, followed by sharing a bottle of locally-produced Grk wine with your new friends. Exploring the world on two wheels lets you experience your surroundings on a deeper level.


VBT offers exceptional value without compromising on quality. Simply put, no other US-based active travel company offers an experience this rich for such a reasonable price. On our tours, you can see more sights, have more local experiences, and enjoy more delicious, authentic meals—all while staying in high-quality, boutique hotels and charming, family-run inns.


All you have to do is show up at the airport—we’ll handle the rest! From tour consultants who help you find the perfect vacation to expert local trip leaders who show you the best place for gelato, we take care of all the little details that make your trip memorable. We book your flights, arrange all your transportation and accommodations, and move your luggage between hotels. Our support vans are available to give you a lift up a hill or quickly fix a flat tire. VBT takes care of your travel details and creates unique itineraries so you can relax and enjoy your small-group vacation from start to finish.


Friendly camaraderie, cultural immersion, and casual comforts are the hallmarks of our vacations. Discover delightful people, beautiful hotels, foreign cultures, and fascinating lifestyles that will enrich your life and provide memories for years to come.

Why we love this operator
Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.
What they’re known for
VBT Cycling are renowned for offering exceptional guided and self-guided bicycle tours worldwide.


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Travel Insurance
We strongly recommend purchasing travel insurance alongside your travel package to safeguard against unforeseen circumstances such as medical expenses, trip cancellations, and other contingencies. It offers you peace of mind and ensures you are prepared for unexpected events that may occur before or during your journey
Visa requirements
Visa requirements vary depending on your country of origin and your country of destination. It is your responsibility to familiarize yourself with the relevant requirements. For a handy tool that can help you quickly find the requirements, please visit this link .
Meals Included

11 meals: 5 breakfasts, 3 lunches, 3 dinners

Age Requirements
13 to 80 years
Additional Information
What to Expect This tour offers easy ride options with only a few gradual hills. It is possible to ride the entire week without the need for assistance, but our VBT support vehicle is always available in cases of inclement weather or for those who wish to shorten their rides. Daily Mileage: 6 - 33 miles| Biking: 1 - 4 hours| Group Size: 20
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